nutrients

Review A Comprehensive Review of Chemistry, Sources and Bioavailability of Omega-3 Fatty Acids

Mateusz Cholewski 1, Monika Tomczykowa 2 and Michał Tomczyk 1,*

1 Department of Pharmacognosy, Faculty of Pharmacy, Medical University of Białystok, ul. Mickiewicza 2a, 15-230 Białystok, Poland; [email protected] 2 Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Białystok, ul. Mickiewicza 2a, 15-230 Białystok, Poland; [email protected] * Correspondence: [email protected]; Tel.: +48-85-748-5694



Received: 12 October 2018; Accepted: 29 October 2018; Published: 4 November 2018


Abstract: Omega-3 fatty acids, one of the key building blocks of cell membranes, have been of particular interest to scientists for many years. However, only a small group of the most important omega-3 polyunsaturated fatty acids are considered. This full-length review presents a broad and relatively complete cross-section of knowledge about omega-3 monounsaturated fatty acids, polyunsaturates, and an outline of their modifications. This is important because all these subgroups undoubtedly play an important role in the function of organisms. Some monounsaturated omega-3s are pheromone precursors in insects. Polyunsaturates with a very long chain are commonly found in the central nervous system and mammalian testes, in sponge organisms, and are also immunomodulating agents. Numerous modifications of omega-3 acids are plant hormones. Their chemical structure, chemical binding (in triacylglycerols, phospholipids, and ethyl esters) and bioavailability have been widely discussed indicating a correlation between the last two. Particular attention is paid to the effective methods of supplementation, and a detailed list of sources of omega-3 acids is presented, with meticulous reference to the generally available food. Both the oral and parenteral routes of administration are taken into account, and the omega-3 transport through the blood-brain barrier is mentioned. Having different eating habits in mind, the interactions between food fatty acids intake are discussed. Omega-3 acids are very susceptible to oxidation, and storage conditions often lead to a dramatic increase in this exposure. Therefore, the effect of oxidation on their bioavailability is briefly outlined.

Keywords: Omega-3 fatty acids; chemistry; sources; bioavailability

1. Chemistry of Omega-3 Fatty Acids Omega-3 fatty acids, called n-3 fatty acids or ω−3 fatty acids (n-3 FAs), are a heterogeneous group of fatty acids with a double bond between the third and fourth carbon atoms from the methyl end (from the ω−1 carbon atom). In general, we distinguish among them monounsaturated fatty acids (MUFAs; one double bond in carbon chain) and polyunsaturated fatty acids (PUFAs; more than one double bond in carbon chain). Conjugated fatty acids (CFAs) are a subset of PUFAs with at least one pair of conjugated double bonds [1], i.e., the double bonds are not separated by methylene bridges, but one single bond. We also mention some examples of modified omega-3 fatty acids like hydroxy fatty acids (HFAs), oxo fatty acids (keto fatty acids) and hydroperoxy fatty acid. Among the hydroxy fatty acids, we distinguish saturated or unsaturated fatty acids, consisting of a long unbranched carbon chain with a carboxyl group at one end and one or more hydroxy groups. Oxo or keto fatty acids are fatty acids having both a carboxy group and a ketonic or aldehydic group in the molecule. Hydroperoxy fatty acids, in turn, carry at least one hydroperoxy group (-OOH) in the

Nutrients 2018, 10, 1662; doi:10.3390/nu10111662 www.mdpi.com/journal/nutrients Nutrients 2018, 10, 1662 2 of 33 molecule. Some authors find the terms long-chain (LC) n-3 PUFAs and omega-3 fatty acids identical in meaning [2], which can be misleading because “omega-3 fatty acids” is a broader term. We assumed all fatty acids with a double bond at the ω−3 carbon atom to be omega-3 fatty acids. Omega-3 fatty acids show cis-trans isomerism with its extension to E-Z configuration [3]. We can speak of geometrical isomerism in the case of omega-3 fatty acids because two carbon atoms with sp2 hybridization connected by a double bond are linked to a hydrogen atom and group of atoms each. In order to determine the type of geometrical isomerism, at the beginning we choose the two most important substituents—one on the left, the second on the right of the double bond. In fatty acids, we have only one group (of atoms) on each side, because the two remaining binding sites occupies a hydrogen atom. In the cis-isomer these two groups are located on the same side of the reference plane (the plane passing through the atoms connected by a double bond and perpendicular to the plane in which these atoms and atoms directly associated with them are situated); in the trans-isomer they are in contrary positions [4]. The E-Z system is a bit more detailed. The mutual placement of the substituents is described by the Cahn-Ingold-Prelog (CIP) rule. The most important is the substituent whose atom directly connecting to the rest of the molecule (directly with the atom forming the double bond) has a higher atomic number (in the case of isotopes, a higher atomic mass). If in this position, in the substituents (on the right or left side of the double bond), there are identical atoms, then (to choose a substituent of greater importance) we take into account subsequent atoms, always choosing atoms with the highest atomic number. If a given atom is connected by multiple bonds, the bond should be replaced by the number of single bonds appropriate for its multiplicity—each atom present at a multiple binding must after transformation have a corresponding number of single bonds (C=C = 2 × C-C). The “E” configuration (from entgegen, German for “opposite”) means that two groups of higher CIP priority (one on the left, the second on the right from the double bond) are on opposite sides of the double bond (in the synperiplanar position). If those groups are on the same side of the double bond (in antyperiplanar position), configuration is defined as “Z” (from zusammen, German for “together”) [5]. For simplicity, according to many authors, we used the terms “cis” and “Z” as well as “trans” and “E” interchangeably. The cis-trans isomerism of fatty acids seems to play a particularly important role in shaping their chemical and biological activity, a good example of which are the various properties of conjugated fatty acid isomers [1]. Naturally occurring fatty acids usually have from four to 28 carbon atoms. However, many of them, especially those found in the brain, retina and spermatozoa, have a longer carbon chain [6–8]. Fatty acids can be divided, depending on the length of the carbon chain, into four basic groups: i. Short-chain fatty acids (SCFAs), sometimes called volatile fatty acids (VFAs), contain from one to six carbon atoms (C1–6), formed as a result of the fermentation of carbohydrates by the gut microbiota in the digestive tract of mammals [9]. ii. Medium-chain fatty acids (MCFAs) have from seven to 12 carbon atoms (C7–12) [10]; according to other sources eight to 14 carbon atoms [11]. iii. Long-chain fatty acids (LCFAs) have from 14 to 18 carbon atoms (C14–18) and constitute the majority of fatty acids taken with food (diet) [12]. iv. Very long-chain fatty acids (VLCFAs) have backbones containing more than 20 carbon atoms (C > 20) [13], or according to other authors no fewer than 20 carbon atoms (C ≥ 20) [12] or even more than 22 carbon atoms (C > 22) [14–16].

There can also be distinguished fatty acid subgroups, such as dietary long-chain saturated fatty acids (C ≥ 16) and long-chain polyunsaturated fatty acids (LCPUFAs/LC PUFAs; C ≥ 18). While dietary long-chain saturated fatty acids do not directly concern the subject of this article, they deserve to be distinguished in the general chemical classification due to the ease of incorporation into the adipose tissue, and therefore, nomen omen, special dietary significance [11]. Fatty acids with nine or fewer carbon atoms are in a liquid state at room temperature [10]. Nutrients 2018, 10, 1662 3 of 33

The most important, but small, group of fatty acids for humans are essential fatty acids (EFAs), which are necessary to maintain homeostasis, cannot be synthesized, or rather cannot be synthesized sufficiently by the organism, and must be supplied with food [17,18]. The significance of fatty acids in the animal diet was discussed by Osborne and Mendel [19] in 1920. In 1929 Burr and Burr [20] proved in their experiments on rats the ‘essential’ nature of some fatty acids. Some authors consider all PUFAs to be essential fatty acids [21] and determine linoleic acid (LA) and alpha-linolenic acid (ALA) as the most important [17,22], calling them “parent essential fatty acids” [23,24]. Others considered only arachidonic and linoleic acids as essential fatty acids because of their importance for the body’s growth and for maintaining the integrity of the skin [21]. The mammalian literature indicates 23 acids as essential, while the aquatic literature quotes only two EFAs—EPA and DHA. Considering the importance of ARA, we can take ARA, DHA and EPA as the most important long-chain PUFAs in mammals and fish [25]. Some animals can synthesize them using LA and ALA as precursors [25,26]. However, those precursors must be available in sufficient quantities [25]. Gurr and Harwood [27] detailed “essential nutrients” in contrast to “essential metabolites”. In the light of this assumption, “essential nutrients” are precursors of “essential metabolites” and cannot be synthesized by organisms for which they are “essential”. Notwithstanding, “essential” is a relative term—human and rats can synthesize LA and ALA from 16:2n-6 and 16:3n-3 contained in green vegetables, i.e., in microalgae, in conditions of defined substrate availability [28–31]. Considering that there is insufficient data showing that any individual PUFA is absolutely necessary during life, Cunnane divided essential fatty acids into ‘conditionally indispensable’ and ‘conditionally dispensable’ [32–34]. The most important data concerning chemistry and sources of omega-3 fatty acids are included in Table1. Nutrients 2018, 10, 1662 4 of 33

Nutrients 2018, 10, x FOR PEER REVIEW Table 1. Omega-3 fatty acids—chemistry and sources. 4 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 4 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 4 of 34 Nutrients 2018, 10, x FOR PEER REVIEW Shorthand 4 of 34 Common MolecularTable 1. Omega-3 fatty acids—chemistry and sources. No IUPACNutrients Name 2018, 10, x FOR PEER REVIEW (Simplified Table 1. OmegaFormula/Structure-3 fatty acids—chemistry Molecular and Weight sources. Sources [Refs.]4 of 34 Nutrients 2018, 10, x FOR PEERName REVIEW Shorthand FormulaTable 1. Omega-3 fatty acids—chemistry and sources. 4 of 34 Common Shorthand Molecular Molecular No IUPAC Name CommonFormula) (Simplified TableMolecular 1. Omega -Formula/3 fattyStructure acids —chemistryMolecular and sources. Sources [Refs.] NutrientsNo 2018,, 10IUPAC,, xx FORFOR Name PEERPEER REVIEWREVIEWName (SimplifiedShorthand Formula Formula/Structure Weight Sources [Refs.] 4 of 34 Common ShorthandFormula) Molecular Molecular No IUPAC Name CommonName (Simplified TableMolecularFormula 1. Omega -Formula/3 fattyStructure acids —chemistryMolecularWeight and sources. Sources [Refs.] NutrientsNo 2018, 10IUPAC, x FOR Name PEER REVIEWName (SimplifiedFormula) TableFormula 1. Omega MONOUNSATURATEDFormula/-3 fattyStructure acids —chemistryWeight FATTY and ACIDSsources. (MUFAs) Sources [Refs.] 4 of 34 Nutrients 2018, 10, x FOR PEER REVIEWName Formula) Formula MONOUNSATURATED FATTY ACIDS (MUFAWeights) 4 of 34 ShorthandFormula) MONOUNSATURATED FATTY ACIDS (MUFAs) Common Shorthand TableMolecular 1. Omega MONOUNSATURATED-3 fatty acids FATTY—chemistry ACIDS Molecular(MUFA ands) sources.0.08% of fatty acid composition (total free fatty acids) of fresh and mature cheese No IUPAC Name Common (Simplified TableMolecular 1. Omega Formula/-3 fattyStructure acids —chemistryMolecular and sources.0.08%0.08% of fatty of acid fatty composition acid composition (totalSources free fatty [Refs acids (total.] ) of freefresh and fatty mature acids) cheese of fresh and mature cheese samples of No IUPAC Name9-lauroleic 9-Namelauroleic (Simplified Formula MONOUNSATURATEDFormula/Structure FATTY ACIDS (MUFAWeights) samples of commercial (with full fatSources content) [Refs Manchego.] -type cheese and Name ShorthandFormula) TableFormula 1. Weight 0.08% of fatty acid composition (total free fatty acids) of fresh and mature cheese 9Common-lauroleic MolecularOmega O -3 fatty acids—chemistryMolecular and sources.samplescommercial of commercial (with (with fullfull fat fat content) content) Manchego Manchego-type-type cheese and cheese and 0.05%/0.07% of the same cheese 1 (9Z)-dodec-9-enoic acid acidCommon/lauroleic Formula)C12:1n-3 MolecularC12H22O2 H 198.306Molecular g/mol 00.05%.08% of/0.07% fatty ofacid the composition same cheese (total samples free (freshfatty acids and mature)) of fresh made and mature from low cheese-fat/full - 1 (9Z)-dodec-9-enoicNo acidIUPAC Nameacid/lauroleic 9-lauroleicC12:1 n-3(Simplified CTable12H22 O1.2 OmegaO -Formula/3 fattyStructure acids —chemistry198.306 g/moland sources.samples of commercial (with full fatSources content) [Refs Manchego.] -type cheese and No1 (9Z)-IUPACdodec-9 Name-enoic acid acid/lauroleic (SimplifiedShorthandC12:1n-3 C12H22O2 MONOUNSATURATEDH Formula/Structure FATTY ACIDS198.306 (MUFA g/mols) 0.05%/0.07% of the same cheese samplesSources (fresh [Refs and.] mature) made from low-fat/full- 9-lNameauroleicacid Formula MONOUNSATURATEDO O FATTY ACIDS (MUFAWeights) samplesfat milksamples ofwith commercial the (fresh addition (with and of 2full mature)g avocadofat content) oil made perManchego 100 from mL- typeof low-fat/full-fatmilk cheese [35] ;and 0.31 % of free milk with the addition of 2 g avocado oil per 1 (9Z)-dodec-9-enoic acid acidCommon/lauroleic Formula)C12:1n-3 MolecularC12H22O2 H 198.306Molecular g/mol 0.05%/0.07% of the same cheese samples (fresh and mature) made from low-fat/full- No IUPAC Name acid acid (SimplifiedShorthandFormula) O Formula/O Structure 0fat.08% milk of withfatty theacid addition composition of 2 g (total avocadoSources free oilfatty [Refs per acids .100] )mL of freshof milk and [35] mature; 0.31% cheese of free 1 (9Z)-dodec-9-enoic acid acidCommon/lauroleic C12:1n-3 MolecularC12H22O2 H 198.306Molecular g/mol 0.05%fatty100 acids/0.07% mL from of ofthe bovine milksame whey cheese [35 ];cream samples 0.31% [36] (fresh of free and fattymature) acids made from low bovine-fat/full- whey cream [36] Nameacid Formula MONOUNSATURATEDO FATTY ACIDS (MUFAWeights) 0fat.08% milk of withfatty theacid addition composition of 2 g (total avocado free oilfatty per acids 100 )mL of freshof milk and [35] mature; 0.31% cheese of free No IUPAC Name 9-lauroleic (SimplifiedFormula) MONOUNSATURATEDO Formula/Structure FATTY ACIDS (MUFAs) samplesfatty acids of fromcommercial bovine (withwhey full cream fatSources content)[36] [Refs Manchego.] -type cheese and H O 9-lNameauroleicacid Formula O Weight fatsamples milk withof commercial the addition (with of 2 full g avocado fat content) oil per Manchego 100 mL -oftype milk cheese [35]; and0.31 % of free 12 22 2 O fatty0.08% acids of fatty from acid bovine composition whey cream (total [36] free fatty acids) of fresh and mature cheese 12 ((99ZE))--dodecdodec--99--enoicenoic acidacid acid/lauroleic- Formula)C12:1C12:1nn--33 CC12HH22OO2 H 198.306198.306 g/molg/mol 0.05%0in.08% Peganum /of0.07% fatty harmala of acid the compositionsame fatty cheeseacids (concentration (totalsamples free (fresh fatty 0.31 andacids% mature))) [37]of fresh made and maturefrom low cheese-fat/full - 12 22 2 MONOUNSATURATEDO O FATTY ACIDS (MUFAs) 12 ((9ZE)-dodec-9-enoic acid acid/lauroleic- C12:1n--3 C12H22O2 H 198.306 g/mol fatty0.05%in Peganum acids/0.07% from harmala of the bovine same fatty whey cheeseacids c ream(concentration samples [36] (fresh 0.31 and% mature)) [37] made from low-fat/full- 2 (9E)-dodec-9-enoic acid - C12:1n-3 C12H22O2 H O 198.306 g/mol in Peganum harmala fatty acids (concentration 0.31%) [37] 9--llauroleicacid 12 22 2 MONOUNSATURATEDO O FATTY ACIDS (MUFAs) fatsamples milk withof commercial the addition (with of 2 full g avocado fat content) oil per Manchego 100 mL --oftypetype milk cheesecheese [35]; and0.31 % of free 2 (9E)-dodec-9-enoic acid - C12:1n-3 C H O H 198.306 g/mol 0in.08% Peganum of fatty harmala acid composition fatty acids (concentration (total free fatty 0.31 acids%)) [37] of fresh and mature cheese O OO acid 12 22 2 OO fat milk with the addition of 2 g avocado oil per 100 mL of milk [35]; 0.31% of free 21 ((99EZ))--dodecdodec--99--enoicenoic acidacid acid/lauroleic- C12:1nn--33 C1212H2222O22 H 198.306198.306 g/molg/mol in0.05% Peganum/0.07% harmala of the samefatty acheesecids (concentration samples (fresh 0.31 and% )mature) [37] made from low-fat/full- 13 (11(9ZZ))--tetradecdodec-9--11enoic-enoic acid acid acid/lauroleic- C12:1C14:1nn--33 CC14HH26OO2 HH O 198.306226.36 g/mol 0fatty0.05%a.08% precursor acids /of0.07% fatty from of of acid the the bovine compositionsex same pheromone whey cheese cream (totalsamples component [36] free (fresh fatty in acidsand Ostrinia mature)) of fresh scapulalis made and maturefrom [38] low cheese-fat/full - 9-lauroleic O samples of commercial (with full fat content) Manchego-type cheese and 14 26 2 H O fatty acids from bovine whey cream [36] 3 (11Z)-tetradec-11-enoic acid - C14:1n-3 C H O O OO 226.36 g/mol a precursor of the sex pheromone component in Ostrinia scapulalis [38] 9-lauroleicacid H O O samplesfat milk withof commercial the addition (with of 2full g avocado fat content) oil per Manchego 100 mL -oftype milk cheese [35]; and0.31 % of free 1 (9Z)-dodec-9-enoic acid acid/lauroleicacid C12:1n-3 C12H22O2 H 198.306 g/mol 0.05%fat milk/0.07% with ofthe the addition same cheese of 2 g samplesavocado (freshoil per and 100 mature) mL of milk made [35] from; 0.31 low% of-fat free/full - 3 (11Z)-tetradec-11-enoic acid - C14:1n-3 C1214H2226O2 HH O 226.36 g/mol a precursor of the sex pheromone component in Ostrinia scapulalis [38] 3 (11Z)-tetradec-11-enoic2 (9E)-dodec acid-9-enoic acid -- C14:1n-3C12:1n-3 C HC HOO OO 226.36198.306 g/molg/mol in Peganum a precursor harmala fatty ofthe acids sex (concentration pheromone 0.31% component) [37] in Ostrinia scapulalis [38] 14 1226 22 22 H O fatty acids from bovine whey cream [36] 312 (11(9ZZE)-)tetradec-dodec-9-11-enoic-enoic acid acid acid/lauroleic- C14:1C12:1n-3 C1412H2622O2 H O 198.306226.36 g/mol g/mol a0.05%infatty precursor Peganum acids/0.07% from harmalaof of the the bovine sex samefatty pheromone whey acheesecids c (concentrationream samples component [36] (fresh 0.31in and Ostrinia% mature)) [37] scapulalis made from[38] low-fat/full- acid 14 26 2 OOO fat milk with the addition of 2 g avocado oil per 100 mL of milk [35]; 0.31% of free 4 (11E)-tetradec-11-enoic acid - C14:1n-3 C H O H OO 226.36 g/mol 13.37% of leaf essential oil of Coriandrum sativum [39]; in Spodoptera littoralis [40] O O 14 26 2 HH OO 4 (11E)-tetradec-11-enoic acid acid- C14:1n-3 C H O H 226.36 g/mol fat13.37 milk% ofwith leaf the essential addition oil ofof 2Coriandrum g avocado sativumoil per 100 [39] mL; in ofSpodoptera milk [35] littoralis; 0.31% of[40] free 2 (9E)-dodec-9-enoic acid - C12:1n-3 C1212H2222O22 O O 198.306 g/mol fattyin Peganum acids from harmala bovine fatty whey acids c (concentrationream [36] 0.31%) [37] 2 (9E)-dodec-9-enoic acid - C12:1n-3 C14H26O2 O O 198.306 g/mol in Peganum harmala fatty acids (concentration 0.31%) [37] 34 ((11ZE)-tetradec-11-enoic acid - C14:1n-3 C14H26O2 H O O 226.36 g/mol a13.37in precursor microalgae% of leaf of —essentialthe1.39 sex% pheromone, 3.12oil of% ,Coriandrum 0.23 component%, 1.33 sativum% of inDunaliella Ostrinia[39]; in Spodopteratertiolectascapulalis, [38] Platimonaslittoralis [40] viridis , O fatty acids from bovine whey cream [36] 3 (11(13Z)E-tetradec/Z)-hexadec-11-enoic-13-enoic acid - C14:1n-3 C14H26O2 H 226.36 g/mol a precursor of the sex pheromone component in Ostrinia scapulalis [38] E 4 (11E)-tetradec-11-enoic acid - n C14:1n-3 C H O O 226.36 g/mol 13.37in microalgae% of leaf —essential1.39%, 3.12oil of% ,Coriandrum 0.23%, 1.33 sativum% ofCoriandrum Dunaliella [39]; in tertiolectaSpodoptera sativum, Platimonas littoralis [40] viridis Spodoptera, littoralis 4 (11 )-tetradec-11-enoic2 (9E)-dodec acid-9-enoic acid -- C14:1 -3C12:1n-3 C14HC122616HO2230O222 O O 226.36198.306 g/molg/mol in Peganum 13.37% harmala of leaf fatty essential acids (concentration oil of 0.31%) [37] [39]; in [40] 5 (13E/Z)-hexadec-13-enoic - C16:1n-3 C H O undefinedH O cis-trans isomerism 254.414 g/mol Nefrochloris salina and Phaeodactylum tricornutum total fatty acids, respectively, also O O in microalgae—1.39%, 3.12%, 0.23%, 1.33% of Dunaliella tertiolecta, Platimonas viridis, 5 acid - C16:1n-3 C1216H2230O22 undefinedOO cis-trans isomerism 254.414 g/mol Nefrochloris salina and Phaeodactylum tricornutum total fatty acids, respectively, also 23 (11((139ZEE))-/-tetradecZdodec)-hexadec-9--11enoic--enoic13- enoicacid acid -- C12:1C14:1nn--33 C 14H 26O 2 HH O 198.306226.36 g/molg/mol ina precursorPeganum harmalaof the sex fatty pheromone acids (concentration component 0.31in Ostrinia%) [37] scapulalis [38] 3 (11Z)-tetradec-11-enoic acid - C14:1n-3 C14H26O2 H O 226.36 g/mol inapresent precursor microalgae in the of— thegonads1.39 sex% ,pheromone and3.12 %larvae, 0.23 of%component, oysters1.33% of fed Dunaliellain wi Ostriniath the tertiolecta mentionedscapulalis, Platimonas[38] microalgae viridis [41], 45 (11E)-tetradecacid-11 -enoic acid - C14:1C16:1n-3 C1416H2630O2 undefinedH cis-trans isomerism 254.414226.36 g/mol g/mol 13.37Nefrochloris% of leaf salina essential and Phaeodactylum oil of Coriandrum tricornutum sativum total[39]; fattyin Spodoptera acids, respectively, littoralis [40] also (13E/Z)-hexadec-13-enoic OO present in the gonads and larvae of oysters fed with the mentioned microalgae [41] 4 (11E)-tetradecacid-11 -enoic acid - C14:1n-3 C1614H3026O2 O O 226.36 g/mol 13.37in% of microalgae—1.39%, leaf essential oil of Coriandrum 3.12%, sativum 0.23%, [39]; in 1.33% Spodoptera of Dunaliellalittoralis [40] tertiolecta, Platimonas viridis, Nefrochloris salina 5 - C16:1n-3 C14H26O2 undefinedH O cis-trans isomerism 254.414 g/mol Nefrochlorisin Brassica napussalina leafand discs Phaeodactylum—3.35%, 1.06 tricornutum%, 1.19% totalof total fatty PG acids, (phosphatidylglycerol), respectively, also 3 (11Z)-tetradec-11-enoic acid - C14:1n-3 C H O OO 226.36 g/mol apresent precursor in the of gonadsthe sex pheromoneand larvae of component oysters fed in wi Ostriniath the mentioned scapulalis [38] microalgae [41] (13E/Z)-hexadec-13-enoicacid undefinedO cis-trans HH inin microalgaeBrassica napus—1.39 leaf% discs, 3.12—%3.35, 0.23%%, 1.06, 1.33%%, 1.19 of Dunaliella% of total tertiolectaPG (phosphatidylglycerol),, Platimonas viridis, 14 26 2 H O O present in the gonads and larvae of oysters fed with the mentioned microalgae [41] 5 34 ((1111(13ZEE))--/tetradectetradecZ)-hexadec--1111---enoicenoic13-enoic acidacid- -- C16:1n-3C14:1nn--33 C HC1414HO2626O22 H 254.414226.36226.36 g/molg/mol g/mol ain13.37PA precursor microalgae (phosphatidicand% of Phaeodactylumleaf of— theessential1.39 sexacid)% ,pheromone 3.12 oiland of% PC, Coriandrum0.23 tricornutum (phosphatidylcholine) %component, 1.33 %sativum of inDunaliellatotal Ostrinia [39]; fattyin fatty tertiolectaSpodopterascapulalis acids, acids,, respectively,Platimonas[38] littoralis respectively, [40] viridis trace , also present in the gonads and larvae of 4 (11E)-tetradec-11-enoic acid - C14:1n-3 16 C 30H O2 O O 226.36 g/mol 13.37in Brassica% of leaf napus essential leaf discs oil— of3.35 Coriandrum%, 1.06% sativum, 1.19% of[39] total; in PGSpodoptera (phosphatidylglycerol), littoralis [40] 1616 3030 22 O O acid56 (13(13EE)-/hexadecZ)-hexadec-13-enoic13-enoic acid -- C16:1C16:1nn--33 CC HH OO undefinedH OO isomerism cis-trans isomerism 254.414254.414 g/molg/mol NefrochlorisPA (phosphatidic salina andacid) Phaeodactylum and PC (phosphatidylcholine) tricornutum total fatty fatty acids, acids, respectively, respectively, also trace H 56 (13E)-hexadecacid-13 -enoic acid -- C16:1n--3 C1616H3030O22 undefinedO cis-trans isomerism 254.414 g/mol inNefrochlorisamounts Brassica in napus salina phosphatidylethano leaf and discs Phaeodactylum—3.35%lamine, 1.06 tricornutum% (PE), 1.19 were% oftotal also total fatty found PG acids, (phosphatidylglycerol), [42] respectively,; in the moth also 4 (11E)-tetradec-11-enoic acid - C14:1n-3 C14H26O2 H O O 226.36 g/mol 13.37PAin microalgae (phosphatidicoysters% of leaf —essential fed1.39 acid)% with, 3.12oiland of%the PC ,Coriandrum 0.23 (phosphatidylcholine) mentioned%, 1.33 sativum% of Dunaliella microalgae [39]; infatty tertiolectaSpodoptera acids, [41 ,respectively, Platimonas littoralis] [40] viridis trace , acid 16 30 2 H O O presentinamounts microalgae in in the phosphatidylethano— gonads1.39% ,and 3.12 larvae%, 0.23lamine of% ,oysters 1.33 (PE)% offed were Dunaliella wi thalso the found mentionedtertiolecta [42];, inPlatimonas microalgae the moth viridis [41] , 6 (13(13E)E-/hexadecZ)-hexadec-13--enoic13-enoic acid - C16:1n-3 C H O O 254.414 g/mol 4 (11(13EE)-/tetradecZ)-hexadec-11--enoic13-enoic acid - C14:1n-3 C14H26O2 H 226.36 g/mol 13.37PApresentSpodoptera (phosphatidic% ofin leafthe littoralis essentialgonads acid) [43] and oil and oflarvae PC Coriandrum (phosphatidylcholine) of oysters sativum fed wi [39]th the; infatty mentionedSpodoptera acids, respectively, littoralismicroalgae [40] trace[41] 65 (13E)-hexadec-13-enoic acid -- C16:1nn--33 C1616H3030O22 undefinedO cis-trans isomerism 254.414254.414 g/molg/mol amountsNefrochloris in salinaphosphatidylethano and Phaeodactylumlamine tricornutum (PE) were total also fattyfound acids, [42] ; respectively,in the moth also 5 - C16:1n-3 C H O undefinedO cis-trans isomerism 254.414 g/mol inNefrochlorisSpodoptera microalgaeBrassica napuslittoralis salina—1.39 leaf and [43]% discs ,Phaeodactylum 3.12 —%3.35, 0.23%%, 1.06, tricornutum1.33%%, 1.19 of Dunaliella% oftotal total fatty tertiolectaPG acids, (phosphatidylglycerol), ,respectively, Platimonas viridis also , acid amountsin Brassicain Brassica in napus phosphatidylethano leaf napus discs—leaf3.35lamine% discs—3.35%,, 1.06 %(PE), 1.19 were% of also total 1.06%, found PG (phosphatidylglycerol), [42] 1.19%; in the of moth total PG (phosphatidylglycerol), PA (phosphatidic (13E/Z)-hexadec-13-enoic OO Spodopterapresent in thelittoralis gonads [43] and larvae of oysters fed with the mentioned microalgae [41] 57 (13Z)-hexadec-13-enoic acid -- C16:1C16:1nn--33 CC1616HH3030OO22 undefinedHH cis-trans isomerism 254.414254.414 g/molg/mol inNefrochlorisPApresentin microalgaemicroalga (phosphatidic in the salina —Heterosigma gonads1.39 andacid)% ,andPhaeodactylum 3.12 and carterae larvae% PC, 0.23 (phosphatidylcholine) of[44]% ,oysters tricornutum1.33 % offed Dunaliella wi totalth the fattyfatty tertiolectamentioned acids,acids, , respectively, respectively,Platimonas microalgae viridis also trace[41] , OO Spodoptera littoralis [43] 6 (13(13EE)-/hexadecZ)-hexadec-13--enoic13-enoic acid - C16:1n-3 C16H30O2 H 254.414 g/mol PA (phosphatidic acid) and PC (phosphatidylcholine) fatty acids, respectively, trace 6 (13E)-hexadec-13-enoic7 (13Z)-hexadec acidacid-13 -enoic acid- - C16:1n-3C16:1n-3 C HC16HO30O2 H O O 254.414254.414 g/mol in microalgaacid) and Heterosigma PC (phosphatidylcholine) carterae [44] fatty acids, respectively, trace amounts in 5 - C16:1n-3 16 C1630H30O22 undefinedO cis-trans isomerism 254.414 g/mol Nefrochlorisin Brassica napus salina leaf and discs Phaeodactylum—3.35%, 1.06 tricornutum%, 1.19% totalof total fatty PG acids, (phosphatidylglycerol), respectively, also 6 (13E)-hexadec-13-enoic acid - C16:1n-3 C H O O 254.414 g/mol presentamountsin Brassica in in thenapus phosphatidylethano gonads leaf discs and —larvae3.35lamine% of, 1.06oysters %(PE), 1.19 fed were% wi of alsoth total the found mentionedPG (phosphatidylglycerol), [42]; in microalgae the moth [41] 16 30 2 H O 7 (13Z)-hexadecacid-13 -enoic acid - C16:1n-3 C H O O 254.414 g/mol in microalga Heterosigma carterae [44] O amounts in phosphatidylethanolamine (PE) were also found [42]; in the moth (15E/Z)-octadec-15-enoic H PAdetected (phosphatidic in pork (4.2 acid) mg/100 and PC g fatty(phosphatidylcholine) acids of the fresh hamfatty of acids, adult respectively, pig, 4.8 mg/100 trace g 7 (13Z)-hexadec-13-enoic acid - C16:1n-3 C16H30O2 H O 254.414 g/mol inpresentSpodopteraPA microalga (phosphatidicphosphatidylethanolamine in thelittoralis Heterosigma gonads acid) [43] and and carterae larvae PC (phosphatidylcholine) [44]of oysters (PE) fed wi wereth the fatty mentioned also acids, found respectively, microalgae [42]; intrace[41] the moth Spodoptera littoralis [43] 1618 3034 22 in Brassica napus leaf discs—3.35%, 1.06%, 1.19% of total PG (phosphatidylglycerol), 68 (13(15E)E-hexadec/Z)-octadec-13--enoic15-enoic acid -- C16:1C18:1nn--33 C16H30O2 undefinedO cis-trans isomerism 254.414282.468 g/molg/mol detected in pork (4.2 mg/100 g fatty acids of the fresh ham of adult pig, 4.8 mg/100 g 6 (13E)-hexadec-13-enoic acid - C16:1n-3 C H O O 254.414 g/mol Spodoptera littoralis [43] 8 acid - C18:1n-3 C18H34O2 undefinedO cis-trans isomerism 282.468 g/mol inamountsfatty Brassica acids in napus ofphosphatidylethano the leaf pork discs loin— of3.35 adult%laminelamine, 1.06 pig) %(PE)(PE) [45], 1.19 )werewere % of alsoalso total foundfound PG (phosphatidylglycerol), [42][42];; inin thethe mothmoth (15E/Z)-octadec-15-enoic H PAdetected (phosphatidic in pork (4.2 acid) mg/100 and PC g fatty (phosphatidylcholine) acids of the fresh ham fatty of acids, adult respectively, pig, 4.8 mg/100 trace g acid 18 34 2 O fatty acids of the pork loin of adult pig) [45]) 68 (13E)-hexadec-13-enoic acid - C16:1C18:1n-3 C16H30O2 undefinedH O cis-trans isomerism 254.414282.468 g/mol 7 (13(15Z)E-/hexadecZ)-octadec-13-enoic15-enoic acid - C16:1n-3 C H O O O 254.414 g/mol dinSpodopteradetectedetected microalga inin littoralis porkbeef Heterosigma (0.217%(4.2 [43] mg/100 (carteraefor gthe fatty [44]grass acids -fed of beef the samplesfresh ham) and of adult0.241 %pig, (for 4. 8 mg/100 g acid 1816 3430 2 H PAamountsSpodopterafatty (phosphatidic acids in littoralisof phosphatidylethano the pork acid) [43] loin and of PC adult (phosphatidylcholine)lamine pig) (PE)[45] )were also fattyfound acids, [42]; respectively,in the moth trace 7 (13Z)-hexadec-13-enoic87 (13Z)-hexadec acid -13-enoic acid- - C16:1n-3C18:1C16:1n-3 C HC16HO30O2 undefinedO cis-trans isomerism 254.414282.468254.414 g/mol indetected microalga in microalga in beef Heterosigma (0.217%Heterosigma (carteraefor the grass[44] -fed carterae beef samples[44] ) and 0.241% (for 6 (13E)-hexadec-13-enoic acid - C16:1n-3 16 C 30H O2 O 254.414 g/mol acid O fattyconventional acids of the beef pork) of totalloin offatty adult acids pig) mass) [45]) [46], cows milk (0.146–0.56 g/100 g of O amounts in phosphatidylethanolamine (PE) were also found [42]; in the moth O Spodopteradetected in littoralis beef (0.217% [43] (for the grass-fed beef samples) and 0.241% (for (15E/Z)-octadec-15-enoic H detected in pork (4.2 mg/100 g fatty acids of the fresh ham of adult pig, 4.8 mg/100 g 7 (13Z)-hexadec-13-enoic acid - C16:1n-3 C1616H3030O22 H 254.414 g/mol conventionalin microalga Heterosigmabeef) of total carterae fatty acids [44] mass) [46], cows milk (0.146–0.56 g/100 g of 7 (13Z)-hexadec-13-enoic acid - C16:1n-3 C18H34O2 254.414 g/mol detectedintotal microalga fatty in acids, beef Heterosigma (0.217% dependently ( carteraefor the on grass [44]applied -fed diet) beef andsamples butter) and [47] 0.241, and% in ( forhuman blood 8 (15E/Z)-octadec-15-enoic - C18:1n-3 C H O undefinedO cis-trans isomerism 282.468 g/mol Spodopteradetected in littoralis pork (4.2 [43] mg/100 g fatty acids of the fresh ham of adult pig, 4.8 mg/100 g 18 34 2 O conventional beef) of total fatty acids mass) [46], cows milk (0.146–0.56 g/100 g of 8 acid - C18:1n-3 C H O undefinedO cis-trans isomerism 282.468 g/mol fattytotal acidsfatty acids,of the dependentlypork loin of adulton applied pig) [45] diet)) and butter [47], and in human blood (15E/Z)-octadec-15-enoic 16 30 2 undefinedH cis-trans conventionaldetected beef in) of pork total fatty (4.2 acids mg/100 mass) [46] g fatty, cows acidsmilk (0.146 of the–0.56fresh g/100 g ham of of adult pig, 4.8 mg/100 g fatty acids of the 7 (13Z)-hexadecacid-13 -enoic acid - C16:1n-3 C H O O 254.414 g/mol fattyin(relative microalga acids abundance of Heterosigmathe pork for loin healthy carterae of adult male[44] pig) — 0.04[45]%) ) [48] and human milk (0.01–0.06% of (15E/Z)-octadec-15-enoic H O totaldetected fatty in acids, pork dependently(4.2 mg/100 g on fatty applied acids diet) of the and fresh butter ham [47] of ,adult and inpig, human 4.8 mg/100 blood g 8 9 (15(15ZE)-/Zoctadec)-octadec-15-15enoic-enoic acid - - C18:1n-3C18:1n-3 C HC18HO34O2 O 282.468282.468 g/molg/mol d(relativeetected abundancein pork (4.2 formg/100 healthy g fatty male acids—0.04 of% the) [48] fresh and ham human of adult milk pig, (0.01 4.–80.06 mg/100% of g O detected in beef (0.217% (for the grass-fed beef samples) and 0.241% (for 78 (13Z)-hexadec-13-enoic acid -- C16:1C18:1nn--33 18 C161834H3034O222 undefinedH cis-trans isomerism 254.414282.468 g/molg/mol in microalga Heterosigma carterae [44] acid89 (15Z)-octadec-15-enoic acid - C18:1n-3 C18H34O2 undefinedH O isomerism cis-trans isomerism 282.468 g/mol totaldetectedtotalpork fattyfatty in acids,acids loinbeef (0.217%ofdependently of transitional adult (for the pig)on and grassapplied mature [45-fed]) diet) beef human and samples buttermilk) fromand [47] 0.241,five and regions %in (humanfor in Chinablood acid O O (relativefatty acids abundance of the pork for loin healthy of adult male pig)—0.04 [45]%) ) [48] and human milk (0.01–0.06% of acid O fattytotal fattyacids acidsof the of pork transitional loin of adult and maturepig) [45] human) milk from five regions in China 9 (15(15ZE)-/octadecZ)-octadec-15--enoic15-enoic acid - C18:1n-3 C18H34O2 H 282.468 g/mol dconventionaletected in pork beef (4.2) of mg/100total fatty g fatty acids acids mass) of [46]the ,fresh cows ham milk of (0.146 adult– 0.56pig, g/1004.8 mg/100 g of g 18 34 2 O (relativeconventional[49], 0.02 abundance–0.29 beef% by) of weightfor total healthy fatty of total acidsmale fatty— mass)0.04 acids% [46]) in[48], humancows and milkhuman milk (0.146 samples milk–0.56 (0.01 collected g/100–0.06 g% of fromof 8 - C18:1n-3 C H O undefinedH O cis-trans isomerism 282.468 g/mol total fatty acids of transitional and mature human milk from five regions in China 9 (15(15ZE)-/octadecZ)-octadecacid-15 --enoic15-enoic acid - C18:1n-3 C18H34O2 282.468 g/mol dfattytotaldetected[49]etected, 0.02fattyacids in–in 0.29acids, of porkbeef the% (0.217%dependently by(4.2pork weight mg/100 loin ((forfor ofof thegthe adulttotalon fatty grassgrassapplied fattypig) acids--fedfed [45]acids diet) of beefbeef )the inand samplessamples freshhuman butter ham) )milk and [47] of samples0.241adult, and %inpig, (( humanforforcollected 4 .8 mg/100 blood from g 8 - C18:1n-3 C18H34O2 undefinedO cis-trans isomerism 282.468 g/mol totalwomandetected fatty in acidsacids, the United of dependently in transitional beef States (0.217% {the on and appliedmean mature (for concetration diet) human the and grass-fed milkbutter for fromboth [47] (five,cis and beef and regions in transhuman samples) in) China blood and 0.241% (for conventional beef) of total acid fattyconventional[49]woman, 0.02acids in–0.29 ofthe thebeef %United bypork)) ofweight total Statesloin fattyofof {the adulttotal acids mean fattypig) mass) concetration [45]acids )[46][46] in ,,human cows for milk bothmilk (0.146 (samplescis and–0.56 trans collected g/100) g offrom O detected(relative abundancein beef (0.217% for healthy (for the male grass—-fed0.04 beef%) [48] samples and human) and 0.241 milk% (0.01 (for –0.06% of 18 34 2 H [49]isomers, 0.02—–0.290.06%% }by [50] weight) of total fatty acids in human milk samples collected from 9 (15Z)-octadec-15-enoic acid - C18:1n-3 C H O O 282.468 g/mol (relativewomanfatty inabundance the acids United mass) for States healthy [{the46 male], mean cows— concetration0.04 milk%) [48] (0.146–0.56 and for humanboth (cis milk and g/100 (0.01 trans–)0.06 g of% of total fatty acids, dependently on applied diet) H total fatty acids, dependently on applied diet) and butter [47], and in human blood 9 (15Z)-octadec-15-enoic acid - C18:1n-3 C18H34O2 O 282.468 g/mol womandetectedconventionaltotalisomers fatty —in in 0.06acidsacids,the beef beef %United of }(0.217%dependently [50]) transitionalof )totalStates (for fatty {the the on and acids grassmeanapplied mature mass)- fedconcetration diet) beefhuman [46] and samples, cows milkbutter for milk )bothfrom and [47] (0.146 ( 0.241fivecis, and and regions–% 0.56in trans( humanfor g/100 )in China bloodg of O totalisomersdetected fatty— in 0.06acids cow% of}’ s[50] milktransitional) (0.102– 0.34and matureg/100 g humanof total milkfatty fromacids, five dependently regions in on China O (relativeand abundance butter [ 47for ],healthy and male in human—0.04%) blood[48] and (relativehuman milk abundance(0.01–0.06% of for healthy male—0.04%) [48] and human O conventional[49](relativedetected, 0.02 abundance–in0.29 cow beef% ’bys )milk ofweight for total (0.102 healthy fattyof– total0.34 acidsmale fattyg/100— mass)0.04 acids g of% [46] )totalin [48] ,human cows fattyand milk human acids,milk (0.146 samples dependently milk–0.56 (0.01 collected g/100–0.06 on g % offrom of H O total fatty acids, dependently on applied diet) and butter [47], and in human blood 9 (15Z)-octadec-15-enoic acid - C18:1n-3 C1818H3434O22 H 282.468 g/mol isomers—0.06%} [50]) 9 (15Z)-octadec-15-enoic9 (15Z)-octadec acid-15-enoic acid - - C18:1n-3C18:1n-3 C18HC 34HOO2 H 282.468282.468 g/mol [49]applied, 0.02 diet)–0.29 and% by butter weight [47] of, total0–0.15 fatty% by acids weight in human of total milk fatty samples acids in collectedhuman milk from O O detected in cow’s milk (0.102–0.34 g/100 g of total fatty acids, dependently on 18 34 2 O total fatty acids of transitional and mature human milk from five regions in China 10 (15E)-octadec-15-enoic acid - C18:1n-3 C H O H O 282.468 g/mol totalwomanapplied fatty indiet) acids,acidsthe and United ofdependently butter transitional States [47] {the, 0on and–0.15 meanapplied mature% by concetration diet)weight human and of milkbutter totalfor bothfrom fatty [47] ( ,fivecisacids and and regions in in transhuman human )in China blood milk O (relativemilk abundance (0.01–0.06% for healthy of totalmale— fatty0.04%) acids[48] and of human transitional milk (0.01–0.06 and% matureof human milk from five regions in 18 34 2 H O detectedsamples incollected cow’s milk from (0.102 wome–0.34n in g/100the United g of total States fatty (the acids, mean dependently concetration on for both 109 ((1515ZE)-octadec-15-enoic acid -- C18:1n--3 C18H34O2 O 282.468 g/mol woman in the United States {the mean concetration for both (cis and trans) H (relative[49]applied[49],, 0.020.02 diet)abundance–0.29 and% by butter weight for healthy [47] of, 0total– 0.15male fatty%— by0.04 acids weight%) in [48] human of and total human milkfatty samples acids milk in(0.01 collectedhuman–0.06 milk% from of 18 34 2 O O totalisomerssamples fatty— collected 0.06acids% }of [50] fromtransitional) wome nand in themature United human States milk (the from mean five concetration regions in forChina both 10 (15E)-octadec-15-enoic acid - C18:1n-3 C H O O 282.468 g/mol 9 (15Z)-octadec-15-enoic acid - C18:1n-3 C18H34O2 HH 282.468 g/mol appliedisomerssamples(cis andChina — diet)transcollected0.06 and [)% 49isomers} [50]], butterfrom 0.02–0.29%) — wome [47]0.06, %0n–) 0.15in[50] the% by byUnited weight weight States of oftotal (the total fattymean fattyacids concetration in acids human for in milk both human milk samples collected from woman in 10 (15E)-octadec-15-enoic acid - C18:1n-3 C18H34O2 O 282.468 g/mol woman in the United States {the mean concetration for both (cis and trans) O total[49]detectedwoman(cis ,and 0.02fatty intrans –in 0.29 acidsthe cow) %Unitedisomers ’of sby milktransitional weight States— (0.1020.06 of {the%– total 0.34)and [50] mean g/100fattymature concetration acids g ofhuman total in human fattymilk for acids, bothfrommilk ( samplesfivecisdependently and regions trans collected in) on China from POLYUNSATURATED FATTY ACIDS (PUFAs) samplesdetected(cis andthe trans collectedin United cow) isomers’s milkfrom States— (0.102wome0.06% {the–n0.34) [50]in theg/100 mean United g of concetration totalStates fatty (the acids, mean fordependently concetration both (cis on for and both trans) isomers—0.06%} [50]) O [49]isomersisomers, 0.02—–0.290.06% }}by [50][50] weight)) of total fatty acids in human milk samples collected from HPOLYUNSATURATED FATTY ACIDS (PUFAs) womanapplied indiet) the and United butter States [47] ,{the 0–0.15 mean% by concetration weight of totalfor both fatty ( cisacids and in trans human) milk 18 34 2 O (cis and trans) isomers—0.06%) [50] 10 (15(11EZ)-,13octadecZ)-hexadeca-15-enoic-11,13 acid- - C18:1n-3 C H O H O 282.468 g/mol applied diet) and butter [47], 0–0.15% by weight of total fatty acids in human milk POLYUNSATURATEDO FATTY ACIDS (PUFAs) womandetected in in the cow United’s milk States (0.102 {the–0.34 mean g/100 concetration g of total fatty for bothacids, ( cisdependently and trans) on 10 (15E)-octadec-15-enoic acid - C18:1n-3 C18H34O2 O 282.468 g/mol samplesdetected collectedin cow’s milkfrom (0.102wome–n0.34 in theg/100 United g of totalStates fatty (the acids, mean dependently concetration on for both 1 - C16:1n-3 C16H28O2 H 252.398 g/mol isomersin the (pheromone)—0.06%} [50] gland) extracts of the navel orangeworm, Amyelois transitella [51] (11Z,13Z)-hexadeca-11,13- POLYUNSATURATEDO FATTY ACIDS (PUFAs) detected in cow’s milk (0.102–0.34 g/100 g of total fatty acids, dependently on applied diet) and O samples collected from women in the United States (the mean concetration for both dienoic acid 16 28 2 H O 1 - C16:1n-3 C H O H O 252.398 g/mol inapplied the (pheromone) diet) and butter gland [47] extracts, 0–0.15 of% the by navelweight orangeworm, of total fatty Amyeloisacids in humantransitella milk [51] (11Z,13Z)-hexadeca-11,13- H isomers—0.06%} [50]) O detected(appliedcis and transdiet) in cow )and isomers’s buttermilk— (0.102 0.06[47],% –00.34)– [50]0.15 g/100 % by g weight of total of fatty total acids, fatty dependentlyacids in human on milk 10 (15E)-octadecdienoic-15 acid-enoic acid - C18:1n-3 C1618H2834O2 H OO 282.468 g/mol 101 (15E)-octadec-15-enoic acid - C18:1C16:1n-3 C18H34O2 O 282.468252.398 g/mol (incis the and (pheromone) trans) isomers gland—0.06 extracts%) [50] of the navel orangeworm, Amyelois transitella [51] 10 (15E)-octadec-15-enoic(11Z,13 acidZ)-hexadeca-11,13- C18:1n-3 C18H34O2 O 282.468 g/mol butter [47], 0–0.15% by weight of total fatty acids in human milk samples collected from women in the O samples collected from women in the United States (the mean concetration for both dienoic acid 16 28 2 HPOLYUNSATURATEDO FATTY ACIDS (PUFAs) detectedsamplesas methyl collectedin ester: cow’ s0.1 milkfrom1–0 .12(0.102 wome% of–n0.34 European in theg/100 United g wels of total States catfish fatty (the oil, acids, mean 0.34 –dependently 0.41concetration% of common on for both 1 - C16:1n-3 C H O H 252.398 g/mol inapplied the (pheromone) diet) and butter gland [47] extracts, 0–0.15 of% the by navelweight orangeworm, of total fatty Amyelois acids in humantransitella milk [51] 10 (15E)-octadecdienoic-15 acid-enoic acid - C18:1n-3 C18H34O2 POLYUNSATURATED FATTY ACIDS282.468 (PUFAs g/mol) as methyl ester: 0.11–0.12% of European wels catfish oil, 0.34–0.41% of common O OO (bleakcis andUnited oil trans (in Area) isomers States (%))— [52] (the0.06; 3,% mean1.1,) [50] 0.9, concetration6.6, 0.4, 4.1, 0.5, 0.5, for 0.3, both 0.1, 11.8 (cis% ofand Chinesetrans ) isomers—0.06%) [50] H appliedsamples(ascis methyl and diet)transcollected ester: )and isomers 0.1 butterfrom1–0—.12 wome 0.06[47]% of,% 0n )European– [50]0.15in the % Unitedby welsweight Statescatfish of total (the oil, fattymean0.34– acids0.41 concetration% in of human common for milk both (11Z,13Z)-hexadeca-11,13- O 10 (15E)-octadec-15-enoic acid - C18:1n-3 C18H34O2 O 282.468 g/mol bleak oil (in Area (%)) [52]; 3, 1.1, 0.9, 6.6, 0.4, 4.1, 0.5, 0.5, 0.3, 0.1, 11.8% of Chinese 1 (11Z,13Z)-hexadeca-11,13- - C16:1n-3 C16H28O2 H 252.398 g/mol in the (pheromone) gland extracts of the navel orangeworm, Amyelois transitella [51] POLYUNSATURATEDO FATTY ACIDS (PUFAs)) samplesascabbage, methyl collected whiteester: cabbage,0.1 from1–0.12 wome %savoy, of nEuropean in kale, the redUnited wels cabbage, Statescatfish brussels (the oil, mean0.34 sprouts,–0.41 concetration% ofcauliflower, common for both 1 dienoic acid - C16:1n-3 C16H28O2 H 252.398 g/mol in(bleakcis the and oil(pheromone) trans (in Area) isomers (%) gland) —[52]0.06 extracts; 3,% 1.1,) [50] 0.9, of the 6.6, navel 0.4, 4.1, orangeworm, 0.5, 0.5, 0.3, Amyelois 0.1, 11.8 %transitella of Chinese [51] (7Z,10Z,13Z)-hexadeca- O POLYUNSATURATED FATTY ACIDScabbage, (PUFAs) white cabbage, savoy, kale, red cabbage, brussels sprouts, cauliflower, 2 (7Z,10dienoicZ,13Z)- acidhexadeca - roughanic acid C16:3n-3 C16H26O2 O 250.382 g/mol (bleakkohlrabi,cis and oil trans ( inswede, Area) isomers cabbage(%)) —[52]0.06 ;lettu 3,% 1.1,)ce, [50] 0.9,parsley 6.6, 0.4,fatty 4.1, acid 0.5, mass 0.5, 0.3,[53] —0.1,system 11.8%atic of Chinesenames (11Z,13Z)-hexadeca-11,13- POLYUNSATURATEDO FATTY ACIDS (PUFAs) cabbage, white cabbage, savoy, kale, red cabbage, brussels sprouts, cauliflower, (11Z7,10,13,13Z)-hexadeca-trienoic acid-11,13 - 16 26 2 O 21 roughanic- acid C16:3C16:1n-3 C16H28O2 H 250.382252.398 g/mol askohlrabi,in methylthe (pheromone) swede, ester: 0.1 cabbage1 gland–0.12% lettuextracts of Europeance, parsley of the welsnavel fatty catfish acidorangeworm, mass oil, 0.34 [53] –—Amyelois0.41system% of transitellaaticcommon names [51] 1 (7Z7,10,13,10Z,13-trienoicZ)-hexadeca acid - - C16:1n-3 C16H28O2 HPOLYUNSATURATED FATTY ACIDS252.398 (PUFAs )g/mol cabbage,asinwere themethyl placed(pheromone) white ester: in cabbage, the0.1 1 linegland–0.12 ‘ αsavoy,% -extractslinolenic of European kale, of acid redthe’ ;welsnavelcabbage, in leaves catfish orangeworm, brussels of oil, many 0.34 sprouts, conifer –Amyelois0.41% species,cauliflower, of transitella common most [51] in 2 dienoic acid roughanic acid C16:3n-3 C16H26O2 OO 250.382 g/mol kohlrabi, swede, cabbage lettuce, parsley fatty acid mass [53]—systematic names Z Z (11(7Z,13,10Z),13-hexadecaZ)-hexadeca-11,13- - O were placed in the line ‘α-linolenic acid’; in leaves of many conifer species, most in (11 ,13 )-hexadeca-11,13 O bleak oil (in Area (%)) [52]; 3, 1.1, 0.9, 6.6, 0.4, 4.1, 0.5, 0.5, 0.3, 0.1, 11.8% of Chinese 7,10,13-trienoic acid 16 26 2 H O 21 roughanic- acid C16:3C16:1n-3 C16H28O2 H 250.382252.398 g/mol kohlrabi,inLarix the leptolepus(pheromone) swede, and cabbage glandTaxus lettuextractsbaccatace, —parsley of4.8 the% andnavel fatty 5.8 acidorangeworm,% of mass fatty [53] acids —Amyeloissystem of lives transitellaatic, respectively names [51] 1 - C16:1n-3 C H O H 252.398 g/molbleakwere in placedoil the (in Areain (pheromone) the (%) line) [52] ‘α-linolenic; 3, 1.1, gland 0.9, acid 6.6,’;extracts in0.4, leaves 4.1, 0.5, of of many0.5, the 0.3, conifer navel 0.1, 11.8 species, orangeworm,% of Chinese most in Amyelois transitella [51] (11Z7,10,13,13Z)--hexadecatrienoic acid-11,13 - 16 28 2 O O as methyl ester: 0.11–0.12% of European wels catfish oil, 0.34–0.41% of common dienoic acid O cabbage,asLarix methyl leptolepus white ester: andcabbage, 0.11 Taxus–0.12 savoy,% baccata of European kale,—4.8 red% and welscabbage, 5.8 catfish% ofbrussels fattyoil, 0.34 acids sprouts,–0.41 of %lives cauliflower, of ,common respectively -dienoic1 acid - C16:1n-3 C16H28O2 H O 252.398 g/mol werein the placed (pheromone) in the line gland ‘α- linolenicextracts of acid the’; navelin leaves orangeworm, of many conifer Amyelois species, transitella most [51] in (7Z,10Z,13Z)-hexadeca- H O cabbage,Larix[54] leptolepus white andcabbage, Taxus savoy, baccata kale,—4.8 red% and cabbage, 5.8% ofbrussels fatty acids sprouts, of lives cauliflower,, respectively dienoic acid O O bleak oil (in Area (%)) [52]; 3, 1.1, 0.9, 6.6, 0.4, 4.1, 0.5, 0.5, 0.3, 0.1, 11.8% of Chinese 2 (7Z,10Z,13Z)-hexadeca- roughanic acid C16:3n-3 C16H26O2 H 250.382 g/mol Larixaskohlrabi,bleak[54] methyl leptolepusoil (swede, inester: Area and 0.1 cabbage (%) 1Taxus–)0 .12[52] %lettubaccata; 3,of 1.1,Europeance,— parsley0.9,4.8 %6.6, and wels fatty0.4, 5.8 4.1,catfish acid% 0.5,of mass fattyoil, 0.5, 0.34 [53]acids0.3,–— 0.1,0.41 systemof 11.8%lives of% atic,common respectivelyof namesChinese 2 7,10,13-trienoic acid roughanic acid C16:3n-3 C16H26O2 O 250.382 g/mol kohlrabi,[54]cabbage, whiteswede, cabbage, cabbage savoy, lettuce, kale, parsley red cabbage,fatty acid brussels mass [53] sprouts,—system cauliflower,atic names 7,10,13-trienoic acid O aswerecabbage, methylas placed methyl white ester: in the cabbage,0.1 ester:1line–0.12 ‘α savoy,%-linolenic 0.11–0.12% of European kale, acid red’; welscabbage,in of leaves catfish European brusselsof oil,many 0.34 sprouts,conifer wels–0.41% species, catfishcauliflower,of common most oil, in 0.34–0.41% of common bleak oil (in Area (7(7Z,10,10Z,13,13Z))--hexadeca-- O [54]werebleak placedoil (in Areain the (%) line) [52] ‘α-linolenic; 3, 1.1, 0.9, acid 6.6,’; in0.4, leaves 4.1, 0.5, of many0.5, 0.3, conifer 0.1, 11.8 species,% of Chinesemost in 2 roughanic acid C16:3n--3 C1616H2626O22 H O 250.382 g/mol bleakLarixkohlrabi, leptolepusoil (swede,in Area and cabbage (%) Taxus) [52] lettubaccata; 3, 1.1,ce,— 0.9,parsley4.8 6.6,% and fatty0.4, 5.8 4.1, acid% 0.5,of mass fatty 0.5, [53][53]0.3,acids —0.1, systemof 11.8lives%atic, respectivelyof namesChinese 7,10,13--trienoictrienoic acidacid H Larixcabbage,(%)) leptolepus white [52 ]; andcabbage, 3, Taxus 1.1, savoy, baccata 0.9, 6.6,kale,—4.8 0.4,red% and cabbage, 4.1, 5.8% 0.5, ofbrussels fatty 0.5, acids 0.3,sprouts, of 0.1, lives cauliflower, 11.8%, respectively of Chinese cabbage, white cabbage, savoy, kale, (7Z,10Z,13Z)-hexadeca- O O cabbage,[54]were placed white in thecabbage, line ‘‘α savoy,--linoleniclinolenic kale, acidacid red’’;; cabbage,inin leavesleaves brusselsofof manymany sprouts, coniferconifer species, species,cauliflower, mostmost inin 2 (7Z,10Z,13Z)-hexadeca- roughanic acid C16:3n-3 C16H26O2 O O 250.382 g/mol kohlrabi, swede, cabbage lettuce, parsley fatty acid mass [53]—systematic names (7Z,10Z ,13Z)-hexadeca-7,10,13-trienoic acidroughanic H [54] red cabbage, brussels sprouts, cauliflower, kohlrabi, swede, cabbage lettuce, parsley fatty acid 2 roughanic acid C16:3n-3 C16H26O2 250.382 g/mol kohlrabi,Larix leptolepus swede, and cabbage Taxus lettubaccatace,— parsley4.8% and fatty 5.8 acid% of mass fattyfatty [53] acidsacids— systemof livesatic,, respectivelyrespectively names 2 C16:3n-3 C16H26O2 O 250.382 g/mol were placed in the line ‘α-linolenic acid’; in leaves of many conifer species, most in 7,10,13-trienoic acid O 7,10,13-trienoic acid acid H O [54] mass [53]—systematic names were placed in the line ‘α-linolenic acid’; in leaves of many conifer O wereLarix[54] placedleptolepus in theand line Taxus ‘α- baccatalinolenic— 4.8acid%’ ;and in leaves 5.8% ofof fattymany acids conifer of lives species,, respectively most in H O Larix leptolepus and Taxus baccataLarix— leptolepus4.8% and 5.8% of fattyTaxus acids baccata of lives, respectively [54] species, most in and —4.8% and 5.8% of fatty acids of lives, O [54] respectively [54]

Nutrients 2018, 10, 1662 5 of 33

Table 1. Cont.

Shorthand Common Molecular No IUPAC Name (Simplified Formula/Structure Molecular Weight Sources [Refs.] Name Formula Formula) Nutrients 2018, 10, x FOR PEER REVIEW 5 of 34 Nutrients 2018, 10, x FOR PEER REVIEW POLYUNSATURATED FATTY ACIDS (PUFAs) 5 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 5 of 34 H O Nutrients 2018, 10, x FOR PEER REVIEW H O 5 of 34 H O O O (4Z,7Z,10Z,13Z)-hexadeca-(4Z,7Z,10Z,13Z)-hexadeca- H O as methylas methyl 4,7,10,13 4,7,10,13-hexadecatetraenoate:-hexadecatetraenoate: 0.09–0.1% of Pontic 0.09–0.1%shad oil, 0.08– of0.16 Pontic% of shad oil, 0.08–0.16% of European wels 3 3 (4Z,7Z,10Z,13Z)-hexadeca-- - C16:4n-3C16:4n-3 C16HC2416HO242O2 O 248.366248.366 g/molg/mol as methyl 4,7,10,13-hexadecatetraenoate: 0.09–0.1% of Pontic shad oil, 0.08–0.16% of 4,7,10,13-tetraenoic3 4,7,10,13 acid -tetraenoic acid - C16:4n-3 C16H24O2 248.366 g/mol Europeancatfish wels oil, catfish 0.11–0.56% oil, 0.11–0.56 of% commonof common bleak bleak oil [52] oil [52] (44,7,10,13Z,7Z,10Z-tetraenoic,13Z)-hexadeca acid - O Europeanas methyl wels4,7,10,13 catfish-hexadecatetraenoate: oil, 0.11–0.56% of c 0.09ommon–0.1 %bleak of Pontic oil [52] shad oil, 0.08–0.16% of 3 - C16:4n-3 C16H24O2 248.366 g/mol 4,7,10,13-tetraenoic acid European wels catfish oil, 0.11–0.56% of common bleak oil [52] (4Z,7Z,10Z,13Z)-hexadeca- as methyl 4,7,10,13-hexadecatetraenoate: 0.09–0.1% of Pontic shad oil, 0.08–0.16% of 3 - C16:4n-3 C16H24O2 248.366 g/mol 4,7,10,13-tetraenoic acid European wels catfish oil, 0.11–0.56% of common bleak oil [52]

O H O H O O (8Z,11Z,14Z)-heptadeca- norlinolenic H O in Salvia nilotica—0.4% of mixed esters and 2.3% of IV fraction (% by gas liquid (8Z,11Z,14Z4)-heptadeca- (8Z,11Z,14Z)-heptadecanorlinolenic- norlinolenic C17:3n-3 C17H28O2 264.409 g/mol in Salvia nilotica—0.4% of mixed esters and 2.3% of IV fraction (% by gas liquid 4 8,11,14-trienoic acid acid n C17:3n-3 C17H28O2 O O 264.409 g/mol chromatographySalvia nilotica) [55] 4 (8Z8,11,14,11Z,14-trienoicZ)-heptadeca acid - norlinolenicacid C17:3 -3 C17H28O2 H 264.409 g/mol chromatographyin Salviain nilotica—) 0.4[55]% of —0.4%mixed esters of and mixed 2.3% of esters IV fraction and (% 2.3% by gas of liquid IV fraction (% by gas liquid chromatography) [55] 8,11,14-trienoic4 acid acid C17:3n-3 C17H28O2 264.409 g/mol 8,11,14-trienoic acid acid O chromatography) [55] (8Z,11Z,14Z)-heptadeca- norlinolenic in Salvia nilotica—0.4% of mixed esters and 2.3% of IV fraction (% by gas liquid 4 C17:3n-3 C17H28O2 264.409 g/mol 0.2% of black cumin (Nigella sativa) seed oil fatty acids [56]; 8% of Cardiospermum 8,11,14-trienoic acid acid 0.2chromatography% of black cumin) [55] (Nigella sativa) seed oil fatty acids [56]; 8% of Cardiospermum halicabum seed oil total fatty acids [57]; as methyl esters: 1.67% of Labeo rohita muscle halicabum0.2%0.2% of black seed of cumin oil black total (Nigella cuminfatty acidssativa ( Nigella[57]) seed; as oil methyl fatty sativa acidsesters:) seed [56] 1.67; 8 oil%% ofof fatty LabeoCardiospermum rohita acids muscle [ 56]; 8% of Cardiospermum halicabum seed oil tissue fatty acids, 1.39% of Cirrhinus mrigata muscle tissue fatty acids, 1.29% of Catla tissuehalicabum fatty seed acids, oil 1.39total% fatty of Cirrhinus acids [57] mrigata; as methyl muscle esters: tissue 1.67 fatty% ofacids, Labeo 1.29 rohita% of muscle Catla 0.2catla%total ofmuscle black fatty tissue cumin acids fatty (Nigella acids [57 sativa ];[58] as); inseed methyl salted oil fatty products esters: acids of [56] 1.67%fish; 8 %roe: of of0.7 Cardiospermum%Labeo of Ikura rohita muscle tissue fatty acids, 1.39% of Cirrhinus catlatissue muscle fatty acids, tissue 1.39 fatty% acidsof Cirrhinus [58]; in mrigata salted products muscle tissue of fish fatty roe: acids, 0.7% of1.29 Ikura% of Catla halicabum(salmon),mrigata seed0.4% muscleoil of totalTarako fatty tissue(pollock), acids fatty[57] 0.7; %as acids, ofmethyl Tobiko esters: 1.29% (flyingfish), 1.67 of% Catlaof 0.4 Labeo% of catla rohita Kazunoko musclemuscle tissue fatty acids [58]; in salted (salmon),catla muscle 0.4 tissue% of Tarako fatty acids (pollock), [58]; in 0.7 salted% of Tobikoproducts (flyingfish), of fish roe: 0.4 0.7%% of of Kazunoko Ikura tissue(herring) fatty total acids, lipids 1.39 [59]% of; 1.6Cirrhinus–1.9% of mrigata salmon muscle eggs total tissue phospholipid fatty acids, 1.29 fraction,% of Cat1– la (herring)(salmon),products total 0.4% lipids of ofTarako fish[59]; (pollock),1.6 roe:–1.9% 0.7% of 0.7 salmon%of of Tobiko Ikura eggs total(flyingfish), (salmon), phospholipid 0.4 0.4%% of fraction, Kazunoko of Tarako 1– (pollock), 0.7% of Tobiko (flyingfish), catla3.6% muscle of salmon tissue eggs fatty tot acidsal triacylglicerol [58]; in salted fraction products [60] ;of 1.1 fish% of roe: wild 0.7 sardine% of Ikura (Sardina 3.6(herring)%0.4% of salmon total of lipids Kazunokoeggs tot[59]al; 1.6triacylglicerol–1.9 (herring)% of salmon fraction total eggs [60] lipidstotal; 1.1 phospholipid% of [59 wild]; 1.6–1.9% sardine fraction, (Sardina of1– salmon eggs total phospholipid fraction, (salmon),pilchardus 0.4) muscle% of Tarako total fatty (pollock), acids (10.7%% of of captive Tobiko sardine (flyingfish), muscle 0.4 total% of fattyKazunoko acids), pilchardus3.6% of salmon) muscle eggs total tot fattyal triacylglicerol acids (1% of fraction captive [60]sardine; 1.1% muscle of wild total sardine fatty (acids),Sardina (herring)0.7%1–3.6% of wild/captive total oflipids salmon [59] sardine; 1.6 eggs– liver1.9% total of salmon fatty triacylglicerol acidseggs total[61]; 0.61phospholipid–0.83 fraction% for fraction, finwhale [60]; 1 1.1% –oils, of wild sardine (Sardina pilchardus) muscle 0.7pilchardus% of wild/captive) muscle total sardine fatty acidsliver total(1% offatty captive acids sardine [61]; 0.61 muscle–0.83% total for finwhalefatty acids), oils, 3.60.13%total– of0.34 salmon% fatty for sealeggs acids oils tot al[62] triacylglicerol (1%; 0.5% of of captive tuna fraction oil [63] sardine [60]; 0.5;% 1.1 of% muscleEpinephelus of wild sardine total fasciatus ( fattySardina acids), 0.7% of wild/captive sardine liver 0.130.7%– 0.34of wild/captive% for seal oils sardine [62]; 0.5 liver% oftotal tuna fatty oil [63]acids; 0.5 [61]%; of0.61 Epinephelus–0.83% for fasciatus finwhale oils, pilchardusmuscletotal triacylglycerols,) muscle fatty acidstotal fatty 0.1 [61% acids of]; E. 0.61–0.83% (1fasciatus% of captive PE and forsardine 0.1 finwhale–0.2 muscle% of E. total fasciatus oils, fatty 0.13–0.34% PC acids),, 0.1– for seal oils [62]; 0.5% of tuna oil [63]; muscle0.13–0.34 triacylglycerols,% for seal oils [62]0.1%; 0.5 of% E. of fasciatus tuna oil PE [63] and; 0.5 0.1%– 0.2of Epinephelus% of E. fasciatus fasciatus PC, 0.1– 0.70.5%% ofof wild/captiveE. retouti muscle sardine triacylglycerols, liver total fatty 0– 0.1acids% of [61] E.; retouti0.61–0.83 PE %and for 0.1 finwhale% of E. oils, 0.5muscle%0.5% of triacylglycerols,E. retouti of Epinephelus muscle 0.1triacylglycerols,% of fasciatus E. fasciatus 0– musclePE0.1 %and of 0.1E. triacylglycerols,–retouti0.2% ofPE E. and fasciatus 0.1% ofPC 0.1%E., 0.1 – of E. fasciatus PE and 0.1–0.2% of E. fasciatus 0.13retouti–0.34 PC% [64] for ;seal 16.4 oils g/100 [62] g; of0.5 the% of milled tuna chiaoil [63] seeds; 0.5 [65]% of; 21Epinephelus% of n-hexane fasciatus extract of retouti0.5% of PC E. [64]retouti; 16.4 muscle g/100 triacylglycerols, g of the milled chia 0–0.1 seeds% of [65]E. retouti; 21% PofE nand-hexane 0.1% extractof E. of muscleSennaPC, italica triacylglycerols, 0.1–0.5% aerial parts of 0.1[66]E.%; retoutiof40 %E. offasciatus Chamaecyparismuscle PE and triacylglycerols, 0.1lawsoniana–0.2% of andE. fasciatus 50% of 0–0.1% PCFokienia, 0.1– of E. retouti PE and 0.1% of E. retouti PC [64]; Sennaretouti italica PC [64] aerial; 16.4 parts g/100 [66] g of; 40 the% ofmilled Chamaecyparis chia seeds lawsoniana [65]; 21% ofand n- hexane50% of Fokieniaextract of 0.5hodginsii%16.4 of E. total g/100retouti fatty muscleg acids of triacylglycerols, the[67]; milled64.04% of chia chia 0–0.1 (Salvia seeds% of E. hispanica retouti [65]; P) 21% Eseed and oil of 0.1 fatty n-hexane% of acids E. extract of Senna italica aerial parts [66]; 40% hodginsiiSenna italica total aerial fatty parts acids [66] [67]; ;40 64.04% of% Chamaecyparis of chia (Salvia lawsoniana hispanica) seedand 50oil% fatty of Fokienia acids retouti[68]of; 0.25 PCChamaecyparis g/100[64]; 16.4 g of g total/100 fattyg lawsonianaof theacid milled methyl chia andesters seeds 50%of [65]milk of; 21fatFokienia% from of n -ewes,hexane hodginsii 2.57 extract g/100 of gtotal fatty acids [67]; 64.04% of chia (Salvia [68]hodginsii; 0.25 totalg/100 fatty g of acidstotal fatty[67]; acid64.04 methyl% of chia esters (Salvia of milkhispanica fat from) seed ewes, oil fatty 2.57 acids g/100 g (9Z,12Z,15Z)-octadeca- Sennaof total italica fatty aerial acid methylparts [66] esters; 40% of of milk Chamaecyparis fat from ewes lawsoniana fed diets and with 50 extruded% of Fokienia 5 (9Z,12Z,15Z)-octadeca- α-linolenic acid C18:3n-3 C18H30O2 278.436 g/mol of[68] total;hispanica 0.25 fatty g/100 acid g) ofmethyl seed total oilfattyesters fatty acid of milk methyl acids fat fromesters [68 ewes ];of 0.25milk fed fat diets g/100 from with ewes, g extruded of 2.57 total g/100 fatty g acid methyl esters of milk fat from ewes, 5 9,12,15-trienoic acid α-linolenic acid C18:3n-3 C18H30O2 278.436 g/mol hodginsiilinseed supplementation total fatty acids [67] (12%; 64.04 linseed% of in chia dry ( Salviamatter) hispanica [69]; 59.5,) seed 57, oil46.4, fatty 50, acids39.8, (9Z,12Z,15Z)-octadeca-(99,12,15Z,12Z,15-trienoicZ)-octadeca αacid-linolenic - O linseedof total2.57 supplementationfatty g/100 acid methyl g of (12%esters total linseed of fatty milk in fat acid dry from matter) methyl ewes [69]fed ;estersdiets 59.5, with57, of 46.4, extruded milk 50, 39.8, fat from ewes fed diets with extruded linseed 5 α-linolenic acid C18:3n-3 C18H30O2 H O 278.436 g/mol [68]58.7,; 0.25 48.9, g/100 41.9, g50.8, of total 54.6, fatty 41.7, acid 10, 6,methyl 8.5, 5.9 esters% of Chineseof milk fat cabbage from ewes, (Brassica 2.57 chinensis g/100 g ), 5 C18:3n-3 C H O H 278.436 g/mol 9,12,15-trienoic acid 18 30 2 O 58.7,linseed 48.9, supplementation 41.9, 50.8, 54.6, 41.7,(12% 10,linseed 6, 8.5, in 5.9 dry% matter)of Chinese [69] cabbage; 59.5, 57, ( Brassica46.4, 50, chinensis 39.8, ), 9,12,15-trienoic acid(9Z,12Z,15Z)-octadecaacid- O ofwhite totalsupplementation cabbage fatty acid (Brassica methyl oleracea esters (12% of), savoymilk linseed fat (Brassica from in ewes oleracea dry fed matter) var.diets sabauda with [69 extruded),]; kale 59.5, (Brassica 57, 46.4, 50, 39.8, 58.7, 48.9, 41.9, 50.8, 54.6, 41.7, O 5 α-linolenic acid C18:3n-3 C18H30O2 H 278.436 g/mol white58.7, 48.9, cabbage 41.9, (50.8,Brassica 54.6, oleracea 41.7, 10,), savoy 6, 8.5, ( Brassica5.9% of Chineseoleracea var. cabbage sabauda (Brassica), kale chinensis(Brassica ), 9,12,15-trienoic acid linseedoleracea10, supplementationconvar. 6, 8.5, acephala 5.9% ofvar. (12% Chinese sabellica linseed), inred cabbage dry cabba matter)ge ( Brassica [69]; 59.5, oleracea 57, chinensis 46.4, var. 50, capitata ),39.8, white ), cabbage (Brassica oleracea), savoy (Brassica O O oleraceawhite cabbage convar. ( acephalaBrassica oleraceavar. sabellica), savoy), red (Brassica cabbage oleracea (Brassica var. oleracea sabauda var.), kale capitata (Brassica), H 58.7,brussels 48.9, sprouts 41.9, 50.8, (Brassica 54.6, 41.7, oleracea 10, 6,var. 8.5, gemmifera 5.9% of ),Chinese cauliflower cabbage (Brassica (Brassica oleracea chinensis ), brusselsoleraceaoleracea convar. sproutsvar. acephala (Brassicasabauda var. oleracea sabellica), var. kale), gemmiferared (Brassica cabba),ge cauliflower (Brassica oleracea oleracea (Brassicaconvar. var. oleracea capitataacephala ), var. sabellica), red cabbage (Brassica oleracea O whiteconvar. cabbage botrytis ( Brassicavar. botrytis oleracea), kohlrabi), savoy ( Brassica(Brassica oleracea oleracea convar. var. sabauda acephala), kale var. (Brassica convar.brussels botrytis sprouts var. (Brassica botrytis oleracea), kohlrabi var. (gemmiferaBrassica oleracea), cauliflower convar. (Brassica acephala oleracea var. oleraceagongylodesvar. convar.capitata), swede acephala (),Brassica brussels var. napussabellica sproutsvar.), red napobrassic cabba (Brassicagea (),Brassica cabbage oleracea oleracea lettuce var. (var.Lactuca capitatagemmifera sativa), ), cauliflower (Brassica oleracea convar. gongylodesconvar. botrytis), swede var. ( Brassicabotrytis), napus kohlrabi var. (napobrassicBrassica oleraceaa), cabbage convar. lettuce acephala (Lactuca var. sativa brusselsvar.botrytis capitata sprouts), parsleyvar. (Brassicabotrytis (Petroselinum oleracea), kohlrabivar. crispum gemmifera ssp. (Brassica ),crispum cauliflower), black oleracea (Brassica salsifyconvar. (oleraceaScorzonera acephala var. gongylodes), swede (Brassica napus var.gongylodes capitata), ),swede parsley (Brassica (Petroselinum napus var. crispum napobrassic ssp. crispuma), cabbage), black lettuce salsify (Lactuca (Scorzonera sativa convar.hispanicavar. botrytis),napobrassica carrot var. (Daucus botrytis carota),), cabbagekohlrabi ssp. sativus (Brassica lettuce), turnip oleracea (-Lactucarooted convar. parsley sativaacephala (Petroselinum var.var. capitata ), parsley (Petroselinum crispum ssp. hispanicavar. capitata), carrot), parsley (Daucus (Petroselinum carota ssp. crispum sativus), ssp. turnip crispum-rooted), black parsley salsify (Petroselinum (Scorzonera gongylodescrispum ssp.), swede tuberosum (Brassica), Florence napus fennelvar. napobrassic (Foeniculuma), cabbage vulgare var. lettuce azoricum (Lactuca) fatty sativa crispumhispanicacrispum ssp.), carrot tuberosum), ( blackDaucus), Florence salsifycarota ssp. fennel ( Scorzonerasativus (Foeniculum), turnip hispanica-rooted vulgare parsley var.), azoricum carrot (Petroselinum) fatty (Daucus carota ssp. sativus), turnip-rooted parsley var.acids capitata mass,), respectively; parsley (Petroselinum 8.7, 9.7, 11.5, crispum 8.3, 10.2,ssp. crispum11.2, 9.3,), 11,black 12.3 salsify% of Chinese(Scorzonera acidscrispum mass, ssp. respectively; tuberosum), Florence 8.7, 9.7, 11.5,fennel 8.3, (Foeniculum 10.2, 11.2, 9.3,vulgare 11, 12.3var.% azoricum of Chinese) fatty hispanicacabbage,(Petroselinum), white carrot cabbage, (Daucus crispum savoy,carota ssp. kale,ssp. sativus redtuberosum cabbage,), turnip -brusselsrooted), Florence parsley sprouts, (Petroselinum cauliflower, fennel (Foeniculum vulgare var. azoricum) fatty acids cabbage,acids mass, white respectively; cabbage, savoy,8.7, 9.7, kale, 11.5, red 8.3, cabbage, 10.2, 11.2, brussels 9.3, 11, sprouts, 12.3% of cauliflower, Chinese crispumkohlrabi,mass, ssp. swede, respectively;tuberosum black), salsify, Florence 8.7,cabbage fennel 9.7, lettuce,(Foeniculum 11.5, c 8.3,arrot, vulgare 10.2, parsley, var. 11.2, Florence azoricum 9.3, fennel) 11, fatty 12.3% seed of Chinese cabbage, white cabbage, savoy, kohlrabi,cabbage, whiteswede, cabbage, black salsify, savoy, cabbage kale, red lettuce, cabbage, carrot, brussels parsley, sprouts, Florence cauliflower, fennel seed acidsfattykale, mass,acids redmass,respectively; cabbage, respectively 8.7, 9.7, brussels [53] 11.5,; in Trichosanthes8.3, sprouts,10.2, 11.2, kirilowii 9.3, cauliflower, 11, (33.7712.3%– of38.66% Chinese kohlrabi, of seed swede, black salsify, cabbage lettuce, carrot, fatkohlrabi,ty acids swede, mass, respectivelyblack salsify, [53] cabbage; in Trichosanthes lettuce, carrot, kirilowii parsley, (33.77 Florence–38.66% fennel of seed seed cabbage,oils) [70] ;white in Linum cabbage, usitatissimum savoy, kale, (depending red cabbage, on the brussels genotype sprouts, it contains cauliflower, from 1.1 to oils)fattyparsley, [70]acids; in mass, Linum Florence respectively usitatissimum fennel [53] (depending; in seedTrichosanthesfatty on the kirilowii acidsgenotype (33.77 mass, it contains–38.66% respectively from of seed 1.1 to [53]; in Trichosanthes kirilowii (33.77–38.66% kohlrabi,65.2% of swede,total fatty black acids salsify, in seeds) cabbage [71] ;lettuce, in paprika carrot, Capsicum parsley, annuum Florence (29.93 fennel% of seed fresh 65.2oils)% [70] of ;total in Linum fatty usitatissimumacids in seeds) (depending [71]; in paprika on the Capsicum genotype annuum it contains (29.93 from% of 1.1 fresh to fatpericarptyof acids seed fatty mass, oils)acids respectively in [70 Jaranda]; in [53] varietyLinum; in Trichosanthes and usitatissimum 30.27% kirilowiiin Jariza (33.77 (dependingvariety)–38.66% [72] of seed on the genotype it contains from 1.1 to 65.2% of pericarp65.2%total of fattytotal fatty acidsfatty acids acidsin Jaranda in in seeds) seeds) variety [71] ;and [in71 p 30.27aprika]; in% paprika Capsicumin Jariza variety) annuumCapsicum [72] (29.93 % annuum of fresh (29.93% of fresh pericarp fatty acids in linolenelaidic H oils)in Turkish [70]; in sage Linum species usitatissimum—Salvia virgata (depending, Salvia on potentillifolia the genotype, Salvia it contains recognita from, Salvia 1.1 to (9E,12E,15E)-octadeca- O linolenelaidic H inpericarp Turkish fatty sage acids species in Jaranda—Salvia variety virgata ,and Salvia 30.27 potentillifolia% in Jariza, Salviavariety) recognita [72] , Salvia 6 acid/elaidolinol C18:3n-3 C18H30O2 O 278.436 g/mol 65.2tomentosa% of total amounts fatty acidsto 0.4, in 0.7, seeds) 1.1 and [71] 1.4; in% p aprikaof seed Capsicum fatty acids, annuum respectively (29.93% [73] of ;fresh (9E,12E,15E)-octadeca- O Jaranda variety and 30.27% in Jariza variety) [72] 6 9,12,15-trienoic acid acidlinolenelaidic/elaidolinol C18:3n-3 C18H30O2 278.436 g/mol tomentosain Turkish amounts sage species to 0.4,— Salvia0.7, 1.1 virgata and 1.4, Salvia% of seedpotentillifolia fatty acids,, Salvia respectively recognita, [73]Salvia; O H (99,12,15E,12E,15-trienoicE)-octadeca acid - enic acid O pericarp0.03% of fatty tobacco acids seed in Jarandaoil fatty varietyacids [74] and 30.27% in Jariza variety) [72] 6 acidenic/elaidolinol acid C18:3n-3 C18H30O2 278.436 g/mol 0.03tomentosa% of tobacco amounts seed to 0.4,oil fatty0.7, 1.1 acids and [74] 1.4 % of seed fatty acids, respectively [73]; linolenelaidic O 9,12,15-trienoic acid linolenelaidic H in Turkish sage species—Salvia virgata, Salvia potentillifolia, Salvia recognita, Salvia (9E,12E,15E)-octadeca-(9E,12E,15E)-octadeca- enic acid O 0.03%in of Turkish tobacco seed sage oil fatty species— acids [74]Salvia virgata, Salvia potentillifolia, Salvia recognita, Salvia tomentosa amounts to 6 acid/elaidolinol C18:3n-3 C18H30O2 278.436 g/mol tomentosa amounts to 0.4, 0.7, 1.1 and 1.4% of seed fatty acids, respectively [73]; 6 9,12,15-trienoicacid/elaidolinolenic acid C18:3n-3 C18H30O2 O 278.436 g/mol 9,12,15-trienoic acid enic acid 0.03%0.4, of tobacco 0.7, 1.1 seed and oil fatty 1.4% acids of [74] seed fatty acids, respectively [73]; 0.03% of tobacco seed oil fatty acids [74] acid

Nutrients 2018, 10, 1662 6 of 33

Table 1. Cont.

Shorthand Common Molecular No IUPAC Name (Simplified Formula/Structure Molecular Weight Sources [Refs.] Name Formula Formula) Nutrients 2018, 10, x FOR PEER REVIEW 6 of 34 Nutrients 2018, 10, x FOR PEER REVIEW POLYUNSATURATED FATTY ACIDS (PUFAs) 6 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 6 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 6 of 34 in musclein muscle samples samples from linseed from oil-fed linseed lambs [75] oil-fed; 0.03 g/100 lambs g of total [75 ];fatty 0.03 acid g/100 g of total fatty acid methyl esters of milk (9Z,11E,15Z)-octadeca-(9Z,11E,15Z)-octadecarumelenic- methylin muscle esters samples of milk from fat linseedfrom ewes, oil-fed 0.52 lambs g/100 [75] g of; 0.03total g/100 fatty gacid of total methyl fatty esters acid of Nutrients7 2018, 10, x FOR PEER REVIEWrumelenic acid C18:3n-3 C18H30O2 278.436 g/mol in muscle samples from linseed oil-fed lambs [75]; 0.03 g/100 g of total fatty acid6 of 34 7 (99,11,15Z,11E,15-trienoicZ)-octadeca acid - C18:3n-3 C18H30O2 278.436 g/mol milkmethylfat fat esters from ewesof ewes,milk fed fat diets 0.52from with ewes, g/100 extruded 0.52 g g/100 oflinseed total g of supplementationtotal fatty fatty acid acid methyl methyl (12% esterslinseed esters of in of milk fat from ewes fed diets with 9,11,15-trienoic7 acid acid rumelenic acid C18:3n-3 C18H30O2 O 278.436 g/mol (99,11,15Z,11E,15-trienoicZ)-octadeca acid - H milkmethylin muscle fat estersfrom samples ewesof milk fromfed fat diets linseedfrom with ewes, oil extruded-fed 0.52 lambs g/100 linseed [75] g of; 0.03supplementationtotal g/100 fatty gacid of total methyl (12% fatty esterslinseed acid of in Nutrients7 2018, 10, x FOR PEER REVIEWrumelenic acid C18:3n-3 C18H30O2 O 278.436 g/mol dry matter)extruded [69] linseed supplementation (12% linseed in dry6 matter)of 34 [69] H O (99,11,15Z,11E,15-trienoicZ)-octadeca acid - O milkmethyl fat esters from ewesof milk fed fat diets from with ewes, extruded 0.52 g/100 linseed g of supplementationtotal fatty acid methyl (12% esterslinseed of in O dry matter) [69] Nutrients7 2018, 10, x FOR PEER REVIEWrumelenic acid C18:3n-3 C18H30O2 H 278.436 g/mol in muscle samples from linseed oil-fed lambs [75]; 0.03 g/100 g of total fatty acid6 of 34 9,11,15-trienoic acid O O drymilk matter) fat from [69] ewes fed diets with extruded linseed supplementation (12% linseed in (9Z,11E,15Z)-octadeca- H methyl esters of milk fat from ewes, 0.52 g/100 g of total fatty acid methyl esters of 7 rumelenic acid C18:3n-3 C18H30O2 O 278.436 g/mol 0.01indry muscle matter)g/100 samplesg [69]of total from fatty linseed acid methyl oil-fed esters lambs of [75]milk; 0.03fat from g/100 ewes, g of total 0.21 fattyg/100 acid g of (99,11,15Z,11E,15-trienoicE)-octadeca acid - milk0.01 fat from g/100 ewes fed g of diets total with fatty extruded acid linseed methyl supplementation esters of (12% milk linseed fat from in ewes, 0.21 g/100 g of total fatty acid O 0.01 g/100 g of total fatty acid methyl esters of milk fat from ewes, 0.21 g/100 g of 8 - C18:3n-3 C18H30O2 278.436 g/mol total fatty acid methyl esters of milk fat from ewes fed diets with extruded linseed (9Z,11E,15E)-octadeca-(9Z,11E,15EZ))--octadeca-- H methyl esters of milk fat from ewes, 0.52 g/100 g of total fatty acid methyl esters of 87 9,11,15-trienoic acid rumelenic- acid C18:3n-3 C18H30O2 278.436 g/mol totaldry0.01in muscle matter) g/100fatty acid gsamples [69]of methyltotal fromfatty esters acidlinseed of methyl milk oil- fedfat esters fromlambs of ewes milk[75] ;fed fat0.03 dietsfrom g/100 withewes, g of extruded 0.21total g/100fatty linseed acidg of 8 - C18:3n-3 C H O O 278.436 g/mol supplementationmethyl esters (12% linseed of milk in dry fat matter) from [69] ewes fed diets with extruded linseed supplementation (12% linseed in (99,11,15Z,11E,15-trienoicE)-octadeca acid - 18 30 2 O milk fat from ewes fed diets with extruded linseed supplementation (12% linseed in 9,11,15-trienoic8 acid(9Z,11E,15Z)-octadeca- - C18:3n-3 C18H30O2 HH 278.436 g/mol supplementationtotal0.01methyl g/100fatty esters acidg of oftotalmethyl milk(12% fatty fatesterslinseed acidfrom of methyl in ewes,milk dry fat matter)0.52esters from g/100 of [69]ewes milk g of fed fat total dietsfrom fatty withewes, acid extruded 0.21 methyl g/100 esterslinseed g of of 7 (9Z,11E,15E)-octadeca- rumelenic acid C18:3n-3 C18H30O2 O 278.436 g/mol 9,11,15-trienoic acid O dry matter)dry matter) [69] [69] 9,11,15-trienoic acid 18 30 2 H milk fat from ewes fed diets with extruded linseed supplementation (12% linseed in 8 - C18:3n-3 C H O OO 278.436 g/mol supplementationtotal fatty acid methyl (12% esterslinseed of in milk dry fat matter) from ewes[69] fed diets with extruded linseed O 9,11,15-trienoic acid H H f0.01ounddry g/100matter) in many g of[69] totalconifer fatty species: acid methyl 0.05% ofesters Abies of fraseri milk fatseed from total ewes, fatty 0.21 acids, g/100 0.03 g% of of (9Z,11E,15E)-octadeca- O O supplementation (12% linseed in dry matter) [69] O 8 - C18:3n-3 C18H30O2 H 278.436 g/mol ftotalound fatty in many acid methylconifer estersspecies: of 0.05milk% fat of fromAbies ewesfraseri fed seed diets total with fatty extruded acids, 0.03 linseed% of 9,11,15-trienoic acid A.0.01 nordmanniana g/100 g of total ssp. fatty nordmanniana acid methyl seed esters total of fatty milk acids, fat from 0.05 ewes,% of A.0.21 numidica g/100 g seed of (9Z,11E,15E)-octadeca- O A.supplementationfound nordmannianafound in many in conifer manyssp. (12% nordmanniana species:linseed conifer in0.05 dry seed% species: matter)of Abiestotal fatty[69]fraseri 0.05% acids, seed of 0.05totalAbies% fatty of A. fraseriacids, numidica 0.03seed seed% of total fatty acids, 0.03% of A. nordmanniana 8 - C18:3n-3 C18H30O2 O 278.436 g/mol totaltotal fattyfatty acids,acid methyl 0.06% estersof A. procera of milk seed fat from total ewesfatty acids,fed diets 0.05 with% of extruded Tsuga chinensis linseed (5Z9,11,15,9Z,12Z-trienoic,15Z)-octadeca acid - Coniferonic H totalA.found0.01 nordmannianassp. fattyg/100 in many acids,nordmanniana g of conifertotal 0.06 ssp. %fatty nordmanniana ofspecies: A. acid proceraseed methyl0.05 %seed total of esters Abiestotal fatty of fattyfraseri milk acids, seedfat from 0.05total 0.05% ewes,% fatty of TsugaA. 0.21acids, ofnumidica A. g/100chinensis 0.03 numidica g%seed of of seed total fatty acids, 0.06% of A. procera 9 C18:4n-3 C18H28O2 O 276.42 g/mol seed total fatty acids, 0.09% of Tsuga heterophylla seed total fatty acids, 1.78% of (5Z(9,9ZZ,11,12EZ,15,15EZ))--octadecaoctadeca-- Coniferonic O supplementation (12% linseed in dry matter) [69] 5,9,12,15-tetraenoic acid acid O totalA. nordmanniana fatty acids, 0.06ssp.% nordmanniana of A. procera seedseed totaltotal fatty acids, 0.05% of A.Tsuga numidica chinensis seed 98 - C18:4C18:3nn-3-3 CC1818HH2830OO2 2 H 276.42278.436 g/mol g/mol seedtotal total fatty fatty acid acids, methyl 0.09 esters% of of Tsuga milk heterophylla fat from ewes seed fed total diets fatty with acids, extruded 1.78% linseed of (5Z,9Z,12Z,15Z)-octadeca-(55,9,12,15Z,99,11,15Z,12Z-tetraenoic-,15trienoicZ)-octadecaConiferonic acid acid - Coniferonicacid O Pseudolarixfoundseed in many totalamabilis conifer fatty seed species: total acids, fatty 0.050.05% acids% of Abies[76] of; 2fraseriTsuga% of Chamaecyparis seed chinensis total fatty lawsonianaseed acids, 0.03 total and% of fatty acids, 0.09% of Tsuga heterophylla seed 9 C18:4n-3 C18H28O2 H OO 276.42 g/mol seedtotal fattytotal fattyacids, acids, 0.06% 0.09 of A.% ofprocera Tsuga seed heterophylla total fatty seed acids, total 0.05 fatty% ofacids, Tsuga 1.78 chinensis% of 9 C18:4n-3 C H O O 276.42 g/mol Pseudolarixsupplementation amabilis (12% seed linseedtotal fatty in dryacids matter) [76]; 2 [69]% of Chamaecyparis lawsoniana and (55,9,12,15Z,9Z,12Z-tetraenoic,15Z)-octadeca acid - Coniferonicacid 18 28 2 O 2.8A. %nordmanniana of Fokienia hodginsii ssp. nordmanniana seed total fattyseed acidstotal fatty[67]; acids,11% of 0.05 Abies% ofvejarii A. numidica Martínez seed leaf 5,9,12,15-tetraenoic9 acid acid C18:4n-3 C18H28O2 HH O 276.42 g/mol fPseudolarixseedoundtotal total in many fatty fattyamabilis acids,conifer acids, seed 0.09 species: total% 1.78% of fatty Tsuga0.05 acids% of heterophylla ofPseudolarix Abies[76]; 2fraseri% seedof Chamaecyparisseed total amabilis total fatty fatty acids,seed lawsoniana acids, 1.78 total 0.03% ofand% fatty of acids [76]; 2% of Chamaecyparis lawsoniana O O 2.8% of Fokienia hodginsii seed total fatty acids [67]; 11% of Abies vejarii Martínez leaf 5,9,12,15-tetraenoic acid acid H O fattytotal acidsfatty acids,[77] 0.06% of A. procera seed total fatty acids, 0.05% of Tsuga chinensis (5Z,9Z,12Z,15Z)-octadeca- Coniferonic fattyA.2.8Pseudolarix %nordmannianaand acidsof Fokienia 2.8%[77] amabilis hodginsii ssp. of seed Fokienianordmanniana totalseed fattytota hodginsiil acidsfattyseed totalacids[76];seed fatty 2[67]% of; acids,11 Chamaecyparis total% of 0.05 Abies fatty% of vejarii acidsA.lawsoniana numidica Martínez [67 and seed]; leaf 11% of Abies vejarii Martínez leaf fatty 9 C18:4n-3 C18H28O2 O 276.42 g/mol inseedfound salted total in products manyfatty acids, conifer of fish 0.09 species: roe:% of 0.8 Tsuga 0.05% of% heterophyllaIkura of Abies (salmon), fraseri seed seed 0.8total% totaloffatty Tarako fatty acids, acids,(pollock), 1.78 %0.03 of %0.4 of% 5,9,12,15-tetraenoic acid acid O totalfatty2.8% fattyacidsof Fokienia acids, [77] hodginsii0.06% of seedA. procera total fattyseed acidstotal fatty[67]; acids,11% of 0.05 Abies% ofvejarii Tsuga Martínez chinensis leaf (5Z,9Z,12Z,15Z)-octadeca- Coniferonic H ofinPseudolarixA. saltedTobiko nordmannianaacids products (flyingfish), amabilis [77] ssp. of seed fish 0.4nordmanniana total %roe: of 0.8fattyKazunoko% ofacids seed Ikura [76] (herring)total (salmon),; 2 fatty% of total acids,Chamaecyparis 0.8 lipids% 0.05 of Tarako[59]% of; lawsoniana2.3A. (pollock), %numidica of wild and seed0.4 % 9 C18:4n-3 C18H28O2 O 276.42 g/mol seedinfatty salted totalacids products fatty [77] acids, of fish0.09 roe:% of 0.8 Tsuga% of heterophylla Ikura (salmon), seed 0.8total% fattyof Tarako acids, (pollock), 1.78% of 0.4% O oftotal Tobiko fatty (flyingfish), acids, 0.06% 0.4 of% A. of procera Kazunoko seed (herring)total fatty total acids, lipids 0.05 [59]% of; 2.3Tsuga% of chinensis wild 5,9,12,15-tetraenoic acid acid H sardine2.8% of (FokieniaSardina hodginsiipilchardus seed) muscle total totalfatty fattyacids acids [67]; (1.511%% of of Abies captive vejarii sardine Martínez muscle leaf (5Z,9Z,12Z,15Z)-octadeca- Coniferonic O sardinePseudolarixofin saltedTobikoin salted( Sardinaproducts (flyingfish), amabilis pilchardus products of seed fish 0.4 total %roe:) muscleof offatty0.8Kazunoko% fish acidstotalof Ikura roe: fatty[76] (herring) (salmon),; 0.8%acids2% of total(1.5 Chamaecyparis of 0.8% lipids Ikura %of of captive Tarako[59] (salmon), ;lawsoniana 2.3sardine (pollock),% of wildmuscle and 0.8% 0.4 % of Tarako (pollock), 0.4% of Tobiko 9 C18:4n-3 C18H28O2 H O 276.42 g/mol totalfattyseed fattyacids total acids), [77]fatty acids, 0.7% of0.09 wild% of/0.6 Tsuga% of heterophyllacaptive sardine seed liver total totalfatty fatty acids, acids 1.78 %[61] of; as 5,9,12,15-tetraenoic acid acid O 2.8sardineof Tobiko% of Fokienia(Sardina (flyingfish), hodginsiipilchardus 0.4 seed%) muscleof totaKazunokol totalfatty fattyacids (herring) acids [67]; total11(1.5%% oflipids of Abies captive [59] vejarii; 2.3 sardine %Martínez of wild muscle leaf HH total(flyingfish), fatty acids), 0.7% 0.4% of wild of/0.6 Kazunoko% of captive sardine (herring) liver total total fatty lipids acids [61] [59; ];as 2.3% of wild sardine (Sardina pilchardus) O O methylinPseudolarix salted ester: products amabilis 0.57– 0.76of seed fish% ofroe:total commo 0.8 fatty% nof acids barbel Ikura [76] oil,(salmon),; 2 1.52% of– 2.04Chamaecyparis 0.8% of PTarakoontic lawsoniana shad (pollock), oil, 0.2and 0.4– % stearidonic acid H O methylfattytotalsardine fattyacids ester:(Sardina acids),[77] 0.57 pilchardus 0.7–0.76% %of ofwild) musclecommo/0.6% ntotal of barbel captive fatty oil, acids sardine 1.52 (1.5–2.04 liver%% of of totalcaptive Pontic fatty sardine shad acids oil, [61]muscle 0.2; as– (6Z,9Z,12Z,15Z)-octadeca- stearidonic acid O O 0.35of2.8 Tobiko%muscle of FokieniaEuropean (flyingfish), total hodginsii welsfatty 0.4 catfish% seed of acids Kazunoko totaoil, l0.28 fatty (1.5%–0.59 (herring)acids% of of[67] captive c ommontotal; 11% lipids of bleak sardineAbies [59] oilvejarii; 2.3 [52] muscle% Martínez; of0.41 wild–0.71 total leaf% fatty acids), 0.7% of wild/0.6% of captive 10 (SDA)/moroctic C18:4n-3 C18H28O2 H 276.42 g/mol inmethyltotal salted fatty ester: products acids), 0.57 0.7– of0.76% fish %of ofwildroe: commo 0.8/0.6%% ofn of barbelIkura captive (salmon),oil, sardine 1.52–2.04 0.8 liver% oftotal TarakoPontic fatty shad(pollock), acids oil, [61] 0.2 0.4; as– % (66,9,12,15Z,9Z,12Z,15-tetraenoicZ)-octadeca acid - O for0.35fatty finwhale% acidsof European [77] oils, 0.79 wels–1.09 catfish% for oil, seal 0.28 oils– 0.59(in weight% of common per cent) bleak [62] oil; 0– [52]0.9%; 0.41 of –0.71% 10 stearidonic(SDA)/morocticstearidonic acid C18:4n-3 C18H28O2 276.42 g/mol sardinesardine (Sardina liver pilchardus total) muscle fatty total acids fatty [ 61acids]; as(1.5 methyl% of captive ester: sardine 0.57–0.76% muscle of common barbel oil, 1.52–2.04% of (66,9,12,15Z,9Z,12Z,15-tetraenoicZ)-octadeca acid - acid O O forof0.35methyl Tobiko finwhale% of ester: European (flyingfish), oils, 0.57 0.79–0.76 wels– 0.41.09% catfish of%% commoof for Kazunoko oil, seal n0.28 oilsbarbel– 0.59 (in(herring) oil,weight% of 1.52 c ommontotal –per2.04 cent)lipids% bleakof [62] P[59]ontic oil; ;0 2.3– [52] 0.9shad%% ;of 0.41 ofoil, wild – 0.20.71 –% 10 stearidonic(SDA)/morocticacid acid C18:4n-3 C18H28O2 H 276.42 g/mol Epinephelustotalin salted fatty productsacids), retouti 0.7 muscle of% fish of wild triacylglycerolsroe:/ 0.60.8% of captiveIkura [64] (salmon), ;sardine mean amounts liver0.8% totalof ofTarako fattyseeds acids(pollock), total [61]fatty; 0.4as % (6Z,9Z,12Z,15Z)-octadeca-(66,9,12,15Z,9Z,12Z,15-tetraenoicZ)-octadeca acidacid - Epinephelussardinefor0.35 finwhale%Pontic of ( SardinaEuropean retouti oils, shad pilchardus 0.79 muscle wels oil,–1.09 catfish triacylglycerols) 0.2–0.35%% muscle for oil, seal total0.28 oils– fatty of0.59(in [64] Europeanweight% acids; meanof c ommon(1.5 per amounts% cent) of welsbleak captive [62] of oilseeds;catfish 0 – sardine[52]0.9 total%; 0.41 of oil, muscle fatty–0.710.28–0.59% % of common bleak oil [52]; 10 (SDA)/morocticacid C18:4n-3 C18H28O2 O 276.42 g/mol acidof Tobiko methyl (flyingfish), esters: 4.73% 0.4 for% ofPrimulaceae Kazunoko, 4.99 (herring)% for Boraginaceaetotal lipids [59], 0.36; 2.3% %for of wild 10 C18:4n-3 C18H28O2 O 276.42 g/mol methyl ester: 0.57–0.76% of common barbel oil, 1.52–2.04% of Pontic shad oil, 0.2– 6,9,12,15-tetraenoic acid stearidonic acid H acidtotalEpinephelusfor finwhale methylfatty acids), retoutiesters: oils, 0.70.79 muscle4.73%%– of1.09 wildfor triacylglycerols% Primulaceaefor/0.6 seal% of oils captive, (in4.99 [64] weight% ;sardine mean for Boraginaceaeper amounts liver cent) total [62] of, fatty0.36 ;seeds 0–%0.9 acids fortotal% of [61] fatty; as 6,9,12,15-tetraenoic(6Z,9 acidZ,12Z,15Z)-(SDA)/morocticoctadeca- acid Hippophae0.35sardine%0.41–0.71% of (European Sardinarhamnoides pilchardus wels for, 0.77 catfish finwhale%) musclefor oil,Cannabis 0.28total oils,– 0.59safattytiva 0.79–1.09%% acids of[78] common; in(1.5 Ribes% of bleak nigrum forcaptive sealoil and [52]sardine oils ;fish 0.41 oilsmuscle (in–0.71 weight% per cent) [62]; 0–0.9% of Epinephelus O 10 (SDA)/moroctic C18:4n-3 C18H28O2 O 276.42 g/mol HippophaemethylacidEpinephelus methyl ester: rhamnoides retouti esters: 0.57– muscle0.76 4.73%, 0.77% of for%triacylglycerols commo for Primulaceae Cannabisn barbel, sa 4.99[64]tiva oil,%; [78]mean 1.52for; Boraginaceae–in 2.04amounts Ribes% of nigrum P ofontic, 0.36seeds and shad% fortotal fish oil, fattyoils 0.2 – 6,9,12,15-tetraenoic acidacid stearidonic acid H [77]fortotal finwhale;retouti 14 fatty% and acids), oils, muscle16.2 0.79 %0.7 of%– 1.09Echium of triacylglycerols wild% for humile/0.6 seal% of oilsssp. captive (in pycnanthum weight [ 64sardine]; per mean seeds liver cent) fattytotal amounts[62] ;acids,fatty 0–0.9 acids %depending of [61] seeds; as total fatty acid methyl esters: 4.73% for (6Z,9Z,12Z,15Z)-octadeca- acid [77]0.35Hippophaeacid;% methyl14 of% Europeanand rhamnoides esters: 16.2% 4.73%wels of, 0.77 Echium catfish for% for Primulaceae humile oil,Cannabis 0.28 ssp.–,0.59 sa 4.99pycnanthumtiva%% of[78] for common ;Boraginaceae in seeds Ribes bleak fattynigrum, 0.36 oilacids, and[52]% for depending;fish 0.41 oils–0.71 % 10 (SDA)/moroctic C18:4n-3 C18H28O2 O 276.42 g/mol onEpinephelusmethyl the location ester: retouti 0.57 [79] –muscle 0.76% oftriacylglycerols common barbel [64] oil,; mean 1.52– amounts2.04% of ofPontic seeds shad total oil, fatty 0.2 – 6,9,12,15-tetraenoic acid stearidonic acid onfor[77]Hippophae thefinwhale;Primulaceae 14 location% and rhamnoides oils, 16.2 [79] 0.79% , of, 4.99%– 0.77 1.09Echium%% forfor forhumile CannabissealBoraginaceae oils ssp. (insa pycnanthumtiva weight [78]; , perin 0.36% seedsRibes cent) nigrumfatty [62] for ;acids, 0Hippophae –and0.9 % dependingfish of oils rhamnoides , 0.77% for Cannabis sativa [78]; (all(6-EZ/,9ZZ)-,12Z,15octadecaZ)--9,11,13,15octadeca-- acid acid0.35 methyl% of European esters: 4.73% wels catfishfor Primulaceae oil, 0.28–, 0.594.99% offor c ommonBoraginaceae bleak, 0.36 oil %[52] for; 0.41 –0.71% 1110 (all-E/Z)-octadeca-9,11,13,15- parinaric(SDA)/moroctic acid C18:4C18:4nn-3-3 CC1818HH2828OO2 2 undefined cis-trans isomerism 276.42276.42 g/mol g/mol 11.34Epinepheluson[77] the;in %14 location%ofRibes andthe retouti methanol16.2 nigrum[79] %muscle of Echium extract andtriacylglycerols humileof fish Spirogyra oilsssp. pycnanthum[64] [rhizoides77; mean]; 14% [80] amounts seeds and fatty of 16.2% seedsacids, total ofdependingEchium fatty humile ssp. pycnanthum seeds fatty acids, 11 6,9,12,15tetraenoic-tetraenoic acid acid parinaric acid C18:4n-3 C18H28O2 undefined cis-trans isomerism 276.42 g/mol 11.34Hippophaefor finwhale% of therhamnoides oils,methanol 0.79, 0.77– 1.09extract%% for for of Cannabis sealSpirogyra oils sa (in tivarhizoides weight [78]; [80] inper Ribes cent) nigrum [62]; 0 and–0.9 fish% of oils (all-E/Ztetraenoic)-octadeca acid-9,11,13,15 - acid acidon the methyl location esters: [79] 4.73% for Primulaceae, 4.99% for Boraginaceae, 0.36% for 11 parinaric acid C18:4n-3 C18H28O2 undefined cis-trans isomerism 276.42 g/mol 62%[77]11.34Epinephelus; depending of14% Parinarium%of andthe retouti methanol16.2 %laurinum muscleon of Echium extract the triacylglycerols seed location humileof oil Spirogyra methyl ssp. [ pycnanthum79 [64]estersrhizoides] ; mean [81] [80] ; amounts seeds53.5% fatty of ofParinarium acids,seeds dependingtotal laurinum fatty (all-E/Ztetraenoic)-octadeca acid-9,11,13,15 - Hippophae rhamnoides, 0.77% for Cannabis sativa [78]; in Ribes nigrum and fish oils 18 28 2 62%acid of methyl Parinarium esters: laurinum 4.73% for seed Primulaceae oil methyl, 4.99 esters% for [81] Boraginaceae; 53.5% of Parinarium, 0.36% for laurinum 11 parinaric acid C18:4n-3 C H O undefined cis-trans isomerism 276.42 g/mol seedon11.34 the oil% location offatty the acids methanol [79] [66] ; 4%extract of Parinarium of Spirogyra macrophyllum rhizoides [80] seed oil [82]; in Impatiens (all-E/Z)-octadeca-tetraenoic acidparinaric undefined cis-trans seed[77]62%; of14oil %Parinarium fatty and acids 16.2 % laurinum[66] of ;Echium 4% ofseed Parinarium humile oil methyl ssp. macrophyllum pycnanthum esters [81] ;seeds 53.5%seed fattyoil of [82] Parinarium acids,; in Impatiens depending laurinum 11 (all-E/Z)-octadeca-9,11,13,15- C18:4n-3 C18H28O2 276.42 g/moledgeworthiiHippophae 11.34% (48%rhamnoides of of the total, 0.77 methanol fatty% foracids) Cannabis [83] extract; in sa Impatienstivaof [78]Spirogyra; inglandulifera Ribes nigrum rhizoides(42.5 and% of fish Impatiens[ 80oils] 11 parinaric acid C18:4n-3 C18H28O2 undefined cis-trans isomerism 276.42 g/mol edgeworthiion11.34seed62% the ofoil% location Parinariumof fatty the (48% acidsmethanol [79] of laurinum [66]total; extract4%fatty ofseed acids) Parinarium of oil Spirogyra [83]methyl; in macrophyllum Impatiensrhizoidesesters [81] [80] glandulifera; 53.5%seed oil of [82]Parinarium (42.5; in% Impatiens of Impatiens laurinum 9,11,13,15-tetraenoic acidtetraenoic acid acid α-parinaric acid isomerism oil)[77] [84]; 14; %in and the seed16.2% oil of of Echium Sebastiana humile brasiliensis ssp. pycnanthum (21.4, 32.5 seeds and fatty35.1 peakacids, area depending % of (all(9Z-E,11/ZE)-,13octadecaE,15Z)-octadeca9,11,13,15-- α-parinaric acid oil)edgeworthiiseed [84] oil; fattyin the(48% acids seed of [66]total oil ;of 4%fatty Sebastiana of acids) Parinarium brasiliensis[83]; inmacrophyllum Impatiens (21.4, 32.5glandulifera seed and oil 35.1 [82] (42.5 peak; in% Impatiens areaof Impatiens % of 1211 parinaric(cis-parinaric acid C18:4n--3 C1818H2828O22 undefined cis-trans isomerism 276.42 g/mol samples11.3462%on the of% Parinariumoflocation from the methanolNational [79] laurinum Parkextract seed of Turvo,of oil Spirogyra methyl Santana rhizoidesesters da [81]Boa [80]; Vista53.5% region of Parinarium and Cacapava laurinum (99,11,13,15Z,11Etetraenoic,13E-tetraenoic,15Z) acid-octadeca acid - edgeworthii (48% of total fatty acids) [83]; in Impatiens glandulifera (42.5% of Impatiens 12 α(-cisparinaric-parinaric acid C18:4n-3 C18H28O2 O 276.42 g/mol samplesoil) [84]62%; frominof the NationalParinarium seed oil ofPark Sebastiana of laurinum Turvo, brasiliensis Santanaseed (21.4,da oilBoa 32.5 methylVista and region 35.1 esters peak and Cacapavaarea [81 %]; of 53.5% of Parinarium laurinum seed oil fatty (all(99,11,13,15Z-,11E/ZE),13-octadecaE-tetraenoic,15Z)-octadeca-9,11,13,15 acid - - acid) H dseedo Sul oil region, fatty acids respectively) [66]; 4% of[85] Parinarium; 30% of Impatiens macrophyllum balsamina seed seed oil [82] oil ;[86] in Impatiens; in 1211 α-(parinariccis-parinaric acid C18:4C18:4nn-3-3 CC1818HH2828OO2 2 undefinedO cis-trans isomerism 276.42276.42 g/mol g/mol 62%samplesoil)11.34 [84] of% Parinarium; offromin thethe National methanolseed laurinum oil ofPark extract Sebastiana seed of Turvo, of oil Spirogyra methylbrasiliensis Santana esters rhizoides (21.4,da [81]Boa 32.5[80]; Vista53.5% and region of35.1 Parinarium peak and areaCacapava laurinum % of tetraenoic acid acid) H O Chrysobalanusdo Sulacids region, [66 icacorespectively)]; 4%(10% of of seed Parinarium[85]; oil30% methyl of Impatiens macrophyllumesters) balsamina[81]; in evening seedseed oil primrose [86] oil; in [82 ]; in Impatiens edgeworthii (48% of total fatty (99,11,13,15Z,11E,13E-tetraenoic,15Z)-octadeca acid - O edgeworthii (48% of total fatty acids) [83]; in Impatiens glandulifera (42.5% of Impatiens O 12 α-parinaric(cis-parinaricacid) C18:4n-3 C18H28O2 H 276.42 g/mol seeddsampleso Sul oil region, fattyfrom acids Nationalrespectively) [66]; Park4% of[85] of Parinarium Turvo,; 30% of Santana Impatiens macrophyllum da balsaminaBoa Vista seed seed regionoil [82] oil ; and [86]in Impatiens ;Cacapava in 9,11,13,15-tetraenoic acid (ChrysobalanusOenothera62%acids) of Parinarium biennis [ 83icaco];) oil (10%laurinum in (3.5Impatiens of × seed10 seed−5 mol/L)oil oil methyl glanduliferamethyl [87] ;ester inesters strippeds) [81] [81](42.5%; ; in Borage53.5% evening ofof (Borago Parinarium Impatiensprimrose officinalis laurinumoil)) oil [ 84]; in the seed oil of Sebastiana brasiliensis α-parinaric acid O O oil) [84]; in the seed oil of Sebastiana brasiliensis (21.4, 32.5 and 35.1 peak area % of H −5 (9Z,11E,13E,15Z)-octadeca-(9Z,11E,13E,15Z)-octadecaacid- acid) (edgeworthiiChrysobalanusdOenotherao Sul region,−4 biennis(48% icacorespectively) of) oil (10%total (3.5 fattyof × seed 10[85] acids) ; mol/L) oil30% methyl[83] of [87] ;Impatiens in ;esterImpatiens in strippeds) balsamina[81] glandulifera; inBorage evening seed (Borago oil(42.5 primrose [86]% officinalis ;of in Impatiens ) oil 18 28 2 (1.6seed × 10oil fatty mol/L) acids [82] [66] ; 4% of Parinarium macrophyllum seed oil [82]; in Impatiens 12 (cis-parinaric n C18:4n-3 C H O O 276.42 g/mol samples from National Park of− 5Turvo, Santana da Boa Vista region and Cacapava 12 9,11,13,15-tetraenoic acid α-parinaricC18:4 acid -3 C18H28O2 276.42 g/mol (1.6oil)(ChrysobalanusOenothera [84](21.4,× 10;− 4in mol/L) biennisthe 32.5 icaco seed [82]) and oil(10% oil (3.5 of 35.1of Sebastiana× seed10 peak mol/L)oil methylbrasiliensis area [87] ;ester in % stripped(21.4,s) of [81] samples 32.5; in Borage andevening 35.1 ( fromBorago peakprimrose Nationalofficinalisarea % of) oil Park of Turvo, Santana da Boa Vista region 9,11,13,15-tetraenoic acid (cis-parinaric O (9Z,11E,13E,15Z)-octadeca- trans-parinaric H edgeworthii (48% of total fatty acids) [83]; in Impatiens glandulifera (42.5% of Impatiens acid) O do Sul region,−4 respectively) [85]−5 ; 30% of Impatiens balsamina seed oil [86]; in 12 (9E,11E,13E,15E)-octadeca- (cis-parinaric C18:4n-3 C18H28O2 H 276.42 g/mol samples(1.6(Oenothera and× 10 from mol/L) Cacapavabiennis National [82]) oil (3.5 Park do × 10 of Sul Turvo, mol/L) region, Santana [87]; in respectively) strippedda Boa Vista Borage region [(85Borago ];and 30% officinalisCacapava of Impatiens) oil balsamina seed oil [86]; in trans-parinaric O 18 28 2 O 13 9,11,13,15-tetraenoic acid α-parinaricacid (β- acid C18:4n-3 C H O O 276.42 g/mol “Chrysobalanusoil)naturally [84]; in occurring the icaco seed (10%” oil [88] of of; Sebastiana inseed Impatiens oil methyl brasiliensis spp. ester [89] (21.4,s) [81] 32.5; in eveningand 35.1 primrose peak area % of (9E,11E,13E,15E)-octadecaacid)- H O −4 9,11,13,15(9Z,11E,13-tetraenoicE,15Z)-octadeca acid - transacid)-parinaric 18 28 2 H d(1.6o Sul × 10 region, mol/L) respectively) [82] [85]; 30% of Impatiens balsamina seed oil [86]; in 13 acid (β- C18:4n-3 C 18H 28O 2 O O 276.42 g/mol “naturallyChrysobalanus occurring” [88] icaco; in Impatiens−(10%5 of spp. seed [89] oil methyl esters) [81]; in evening primrose (Oenothera biennis) oil 12 (9E,11E,13E,15E)-octadeca- parinaric(cis-parinaric acid) C18:4n-3 C H O H 276.42 g/mol (Oenotherasamples from biennis National) oil (3.5 Park × 10 of mol/L)Turvo, [87]Santana; in stripped da Boa VistaBorage region (Borago and officinalis Cacapava) oil 9,11,13,159,11,13,15-tetraenoic-tetraenoic acid acid O 13 transacid-parinaric (β- C18:4n-3 C18H28O2 OO 276.42 g/mol Chrysobalanus“naturally occurring icaco−5 (10%” [88] of; inseed Impatiens oil methyl spp. ester [89]s) [81]; in evening primrose −4 parinaric acid) O −4 acid) H H do Sul region,× respectively) [85]; 30% of Impatiens balsamina seed oil [86]; in × (99,11,13,15E,11E,13E-tetraenoic,15E)-octadeca acid - (1.6 (3.5× 10 mol/L)10 [82]mol/L) −5 [87]; in stripped Borage (Borago officinalis) oil (1.6 10 mol/L) [82] 13 parinaricacid ( βacid)- C18:4n-3 C18H28O2 O O 276.42 g/mol (“Oenotheranaturally biennisoccurring) oil” (3.5[88] ;× in 10 Impatiens mol/L) [87]spp.; [89]in stripped Borage (Borago officinalis) oil Chrysobalanus icaco (10% of seed oil methyl esters) [81]; in evening primrose 9,11,13,15-tetraenoic acid trans-parinaric −4 (9Z,15Z)-octadeca-9,15- parinaric acid) O 3.1(1.6– 5.4%× 10 of mol/L) fatty acids[82] in pulp of mango fruit, 1% of mango peel total fatty acids (9E,11E,13E,15E)-transoctadeca-parinaric- 18 32 2 H −5 1413 (9Z,15Z)-octadeca-9,15- Mangifericacid (β -acid C18:2C18:4n--33 C 18H 28O 2 280.452276.42 g/molg/mol 3.1“(naturallyOenothera–5.4% of occurring fattybiennis acids) oil” [88]in(3.5 pulp; ×in 10 Impatiens of mol/L)mango spp. [87]fruit, ;[89] in 1% stripped of mango Borage peel (totalBorago fatty officinalis acids ) oil dienoic acid O (Mangifera indica L.) [90]; in muscle samples from linseed oil-fed lambs [75] 14 9,11,13,15-tetraenoic acid Mtransangiferic-parinaric acid C18:2n-3 C18H32O2 H O 280.452 g/mol −4 (9Z,15Z)-octadeca-9,15- O 3.1(1.6–5.4% × 10 of mol/L) fatty acids [82] in pulp of mango fruit, 1% of mango peel total fatty acids (9E,11E,13E,15E)-octadeca-(9E,11Edienoic,13E,15E acid)-octadeca acid- parinaric acid) H (Mangifera indica L.) [90]; in muscle samples from linseed oil-fed lambs [75] 1314 Mangifericacid (β- acid C18:4C18:2n-3 C18H2832O2 H O 280.452276.42 g/mol g/mol “naturally occurring” [88]; in Impatiens spp. [89] 13 (9Z,15dienoicZ)-octadeca acid -9,15- C18:4n-3 C18H28O2 O 276.42 g/mol(3.1Mangifera–5.4% “naturally of indica fatty L.)acids occurring” [90] in; inpulp muscle of mango [samples88]; fruit, in fromImpatiens 1% linseedof mango oilspp. -peelfed lambstotal [89 ]fatty [75] acids 9,11,13,15-tetraenoic acid trans-parinaric H O 9,11,13,15-tetraenoic14 acid (β-parinaricMangiferic acid C18:2n-3 C18H32O2 OO 280.452 g/mol (9E,11E,13E,15E)-octadeca- parinaric acid) H 13 (all-E/Zdienoic)-octadeca acid- 11,15- acid (β- C18:4n-3 C18H28O2 276.42 g/mol in(Mangifera“ naturallybeef and indica muttonoccurring L.) tallow [90]” [88]; in—; musclein11 EImpatiens, 15 Esamples; 11 Zspp.(E), from [89]15E (linseedZ); 11Z ,oil 15-Zfed isomers lambs [91][75]; 11E, 15 (all(99,11,13,15Z-E,15/ZZ)-)octadeca-octadeca-tetraenoic-11,15-9,15 acidacid)-- - C18:2n-3 C18H32O2 undefinedH O O O cis-trans isomerism 280.452 g/mol in3.1 beef–5.4% and of muttonfatty acids tallow in pulp—11 Eof, 15mangoE; 11Z fruit,(E), 15 1%E( ofZ); mango 11Z, 15 peelZ isomers total fatty [91] ;acids 11E, 1514 dienoic acid Mparinaricangiferic- acid)acid C18:2n--3 C1818H3232O22 undefined cis-trans isomerism 280.452 g/mol 15Z isomer in muscle samples from linseed oil-fed lambs [75] (all-E/dienoicZ)-octadeca acid- 11,15- O 15(inMangifera Zbeef isomer and indica inmutton muscle L.) tallow [90] samples; in— muscle11 fromE, 15 E sampleslinseed; 11Z(E oil),from 15-fedE (linseedZ lambs); 11Z ,oil[75] 15-fedZ isomers lambs [75][91] ; 11E, 15 (9Z,15Z)-octadeca-9,15- - C18:2n-3 C18H32O2 HundefinedO cis-trans isomerism 280.452 g/mol 3.1–5.4% of fatty acids in pulp of mango fruit, 1% of mango peel total fatty acids 14 (all-E/Zdienoic)-octadeca acid- 11,15- Mangiferic acid C18:2n-3 C18H32O2 280.452 g/mol 15in Zbeef isomer and muttonin muscle tallow samples—11 Efrom, 15E linseed; 11Z(E ),oil 15-fedE(Z lambs); 11Z ,[75] 15Z isomers [91]; 11E, 15 dienoic acid - C18:2n-3 C18H32O2 undefinedO cis-trans isomerism 280.452 g/mol (Mangifera indica L.) [90]; in muscle samples from linseed oil-fed lambs [75] (9Z,15Z)-octadeca-(9Z,15dienoicZ)-octadeca acidMangiferic -9,15- H O 153.1Z– 3.1–5.4%isomer5.4% of in fatty muscle of acids fatty samples in pulp acids from of mango inlinseed pulp fruit, oil of-1%fedmango oflambs mango [75] fruit,peel total 1% fatty of acids mango peel total fatty acids 14 14 (all-E/Z)-octadeca-11,15- MangifericC18:2 acid n-3C18:2n-3 C HC18HO32O2 280.452280.452 g/mol g/mol in beef and mutton tallow—11E, 15E; 11Z(E), 15E(Z); 11Z, 15Z isomers [91]; 11E, 15 dienoic acid - C18:2n-3 18 C1832H32O22 undefinedO cis-trans isomerism 280.452 g/mol (Mangifera indica L.) [90]; in muscle samples from linseed oil-fed lambs [75] 9,15-dienoic acid dienoic acid acid H O 15Z (isomerMangifera in muscle indica samplesL.) from [90 linseed]; in muscle oil-fed lambs samples [75] from linseed oil-fed lambs [75] (all-E/Z)-octadeca-11,15- in beef and mutton tallow—11E, 15E; 11Z(E), 15E(Z); 11Z, 15Z isomers [91]; 11E, 15 - C18:2n-3 C18H32O2 undefinedO cis-trans isomerism 280.452 g/mol dienoic acid 15Z isomer in muscle samples from linseed oil-fed lambs [75] (all-E/Z)-octadeca-11,15- in beef and mutton tallow—11E, 15E; 11Z(E), 15E(Z); 11Z, 15Z isomers [91]; 11E, 15 - C18:2n-3 C18H32O2 undefined cis-trans isomerism 280.452 g/mol dienoic acid 15Z isomer in muscle samples from linseed oil-fed lambs [75]

Nutrients 2018, 10, 1662 7 of 33

Table 1. Cont.

Shorthand Common Molecular No IUPAC Name (Simplified Formula/Structure Molecular Weight Sources [Refs.] Name Formula Formula) POLYUNSATURATED FATTY ACIDS (PUFAs) (all-E/Z)-octadeca- undefined cis-trans in beef and mutton tallow—11E, 15E; 11Z(E), 15E(Z); 11Z, 15Z isomers [91]; 11E, 15Z isomer in muscle 15 Nutrients 2018, 10, x FOR PEER- REVIEW C18:2n-3 C H O 280.452 g/mol 7 of 34 11,15-dienoic acid 18 32 2 isomerism samples from linseed oil-fed lambs [75]

Nutrients 2018, 10, x FOR PEER REVIEW O 7 of 34 Nutrients 2018, 10, x FOR PEER REVIEW H 7 of 34 (12Z,15NutrientsZ)-octadeca- 2018(12Z,,15 10Z,) -xoctadeca FOR PEER-12,15- REVIEW O 7 of 34 Nutrients16 2018, 10, x FOR PEER REVIEW - C18:2n-3 C18H32O2 O 280.452 g/mol in muscle samples from linseed oil-fed lambs [75] 7 of 34 16 dienoic acid - C18:2n-3 C18H32O2 H 280.452 g/mol in muscle samples from linseed oil-fed lambs [75] 12,15-dienoic acid O (12Z,15Z)-octadeca-12,15- H O O 18 32 2 O 16 (12Z,15Z)-octadeca-12,15- - C18:2n-3 C H O H O 280.452 g/mol in muscle samples from linseed oil-fed lambs [75] dienoic acid H 16 (all-E/Z)-octadeca-10,15- - C18:2n-3 C18H32O2 O 280.452 g/mol in muscle samples from linseed oil-fed lambs [75] (12Z,15Z)-octadeca-12,15- 18 32 2 17 dienoic acid - C18:2n-3 C H O undefinedO cis-trans isomerism 280.452 g/mol in beef and mutton tallow—10Z, 15Z; 10Z(E), 15E(Z) isomers [92] (all-E/Z)-octadeca-16 (12Z,15dienoicZ)-octadeca acid -12,15- - C18:2n-3 C18H32O2 undefined cis-trans 280.452 g/mol in muscle samples from linseed oil-fed lambs [75] 16 dienoic acid - C18:2n-3 C18H32O2 280.452 g/mol in muscle samples from linseed oil-fed lambs [75] 17 (all-E/Zdienoic)-octadeca acid- 10,15-- C18:2n-3 C18H32O2 280.452 g/mol in beef and mutton tallow—10Z, 15Z; 10Z(E), 15E(Z) isomers [92] 10,15-dienoic17 acid - C18:2n-3 C18H32O2 undefinedisomerism cis-trans isomerism 280.452 g/mol Iinn beefSterculia and urensmutton seeds tallow (2.96—%10 ofZ, the15Z total; 10Z( lipid)E), 15 [91]E(Z;) inisomers Hibiscus [92] sabdariffa seed oil (all-E/Zdienoic)-octadeca acid- 10,15- 17 - C18:2n-3 C18H32O2 undefined cis-trans isomerism 280.452 g/mol (in0.2 beef% of and total mutton fatty acids) tallow [93]—10; 2.2Z, 215–6Z.59; 10Z( mg/gE), of15 EPlatymonas(Z) isomers subcordiformis [92] dry (all-E/Zdienoic)-octadeca acid- 10,15- 17 (all-E/Z)-octadeca-10,15- - C18:2n-3 C18H32O2 undefined cis-trans isomerism 280.452 g/mol Iinn beefSterculia and urensmutton seeds tallow (2.96—%10 ofZ, the15Z total; 10Z( lipid)E), 15 [91]E(Z;) inisomers Hibiscus [92] sabdariffa seed oil 17 dienoic acid - C18:2n-3 C18H32O2 undefined cis-trans isomerism 280.452 g/mol inweight beefIn andSterculia mutton24 to 42.04 tallow urens mg/g—seeds 10ofZ Porphyridium, 15Z (2.96%; 10Z(E), cruentum 15 ofE( theZ) isomers dry total weight [92] lipid) [94];[ 3.9791]; g/kg in Hibiscus sabdariffa seed oil (0.2% of total fatty dienoic acid I(n0.2 Sterculia% of total urens fatty seeds acids) (2.96 [93]%; 2.2of the2–6 .59total mg/g lipid) of [91]Platymonas; in Hibiscus subcordiformis sabdariffa seeddry oil soybeanIn Sterculiaacids) unit urens [[95]93 ;seeds]; 6.7 2.22–6.598– (2.968.73%% of of total the mg/g total fatty lipid) ofacidsPlatymonas [91]in Torreya; in Hibiscus grandis subcordiformis sabdariffa kernel oilseed [96] oil; dry weight and 24 to 42.04 mg/g of I(weightn0.2 Sterculia% of and total urens 24 fatty to seeds42.04 acids) mg/g(2.96 [93]% of; 2.2of Porphyridium the2–6 .59total mg/g lipid) cruentum of [91]Platymonas; in dry Hibiscus weight subcordiformis sabdariffa [94]; 3.97 seeddry g/kg oil 31.44(0.2%% of of total Pittosporum fatty acids) undulatum [93]; 2.2 seed2–6.59 oil mg/g total offatty Platymonas acids [97] subcordiformis; 8.5% of total dry neutral (weightsoybean0.2%Porphyridium of and totalunit 24 [95]fatty to ;42.04 6.7acids)8 – cruentummg/g8 .73[93]% of; of2.2 Porphyridium total2–6dry.59 fatty mg/g weight acids cruentum of Platymonasin Torreya [94 dry]; weightgrandis 3.97subcordiformis g/kg [94]kernel; 3.97 soybean oildry g/kg [96] ; unit [95]; 6.78–8.73% of total fatty acids in lipidsweight and and 15.5 24 %to of42.04 free mg/g fatty ofacids Porphyridium of cork Phellodendron cruentum dry lavalei weight see ds[94] [98]; 3.97; 0.49 g/kg eicosatrienoic weightsoybean31.44Torreya% andof unit Pittosporum 24 [95] grandisto ;42.04 6.78 undulatum –mg/g8.73kernel% of of Porphyridium total seed oil fatty oil [96 total ];acids cruentum 31.44% fatty in Torreya acids dry of [97] weightgrandisPittosporum; 8.5% [94]kernel of ;total 3.97 oil neutralg/kg undulatum[96] ; seed oil total fatty acids [97]; 8.5% of g/100gsoybean of unit Pinus [95] halepensis; 6.78–8.73 seed% of oil total total fatty fatty acids acids in [99] Torreya; 0.2% grandis of black kernel cumin oil ( Nigella[96]; acid soybean31.44lipids% and of unit Pittosporum15.5 [95]% of; 6.7 free8 undulatum–8 fatty.73% acidsof total seed of fatty corkoil total Phellodendronacids fatty in Torreya acids lavalei [97] grandis; 8.5see% dskernel of [98] total ;oil 0.49 neutral [96] ; (11Z,14Z,17Zeicosatrienoic)-icosa- eicosatrienoic sativa31.44total%) seed of Pittosporum neutraloil fatty acids lipidsundulatum [56]; and0.01 seed–0.1 15.5% oil% fortotal finwhale of fatty free acids oils, fatty [97] <0.01; acids8.5–0.03% of% oftotal for cork sealneutral oilsPhellodendron lavalei seeds [98]; 0.49 g/100g of 18 (ETE)/homo- 20:3n-3 C20H34O2 306.49 g/mol 31.44lipidsg/100g% and ofof Pinus Pittosporum15.5% halepensis of free undulatum fatty seed acids oil seed total of corkoil fatty total Phellodendron acids fatty [99] acids; 0.2 lavalei [97]% of; 8.5blacksee%ds of cumin[98] total; 0.49 neutral(Nigella 11,14,17-trienoic acidacid eicosatrienoic (inlipids weightPinus and per15.5 halepensis cent)% of free[62] ;fatty 3.3seed% acids of Ephedra oil of totalcork gerardiana Phellodendron fatty seed acids lavaleilipids [99 andsee];ds 0.2% 2.2 [98]% of; of0.49 black cumin (Nigella sativa) seed oil fatty alpha-acidlinolenic O g/100g of Pinus halepensis seed oil total fatty acids [99]; 0.2% of black cumin (Nigella (11Z,14Z,17Z)-icosa-(11Z,14Z,17Z)-icosa- eicosatrienoicacid H lipidssativa) and seed 15.5 oil %fatty of freeacids fatty [56] acids; 0.01 –of0.1 cork% for Phellodendron finwhale oils, lavalei <0.01 see–0.03ds [98]% for; 0.49 seal oils 18 eicosatrienoic(ETE)/homo- 20:3n-3 C20H34O2 306.49 g/mol Cimicifugag/100g of Pinus racemosa halepensis seed oil seed [100] oil; 0.15total% fatty and acids0.16% [99] of ISA; 0.2 %Brown of black and cumin Arucana (Nigella hen 18 (11Z,14Z,17Z(ETE)/homo-)-icosa- acid 20:3n-3 C20H34O2 O 306.49 g/mol g/100gsativaacids) seedof Pinus oil [56 fatty halepensis]; 0.01–0.1% acids seed[56]; oil0.01 fortotal–0.1 finwhale %fatty for acids finwhale [99] oils, ;oils, 0.2 <0.01–0.03%% <0.01 of black–0.03 cumin% for seal for(Nigella oils seal oils (in weight per cent) [62]; 3.3% of 18 11,14,17-trienoic acid (ETE)/homo- 20:3n-3 C20H34O2 306.49 g/mol (in weight per cent) [62]; 3.3% of Ephedra gerardiana seed lipids and 2.2% of 11,14,17-trienoic acid(11Z,14Z,17Z)-icosa- alpha-acidlinolenic O eggsativa yolk) seed total oil lipids, fatty acids respectively [56]; 0.01 [101]–0.1;% 0.1, for 0.2, finwhale 0.1, 0.2, oils, 0.2, <0.01 0.2, 0.1–0.03% of% whitefor seal oils 11,14,17(11Z,14Z-trienoic,17Zalpha)-icosa acid- 20 34 2 H sativa(in weightEphedra) seed per oil cent)fatty gerardiana acids[62]; 3.3 [56]%; of0.01 Ephedra–0.1% gerardianafor finwhale seed oils, lipids <0.01 Cimicifugaand–0.03 2.2%% for of seal racemosa oils 18 -linolenicalpha(ETE)-linolenic/homo- 20:3n-3 C H O O 306.49 g/mol cabbage,Cimicifuga kale, racemosa red cabbage, seed oil brussels[100]seed; 0.15 sprouts, lipids% and 0.16cauliflower, and% of 2.2% ISA cabb Brown of age and lettuce, Arucana parsley hen seed oil [100]; 0.15% and 0.16% of ISA 18 11,14,17-trienoic acid (ETE)acid/homo - 20:3n-3 C20H34O2 H O 306.49 g/mol (in weight per cent) [62]; 3.3% of Ephedra gerardiana seed lipids and 2.2% of 11,14,17-trienoic acid alpha-linolenic O (inCimicifugaegg weight yolk total racemosaper lipids,cent) seed [62] respectively; oil3.3 [100]% of ;Ephedra [101]0.15%; 0.1,and gerardiana 0.2, 0.16 0.1,% of seed0.2, ISA 0.2, lipids Brown 0.2, and 0.1 and% 2.2 of Arucana% white of hen acid alpha-acidlinolenic H O O fattyCimicifugaBrown acid mass; racemosa and 0.1, seed0.1, Arucana 0.1, oil [100]0.2, 0.1, hen; 0.15 0.2,% egg traces, and yolk0.16 0.1,% 0.1totalof %ISA of lipids,Brown Chinese and respectivelycabbage, Arucana white hen [101]; 0.1, 0.2, 0.1, 0.2, 0.2, 0.2, 0.1% of white H egg yolk total lipids, respectively [101]; 0.1, 0.2, 0.1, 0.2, 0.2, 0.2, 0.1% of white acid O Cimicifugacabbage, kale, racemosa red cabbage, seed oil [100]brussels; 0.15 sprouts,% and 0.16cauliflower,% of ISA cabbBrownage and lettuce, Arucana parsley hen acid O cabbage,egg cabbage,yolk savoy,total lipids, kale, kale, respectivelyred red cabbage, cabbage, [101] brussels; 0.1, brussels sprouts,0.2, 0.1, 0.2,cauliflower, sprouts, 0.2, 0.2, 0.1 kohlrabi, cauliflower,% of white swede cabbage lettuce, parsley fatty acid mass; 0.1, eggcabbage,fatty yolk acid totalkale, mass; lipids,red 0.1, cabbage, 0.1, respectively 0.1, brussels0.2, 0.1, [101] 0.2,sprouts,; 0.1,traces, 0.2, cauliflower, 0.1, 0.1, 0.1 0.2,% 0.2, of cabb Chinese 0.2,age 0.1 lettuce,% cabbage, of white parsley white seedcabbage, fatty kale, acid redmass cabbage, [53]—systematic brussels sprouts, names werecauliflower, placed incabb theage line lettuce, ‘α-linolenic parsley cabbage,fatty0.1, acid kale,savoy, 0.1,mass; red 0.2, 0.1,kale, cabbage, 0.1, 0.1, red 0.1, cabbage, 0.2, brussels0.2, traces,0.1, brussels 0.2,sprouts, traces, 0.1, sprouts, cauliflower, 0.1%0.1, 0.1 cauliflower,% of of cabb Chinese Chineseage kohlrabi, lettuce, cabbage, cabbage, parsleyswede white white cabbage, savoy, kale, red cabbage, acidfatty’ acid mass; 0.1, 0.1, 0.1, 0.2, 0.1, 0.2, traces, 0.1, 0.1% of Chinese cabbage, white fattycabbage,seedbrussels fattyacid savoy, mass;acid mass 0.1, sprouts,kale, 0.1, [53] red 0.1,— cabbage,systematic 0.2, cauliflower, 0.1, brussels 0.2, names traces, sprouts, were kohlrabi, 0.1, placed0.1 cauliflower,% of in swedeChinese the line kohlrabi, cabbage, seed‘α-linolenic swede fatty white acid mass [53]—systematic names were incabbage, salted productssavoy, kale, of fish red roe:cabbage, 2.1% brusselsof Ikura sprouts,(salmon), cauliflower, 0.6% of Tarako kohlrabi, (pollock), swede 0.5 % cabbage,seedacid’ fatty savoy, acid mass kale, [53] red— cabbage,systematic brussels names sprouts, were placed cauliflower, in the line kohlrabi, ‘α-linolenic swede ofseed Tobikoplaced fatty (flyingfish),acid in mass the [53] 0.4 line—%systematic of ‘α Kazunoko-linolenic names (herring) acid’were placedtotal lipids in the [59] line; 2.9 ‘α–-3.8linolenic% of seedacidin salted’ fatty products acid mass of [53]fish— roe:systematic 2.1% of Ikuranames (salmon), were placed 0.6% in of the Tarako line ‘ α(pollock),-linolenic 0.5 % salmonacid’ eggs total triacylglicerol fraction [48]; as methyl 8,11,14,17- O acidin salted’in salted products products of fish roe: 2.1 of% fish of Ikura roe: (salmon), 2.1% of 0.6 Ikura% of Tarako (salmon), (pollock), 0.6% 0.5% of Tarako (pollock), 0.5% of Tobiko H eicosatetraenoate:of Tobiko (flyingfish), 0.19 –0.40.24% %of ofKazunoko common (herring) barbel oil, total 0.82 lipids–1.44 %[59] of; P2.9ontic–3.8 shad% of oil, ofin Tobikosalted products (flyingfish), of fish 0.4 %roe: of 2.1Kazunoko% of Ikura (herring) (salmon), total 0.6 lipids% of Tarako[59]; 2.9 (pollock),–3.8% of 0.5% O insalmon salted eggs products total triacylglicerolof fish roe: 2.1 fraction% of Ikura [48] (salmon),; as methyl 0.6 8,11,14,17% of Tarako- (pollock), 0.5% O 0.34of Tobiko–(flyingfish),1% of (flyingfish), European 0.4%wels 0.4% catfish of of Kazunoko Kazunoko oil, 0.17 (herring)–0.35% (herring) of total common lipids total bleak [59]; lipidsoil2.9 –[52]3.8;% 0.35[ of59 –]; 2.9–3.8% of salmon eggs total triacylglicerol (8Z,11Z,14Z,17Z)-icosa- eicosatetraenoic H ofsalmon Tobiko eggs (flyingfish), total triacylglicerol 0.4% of Kazunoko fraction [48](herring); as methyl total lipids8,11,14,17 [59]-; 2.9–3.8% of 19 C20:4n-3 C20H32O2 O 304.474 g/mol 0.78eicosatetraenoate:% for finwhale 0.19 oils,– 0.240.07%–0.26 of commo% for sealn barbel oils (in oil, weight 0.82– 1.44per %cent) of P [62]ontic; 0.4 shad–0.8 oil,% of H salmonfraction eggs total [48 triacylglicerol]; as methyl fraction 8,11,14,17-eicosatetraenoate: [48]; as methyl 8,11,14,17- 0.19–0.24% of common barbel oil, 0.82–1.44% of 8,11,14,17-tetraenoic acid acid (ETA) O O salmoneicosatetraenoate:0.34–1% eggs of European total triacylglicerol0.19 wels–0.24 catfish% of fractioncommo oil, 0.17n [48] –barbel0.35; as% methyl oil,of common 0.82 8,11,14,17–1.44 bleak% of- Poilontic [52] shad; 0.35 oil,– H O Epinephelus retouti muscle triacylglycerols [64]; 0.06% of Agathis robusta seed lipids (8Z,11Z,14Z,17Z)-icosa- eicosatetraenoic O 0.34eicosatetraenoate:–Pontic1% of European shad 0.19 oil,wels–0.24 0.34–1%catfish% of commo oil, 0.17 ofn European–barbel0.35% oil,of common 0.82 wels–1.44 bleak% catfish of Poilontic [52] oil, shad; 0.35 0.17–0.35% oil,– of common bleak oil [52]; 0.35–0.78% 19 C20:4n-3 C20H32O2 H 304.474 g/mol eicosatetraenoate:0.78% for finwhale 0.19 oils,– 0.240.07%–0.26 of commo% for sealn barbel oils (in oil, weight 0.82–1.44 per% cent) of P [62]ontic; 0.4 shad–0.8 oil,% of (8Z,11Z,14Z,17Z)-icosa-(8Z,11Z,14Z,17eicosatetraenoicZ)-icosa- eicosatetraenoic O [67]0.34;– in1% lipids of European of bovine wels liver catfish [102] ;oil, in herring0.17–0.35 (Clupea% of common harrengus bleak), mackerel oil [52] (; Scomber0.35– 19 8,11,14,17-tetraenoic acid acid (ETA) C20:4n-3 C20H32O2 O 304.474 g/mol 0.78% for finwhale oils, 0.07–0.26% for seal oils (in weight per cent) [62]; 0.4–0.8% of 19 8,11,14,17(8Z,11Z,14-tetraenoicZ,17Z)-icosa acid- eicosatetraenoicacid (ETA)C20:4 n-3 C20H32O2 304.474 g/mol 0.34Epinephelus–for1% of finwhale Europeanretouti muscle wels oils, triacylglycerolscatfish 0.07–0.26% oil, 0.17– [64]0.35 for; %0.06 sealof% common of oils Agathis (inbleak robusta weight oil [52] seed; 0.35 per lipids– cent) [62]; 0.4–0.8% of Epinephelus retouti 8,11,14,17-tetraenoic19 (8 acidZ,11Z,14Z,17Zacid)-icosa (ETA)- eicosatetraenoic C20:4n-3 C20H32O2 304.474 g/mol scombus0.78% for) and finwhale capelin oils, (Mallotus 0.07–0.26 villosus% for) sealbody oils oils (in in weight amounts per of cent) 5, 15 [62] and; 0.44 mg/g–0.8% of of 19 8,11,14,17-tetraenoic acid acid (ETA) C20:4n-3 C20H32O2 304.474 g/mol 0.78Epinephelus[67];% in for lipids finwhale retouti of bovine muscle oils, liver0.07 triacylglycerols– [102]0.26%; infor herring seal [64] oils (;Clupea 0.06(in weight% harrengusof Agathis per cent)), robustamackerel [62]; 0.4seed (Scomber–0.8 lipids% of 8,11,14,17-tetraenoic acid acid (ETA) fattyEpinephelusmuscle acids, respectively,retouti triacylglycerols muscle in triacylglycerols menhaden [ 64(Brevoortia]; [64] 0.06%; 0.06 spp.)% of of oil Agathis and Indian robusta robusta oil sardineseed lipids seed lipids [67]; in lipids of bovine liver [102]; Epinephelus[67]scombus; in lipids) and retouti capelinof bovine muscle (Mallotus liver triacylglycerols [102] villosus; in herring) body [64] oils(;Clupea 0.06 in% amounts harrengusof Agathis of), 5, robustamackerel 15 and seed4 ( mg/gScomber lipids of ([67]Sardinella;in in lipids herring longiceps of bovine ()—Clupea19 liver and [102]6 harrengus mg/g; in o herringf fatty), ac mackerel(Clupeaids, respectively harrengus (Scomber), [103] mackerel scombus (Scomber) and capelin (Mallotus villosus) body oils in [67]scombusfatty; inacids, lipids) and respectively, capelinof bovine (Mallotus liver in menhaden [102] villosus; in herring )( bodyBrevoortia oils(Clupea inspp.) amounts harrengus oil and of ),Indian 5, mackerel 15 and oil sardine4 ( mg/gScomber of 8.9scombus weight) and % ofcapelin Biota orientalis(Mallotus seed villosus oil )[104] body; 0.12oils –in0.57 amounts% of Sargassum of 5, 15 and spp. 4 total mg/g fatty of scombusfatty(Sardinellaamounts acids,) and longiceps respectively, capelin of)— 5,(Mallotus1915 inand menhaden and 6 villosusmg/g 4mg/g o )f( bodyBrevoortiafatty acoils ofids, fatty inspp.) respectivelyamounts oil acids, and of Indian 5,[103] respectively, 15 and oil sardine4 mg/g of in menhaden (Brevoortia spp.) oil and Indian acidsfatty acids,[105]; respectively,1% of Caltha palustrisin menhaden seed oil(Brevoortia [106]; in spp.)many oil conifer and Indian species, oil most sardine in (5Z,11Z,14Z,17Z)-icosa- juniperonic fatty(8.9Sardinella weightoil acids, sardine longiceps %respectively, of Biota) (—Sardinella orientalis19 inand menhaden 6 seedmg/g longiceps oil o f([104] Brevoortiafatty; ac0.12)—19ids, –spp.)0.57 respectively% and oil of and Sargassum 6 Indian mg/g [103] oilspp. of sardine total fatty fatty acids, respectively [103] 20 C20:4n-3 C20H32O2 304.474 g/mol Gnetum(Sardinella gnemon longiceps, Chaemaecyparis)—19 and 6 mg/g thyoides of ,fatty Cephalotaxus acids, respectively sinensis, Taxus [103] cuspidata , 5,11,14,17-tetraenoic acid acid (8.9Sardinella weight longiceps% of Biota)— orientalis19 and 6 seedmg/g oil o f[104] fatty; ac0.12ids,–0.57 respectively% of Sargassum [103] spp. total fatty O Pseudolarixacids [105]; amabilis1% of Caltha, Araucaria palustris angustifolia seed oil, [106]Agathis; in australismany conifer, Zamia species, furfuracea most—12.9, in (5Z,11Z,14Z,17Z)-icosa- juniperonic H acids8.9 weight [105] ;% 1% of of Biota Caltha orientalis palustris seed seed oil oil[104] [106]; 0.12; in– many0.57% coniferof Sargassum species, spp. most total in fatty 20 C20:4n-3 C20H32O2 304.474 g/mol 8.9Gnetum weight8.9 gnemon weight % of ,Biota Chaemaecyparis % orientalis of Biota seed thyoides orientalis oil [104], Cephalotaxus; 0.12seed–0.57 oil sinensis% of [104 Sargassum, Taxus]; 0.12–0.57% cuspidata spp. total, fatty of Sargassum spp. total fatty acids [105]; 1% of (5Z,11Z,14Z,17Z)-icosa- juniperonic O 7.7, 6.8, 6.8, 6.3, 6.3, 6.1, 6, % of leaf fatty acids, respectively [54,77] 20 5,11,14,17-tetraenoic acid acid C20:4n-3 C20H32O2 304.474 g/mol Gnetumacids [105] gnemon; 1% ,of Chaemaecyparis Caltha palustris thyoides seed oil, Cephalotaxus [106]; in many sinensis conifer, Taxus species, cuspidata most, in (5Z,11Z,14Z,17Z)-icosa-(5Z,11Z,14Z,17Zjuniperonic)-icosa- juniperonic O acidsPseudolarixCaltha [105]; amabilis1% palustris of Caltha, Araucaria palustrisseed angustifolia oil seed [106 oil ,[106] ];Agathis in; in many australismany conifer conifer, Zamia species, furfuracea species, most—12.9, in most in Gnetum gnemon, Chaemaecyparis thyoides, 5,11,14,17(5Z,11Z,14-tetraenoicZ,17Z)-icosa acid- juniperonicacid 20 32 2 H 13% of Undaria pinnatifida essential oil composition [107]; 3.05 g/100 g (as methyl 20 20 C20:4n-3C20:4n-3 C HC HOO O 304.474304.474 g/mol PseudolarixGnetum gnemon amabilis, Chaemaecyparis, Araucaria angustifolia thyoides, ,Cephalotaxus Agathis australis sinensis, Zamia, Taxus furfuracea cuspidata—12.9,, 20 5,11,14,17-tetraenoic acid acid C20:4n-3 20 C2032H32O22 H O 304.474 g/mol Gnetum7.7, 6.8, 6.gnemon8, 6.3,, 6.3,Chaemaecyparis 6.1, 6, % of leaf thyoides fatty, Cephalotaxusacids, respectively sinensis [54,77], Taxus cuspidata, 5,11,14,17-tetraenoic5,11,14,17 acid -tetraenoic acidacid acid O ester:PseudolarixCephalotaxus 3.15% amabilis of fatty, acids)Araucaria sinensis muscle angustifolia, Taxustissue of, cuspidataAgathis Labeo rohita australis,, 2.51Pseudolarix, Zamia g/100 furfuraceag (as methyl amabilis—12.9, ester: , Araucaria angustifolia, Agathis australis, H O O Pseudolarix7.7, 6.8, 6.8, amabilis 6.3, 6.3,, 6.1,Araucaria 6, % of angustifolia leaf fatty acids,, Agathis respectively australis, Zamia [54,77] furfuracea —12.9, H 2.5113%% of of Undaria fatty acids) pinnatifida muscle essential tissue of oil Cirrhinus composition mrigata [107], 3.15; 3.05 g/ 100g/100 g (as g (as methyl methyl ester: O 137.7,% 6.8, Zamiaof Undaria 6.8, 6.3, furfuracea pinnatifida6.3, 6.1, 6, —12.9,essential% of leaf oilfatty 7.7, composition acids, 6.8, respectively 6.8, [107] 6.3,; 3.05 6.3, [54,77] g/ 6.1,100 g 6,(as% methyl of leaf fatty acids, respectively [54,77] O 7.7,ester: 6.8, 3.15 6.8,% 6.3,of fatty 6.3, 6.1,acids) 6, %muscle of leaf tissue fatty acids,of Labeo respectively rohita, 2.51 [54,77] g/100 g (as methyl ester: 3.0513%% of of Undaria fatty acids) pinnatifida muscle essential tissue of oil Catla composition catla [58] ;[107] in salted; 3.05 pr g/oducts100 g (as of methylfish roe: 13ester:2.51%% of 3.15of Undaria fatty% of acids) fattypinnatifida acids) muscle essentialmuscle tissue tissueof oil Cirrhinus composition of Labeo mrigata rohita [107],, 3.152.51; 3.05 gg// 100100g/100 gg (as(asg (as methylmethyl methyl ester:ester: 13.6ester:%13% 3.15of Ikura% of ofUndaria (salmon),fatty acids) 18.8pinnatifida muscle% of Tarakotissue essentialof (pollock), Labeo rohita 7% oil, of2.51 compositionTobiko g/100 (flyingfish), g (as methyl [107 15 ester:%]; 3.05 g/100 g (as methyl ester: 3.15% of fatty ester:2.513.05% 3.15of fatty% of acids) fatty acids) muscle muscle tissue tissueof CirrhinusCatla of catlaLabeo mrigata [58] rohita; in,, salted3.152.51 gg/ /pr100100oducts gg (as(as methylofmethyl fish roe: ester:ester: eicosapentaeno of2.51 Kazunoko%acids) of fatty muscle(herring) acids) muscle total tissue lipidstissue of [59]ofLabeo Cirrhinus; 8.7–10.6 rohita mrigata% of, salmon 2.51, 3.15 g/100 geggs/100 total g g(as (asphospholipid methyl methyl ester: ester: 2.51% of fatty acids) muscle tissue of 2.513.0513.6% of fattyIkura acids) (salmon), muscle 18.8 tissue% of Tarakoof CirrhinusCatla (pollock), catla mrigata [58] ;7 in%, salted3.15of Tobiko g/ pr100oducts (flyingfish),g (as methylof fish 15 roe:ester:% (5Z,8Z,11Z,14Z,17Z)-icosa- ic acid fraction,3.05% of 8.3fatty–10.3 acids)% of muscle salmon tissue eggs oftot Catlaal triacylglicerol catla [58]; in fraction salted pr [60]oducts; 13.6 of% fishof wild roe: 21 eicosapentaeno C20:5n-3 C20H30O2 302.458 g/mol 3.0513.6of Kazunoko%Cirrhinus of fattyIkura (herring) acids) (salmon), mrigata muscle total 18.8, lipidstissue 3.15% of Tarako[59]of g/100 Catla; 8.7 (pollock), –catla10.6 g (as %[58] of ; methyl7 salmonin% saltedof Tobiko eggs pr ester:oducts total(flyingfish), 3.05%phospholipidof fish 15roe: of% fatty acids) muscle tissue of Catla catla [58]; 5,8,11,14,17-pentaenoic acid (EPA)/timnodo sardine13.6% of ( SardinaIkura (salmon), pilchardus 18.8) muscle% of Tarako total fatty (pollock), acids (9.2 7%% of of Tobiko captive (flyingfish), sardine muscle 15% (5Z,8Z,11Z,14Z,17Z)-icosa- eicosapentaenoic acid 13.6offraction, Kazunoko%in of salted 8.3Ikura– 10.3(herring) (salmon), products% of salmon total 18.8 lipids of% eggs of fish Tarako[59] tot roe:al; 8.7 triacylglicerol (pollock),–10.6 13.6%% of 7 ofsalmon% fraction Ikuraof Tobiko eggs [60] (salmon), total(flyingfish),; 13.6 phospholipid% of 18.8%wild 15% of Tarako (pollock), 7% of Tobiko (flyingfish), 21 eicosapentaenonic acid C20:5n-3 C20H30O2 O 302.458 g/mol totalof Kazunoko fatty acids), (herring) 6.5% oftotal wild lipids/7.2% [59] of ;captive 8.7–10.6 sardine% of salmon liver total eggs fatty total acids phospholipid [61]; as (5Z,8Z,11Z,14Zeicosapentaenoic,17Z)-icosa- eicosapentaenoic acid offraction, Kazunoko 8.3– 10.3(herring)% of salmon total lipids eggs [59] total; 8.7 triacylglicerol–10.6% of salmon fraction eggs [60] total; 13.6 phospholipid% of wild 21 5,8,11,14,17-pentaenoic acid (EPA)/timnodo C20:5n-3 C20H30O2 H 302.458 g/mol methylsardine ester:(Sardina 2.32 pilchardus–3.41% of) musclecommon total barbel fatty oil, acids 2.57 (9.2–3.8%% of of captive Pontic shadsardine oil, muscle 2.41– 5,8,11,14,17(5Z,8Z,11Z-,14pentaenoicZ,17Z)-icosa acid- (EPA)ic/ timnodoacid sardinefraction,15% ( Sardina8.3 of–10.3 Kazunoko pilchardus% of salmon) muscle (herring)eggs tottotalal triacylglicerolfatty total acids lipids (9.2 fraction% of [59 captive]; [60] 8.7–10.6%; sardine13.6% of muscle wild of salmon eggs total phospholipid fraction, (5Z,8Z,11Z,1421Z ,17Z(5)-icosa-Z,8Z,11Z,14Z,17Z)-icosaacid- nicic acid acid C20:5n-3 C20H30O2 O 302.458 g/mol fraction,total fatty 8.3 acids),–10.3 %6.5 of% salmon of wild eggs/7.2% tot ofal captive triacylglicerol sardine fractionliver total [60] fatty; 13.6 acids% of [61] wild; as 21 21 5,8,11,14,17-pentaenoic acid (EPA)/timnodoC20:5n-3C20:5n-3 C HC20HO30O2 O 302.458302.458 g/mol 6.1sardine%8.3–10.3% of European(Sardina pilchardus wels of salmon catfish) muscle oil, eggs 0.51 total–1.36 totalfatty% acidsof triacylglicerol common (9.2% ofbleak captive oil [52] fractionsardine; 1.82 –muscle3.72 [60%]; 13.6% of wild sardine (Sardina pilchardus) 5,8,11,14,17-pentaenoic acid (EPA)nic/timnodo acid 20 30 2 H O sardinetotalmethyl fatty ester:(Sardina acids), 2.32 pilchardus 6.5–3.41% of% ofwild) musclecomm/7.2%on total of barbel captive fatty oil, acids sardine 2.57 (9.2–3.8 liver%% of of totalcaptive Pontic fatty shadsardine acids oil, [61]muscle 2.41; as– 5,8,11,14,17-pentaenoic acid (EPA)/timnodonicnic acid H fortotal finwhale fatty acids), oils, 6.376.5%– 8.12of wild% for/7.2 seal% of oils captive (in weight sardine per liver cent) total [62] fatty; 1.8– acids3.5% of[61] ; as nic acid O totalmethylmuscle fatty ester: acids), 2.32 total 6.5–3.41%fatty of% ofwild comm acids/7.2%on of (9.2%barbel captive oil, of sardine 2.57 captive–3.8 liver% of sardinetotal Pontic fatty shad acids muscle oil, [61] 2.41; totalas– fatty acids), 6.5% of wild/7.2% of captive H O O Variola6.1% of louti European muscle wels triacylglycerols catfish oil, 0.51 [64]–;1.36 2%% of of Rhododendron common bleak sochadzeae oil [52] ;leaves 1.82–3.72 fatty% acid H 6.1methyl% of ester:European 2.32 –wels3.41% catfish of comm oil, on0.51 barbel–1.36% oil, of 2.57 common–3.8% bleakof Pontic oil [52] shad; 1.82 oil,– 2.413.72–% O methylfor finwhalesardine ester: oils, 2.32 liver –6.373.41– total%8.12 of% comm for fatty sealon acidsoilsbarbel (in oil,weight [61 2.57]; as–per3.8 methyl %cent) of P [62]ontic;ester: 1.8 shad–3.5 oil,% 2.32–3.41% of 2.41 – of common barbel oil, 2.57–3.8% of O acids6.1% of(in European hexan extract) wels catfish[108] oil, 0.51–1.36% of common bleak oil [52]; 1.82–3.72% O 6.1forVariola% finwhale of loutiEuropean muscle oils, 6.37 wels triacylglycerols–8.12 catfish% for oil, seal 0.51 [64] oils–1.36; 2(in%% ofweight of Rhododendron common per cent) bleak sochadzeae[62] oil; 1.8[52]–3.5; leaves1.82% of–3.72 fatty% for finwhalePontic oils, shad 6.37 oil,–8.12 2.41–6.1%% for seal oils of(in Europeanweight per cent) wels [62];catfish 1.8–3.5% oil,of 0.51–1.36% of common bleak oil [52]; forVariolaacids finwhale (in louti hexan muscle oils, extract) 6.37 triacylglycerols–8.12 [108]% for seal [64] oils; 2(in% ofweight Rhododendron per cent) sochadzeae[62]; 1.8–3.5 leaves% of fatty Variola louti muscle triacylglycerols [64]; 2% of Rhododendron sochadzeae leaves fatty Variolaacids1.82–3.72% (in louti hexan muscle extract) triacylglycerols for [108] finwhale [64] oils,; 2% 6.37–8.12%of Rhododendron forsochadzeae seal oilsleaves (in fatty weight per cent) [62]; 1.8–3.5% of Variola louti acids (in hexan extract) [108] acidsmuscle (in hexan triacylglycerolsextract) [108] [64]; 2% of Rhododendron sochadzeae leaves fatty acids (in hexan extract) [108]

Nutrients 2018, 10, 1662 8 of 33

Table 1. Cont.

Shorthand Molecular No IUPAC Name Common Name (Simplified Formula/Structure Molecular Weight Sources [Refs.] Formula Formula) Nutrients 2018, 10, x FOR PEER REVIEW 8 of 34 Nutrients 2018, 10, x FOR PEER REVIEW POLYUNSATURATED FATTY ACIDS (PUFAs) 8 of 34 Nutrients 2018, 10, x FOR PEER REVIEW as methylas methyl 6,9,12,15,18 6,9,12,15,18-heneicosapentaenoate:-heneicosapentaenoate: 0.06–0.12% of common 0.06–0.12% barbel oil,8 of of34 common barbel oil, 0.07–0.08% of 0.07as methyl–0.08% 6,9,12,15,18 of Pontic shad-heneicosapentaenoate: oil, 0.09% of European 0.06 wels–0.12 catfish% of common oil [52] ;barbel 0.2–0.4 oil,% of O 0.07–Pontic0.08% of shadPontic shad oil, 0.09%oil, 0.09% of of EuropeanEuropean wels wels catfish catfish oil [52]; oil0.2–0.4 [52%]; of 0.2–0.4% of diatom Skeletonema costatum Nutrients 2018, 10, x FOR PEER REVIEW H diatom Skeletonema costatum total fatty acids, 0.1–0.2% of copepods Calanus and8 of 34 O as methyl 6,9,12,15,18-heneicosapentaenoate: 0.06–0.12% of common barbel oil, Nutrients 2018, 10, x FOR PEER REVIEW H diatomtotal Skeletonema fatty acids, costatum 0.1–0.2% total fatty acids, of copepods 0.1–0.2% of copepodsCalanus Calanusand Centropages and8 of 34 sp. total fatty acids, <0.1% of O Centropages sp. total fatty acids, <0.1% of copepods Temora longicornia total fatty (6Z,9Z,12Z,15Z,18Z)- heneicosapenta 0.07Centropages–0.08% ofsp. P ontictotal fattyshad acids, oil, 0.09 <0.1% %of ofEuropean copepods wels Temora catfish longicornia oil [52]; total0.2–0.4 fatty% of (6Z,9Z,12Z,15Z,18Z)-henicosa-(6Z,9Z,12heneicosapentaenoicZ,15Z,18Z)- heneicosapenta O O acids,copepods 0.2–0.7% of euphausidTemora longicornia Meganyctiphanestotal norvegica fatty total acids, fatty acids, 0.2–0.7% 0.1–1.1% of of euphausid Meganyctiphanes norvegica 22 henicosa-6,9,12,15,18- enoic acid C21:5n-3 C21H32O2 H 316.485 g/mol asdiatom methyl Skeletonema 6,9,12,15,18 costatum-heneicosapentaenoate: total fatty acids, 0.10.06–0.2–0.12% of% ofcopepods common Calanus barbel andoil, 22 C21:5n-3 C21H32O2 316.485 g/mol euphausidacids, 0.2–0.7 Euphausia% of euphausid sp. total Meganyctiphanes fatty acids, 0.1–0.3 norvegica% of herring total fatty oil Clupea acids, harengus 0.1–1.1% of 6,9,12,15,18-pentaenoic22 acidhenicosapentaenoic-6,9,12,15,18acid acid (HPA)- enoic(HPA) acid C21:5n-3 C21H32O2 316.485 g/mol 0.07Centropagesas –methyltotal0.08% fattyof6,9,12,15,18sp. P ontictotal acids, fattyshad-heneicosapentaenoate: acids, oil, 0.1–1.1% 0.09 <0.1% %of ofEuropean of copepods euphausid 0.06 wels –Temora0.12 catfish% oflongicorniaEuphausia common oil [52]; total0.2 barbel–sp.0.4 fatty% oil, total of fatty acids, 0.1–0.3% of herring oil (6Z,9Z,12Z,15Z,18Z)- heneicosapenta O O totaleuphausid fatty acids, Euphausia 0.19% sp. of totalsturgeon fatty oilacids, Acipenser 0.1–0.3 oxyrhynchus% of herring total oil Clupea fatty acids, harengus 0.2– pentaenoic acid (HPA) H diatom0.07–0 .08Skeletonema% of Pontic costatum shad oil, total 0.09 fatty% of acids, European 0.1–0.2 wels% of catfish copepods oil [52] Calanus; 0.2– 0.4and% of O acids,Clupea 0.2–0.7% harengus of euphausidtotal Meganyctiphanes fatty acids, norvegica 0.19% total of fatty sturgeon acids, 0.1 oil–1.1Acipenser% of oxyrhynchus total fatty acids, 22 henicosa-6,9,12,15,18- enoic acid C21:5n-3 C21H32O2 316.485 g/mol total fatty acids, 0.19% of sturgeon oil Acipenser oxyrhynchus total fatty acids, 0.2– H Centropages0.6diatom% of mackerel Skeletonema sp. total oil fattyScombercostatum acids, scrombrus total <0.1 fatty% of total acids, copepods fatty 0.1 –acids,0.2 Temora% of0.1 copepodslongicornia–0.9% of fin Calanus total whale fatty and O euphausid0.6% of mackerel Euphausia oil Scomber sp. total scrombrus fatty acids, total 0.1 –fatty0.3% acids, of herring 0.1–0.9 oil% Clupea of fin whaleharengus (6Zpentaenoic,9Z,12Z,15Z acid,18Z )- heneicosapenta(HPA) (Balaenopterus0.2–0.6% physalus of mackerel) blubber total oil fattyScomber acids, 0.2 scrombrus% of dolphintotal (Tursiops fatty truncatus acids,) 0.1–0.9% of fin whale (Balaenopterus O acids,totalCentropages fatty 0.2– 0.7acids, %sp. of total0.19 euphausid% fatty of sturgeon acids, Meganyctiphanes <0.1 oil% Acipenser of copepods norvegica oxyrhynchus Temora total longicornia totalfatty fattyacids, acids,total 0.1– fatty1.1 0.2%– of 22 henicosa(6Z,9Z,12-6,9,12,15,18Z,15Z,18Z-)- heneicosapentaenoic acid C21:5n-3 C21H32O2 316.485 g/mol milk(Balaenopterusphysalus total fatty physalus acids [109]) blubber total fatty acids, 0.2% of dolphin (Tursiops Tursiopstruncatus) truncatus euphausid0.6acids,% of 0.2mackerel– Euphausia0.7%) of blubberoil euphausid Scomber sp. total totalscrombrus fattyMeganyctiphanes acids, fatty total 0.1 acids, –fatty0.3 norvegica% acids, of 0.2% herring 0.1 total of–0.9 oilfatty dolphin% Clupea of acids, fin whaleharengus 0.1 ( – 1.1 % of ) milk total fatty acids [109] 22 henicosapentaenoic-6,9,12,15,18 acid - enoic(HPA) acid C21:5n-3 C21H32O2 316.485 g/mol milk total fatty acids [109] totalineuphausid Lepidium fatty acids, sativiumEuphausia 0.19 %seed sp.of sturgeon oiltotal (47 fatty.66 %oil acids, of Acipenser total 0.1 fatty–0.3 oxyrhynchus %acids) of herring [110] total; traceoil fattyClupea amount acids, harengus in0.2 weed– pentaenoic acid (HPA) (inBalaenopterus Lepidiumin Lepidium sativium physalus sativiumseed) blubber oil (47 .66totalseed% fattyof oiltotal acids, (47.66% fatty 0.2 acids)% of of [110]dolphin total; trace (Tursiops fatty amount acids) truncatus in weed [110) ]; trace amount in weed seed oil, 0.6seedtotal% ofoil, fatty mackerel largely acids, charlock oil0.19 Scomber% of [111] sturgeon scrombrus; in salami oil totalAcipenser-type fatty sausage oxyrhynchusacids, made 0.1–0.9 oftotal% Baltic of fatty fin herring whale acids, fillets,0.2– milkseed totaoil, largelyl fatty acids charlock [109] [111] ; in salami-type sausage made of Baltic herring fillets, (porkBalaenopterus0.6%largely and of mackerel lard physalus(from charlock oil < Scomber)0.2 blubber to [ 1110.3 scrombrus% total]; during in fatty salami-type total ripening) acids, fatty 0.2 acids,[112]% of ; sausagedolphin 0.1in shade–0.9% ( Tursiops driedof made fin neemwhale truncatus of Baltic) herring fillets, pork and lard (13Z,16Z,19Z)-docosa- docosatrienoic inpork Lepidium and lard sativium (from seed< 0.2 oilto 0.3(47%.66 during% of total ripening) fatty acids) [112] ;[110] in shade; trace dried amount neem in weed 23 C22:3n-3 C22H38O2 334.544 g/mol (Azadirachta indica) flower powder present to an extent of 5.7% in the total lipid (13Z,16Z,19Z)-docosa- (1313,16,19Z,16Z-,19trienoicdocosatrienoicZ)-docosa acid - docosatrienoicacid (DTrE) milkseed(Balaenopterus(from totaoil, largelyl fatty < acids 0.2physalus charlock to [109]) 0.3% blubber[111] ; duringin total salami fatty- ripening)type acids, sausage 0.2% made [of112 dolphin ];of inBaltic ( shadeTursiops herring truncatus dried fillets, neem) (Azadirachta indica) flower 23 C22:3n-3 C22H38O2 O 334.544 g/mol (Azadirachta indica) flower powder present to an extent of 5.7% in the total lipid 23 C22:3n-3 C22H38O2 H 334.544 g/mol [113]; in eggs (2.92–3.23%), embryos (3.28–3.76%) and larvae (0–3.65%) of 13,16,19-trienoic acid acid (DTrE) O inmilk Lepidium total fattysativium acids seed [109] oil (47.66% of total fatty acids) [110]; trace amount in weed 13,16,19-trienoic acid acid (DTrE) O porkpowder and lard (from present < 0.2 to to 0.3 an% during extent ripening) of 5.7% [112] in; in the shade total dried lipid neem [113]; in eggs (2.92–3.23%), embryos (13Z,16Z,19Z)-docosa- docosatrienoic H Oncorhynchus[113]; in eggs (2.92mykiss–3.23 (from%), 0embryos to 3.76% (3.28 of total–3.76 fatty%) and acids) larvae [114] (0; –in3.65 muscle%) of tissue and 23 C22:3n-3 C22H38O2 O 334.544 g/mol seed(Azadirachtain Lepidium oil, largely indicasativium charlock) flower seed [111] powderoil (47; in.66 salami present% of -totaltype to an fattysausage extent acids) made of [110]5.7 %of; inBaltictrace the amounttotalherring lipid infillets, weed 13,16,19-trienoic acid acid (DTrE) Oncorhynchus(3.28–3.76%) mykiss (from and 0 larvae to 3.76% (0–3.65%)of total fatty acids) of Oncorhynchus [114]; in muscle tissue mykiss and (from 0 to 3.76% of total fatty O porkliverseed andof oil, Diplodus lardlargely (from vulgaris charlock < 0.2 (0.8 to [111] 0.3–11.6%; in during% salami of total ripening)-type fatty sausage acids) [112] [115];made in shade of Baltic dried herring neem fillets, (13Z,16Z,19Z)-docosa- docosatrienoic H [113]liver ;of in Diplodus eggs (2.92 vulgaris–3.23% (0.8), embryos–11.6% of(3.28 total–3.76 fatty%) acids) and larvae [115] (0–3.65%) of 23 C22:3n-3 C22H38O2 O 334.544 g/mol (asAzadirachtapork methylacids) and esters:lard indica [114 (from 1.45) ];flower % in< 0.2of muscle powderLabeo to 0.3 rohita% presentduring tissue muscle ripening) to and antissue extent liver fatty[112] of ; acids, of5.7in %shadeDiplodus in1.86 the dried% total of Cirrhinusneem vulgarislipid (0.8–11.6% of total fatty acids) [115] 13,16,19(13Z,16-Ztrienoic,19Z)-docosa acid - docosatrienoicacid (DTrE) Oncorhynchusas methyl esters: mykiss 1.45 (from% of Labeo 0 to 3 rohita.76% ofmuscle total fattytissue acids) fatty [114]acids,; in1.86 muscle% of Cirrhinus tissue and O mrigata muscle tissue fatty acids, 1.09% of Catla catla muscle tissue fatty acids [58]; 23 C22:3n-3 C22H38O2 H 334.544 g/mol [113](Azadirachta; in eggs indica(2.92–)3.23 flower%), embryospowder present(3.28–3.76 to %an) andextent larvae of 5.7 (0%– 3.65in the%) totalof lipid 13,16,19-trienoic acid acid (DTrE) livermrigata of Diplodusmuscle tissue vulgaris fatty (0.8 acids,–11.6 1.09% of% total of Catla fatty catla acids) muscle [115] tissue fatty acids [58]; OO in saltedas methyl products esters:of fish roe: 1.45% 5.6% of of IkuraLabeo (salmon), rohita 1.0muscle% of Tarako tissue (pollock), fatty 2.8 acids,% 1.86% of Cirrhinus mrigata muscle H Oncorhynchusas[113] methyl; in eggsesters: mykiss (2.92 1.45– 3.23(from% of% Labeo ),0 embryosto 3 rohita.76% of(3.28muscle total–3.76 fattytissue%) acids)and fatty larvae [114]acids, ;(0 in1.86–3.65 muscle%% of) ofCirrhinus tissue and O in salted products of fish roe: 5.6% of Ikura (salmon), 1.0% of Tarako (pollock), 2.8% liverofOncorhynchus Tobikotissue of Diplodus (flyingfish), fatty mykiss vulgaris acids, (from1.3 (0.8% of–0 1.09%1 toKazunoko1.6 3%.76 of% of total of Catla(herring)total fatty fatty catlaacids) total acids) [115] musclelipids [114] [59]; in tissue; muscle6.3–8.1% fattytissue of and acids [58]; in salted products of fish roe: mrigataof Tobiko muscle (flyingfish), tissue fatty 1.3% acids, of Kazunoko 1.09% of (herring) Catla catla total muscle lipids tissue [59] ;fatty 6.3–8.1 acids% of [58] ; assalmonliver methyl5.6% of eggs Diplodus esters: of total Ikura 1.45 vulgarisphospholipid% (salmon),of (0.8Labeo–1 rohita1.6fraction,% 1.0%ofmuscle total 4.9– offatty 6tissue%Tarako of acids) salmonfatty [115]acids, (pollock), eggs 1.86 total% triacylglicerolof 2.8%Cirrhinus of Tobiko (flyingfish), 1.3% of Kazunoko docosapentaen insalmon salted eggs products total phospholipidof fish roe: 5.6 fraction,% of Ikura 4.9 (salmon),–6% of salmon 1.0% ofeggs Tarako total (pollock),triacylglicerol 2.8% (7Z,10Z,13Z,16Z,19Z)- docosapentaen mrigatafractionas methyl muscle [60] esters:; 1.6 tissue% 1.45of wildfatty% of sardine acids,Labeo 1.09rohita (Sardina% muscleof Catla pilchardus tissue catla muscle )fatty muscle acids, tissue total 1.86 fatty% of acids Cirrhinus [58](2%; of (7Z,10Z,13Z,16Z,19Z)- oic acid offraction Tobiko(herring) [60] (flyingfish),; 1.6% total of wild 1.3 lipids% sardine of Kazunoko [59 (Sardina]; 6.3–8.1% (herring) pilchardus total of) muscle salmonlipids total[59]; eggsfatty6.3–8.1 acids total% of (2 % phospholipid of fraction, 4.9–6% of salmon 24 docosa-7,10,13,16,19- C22:5n-3 C22H34O2 330.512 g/mol captive sardine muscle total fatty acids), 2.7% of wild/2.4% of captive sardine liver (DPA)/clupanooic acid insalmonmrigata salted eggs muscleproducts total tissue phospholipidof fish fatty roe: acids, 5.6 fraction,% 1.09 of Ikura% of4.9 Catla(salmon),–6% ofcatla salmon 1.0muscle% ofeggs Tarakotissue total fatty (pollock),triacylglicerol acids [58]2.8%; 24 docosapentaenoic-docosapentaenoic7,10,13,16,19 acid - docosapentaen C22:5n-3 C22H34O2 330.512 g/mol totalcaptiveeggs fatty sardine acids total muscle[61] triacylglicerol; as totalmethyl fatty ester: acids), 0.6 fraction– 2.71.15%% of of wild [common60/];2.4 1.6%% ofbarbel captive of oil, wild sardine0.44– sardine0.83 liver% of (Sardina pilchardus) muscle total fatty (7Z,10Z,13Z,16Z,19Z)- (DPA)/clupano O offractionin Tobiko salted [60] (flyingfish),products; 1.6% of of wild 1.3fish% sardineroe: of Kazunoko 5.6 %(S ofardina Ikura (herring) pilchardus (salmon), total) muscle 1.0 lipids% of total[59] Tarako; fatty6.3– (pollock),8.1 acids% of (2 % 2.8 of% pentaenoic acid donic acid H total fatty acids [61]; as methyl ester: 0.6–1.15% of common barbel oil, 0.44–0.83% of (7Z,10Z,13Z,16Z,19Z)-docosa- acid oic acid O Ponticacids shad (2%oil, 1.04 of–2.82 captive% of European sardine wels muscle catfish oil, total 0.06– fatty0.23% of acids), common 2.7% of wild/2.4% of captive sardine liver 24 docosa-7,10,13,16,19- donic acid C22:5n-3 C22H34O2 H 330.512 g/mol salmoncaptiveof Tobiko eggssardine (flyingfish), total muscle phospholipid total1.3% fattyof Kazunokofraction, acids), 2.74.9 (herring)%–6 %of ofwild salmon total/2.4 %lipids eggsof captive [59] total; 6.3 triacylglicerolsardine–8.1% ofliver 24 C22:5n-3 C H O O 330.512 g/mol Pontic shad oil, 1.04–2.82% of European wels catfish oil, 0.06–0.23% of common docosapentaen(DPA)/clupano 22 34 2 bleak oil [52]; 1.07–2.28% for finwhale oils, 2.64–4.74% for seal oils (in weight per 7,10,13,16,19-pentaenoic acid(7Z,10pentaenoicZ(DPA)/clupanodonic,13Z,16 Zacid,19 Z)- O fractiontotalsalmontotal fatty [60] eggs acids fatty; 1.6 total %[61] acidsof phospholipid; aswild methyl sardine [61]; ester: asfraction, (Sardina methyl0.6–1.15 4.9pilchardus%–6 ester:%of ofcommon )salmon muscle 0.6–1.15% barbel eggs total tot fattyoil,al of 0.44triacylglicerol acids common–0.83 (2% of barbel oil, 0.44–0.83% of Pontic shad docosapentaendonicoic acid acid O cent)bleak [62]oil [52]; 1.34; 1.07% of– 2.28tuna% oil for [51] finwhale; 1.9–3.3 oils,% of 2.64 Variola–4.74 louti% for muscle seal oils triacylglycerols (in weight per 24 docosa(7Z,10Z-7,10,13,16,19,13Z,16Z,19Z- )- C22:5n-3 C22H34O2 H 330.512 g/mol captivefraction sardine [60]; 1.6 muscle% of wild total sardine fatty acids), (Sardina 2.7 %pilchardus of wild/)2.4 muscle% of captive total fatty sardine acids liver (2% of acid (DPA)/clupanooic acid Pcent)onticoil, [62] shad 1.04–2.82%; 1.34 oil,% 1.04 of tuna–2.82 oil% of of[51] European European; 1.9–3.3% wels of wels Variola catfish catfish louti oil, 0.06muscle oil,–0.23 triacylglycerols 0.06–0.23%% of common of common bleak oil [52]; 1.07–2.28% for 24 docosapentaenoic-7,10,13,16,19 acid - C22:5n-3 C22H34O2 O 330.512 g/mol total[64]captive; fatty13.8/16.7 sardine acids% [61]of muscle wether/eve; as methyl total fatty (ester:lamb) acids), 0.6 raw–1.15 2.7meat% offatty wildcommon acids/2.4 %[116] barbel of captive; 0.07 oil,% 0.44 sardineand– 0.831.6% liver% of of (DPA)/clupanodonic acid O bleak[64];finwhale 13.8/16.7 oil [52]; %1.07 of oils,– wether/eve2.28% 2.64–4.74% for finwhale (lamb) raw oils, for meat 2.64 seal– fatty4.74 oils% acids for (in seal[116] weight oils; 0.07 (in% weightper and 1.6% cent) per of [62]; 1.34% of tuna oil [51]; 1.9–3.3% of pentaenoic acid H PHormosiratotalontic fattyshad banksii acids oil, 1.04 [61]and–;2.82 Dictyotaas methyl% of Europeandichomota ester: 0.6 welstotal–1.15 catfishfatty% of acids, common oil, 0.06 respectively –barbel0.23% oil,of [117] common 0.44 –0.83 % of donic acid O cent)Hormosira [62]; 1.34banksii% of and tuna Dictyota oil [51] dichomota; 1.9–3.3% total of Variola fatty acids, louti musclerespectively triacylglycerols [117] H O Variola louti bleak15.44Pontic goil/ 100shad [52] g; oil,(as1.07 methyl1.04–2.28muscle–2.82% ester: for% offinwhale 17.98 European triacylglycerols% ofoils, fatty wels 2.64 acids) catfish–4.74 %muscle [oil, 64for ];0.06seal tissue 13.8/16.7%– oils0.23 of(in% Labeo ofweight common rohita of per wether/eve, (lamb) raw meat fatty [64]15.44; 13.8/16.7 g/100 g %(as of methyl wether/eve ester: (17.98lamb)% raw of fatty meat acids) fatty muscleacids [116] tissue; 0.07 of %Labeo and rohita 1.6% ,of O 18.07 g/100 g (as methyl ester: 8.07% of fatty acids) muscle tissue of Cirrhinus O cent)Hormosirableakacids [62] oil; [52]1.34banksii [116;% 1.07 of and]; –tuna2.28 0.07% Dictyota %oil for [51]and finwhaledichomota; 1.9– 1.6%3.3 %oils, total of of 2.64Variola fattyHormosira–4.74 acids, louti% for musclerespectively seal banksii oilstriacylglycerols (in [117]and weight Dictyota per dichomota total fatty acids, H 18.07 g/100 g (as methyl ester: 8.07% of fatty acids) muscle tissue of Cirrhinus O [64]mrigatacent); 13.8/16.7 [62], 17.98; 1.34% g /%of100 ofwether/eve gtuna (as methyloil [51] (lamb) ;ester: 1.9– raw3.3 15.4% meat %of ofVariola fattyfatty acidsloutiacids) muscle [116] muscle; 0.07 triacylglycerols tissue% and of 1.6% Catla of H 15.44mrigatarespectively g/,100 17.98 g (as g/100 methyl g [(as117 ester: methyl] 17.98 ester:% of 15.4 fatty% ofacids) fatty muscle acids) muscletissue of tissue Labeo of rohita Catla, O catla [58]; in salted products of fish roe: 17.4% of Ikura (salmon), 22.2% of Tarako Hormosira18.07[64]; g13.8/16.7/100 banksii g (as% methylofand wether/eve Dictyota ester: dichomota8.07 (lamb)% of raw fatty total meat acids) fatty fatty acids, muscle acids respectively tissue [116] ;of 0.07 Cirrhinus [117]% and 1.6% of O O catla [58]; in salted products of fish roe: 17.4% of Ikura (salmon), 22.2% of Tarako H 15.44(pollock),Hormosira15.44 g/100 27.9 gbanksii g/100 (as% ofmethyl and Tobiko g Dictyota (asester: (flyingfish), methyl 17.98 dichomota% of ester:22.6 fatty total% ofacids) fatty 17.98%Kazunoko acids,muscle ofrespectively (herring) tissue fatty of acids)totalLabeo [117] lipids rohita muscle [59], ; tissue of Labeo rohita, 18.07 g/100 g docosahexaenoi mrigata(pollock),, 17.98 27.9 g%/100 of Tobiko g (as methyl (flyingfish), ester: 15.422.6%% ofof fattyKazunoko acids) (herring)muscle tissue total oflipids Catla [59] ; (4Z,7Z,10Z,13Z,16Z,19Z)- docosahexaenoi 18.072615.44–29.2 g /g%100/100 of g salmon g(as (as methyl methyl eggs ester: totalester: 8.07phospholipid 17.98% %of offatty fatty acids)fraction, acids) muscle muscle12.5– tissue15.3 tissue% ofof ofCirrhinussalmon Labeo eggsrohita , (4Z,7Z,10Z,13Z,16Z,19Z)- c acid O O catla26–29.2(as [58]%; methyl inof saltedsalmon products ester: eggs total 8.07% of phospholipidfish roe: of 17.4 fatty% fraction, of acids) Ikura 12.5 (salmon), muscle–15.3% 22.2 of tissue salmon% of Tarako of eggsCirrhinus mrigata, 17.98 g/100 g (as methyl 25 docosa-4,7,10,13,16,19- C22:6n-3 C22H32O2 H 328.496 g/mol total triacylglicerol fraction [60]; 14.8% of wild sardine (Sardina pilchardus) muscle c acid O mrigata18.07 g, /17.98100 g g (as/100 methyl g (as methyl ester: 8.07 ester:% of15.4 fatty% of acids) fatty muscleacids) muscle tissue of tissue Cirrhinus of Catla (DHA)/cervoni 22 32 2 (pollock), 27.9% of Tobiko (flyingfish), 22.6% of Kazunoko (herring) total lipids [59]; 25 docosahexaenoic-4,7,10,13,16,19 acid - docosahexaenoi C22:6n-3 C H O H 328.496 g/mol totaltotalester: fattytriacylglicerol acids 15.4% (13.4 fraction% of of fatty captive [60]; acids) 14.8 sardine% of muscle musclewild sardine total tissue fatty (Sardina ofacids), Catlapilchardus 12.8 catla% of) muscle [58]; in salted products of fish roe: 17.4% of (4Z,7Z,10Z,13Z,16Z,19Z)- (DHA)/cervonic acid O catla26mrigata–29.2 [58]%,; 17.98inof saltedsalmon g/100 products eggs g (as total methyl of phospholipidfish ester: roe: 17.415.4%% fraction, ofof Ikurafatty 12.5 acids)(salmon),–15.3 muscle% 22.2 of salmontissue% of Tarako of eggs Catla hexaenoic acid c acid wildtotalIkura/ fatty17.1% acids of (salmon), captive (13.4% sardine of captive 22.2% liver sardine oftotal Tarako fatty muscle acids (pollock),total [61] fatty; as methyl acids), 27.9% ester:12.8%of 1.36 of Tobiko–2.5% (flyingfish), 22.6% of Kazunoko 25 docosa-4,7,10,13,16,19- c acid C22:6n-3 C22H32O2 O 328.496 g/mol (pollock),tocatlatal triacylglicerol [58] ;27.9 in salted% of Tobikofraction products (flyingfish), [60] of ;fish 14.8 roe:% 22.6of 17.4 wild% %of sardineof Kazunoko Ikura ( Sardina(salmon), (herring) pilchardus 22.2 total% of )lipids muscleTarako [59] ; docosahexaenoicdocosahexaenoi(DHA)/cervoni ofwild common/17.1% ofbarbel captive oil, sardine4.15–6.47 liver% of total Pontic fatty shad acids oil, [61] 1.44; as–3.83 methyl% of ester:European 1.36 –wels2.5% (4Z,7Zhexaenoic,10Z,13Z,16 acidZ,19 Z)- 26total(pollock),–29.2(herring) fatty% of acids 27.9 salmon% (13.4 totalof eggsTobiko% of lipids totalcaptive (flyingfish), phospholipid [sardine59]; 26–29.2%22.6 muscle %fraction, of Kazunokototal of12.5 fatty salmon–15.3 acids),(herring)% of 12.8 salmon eggs total% of lipids totaleggs [59] phospholipid; fraction, 12.5–15.3% of (4Z,7Z,10Z,13Z,16Z,19Z)-docosa- acid docosahexaenoic acid catfishof common oil, 0.13 barbel–0.42 oil,% of4.15 common–6.47% ofbleak Pontic oil [52]shad; 2.74 oil, –1.446.23–%3.83 for% finwhale of European oils, wels5.14– 25 (4docosaZ,7Z,10-4,7,10,13,16,19Z,13Z,16Z,19-Z)- C22:6n-3 C22H32O2 328.496 g/mol to26tal– 29.2triacylglicerol% of salmon fraction eggs total [60] ;phospholipid 14.8% of wild fraction, sardine 12.5(Sardina–15.3 pilchardus% of salmon) muscle eggs 25 (DHA)/cervonic acidC22:6 n-3 C22H32O2 328.496 g/mol wildcatfishsalmon/17.1 oil,% 0.13 of captive– eggs0.42% sardine totalof common triacylglicerol liver bleak total fattyoil [52] acids; 2.74 fraction [61]–6.23; as% methyl for [60 finwhale]; ester: 14.8% 1.36oils, of– 5.142.5 wild%– sardine (Sardina pilchardus) muscle 4,7,10,13,16,19-hexaenoic25 aciddocosahexaenoic-4,7,10,13,16,19(DHA)/cervonic acid - C22:6n-3 C22H32O2 328.496 g/mol total8.22total% fatty triacylglicerolfor seaacidsl oils (13.4 (in %fraction weight of captive [60]per ; cent) sardine14.8% [62] of muscle ;wild 14.8 –sardine 19.4total% fatty of (Sardina Epinephelus acids), pilchardus 12.8 fasciatus% of) muscle (DHA)/cervonic acid of8.22 common%total for sea fattybarbell oils acids(inoil, weight 4.15 (13.4%–6.47 per% cent) of ofPontic [62] captive; shad14.8– 19.4oil, sardine 1.44% of– 3.83Epinephelus muscle% of European fasciatus total wels fatty acids), 12.8% of wild/17.1% of hexaenoic acidacid wildmusccletotal/17.1 fatty triacylglycerols% acidsof captive (13.4 %sardine of[64] captive liver sardinetotal fatty muscle acids total [61] ;fatty as methyl acids), ester: 12.8 %1.36 of –2.5% c acid catfishmuscclecaptive oil, triacylglycerols 0.13– sardine0.42% of [64]common liver total bleak fattyoil [52]; acids 2.74–6.23 [61% ];for as finwhale methyl oils, ester: 5.14– 1.36–2.5% of common barbel oil, of8.22wild common%/ 17.1for sea% barbel ofl oils captive (inoil, weight 4.15 sardine–6.47 per liver% cent) of totalPontic [62] fatty; shad14.8 acids– 19.4oil, 1.44[61]% of;– as3.83Epinephelus methyl% of European ester: fasciatus 1.36 wels –2.5 % (12Z,15Z,18Z,21Z)- (12Z,15Z,18Z,21Z)- catfishmusccleof common4.15–6.47% oil, triacylglycerols 0.13 barbel–0.42 %oil, of of 4.15 Pontic [64]common– 6.47% shad bleak of Pontic oil oil, [52] shad 1.44–3.83%; 2.74 oil,– 6.231.44%–3.83 for of %finwhale Europeanof European oils, 5.14 wels wels– catfish oil, 0.13–0.42% of common 26 tetracosa-12,15,18,21- - C24:4n-3 C24H40O2 360.582 g/mol 1.3% of Baltic herring (Clupea harengus) total fatty acids [118] 8.22catfish% for oil, sea 0.13l oils–0.42 (in %weight of common per cent) bleak [62] oil; 14.8 [52]–;19.4 2.74%– 6.23of Epinephelus% for finwhale fasciatus oils, 5.14– 26 tetracosa-12,15,18,21- - C24:4n-3 C24H40O2 H O 360.582 g/mol 1.3%bleak of Balti oilc herring [52]; (Clupea 2.74–6.23% harengus) fortotal finwhalefatty acids [118] oils, 5.14–8.22% for seal oils (in weight per cent) [62]; tetraenoic acid (12Z,15Z,18Z,21Z)- H O musccle8.22% for triacylglycerols seal oils (in weight [64] per cent) [62]; 14.8–19.4% of Epinephelus fasciatus tetraenoic acid O 14.8–19.4% of Epinephelus fasciatus musccle triacylglycerols [64] 26 tetracosa-12,15,18,21- - C24:4n-3 C24H40O2 O 360.582 g/mol 1.3musccle% of Balti triacylglycerolsc herring (Clupea [64] harengus) total fatty acids [118] (12tetraenoicZ,15Z,18Z acid,21Z )- H O (12Z,15Z,18Z,2126Z )- tetracosa(12Z,15-12,15,18,21Z,18Z,21Z)-- - C24:4n-3 C24H40O2 O 360.582 g/mol 1.3% of Baltic herring (Clupea harengus) total fatty acids [118] H O 26 tetracosa-12,15,18,21-tetraenoic26 tetracosatetraenoic-12,15,18,21 acid -- - C24:4n-3C24:4n-3 C24HC4024HO402O2 360.582360.582 g/mol g/mol 1.3% 1.3% of Balti ofc Balticherring ( herringClupea harengus (Clupea) total harengusfatty acids [118]) total fatty acids [118] acid tetraenoic acid H OO O

Nutrients 2018, 10, 1662 9 of 33

Table 1. Cont.

Shorthand Common Molecular No IUPAC Name (Simplified Formula/Structure Molecular Weight Sources [Refs.] Name Formula Formula) Nutrients 2018, 10, x FOR PEER REVIEW 9 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 9 of 34 Nutrients 2018, 10, x FOR PEER REVIEW POLYUNSATURATED FATTY ACIDS (PUFAs) 9 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 9 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 9 of 34 (9Z,12NutrientsZ,15Z,18 2018Z,21(9Z, Z,1210)-Z, ,15x FORZ,18Z ,21PEERZ)- REVIEW 9 of 34 Nutrients 2018(9Z, ,1210Z, ,15x FORZ,18Z PEER,21Z)- REVIEW 9 of 34 27 tetracosa-9,12,15,18,21-27 tetracosa(9Z,12Z,15-9,12,15,18,21Z,18Z,21Z)-- -- C24:5n-3C24:5n-3 C24HC2438HO38O22 358.566358.566 g/mol 1.4% 1.4% of Balti ofc herring Baltic total herring fatty acids total [118] fatty acids [118] 27 tetracosa-9,12,15,18,21- - C24:5n-3 C24H38O2 358.566 g/mol 1.4% of Baltic herring total fatty acids [118] (9Zpentaenoic,12Z,15Z,18 acidZ,21 Z)- O pentaenoic27 acidtetracosa-9,12,15,18,21- - C24:5n-3 C24H38O2 H 358.566 g/mol 1.4% of Baltic herring total fatty acids [118] (9Zpentaenoic,12Z,15Z,18 acidZ,21 Z)- O 27 tetracosa-9,12,15,18,21- - C24:5n-3 C24H38O2 H 358.566 g/mol 1.4% of Baltic herring total fatty acids [118] pentaenoic acid O O 27 tetracosa(9Z,12Z,15-9,12,15,18,21Z,18Z,21Z)-- - C24:5n-3 C24H38O2 H 358.566 g/mol 1.4% of Baltic herring total fatty acids [118] pentaenoic acid OO O (9Z,12Z,15Z,18Z,21Z)- 24 38 2 H O O 27 tetracosapentaenoic-9,12,15,18,21 acid - - C24:5n-3 C H O O 358.566 g/mol 1.4% of Baltic herring total fatty acids [118] H O O 27 tetracosapentaenoic-9,12,15,18,21 acid - - C24:5n-3 C24H38O2 O O 358.566 g/mol 1.4% of Baltic herring total fatty acids [118] H O O O pentaenoic acid H OO H O O H (6Z,9Z,12Z,15Z,18Z,21Z)- O (6Z,9Z,12Z,15Z,18(6ZZ,21,9Z,12Z)-Z,15Z,18Z,21Z)- O O 28 tetracosa-6,9,12,15,18,21- nisinic acid C24:6n-3 C24H36O2 H 356.55 g/mol 0.9% of Baltic herring total fatty acids [118] (6Z,9Z,12Z,15Z,18Z,21Z)- O O 28 tetracosa-6,9,12,15,18,21- nisinic acid C24:6n-3 C24H36O2 356.55 g/mol 0.9% of Baltic herring total fatty acids [118] 28 tetracosa-6,9,12,15,18,21-(6Z,9Zhexaenoic,12Z,15Z ,18acidnisinicZ,21 Z)- acid C24:6n-3 C24H36O2 H O 356.55 g/mol 0.9% of Baltic herring total fatty acids [118] 28 tetracosa-6,9,12,15,18,21- nisinic acid C24:6n-3 C24H36O2 356.55 g/mol 0.9% of Baltic herring total fatty acids [118] (6Z,9Zhexaenoic,12Z,15Z,18 acidZ,21 Z)- hexaenoic28 acidtetracosahexaenoic-6,9,12,15,18,21 acid - nisinic acid C24:6n-3 C24H36O2 O 356.55 g/mol 0.9% of Baltic herring total fatty acids [118] 28 (6tetracosaZ,9Zhexaenoic,12-Z6,9,12,15,18,21,15Z ,18acidZ,21 Z)-- nisinic acid C24:6n-3 C24H36O2 356.55 g/mol 0.9% of Baltic herring total fatty acids [118] 28 (6tetracosaZ,9Zhexaenoic,12-Z6,9,12,15,18,21,15Z,18 acidZ,21 Z)-- nisinic acid C24:6n-3 C24H36O2 356.55 g/mol 0.9% of Baltic herring total fatty acids [118]

28 tetracosahexaenoic-6,9,12,15,18,21 acid - nisinic acid C24:6n-3 C24H36O2 356.55 g/mol 0.9% of Baltic herring total fatty acids [118] hexaenoic acid (11Z,14Z,17Z,20Z,23Z)- (11Z,14Z,17Z,20Z,23Z)- 26 42 2 (11Z,14Z,1729 Z,20Zhexacosa(11,23ZZ,14)-Z-,1711,14,17,20,23Z,20Z,23Z)-- - C26:5n-3 C H O 386.62 g/mol 0.5% of of Baltic herring total fatty acids [118] 29 hexacosa-11,14,17,20,23- - C26:5n-3 C26H42O2 386.62 g/mol 0.5% of of Baltic herring total fatty acids [118] pentaenoic acid O (11Z,14Z,17Z,20Z,23Z)- 26 42 2 H 29 hexacosa-11,14,17,20,23-29 hexacosa-11,14,17,20,23- -- C26:5n-3C26:5n-3 C HC HOO O 386.62386.62 g/mol 0.5% 0.5% of of Balti ofc of herring Baltic total herring fatty acids total [118]fatty acids [118] (11Zpentaenoic,14Z,17Z,20 acidZ,23 Z)- 26 42 2 H 29 hexacosa-11,14,17,20,23- - C26:5n-3 C26H42O2 O 386.62 g/mol 0.5% of of Baltic herring total fatty acids [118] pentaenoic acid O H O O pentaenoic29 acidhexacosa(11Z,14Z-,1711,14,17,20,23Z,20Z,23Z)-- - C26:5n-3 C26H42O2 O 386.62 g/mol 0.5% of of Baltic herring total fatty acids [118] pentaenoic acid H H O O 29 hexacosa(11Z,14Z-,1711,14,17,20,23Z,20Z,23Z)-- - C26:5n-3 C26H42O2 H O 386.62 g/mol 0.5% of of Baltic herring total fatty acids [118] pentaenoic acid H O O O H 29 hexacosa-11,14,17,20,23- - C26:5n-3 C26H42O2 OO O 386.62 g/mol 0.5% of of Baltic herring total fatty acids [118] pentaenoic acid H O H (8Z,11Z,14Z,17Z,20Z,23Z)- OO O O pentaenoic acid H (8Z,11Z,14Z,17Z,20Z,23Z)- H O 30 hexacosa-8,11,14,17,20,23- - C26:6n-3 C26H40O2 O 384.604 g/mol 0.7% of Baltic herring total fatty acids [118] (8Z,11Z,14Z,17Z,20Z,23Z)- O 30 hexacosa-8,11,14,17,20,23- - C26:6n-3 C26H40O2 H O 384.604 g/mol 0.7% of Baltic herring total fatty acids [118] (8Z,11Z,14Z,17Z,20(8Z,11,23hexaenoicZ,14Z)-Z,17Z ,20acidZ ,23Z)- O 30 hexacosahexaenoic-8,11,14,17,20,23 acid - - C26:6n-3 C26H40O2 H O 384.604 g/mol 0.7% of Baltic herring total fatty acids [118] 30 (8hexacosaZ,11Z,14-8,11,14,17,20,23Z,17Z,20Z,23Z)-- - C26:6n-3 C26H40O2 384.604 g/mol 0.7% of Baltic herring total fatty acids [118] 30 hexacosa-8,11,14,17,20,23-hexaenoic acid - C26:6n-3 C26H40O2 O 384.604 g/mol 0.7% of Baltic herring total fatty acids [118] 30 (8hexacosaZ,11hexaenoicZ,14-8,11,14,17,20,23Z,17Z ,20acidZ ,23Z)-- - C26:6n-3 C26H40O2 384.604 g/mol 0.7% of Baltic herring total fatty acids [118] hexaenoic30 acid(8hexacosaZ,11Z,14-8,11,14,17,20,23Z,17Z,20Z,23Z)-- - C26:6n-3 C26H40O2 384.604 g/mol 0.7% of Baltic herring total fatty acids [118] hexaenoic acid 30 hexacosa(15Zhexaenoic,18Z-8,11,14,17,20,23,21Z,24 acidZ,27 Z)- - - C26:6n-3 C26H40O2 384.604 g/mol 0.7% of Baltic herring total fatty acids [118] (15Z,18Z,21Z,24Z,27Z)- hexaenoic acid 30 50 2 31 triaconta(15Z,18Z-,2115,18,21,24,27Z,24Z,27Z)-- - C30:5n-3 C H O 442.728 g/mol as a methyl ester: 7% of Cliona celata total methyl esters [119] 31 triaconta-15,18,21,24,27- - C30:5n-3 C30H50O2 O 442.728 g/mol as a methyl ester: 7% of Cliona celata total methyl esters [119] H (15Zpentaenoic,18Z,21Z,24 acidZ,27 Z)- O 31 triaconta-15,18,21,24,27- - C30:5n-3 C30H50O2 O 442.728 g/mol as a methyl ester: 7% of Cliona celata total methyl esters [119] (15Z,18Z,21Z,24Z,27pentaenoicZ)- acid H (15Z,18Z,21Z,24Z,27Z)- O 31 triaconta-15,18,21,24,27- - C30:5n-3 C30H50O2 O 442.728 g/mol as a methyl ester: 7% of Cliona celata total methyl esters [119] pentaenoic acid H (19Z,22Z,25Z,28Z,31Z)- O (15Z,18Z,21Z,24Z,27Z)- 30 50 2 O 31 triaconta-15,18,21,24,27-31 triacontapentaenoic-15,18,21,24,27 acid - -- C30:5n-3C30:5n-3 C30HC50HOO2 H 442.728442.728 g/mol as a asmethyl a methyl ester: 7%ester: of Cliona 7% celata of totalCliona methyl celata esterstotal [119] methyl esters [119] (19Z,22Z,25Z,28Z,31Z)- O 34 58 2 O 3231 tetratriacontatriaconta(15Z,18Z-,2115,18,21,24,27-19,22,25,28,31Z,24Z,27Z)-- - -- C34:5C30:5n--3 C30H50O2 H 498.836442.728 g/mol 12.4as a %methyl of the ester: phospholipid 7% of Cliona fatty celata acids total from methyl Petrosia esters pellasarca [119] [120] (19Zpentaenoic,22Z,25Z,28 acidZ,31 Z)- O pentaenoic32 acidtetratriaconta-19,22,25,28,31- - C34:5n-3 C34H58O2 H O O 498.836 g/mol 12.4% of the phospholipid fatty acids from Petrosia pellasarca [120] H 31 triaconta(19Zpentaenoic,22Z-,2515,18,21,24,27Z,28 acidZ,31 Z)-- - C30:5n-3 C30H50O2 O O 442.728 g/mol as a methyl ester: 7% of Cliona celata total methyl esters [119] 32 tetratriaconta-19,22,25,28,31- - C34:5n-3 C34H58O2 H 498.836 g/mol 12.4% of the phospholipid fatty acids from Petrosia pellasarca [120] O O pentaenoic acid O O (19Z,22Z,25Z,28Z,31Z)- H 32 tetratriacontapentaenoic-19,22,25,28,31 acid - - C34:5n-3 C34H58O2 H 498.836 g/mol 12.4% of the phospholipid fatty acids from Petrosia pellasarca [120] pentaenoic acid O O O (19Z,22Z,2532 Z,28tetratriacontaZ(19,31ZZ,22)-Z,25-Z19,22,25,28,31,28Z,31Z)- - - C34:5n-3 C34H58O2 H 498.836 g/mol 12.4% of the phospholipid fatty acids from Petrosia pellasarca [120] pentaenoic acid O O (23Z,34Z)-heptatriaconta- H 32 tetratriaconta(19Z,22Z,25-19,22,25,28,31Z,28Z,31Z)- - - C34:5n-3 C3734H7058O22 498.836 g/mol 12.4% of the phospholipid fatty acids from Petrosia pellasarca [120] 32 tetratriaconta-19,22,25,28,31-33 (23Z,34pentaenoicZ)-heptatriaconta acid --- C34:5n-3C37:2n-3 C HC HOO O 498.836546.965 g/mol in a CHCl3 12.4% extract of the of Iranian phospholipid Rosa x damascena fatty (Rosaceae acids) from[121] Petrosia pellasarca [120] 34 58 2 O 23,34-dienoic acid H 3233 tetratriaconta(23Z,34Z)-heptatriaconta-19,22,25,28,31- - - C34:5C37:2n-3 C3437H5870O2 498.836546.965 g/mol 12.4in a %CHCl3 of the extract phospholipid of Iranian fatty Rosa acids x damascena from Petrosia (Rosaceae pellasarca) [121] [120] pentaenoic acid O 23,34-dienoic acid O O 33 - C37:2n-3 C37H70O2 H 546.965 g/mol in a CHCl3 extract of Iranian Rosa x damascena (Rosaceae) [121] pentaenoic acid(23Z,34Z)-heptatriaconta- H O 23,34-dienoic acid O H 33 pentaenoic acid - C37:2n-3 C37H70O2 O 546.965 g/mol in a CHCl3 extract of Iranian Rosa x damascena (Rosaceae) [121] (23Z,34Z)-heptatriaconta- O O 33 23,34-dienoic acid - C37:2n-3 VERY LONGC37H70-CHAINO2 FATTYH ACIDS WITH AN UNDEFINED POSITION546.965 g/mol OF DOUBLE in a BONDS CHCl3 extract of Iranian Rosa x damascena (Rosaceae) [121] O (23Z,34Z)-heptatriaconta- O 23,34-dienoic acid VERY LONG-CHAIN FATTYH ACIDS WITH AN UNDEFINED POSITION OF DOUBLE BONDS 3433 - -- CC37:224:4n--3 C2437H4070O22 O - 360.582546.965 g/mol inin rama CHCl3 and bullextract spermatozoa of Iranian Rosa[7] x damascena (Rosaceae) [121] O VERY LONG-CHAIN FATTYH ACIDS WITH AN UNDEFINED POSITION OF DOUBLE BONDS (23Z,34Z)-heptatriaconta-(23Z23,34,34Z)--dienoicheptatriaconta acid - 24 40 2 34 - - C24:4n-3 C H O O - 360.582 g/mol in ram and bull spermatozoa [7] 33 - C37:2n-3 C37H70O2 546.965 g/mol in a CHCl3 extract of Iranian Rosa x damascena (Rosaceae) [121] 33 35 - -- C37:2n-3C24:5n-3 VERY C LONGHC24HO38-CHAINO2 FATTYO ACIDS WITH- AN UNDEFINED546.965 358.566POSITION g/mol OF DOUBLEin bovine BONDS in a retina CHCl3 [8]; in extract ram spermatozoa of Iranian [7] Rosa x damascena (Rosaceae)[121] 34 23,34-dienoic- acid - C24:4n-3 37 C2470H40O22 H - 360.582 g/mol in ram and bull spermatozoa [7] 23,34-dienoic35 acid - - C24:5n-3 VERY LONGC24H38-CHAINO2 FATTYO ACIDS WITH- AN UNDEFINED 358.566POSITION g/mol OF DOUBLEin bovine BONDS retina [8]; in ram spermatozoa [7] 34 - - C24:4n-3 C24H3640O2 O - 360.582 g/mol in ram and bull spermatozoa [7] 3635 - - C24:624:5n-3 C24H38O2 H - 358.566356.55 g/mol g/mol in bovine retina [8];; inin ramram spermatozoaspermatozoa [7] 3436 - - C24:424:6n-3 VERY LONGC24H4036-CHAINO2 FATTYO ACIDS WITH- AN UNDEFINED 360.582POSITION356.55 g/molg/mol OF DOUBLEin rambovine BONDS and retina bull spermatozoa[8]; in ram spermatozoa [7] [7] 3735 - - C26:424:5n-3 C2624H4438O2 - 388.636358.566 g/mol in rambovine spermatozoa retina [8]; in[7] ram spermatozoa [7] 36 - - C24:6n-3 VERY LONGC24H36-CHAINO2 FATTY ACIDS WITH- AN UNDEFINED POSITION356.55 g/mol OF DOUBLEin bovine BONDS retina [8]; in ram spermatozoa [7] 343537 - - C24:424:526:4n-3 C2426H403844O2 - 360.582358.566388.636 g/mol in rambovine andspermatozoa retina bull spermatozoa[8]; in[7] ram spermatozoa [7] [7] 3836 - - C26:524:6n-3 C2624H4236O2 - 386.62356.55 g/mol in rambovine spermatozoa retina [8]; in[7] ram spermatozoa [7] 3734 - - CVERY26:424:4n-3 LONG-CHAINC2624H4440O2 FATTY ACIDS- WITH AN388.636360.582 UNDEFINED g/mol in ram POSITION spermatozoaand bull spermatozoa [7] OF DOUBLE [7] BONDS 353638 - - C24:524:626:5n-3 C2426H383642O2 - 358.566356.55386.62 g/molg/mol in bovineram spermatozoa retina [8]; in [7] ram spermatozoa [7] 3937 - - C26:526:4n-3 C26H4244O2 - 388.636386.62 g/mol g/mol in bovineram spermatozoa retina [8] [7] 3835 - - C26:524:5n-3 C2624H4238O2 - 358.566386.62 g/mol g/mol in rambovine spermatozoa retina [8]; in[7] ram spermatozoa [7] 363739 - - C24:626:426:5n-3 C2426H364442O2 - 388.636356.55386.62 g/mol g/mol in bovineram spermatozoa retina [8]; in[7] ram spermatozoa [7] 344038- - -- C24:4n-3C26:626:5n-3 C HC26HO4042O2 -- 360.582384.604386.62 g/molg/mol g/mol in ram in spermatozoa ram and bull[7] spermatozoa [7] 3936 - - C26:524:6n-3 24 C262440H4236O22 - 386.62356.55 g/mol in bovine retina [8] ; in ram spermatozoa [7] 373840 - - C26:426:526:6n-3 C26H444240O2 - 388.636384.604386.62 g/molg/mol in ram spermatozoa [7] 4139 - - C26:626:5n-3 C26H4042O2 - 384.604386.62 g/molg/mol in bovine retina [8] 4037 - - C26:626:4n-3 C26H4044O2 - 384.604388.636 g/mol in ram spermatozoa [7] 35383941- - -- C24:5n-3C26:526:6n-3 C HC26HO4240O2 -- 358.566384.604386.62 g/mol g/mol in rambovine in spermatozoa bovine retina [8] retina [7] [8]; in ram spermatozoa [7] 4240 - - C28:526:6n-3 24 C282638H4640O22 - 414.674384.604 g/mol in bovineram spermatozoa retina [8]; in[7] ram and bull spermatozoa [7] 4138 - - C26:626:5n-3 C26H4042O2 - 384.604386.62 g/molg/mol in bovineram spermatozoa retina [8] [7] 394042 - - C26:526:628:5n-3 C2628H424046O2 - 384.604414.674386.62 g/mol g/mol in bovineram spermatozoa retina [8] ; in[7] ram and bull spermatozoa [7] 4341 - - C28:626:6n-3 C2826H4440O2 - 412.658384.604 g/mol in bovine retina [8]; in ram and bull spermatozoa [7] 4239 - - C28:526:5n-3 C2826H4642O2 - 414.674386.62 g/molg/mol in bovine retina [8]; in ram and bull spermatozoa [7] 36404143- - -- C24:6n-3C26:628:6n-3 C24HC262836HO4044O22 -- 356.55384.604412.658 g/molg/mol in rambovine in spermatozoa bovine retina [8] retina ; in[7] ram [and8]; bull inram spermatozoa spermatozoa [7] [7] 4442 - - C30:528:5n-3 C3028H5046O2 - 442.728414.674 g/mol in bovine retina [8]; in ram and bull spermatozoa [7] 4340 - - C28:626:6n-3 C2826H4440O2 - 412.658384.604 g/mol in bovineram spermatozoa retina [8]; in [7] ram and bull spermatozoa [7] 414244 - - C26:628:530:5n-3 C262830H404650O2 - 384.604414.674442.728 g/mol in bovine retina [8] ; in ram and bull spermatozoa [7] 4543 - - n C30:628:6n-3 C3028H4844O2 - 440.712412.658 g/mol in bovine retina [8]; in ram and bull spermatozoa [7] 374441- - -- C26:4 -3C30:526:6n-3 C26HC302644HO5040O22 -- 388.636442.728384.604 g/mol in bovine in ram retina spermatozoa [8]; in ram and bull [7] spermatozoa [7] 424345 - - C28:528:630:6n-3 C2830H464448O2 - 414.674412.658440.712 g/mol in bovine retina [8];; inin ramram andand bullbull spermatozoaspermatozoa [7] 44 - - C30:5n-3 C30H50O2 - 442.728 g/mol in bovine retina [8]; in ram and bull spermatozoa [7] 4542 - - C30:628:5n-3 C3028H4846O2 - 440.712414.674 g/mol in bovine retina [8];; inin ramram andand bullbull spermatozoaspermatozoa [7] 4344 - - C28:630:5n-3 C2830H4450O2 - 412.658442.728 g/mol in bovine retina [8]; in ram and bull spermatozoa [7] 38 45- - -- C26:5n-3C30:6n-3 C26HC3042HO48O22 -- 386.62440.712 g/molg/mol in bovine in ram retina spermatozoa [8]; in ram and bull [7] spermatozoa [7] 4443 - - C30:528:6n-3 C3028H5044O2 - 442.728412.658 g/mol in bovine retina [8]; in ram and bull spermatozoa [7] 45 - - C30:6n-3 C30H48O2 - 440.712 g/mol in bovine retina [8]; in ram and bull spermatozoa [7] 4544 - - C30:630:5n-3 C30H4850O2 - 440.712442.728 g/mol in bovine retina [8]; in ram and bull spermatozoa [7] 45 - - C30:6n-3 C30H48O2 - 440.712 g/mol in bovine retina [8]; in ram and bull spermatozoa [7]

Nutrients 2018, 10, 1662 10 of 33

Table 1. Cont.

Shorthand Common Molecular No IUPAC Name (Simplified Formula/Structure Molecular Weight Sources [Refs.] Name Formula Formula) VERY LONG-CHAIN FATTY ACIDS WITH AN UNDEFINED POSITION OF DOUBLE BONDS

39 - - C26:5n-3 C26H42O2 - 386.62 g/mol in bovine retina [8]

40 - - C26:6n-3 C26H40O2 - 384.604 g/mol in ram spermatozoa [7]

41 - - C26:6n-3 C26H40O2 - 384.604 g/mol in bovine retina [8]

42 - - C28:5n-3 C28H46O2 - 414.674 g/mol in bovine retina [8]; in ram and bull spermatozoa [7]

43 - - C28:6n-3 C28H44O2 - 412.658 g/mol in bovine retina [8]; in ram and bull spermatozoa [7]

44 - - C30:5n-3 C30H50O2 - 442.728 g/mol in bovine retina [8]; in ram and bull spermatozoa [7]

45 - - C30:6n-3 C30H48O2 - 440.712 g/mol in bovine retina [8]; in ram and bull spermatozoa [7]

46 - - C32:5n-3 C32H54O2 - 470.782 g/mol in bovine retina [8]

47 - - C32:6n-3 C32H52O2 - 468.766 g/mol in bovine retina [8]—main component of VLC-PUFA-PC of bovine retina [122]; in bull spermatozoa [7] 48Nutrients - 2018, 10, x FOR PEER - REVIEW C32:7n-3 C H O - 466.75 g/mol in ram and bull spermatozoa [7] 10 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 32 50 2 10 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 10 of 34 49 - - C34:5n-3 C34H58O2 - 498.836 g/mol in bovine retina [8] Nutrients46 2018, 10, x FOR- PEER REVIEW - C32:5n-3 C32H54O2 - 470.782 g/mol in bovine retina [8] 10 of 34 Nutrients46 2018, 10, x -FOR PEER REVIEW - C32:5n-3 C32H54O2 - 470.782 g/mol inin bovine bovine retina retina [8] [8] —main component of VLC-PUFA-PC of bovine retina [122]10; inof 34 47 - - C32:6n-3 C32H52O2 - 468.766 g/mol in bovine retina [8]—main component of VLC-PUFA-PC of bovine retina [122]; in ram and bull 46 - - C32:5n-3 C32H54O2 - 470.782 g/mol ininbull bovine bovine spermatozoa retina retina [8] [8] —[7] main component of VLC-PUFA-PC of bovine retina [122]; in 5047- - -- C34:6n-3C32:6n-3 C34CH32H5652O22 -- 496.82468.766 g/molg/mol 46 - - C32:5n-3 C32H54O2 - 470.782 g/mol bullinin bovine bovine spermatozoa retina retina [8] [8][7] — main [7] component of VLC-PUFA-PC of bovine retina [122]; in 48 - - C32:7n-3 C32H50O2 - 466.75 g/mol in ram and bull spermatozoa [7] 4746 - - C32:632:5n-3 C32H5254O2 - 468.766470.782 g/mol in bovine retina [8] 48 - - C32:7n-3 C32H50O2 - 466.75 g/mol ininbull rambovine spermatozoa and retina bull spermatozoa [8] [7]—main component [7] of VLC-PUFA-PC of bovine retina [122]; in 49 - - C34:5n-3 C34H58O2 - 498.836 g/mol in bovine retina [8] 5147 - - -- C36:5n-3C32:6n-3 C36CH3262H52OO2 -- 526.89468.766 g/mol g/mol in bovine in bovine retina [8] retina—main [ 8component] of VLC-PUFA-PC of bovine retina [122]; in 494847 - - - - CC34:532:732:6nn-3-3 CC3432HH585052OO2 2 - - 498.836468.766466.75 g/molg/mol g/mol inbullin bovine ram spermatozoa and retina bull [8] spermatozoa [7] [7] bullin bovine spermatozoa retina [8] [7]— main component of VLC-PUFA-PC of bovine retina [122]; in 4850 - - - - CC32:734:6nn-3-3 CC3234HH5056OO2 2 - - 466.75496.82 g/mol g/mol in ram and bull spermatozoa [7] 49 - - C34:5n-3 C34H58O2 - 498.836 g/mol ininram bovine bovine and retinabull retina spermatozoa [8] [8]— main component [7] of VLC-PUFA-PC of bovine retina [122]; in 525048------C36:6n-3CC34:632:7nn-3- 3 C36CHC3432H60H5650OO22 2 -- - 524.874496.82466.75 g/mol g/molg/mol in ram in bovineand bull spermatozoa retina [8] [7] 49 - - C34:5n-3 C34H58O2 - 498.836 g/mol raminin bovine bovine and bull retina retina spermatozoa [8] [8] —main [7] component of VLC-PUFA-PC of bovine retina [122]; in 51 - - C36:5n-3 C36H62O2 - 526.89 g/mol in bovine retina [8] 5049 - - C34:634:5n-3 C34H5658O2 - 498.836496.82 g/mol g/mol in bovine retina [8] 5351- - -- C36:6n-3C36:5n-3 C36CH36H6062O22 -- 524.874526.89 g/mol g/mol ininram bovinebovine in and normal retinabullretina spermatozoa [8][8] human —main component [7] brain [122 of VLC] -PUFA-PC of bovine retina [122]; in 5052 - - - - CC34:636:6nn-3-3 CC3436HH5660OO2 2 - - 496.82524.874 g/mol g/mol in bovine retina [8] —main component of VLC-PUFA-PC of bovine retina [122]; in 525150 - - - - CC36:636:534:6nn-3-3 CC363634HH606256OO2 2 - - 524.874526.89496.82 g/molg/mol inramin bovine bovine and bull retina retina spermatozoa [8] [8] [7] 53 - - C36:6n-3 C36H60O2 - 524.874 g/mol ramin normal and bull human spermatozoa brain [122] [7] 535152 ------CCC36:636:536:6nnn--33-3 CCC363636HH606260OO22 2 MODIFICATIONS-- - OF524.874526.89524.874 OMEGA-3 g/molg/mol g/mol FATTYininin normalbovine bovine ACIDS retinahuman retina [8] [8] brain [122] 51 - - C36:5n-3 C36H62O2 MODIFICATIONS- OF OMEGA-3 FATTY526.89 ACIDS g/mol in bovine retina [8] 5253 - - - - CC36:636:6nn-3-3 CC3636HH6060OO2 2 MODIFICATIONSH O - - OF OMEGA-3 FATTY524.874524.874 ACIDS g/mol g/mol inin bovine normal retina human [8] brain [122] 36 60 2 H O 52 (8Z)-5--oxo -11- - 5C-oxo,36:6n 11-3- C H O O O - O 524.874 g/mol in bovine retina [8] 53 - - C36:6n-3 C36H60O2 - OH 524.874 g/mol in normal human brain [122] (8Z)-5-oxo-11-hydroxyundec- 5-oxo, 11-OH, MODIFICATIONS OF OMEGAH -3 FATTY ACIDS (8Z)-5-oxo-11- 5-oxo, 11- H OO O O OH 531 hydroxyundec- -8-enoic acid - OHC36:6, 11n--O3 - CC1736H2860O102 - O 524.874392.40 g/mol g/mol in normalYoungia humanjaponica brain [123] [122] 1 - C17H28O10 MODIFICATIONS OF OMEGAH O -3 FATTY392.40 ACIDS g/mol in Youngia japonica [123] 17 28 10 OH 8-enoic acid1 11-O-glucoside hydroxyundec(8Z)-5-oxo-8-enoic-11- acid 11-O-Glu-C11:1- OH5-oxo,, 11n-3- O11-- C H O H O O O O O O OH 392.40 g/mol in Youngia japonica [123] HO 11-O-glucoside Glu-C11:1n-3 MODIFICATIONS OF OMEGAH -3 FATTY ACIDS OH OH H O 1 hydroxyundec11(8-ZO)--glucoside5-oxo-8--11enoic- acid - Glu5OH--oxo,C11, 11 :111-nO--3- C17H28O10 O O HO O O O O OH 392.40 g/mol in Youngia japonica [123] HOH OH (8Z)-5-oxo-11- 5-oxo, 11- O O O O OH 1 hydroxyundec11-O-glucoside-8-enoic acid - GluOH-,C11 11-:1On- -3 C17H28O10 OHO HO 392.40 g/mol in Youngia japonica [123] OH H (9Z)-12-oxododec-9-enoic 12-oxo- 17 28 10 OH 1 hydroxyundec-8-enoic acid - OH, 11-O- C H O O O O 392.40 g/mol in Youngia japonica [123] 2 11-O-glucoside - Glu-C11:1n-3 C12H20O3 O HO H 212.289 g/mol present in many plants in large quantities, inter alia, in mature soybeans [124,125] Z (9Z)-12-oxododec-9-enoic 12-oxo- OH OH (9 )-12-oxododec- acid C12:1n-3 H 2 11-O-glucoside - Glu-C11:1n-3 C12H20O3 O HO O 212.289 g/mol present in many plants in large quantities, inter alia, in mature soybeans [124,125] 2 - 12-oxo-C12:1n-3 C12H20O3 OH H 212.289 g/mol present in many plants in large quantities, inter alia, in mature soybeans [124,125] (9Z)-12-oxododecacid -9-enoic C12:112-oxon-3- H O 9-enoic acid O 2 - C12H20O3 O 212.289 g/mol present in many plants in large quantities, inter alia, in mature soybeans [124,125] O H H (9Z)-12-oxododecacid -9-enoic 12C12:1-oxon--3 H O 12 20 3 H 2 (9Z) --1212--oxododechydroxydodec-9-enoic-9- - 12-OHoxo- C H O O H 212.289 g/mol present in many plants in large quantities, inter alia, in mature soybeans [124,125] acid C12:1n-3 H O O O 23 HDA- C12H2022O3 H 212.289214.305 g/mol presentwidespread in many among plants plants in large[126– quantities,128] inter alia, in mature soybeans [124,125] O H (9Z) -12-hydroxydodec-9- 12-OH- O (9Z) enoicacid acid C12:1n-3 12 22 3 H O O 3 HDA C H O H O 214.305 g/mol widespread among plants [126–128] H (9Z) -12enoic-hydroxydodec acid -9- C12:112-OHn-3- O O 3 HDA C12H22O3 O O 214.305 g/mol widespread among plants [126–128] 3 -12-hydroxydodec-9-enoic HDA 12-OH-C12:1n-3 C12H22O3 H H 214.305 g/mol widespread among plants [126–128] (9Z) -12-hydroxydodecenoic acid -9- 12C12:1-OHn--3 O O 12 22 3 O H O 3 (9Z) -12-hydroxydodec-9- HDA 12-OH- C H O H 214.305 g/mol widespread among plants [126–128] acid (9Z,11E,15Z)-13- 13- O O enoic acid C12:1n-3 12 22 3 H O 3 HDA C H O H O 214.305 g/mol widespread among plants [126–128] O 4 hydroperoxyoctadeca(9Z,11enoicE,15 acidZ)-13 - - 13-LnHPO hydroperoxyC12:113- n-3 C18H30O4 310.43 g/mol in apple and tomato fruits [129] O H O 18 30 4 O 4 hydroperoxyoctadeca9,11,15(9Z,11-trienoicE,15Z)- 13acid- - 13-LnHPO hydroperoxy-C18:313-n-3 C H O O 310.43 g/mol in apple and tomato fruits [129] H H O (9Z,11E,15Z)-13- O O 4 hydroperoxyoctadeca9,11,15(9Z,11-trienoicE,15Z)- 13acid- - 13-LnHPO hydroperoxy-C18:313-n-3 C18H30O4 H O 310.43 g/mol in apple and tomato fruits [129] H O 13-hydroperoxy- O (9Z,11E,15Z)-13- 13- O O 4 hydroperoxyoctadeca9,11,15-trienoic acid- 13-LnHPO hydroperoxy-C18:3n-3 C18H30O4 O 310.43 g/mol in apple and tomato fruits [129] 4 hydroperoxyoctadeca- 13-LnHPO C18H30O4 H 310.43 g/mol in apple and tomato fruits [129] 18 30 4 O H 4 hydroperoxyoctadeca- 13-LnHPOC18:3 n-3hydroperoxy C H O O 310.43 g/mol in apple and tomato fruits [129] 9,11,15-trienoic acid -C18:3n-3 O O (9Z,11E,13E,15Z)-4- H H 9,11,15-trienoic acid O 9,11,15-trienoic acid -C18:3n-3 O O O 4-oxo- H (9Z,11E,13E,15Z)-4- 18 26 3 O 5 oxooctadeca-9,11,13,15- - C H O O H 290.403 g/mol as a methyl ester—18% of Chrysobalanus icaco seed oil [81] 4-oxo- O O 5 oxooctadeca(9Z,11E,13-9,11,13,15E,15Z)-4-- - C18:4n-3 C18H26O3 O 290.403 g/mol as a methyl ester—18% of Chrysobalanus icaco seed oil [81] tetraenoic acid O O H C18:44-oxon-3- O 5 oxooctadeca(9Ztetraenoic,11E,13E-,159,11,13,15 acidZ) -4- - - C18H26O3 H 290.403 g/mol as a methyl ester—18% of Chrysobalanus icaco seed oil [81] (9Z,11E,13E,15Z)-4- C4-18:4oxon--3 O O (9Z,11E,13E,15Z)-4- 18 26 3 5 oxooctadecatetraenoic-9,11,13,15 acid - - 4-oxo- C H O O 290.403 g/mol as a methyl ester—18% of Chrysobalanus icaco seed oil [81] 5 oxooctadeca-9,11,13,15- 2-Hydroxy- - C18:4n-3 C18H26O3 290.403 g/mol as a methyl ester—18% of Chrysobalanus icaco seed oil [81] 5 oxooctadeca-9,11,13,15-tetraenoic(9Z,12Z,15 acidZ)-2 - - 4-oxo-C18:4Cn18:4-3n-3 C18H26O3 290.403 g/mol as a methyl ester—18% of Chrysobalanus icaco seed oil [81] linolenic2-Hydroxy acid/α- - 2-OH- (9tetraenoicZ,12Z,15Z acid)-2- O tetraenoic6 acidhydroxyoctadeca-9,12,15- linolenic acid/α- 2-OH- C18H30O3 294.435 g/mol 5.4% of Salvia nilotica seed oil [55] hydroxylinolenic2-Hydroxy- C18:3n-3 O 6 hydroxyoctadeca(9trienoicZ,12Z,15 acidZ-9,12,15)-2 - - C18H30O3 294.435 g/mol 5.4% of Salvia nilotica seed oil [55] hydroxylinoleniclinolenic2-Hydroxyacid acid/α - - C18:32-OHn-3- H O O H 6 hydroxyoctadeca(9trienoicZ,12Z,15 acidZ)-- 29,12,15- - C18H30O3 O 294.435 g/mol 5.4% of Salvia nilotica seed oil [55] linolenichydroxylinolenic2-Hydroxyacid acid/α - - 2-OH- H O O H (9Z,12Z,15Z)-2- C18:3n-3 O H 6 hydroxyoctadecatrienoic acid-9,12,15 - C18H30O3 O 294.435 g/mol 5.4% of Salvia nilotica seed oil [55] linolenic acid/α- 2-OH- H O O H hydroxylinolenicacid O H 6 hydroxyoctadeca-9,12,15- C18:3n-3 C18H30O3 294.435 g/mol 5.4% of Salvia nilotica seed oil [55] trienoic acid O hydroxylinolenic C18:3n-3 H O O H acid HO trienoic acid O 2.1% of the seed oil of Lesquerella auriculata (this fatty acid is a major component of acid H O O H O H 2.1% of the seed oil of Lesquerella auriculata (this fatty acid is a major component of (9Z,12R,15Z)-12- O Lesquerella species seed oils from southeastern regions of the U.S.) [130]; the largest OH 12-OH- O 7 hydroxyoctadeca(9Z,12R,15Z)-12--9,15- densipolic acid C18H32O3 296.451 g/mol Lesquerella2.1average% of thecontent species seed inoil seed the of Lesquerellaoilsseeds from of the southeastern auriculata eastern U.S.(this regions species: fatty acidof L.the isperforata U.S.)a major [130], L. component stonensis; the largest, L. of 12-OH- O C18:2n-3 18 32 3 2.1% of the seed oil of Lesquerella auriculata (this fatty acid is a major component of 7 hydroxyoctadeca(9Zdienoic,12R,15 acidZ)--129,15 - - densipolic acid C H O O 296.451 g/mol averageLesquerelladensipila content, L. species lyrata in, theandseed seeds L oils. lescuria fromof the— southeastern easternover 40% U.S. of species:regionstotal fatty ofL. perforatatheacids U.S.) [131], [130]L.; stonensisin ;cv the Linola largest, L. C18:212-OHn-3- 2.1% of the seed oil of Lesquerella auriculata (this fatty acid is a major component of 7 hydroxyoctadeca(9Zdienoic,12R,15 acidZ)-12 -9,15- - densipolic acid C18H32O3 296.451 g/mol densipilaLesquerellaaverage989 Linum, L.content species lyratausitatissimum ,in andseed the L seedsoils. lescuria(low from of linolenic —the southeasternov easterner 40%flax) U.S.of seeds totalregions species: at fatty levels of L.acidsthe perforataof U.S.) 0.[131]2 to [130], ; 1 L.in% stonensis cv;[132] the Linola largest , L. (9Z,12R,15Z)-12- 12C18:2-OHn--3 Lesquerella species seed oils from southeastern regions of the U.S.) [130]; the largest 7 hydroxyoctadecadienoic acid-9,15 - densipolic acid 12-OH- C18H32O3 296.451 g/mol 989averagedensipila Linum content, L.usitatissimum lyrata in, theand seeds L(low. lescuria oflinolenic the— easternov erflax) 40% U.S. seeds of species:total at levels fatty L. acidsofperforata 0.2 [131]to ,1 L.%; in stonensis[132] cv Linola , L. C18:2n-3 O 7 hydroxyoctadeca-9,15- densipolic acid C18H32O3 H 296.451 g/mol average content in the seeds of the eastern U.S. species: L. perforata, L. stonensis, L. dienoic acid C18:2n-3 O densipila989 Linum, L. usitatissimumlyrata, and L. lescuria(low linolenic—over flax)40% ofseeds total at fatty levels acids of 0. [131]2 to ;1 in% cv[132] Linola dienoic acid H densipila, L. lyrata, and L. lescuria—over 40% of total fatty acids [131]; in cv Linola O 989 Linum usitatissimum (low linolenic flax) seeds at levels of 0.2 to 1% [132] H 989 Linum usitatissimum (low linolenic flax) seeds at levels of 0.2 to 1% [132] O H O H

Nutrients 2018, 10, x FOR PEER REVIEW 10 of 34 Nutrients 2018, 10, x FOR PEER REVIEW 10 of 34

46 - - C32:5n-3 C32H54O2 - 470.782 g/mol in bovine retina [8] 46 - - C32:5n-3 C32H54O2 - 470.782 g/mol in bovine retina [8]— main component of VLC-PUFA-PC of bovine retina [122]; in 47 - - C32:6n-3 C32H52O2 - 468.766 g/mol bullin bovine spermatozoa retina [8] [7]— main component of VLC-PUFA-PC of bovine retina [122]; in 47 - - C32:6n-3 C32H52O2 - 468.766 g/mol bull spermatozoa [7] 48 - - C32:7n-3 C32H50O2 - 466.75 g/mol in ram and bull spermatozoa [7] 48 - - C32:7n-3 C32H50O2 - 466.75 g/mol in ram and bull spermatozoa [7] 49 - - C34:5n-3 C34H58O2 - 498.836 g/mol in bovine retina [8] 49 - - C34:5n-3 C34H58O2 - 498.836 g/mol in bovine retina [8]— main component of VLC-PUFA-PC of bovine retina [122]; in 50 - - C34:6n-3 C34H56O2 - 496.82 g/mol ramin bovine and bull retina spermatozoa [8]—main [7]component of VLC-PUFA-PC of bovine retina [122]; in 50 - - C34:6n-3 C34H56O2 - 496.82 g/mol ram and bull spermatozoa [7] 51 - - C36:5n-3 C36H62O2 - 526.89 g/mol in bovine retina [8] 51 - - C36:5n-3 C36H62O2 - 526.89 g/mol in bovine retina [8] 52 - - C36:6n-3 C36H60O2 - 524.874 g/mol in bovine retina [8] 52 - - C36:6n-3 C36H60O2 - 524.874 g/mol in bovine retina [8] 53 - - C36:6n-3 C36H60O2 - 524.874 g/mol in normal human brain [122] 53 - - C36:6n-3 C36H60O2 MODIFICATIONS- OF OMEGA-3 FATTY524.874 ACIDS g/mol in normal human brain [122] H MODIFICATIONSO OF OMEGA-3 FATTY ACIDS H O (8Z)-5-oxo-11- 5-oxo, 11- O O O OH H (8Z)-5-oxo-11- 5-oxo, 11- O O O 17 28 10 O OH 1 hydroxyundec-8-enoic acid - OH, 11-O- C H O H O 392.40 g/mol in Youngia japonica [123] OH 1 hydroxyundec-8-enoic acid - OH, 11-O- C17H28O10 O 392.40 g/mol in Youngia japonica [123] 11-O-glucoside Glu-C11:1n-3 HO O OH OH 11-O-glucoside Glu-C11:1n-3 HO O OH O (9Z)-12-oxododec-9-enoic 12-oxo- H 2 - C12H20O3 212.289 g/mol present in many plants in large quantities, inter alia, in mature soybeans [124,125] (9Z)-12-oxododec-9-enoic 12-oxo- O H acid C12:1n-3 H 2 - C12H20O3 O 212.289 g/mol present in many plants in large quantities, inter alia, in mature soybeans [124,125] Nutrients 2018, 10, 1662 acid C12:1n-3 H O 11 of 33 H O O H (9Z) -12-hydroxydodec-9- 12-OH- O 12 22 3 O 3 (9Z) -12-hydroxydodec-9- HDA 12-OH- C H O H 214.305 g/mol widespread among plants [126–128] enoic acid C12:1n-3 O 3 HDA C12H22O3 214.305 g/mol widespread among plants [126–128] enoic acid C12:1n-3 H O O H O (9Z,11E,15Z)-13- 13- O TableH O 1. Cont. O 4 hydroperoxyoctadeca(9Z,11E,15Z)-13- - 13-LnHPO hydroperoxy13- C18H30O4 310.43 g/mol in apple and tomato fruits [129] 18 30 4 4 hydroperoxyoctadeca9,11,15-trienoic acid - 13-LnHPO hydroperoxy-C18:3n-3 C H O O 310.43 g/mol in apple and tomato fruits [129] H 9,11,15-trienoic acid Shorthand-C18:3n-3 O H O Molecular O No IUPAC Name Common Name (Simplified Formula/StructureO Molecular Weight Sources [Refs.] O H Formula O (9Z,11E,13E,15Z)-4- H Formula)4-oxo- O O 5 oxooctadeca(9Z,11E,13-E9,11,13,15,15Z)-4- - - C18H26O3 290.403 g/mol as a methyl ester—18% of Chrysobalanus icaco seed oil [81] C418:4-oxon-3 O 5 oxooctadeca-9,11,13,15- - C18H26O3 290.403 g/mol as a methyl ester—18% of Chrysobalanus icaco seed oil [81] tetraenoic acid C18:4n-3 MODIFICATIONS OF OMEGA-3 FATTY ACIDS tetraenoic acid

2-Hydroxy- 2-Hydroxy- (9Z,12Z,15Z)-2- (9Z,12Z,15Z)-2- αlinolenic2-Hydroxy acid/α- - 2-OH- (9Z,12linolenicZ,15Z)-2- acid/ - O 6 hydroxyoctadeca-9,12,15-6 hydroxyoctadeca-9,12,15- linolenic2-OH-C18:3 acid/α- 2n-OH-3 - C HC18HO30O3 294.435294.435 g/mol 5.4% 5.4% of Salvia of niloticaSalvia seed nilotica oil [55] seed oil [55] hydroxylinolenic C18:3n-3 18 30 3 O 6 hydroxyoctadecatrienoichydroxylinolenic acid-9,12,15 - C18H30O3 294.435 g/mol 5.4% of Salvia nilotica seed oil [55] hydroxylinolenicacid C18:3n-3 H O O H trienoic acid trienoic acid acid acid H O O H H O H O O 2.1% of the seed oil of Lesquerella auriculata (this fatty acid is a major component of O 2.1% of the seed oil of Lesquerella auriculata (this fatty acid is a major component of Lesquerella (9Z,12R,15Z)-12- Lesquerella2.1% of the species seed oil seed of Lesquerella oils from southeasternauriculata (this regions fatty acid of the is aU.S.) major [130] component; the largest of (9Z,12R,15Z)-12- 12-OH- species seed oils from southeastern regions of the U.S.) [130]; the largest average content in the 7 hydroxyoctadeca(9Z,12R,15Z)-12-9,15- - densipolic acid C18H32O3 296.451 g/mol averageLesquerella content species in seedthe seeds oils from of the southeastern eastern U.S. regions species: of L. the perforata U.S.) [130], L. stonensis; the largest, L. C1218:2-OHn--3 7 hydroxyoctadeca-9,15- densipolic acid C18H32O3 296.451 g/mol average content in the seeds of the eastern U.S. species: L. perforata, L. stonensis, L. 7 hydroxyoctadeca-9,15- dienoicdensipolic acid acid 12-OH-C18:2C18:2n-3n-3 C18H32O3 296.451 g/mol densipilaseeds, L. lyrata of the, and eastern L. lescuria U.S.—over species: 40% of totalL. fatty perforata acids [131], L.; in stonensis cv Linola , L. densipila, L. lyrata, dienoic acid dienoic acid 989densipila Linumand, L. L.usitatissimum lyrata lescuria, and L—over .(low lescuria linolenic— 40%over flax) 40% of seedstotalof total at fatty fattylevels acids acidsof 0. 2[131] to [ 1311;% in [132] cv]; inLinola cv Linola 989 Linum usitatissimum 989 Linum usitatissimum (low linolenic flax) seeds at levels of 0.2 to 1% [132] O Nutrients 2018, 10, x FOR PEER REVIEW H (low linolenic flax) seeds at levels of 0.2 to 1% [132] 11 of 34 Nutrients 2018, 10, x FOR PEER REVIEW O 11 of 34 H

H O H O

O O

(11Z,17Z)-14-hydroxyicosa-(11Z,17Z)-14-hydroxyicosa- 14-OH- 32% 32%of the ofseed the oil of seed Lesquerella oil of auriculataLesquerella [130]; the auriculata largest average[130 content]; the in largest the average content in the seeds of 8 8 (11Z,17Z)-14-auricolichydroxyicosa acid- auricolic14-OH-C20:2 acid 14n-OH-3 - C HC20HO36O3 324.505324.505 g/mol 32% of the seed oil of Lesquerella auriculata [130]; the largest average content in the 8 11,17-dienoic acid auricolic acid C20:2n-3 20 C3620H363O3 324.505 g/mol seeds of L. auriculata and L. densiflora—over 30% of total fatty acids [131] 11,17-dienoic acid 11,17-dienoic acid C20:2n-3 seedsL. of auriculata L. auriculataand and L.L. densiflora densiflora—over—over 30% of total 30% fatty of acids total [131] fatty acids [131]

O H O H (2E,6E,10Z)-7-ethyl-3,ll- (2E,6E,10Z)-7-ethyl-3,ll- O CH3 H (2E,6E,10Z)-7-ethyl-3,ll-dimethyl-dimethyl-2,6,10- 3,11-diMe,7- O CH3 H 9 dimethyl-2,6,10- - 3,11-diMe,3,11-diMe,7- C17H28O2 O CH 264.41 g/mol converted to the juvenile hormon in the moth Hyalophora cecropia males [133] 3 9 tridecatrienoic acid (also as a - Et-C13:3n-3 C17H28O2 CH3 264.41 g/mol converted to the juvenile hormon in the moth Hyalophora cecropia males [133] 9 2,6,10-tridecatrienoic acid - C17H28O2 O CH3 264.41 g/mol converted to the juvenile hormon in the moth Hyalophora cecropia males [133] tridecatrienoic acid (also as a Et-C13:3n-3 CH3 methyl ester) 7-Et-C13:3n-3 (also as a methyl ester) methyl ester)

Nutrients 2018, 10, 1662 12 of 33

2. Sources of Omega-3 Fatty Acids In the years 2003–2008 people in the US consumed, with food, on average 0.17 g/day (median intake 0.11 g/day) of long-chain omega-3 fatty acids (DHA, EPA and EPA equivalents (5% from conversion of ALA, 33% from conversion of SDA)), i.e., lower than the recommended 0.5 g/day. Among people consuming omega-3 fatty acids in the group below or at the 15th percentile of omega−3 FAs total consumption, the most important source of omega-3 acids were cereal products (36%), while in the group above or at the 85th percentile, the dominant source was fish (fish and mixtures; 71%—in contrast to the low-intake group, where the fish consumption was 1%). In both groups, the intake of seeds and nuts was low, and vegetables were consumed at 9% and 2%, respectively [134]. As can be easily seen, the share of omega-3 fatty acids in the diet is most affected by the supply of fish, because they are the primary source of EPA and DHA for humans [135]. This is due to the fact that the food of many fish are algae rich in EPA and DHA, and other organisms consuming algae, like fish or marine invertebrates [136,137]. Microalgae play a key role in the primary production of PUFAs and are their main source in seawater. Marine invertebrates are also an important and basic source of omega-3 PUFAs due to their ability to synthesize some of them de novo, for example, oyster Crassostrea gigas can produce EPA and DHA by consuming microalgae that do not contain both [137]. Seafood contains many valuable omega-3 acids. However, their frequent consumption exposes the human body to the neurotoxic effect of methyl mercury, which is especially harmful for the development of the central nervous system of the fetus [138]. Therefore, it is advisable to look for other sources of these fatty acids, and to include them in a balanced diet. EPA occurs in large amounts in herring (15% of total lipids) [59], wild sardine (13.6% of muscle total FAs) [61] and pollock roe (18.8%) [59]. In plants, it is rather rare. Mention should be made of Undaria pinnatifida (13% of essential oil composition) [107] and Rhododendron sochadzeae (2% of leaf FA hexan extract) [108]. The main sources of DHA are flyingfish, herring, pollock and salmon roe (27.9%, 22.6%, 22.2%, and 17.4% of total lipids, respectively) [59], Cirrhinus mrigata (18.07 g/100 g muscle tissue FAs), and Catla catla (17.98 g/100 g muscle tissue FAs) [58]. The presence of this acid in the jackalberry (4.65 g FA per 100 g oil Diospyros mespiliformis) is noteworthy [139]. As mentioned above, both EPA and DHA are also synthesized from ALA using enzymes—desaturases and elongases [17,22,26,134], although in humans this process is insufficient—the conversion rate is 10–14% for men and women, respectively [136,140]. According to other authors, ALA is converted to EPA with a yield of 0.2 to 21% (in adult men 8%), and to DHA of zero to 9% (in women more than 9%) [141]. DHA can also be a substrate for the creation of EPA and vice versa (the conversion efficiency of EPA to DHA is < 0.1% in adult men) [141,142]. Moreover, ALA is a precursor of DPA as well [143]. α-Linolenic acid (ALA) is common in the higher plants and algae [22]. Rich sources of ALA also include Linum usitatissimum (depending on the genotype it contains from 1.1 to 65.2% of total fatty acids in seeds) [71], chia Salvia hispanica (64.04% of seed oil fatty acids and 16.4 g/100 g of milled chia seeds) [65,68], Trichosanthes kirilowii (33.77–38.66% of seed oils) [70], paprika Capsicum annuum (29.93% of fresh pericarp fatty acids in the Jaranda variety and 30.27% in the Jariza variety) [72], and many others. The content of ALA in fish is small, for example 1.1% in wild sardine (Sardina pilchardus) muscle total FAs [61]. 8(Z),11(Z),14(Z)-Heptadecatrienoic acid, also called norlinolenic acid, was identified in Salvia nilotica [0.4% of mixed esters and 2.3% of IV fraction (% by gas liquid chromatography)] [55]. (all trans)-9,12,15-Octadecatrienoic acid (linolenelaidic acid) is present in Turkish sage species, and the weight per cent of seed FAs of Salvia virgata, Salvia potentillifolia, Salvia recognita, Salvia tomentosa amounts to 0.4, 0.7, 1.1, and 1.4%, respectively [73]. Nicotiana tabacum also contains linolenelaidic acid but in a minor amount, which is 0.03% of tobacco seed oil FAs [74]. Nutrients 2018, 10, 1662 13 of 33

(9Z,12Z,15Z)-2-Hydroxyoctadeca-9,12,15-trienoic acid (2-hydroxylinolenic acid, alpha-hydroxylinolenic acid) is a little known hydroxy acid found in Salvia nilotica (5.4% of Salvia nilotica seed oil) [55]. (11Z,14Z,17Z)-Icosa-11,14,17-trienoic acid (eicosatrienoic acid), sometimes named homo-alpha-linolenic acid, rarely occurs in animal sources—hen egg yolk contains this acid in the amount of only 0.15 – 0.16% of total lipids [101]. Much more was found in Torreya grandis kernel oil (6.78–8.73% of total FAs) [96] and cork Phellodendron lavalei seeds [15.5% of free fatty acids (FFAs)] [98], but the largest amount is contained in Pittosporum undulatum seed oil (31.44% of total FAs) [97]. Close derivatives of alpha-linolenic acid are two acids included in the minor polyenoic acids group [75]. Rumelenic acid (cis-9, trans-11, cis-15-octadecatrienoic acid) is formed by the isomerization of alpha-linolenic acid, while cis-9, trans-11, trans-15-octadecatrienoic acid is the isomer of rumelenic acid. Both acids are found in ruminants, for example in sheep’s milk [69,75]. Docosapentaenoic acid (DPA; (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid), tradinionally called clupanodonic acid, shows structural similarity to EPA but has two more carbon atoms in the chain. Significant amounts are present in meat (13.8/16.7% of wether/ewe (lamb) raw meat FAs) [116], fish roe (5.5% of salmon roe total lipids [59], fish oils (1.04–2.82% of European wels catfish oil) [52], seal oil (2.64–4.74%) [62], and fish muscle (1.6% of wild sardine (Sardina pilchardus) muscle total fatty acids) [61]. DPA sporadically occurs in algae such as Hormosira banksii and Dictyota dichomota (0.07% and 1.6% of total FAs, respectively) [117]. Stearidonic acid (SDA; moroctic acid) is common in plants and fishes. Salmon roe contains a small SDA portion (0.8% of total lipids) [59]; a little more in wild sardine (2.3% of muscle total FAs) [61]. SDA occurs in many plants but in small amounts, except for plants from the families Primulaceae and Boraginaceae, where it can be found in relative big concentrations (mean amounts of 4.73 and 4.99% of seeds total FA methyl esters, respectively). Hippophae rhamnoides (Elaeagnaceae) seeds contain only 0.36% SDA [78]. Particularly noteworthy is Echium humile ssp. pycnanthum, in which seeds had SDA content estimated at up to 16.2% of total FAs [79]. (7Z,10Z,13Z)-Hexadeca-7,10,13-trienoic acid (roughanic acid) occurs in many plants and in fish oils, but usually in small amounts. As a result of reactions catalyzed by lipoxygenases, this is converted to oxygenated metabolites such as 7-, 8-, 10-, 11-, 13-, 14-hydroperoxides, and bis-allylic 9-hydroperoxide. However, hydroxy derivatives of roughanic acid are also present in plants rich in alpha-linolenic acid and not roughanic acid, including soybean and pea seedlings [144]. Omega-3 monounsaturated fatty acids are a small group, although with an undeniable role in nature—some such as (Z)-11-tetradecenoic acid, (E)-11-tetradecenoic acid and (10E,13Z)-10,13-heksadecadienoic acid are pheromone precursors in insects [38]. As contained in generally available food sources, 13Z-hexadecenoic acid, 15Z-octadecenoic acid, 9E-dodecenoic acid and 11E-tetradecenoic acid are especially worth noting. 15Z-octadecenoic acid, found in beef [46], pork [45], cows milk and butter [47], and mature human milk, is relatively common [49,50]. 11E-tetradecenoic acid occurs in Coriandrum sativum, whose leaf essential oil contains 13.37% of this acid [39]. Conjugated fatty acids still require detailed research, as some of them (conjugated linoleic acid) have antitumor activity and a number of properties that give benefits in the fight against hypertension, obesity and diabetes [1,145]. Conjugated omega-3 fatty acids, important from the point of view of their availability in food, are alpha- and beta-parinaric acid. Trans-parinaric acid, also called beta-parinaric acid [88], has all the bonds in the trans configuration. In the case of cis-parinaric acid (alpha-parinaric acid [146]), however, the name is somewhat misleading, because its isomerism can be described as cis-trans-trans-cis [147]. Parinaric acid, due to its natural ability of fluorescence and high susceptibility to free radicals, is used (as cis-parinaric acid) as an indicator of lipid peroxidation in cell membranes [148–154] and (as trans-parinaric acid) to assess the effect of temperature change on cell membranes [88,155]. Some organisms are able to convert nonconjugated fatty acids into conjugated counterparts [156]. In addition to tetraenoic parinaric acid, in plants mainly conjugated trienoic acids Nutrients 2018, 10, 1662 14 of 33 are found with 18 and 17 carbon atoms. Acetylenic and dienoic ones may have a different number of methylene bridges [157]. Parinarium laurinum seeds are the richest in alpha-parinaric acid sources (62% of seed oil methyl esters) [81]. Very long-chain fatty acids (VLCFAs; C > 22) play many important roles in the body, including modulating the functions of neutrophils. While their activity decreases with increasing carbon chain length, they remain efficient superoxide production activators in neutrophils, much better than N-formylmethionyl-leucyl-phenylalanine (FMLP) [15]. VLCFAs also have the ability to regulate PKC activity [16]. However, this still requires further research, especially in vivo. Their predisposed location in the body is also interesting—they are found in large amounts in the human brain [7,122,158,159], bovine retina [8,122], ram, bull, boar, and human spermatozoa [7,14] as well as in rat testicles [160], cultures of mouse spermatides and spermatocytes [161], and human vascular endothelial cells culture [162]. The VLC n-3 FAs acids have been found in dipolyunsaturated phosphatydylcholines of bovine retina and sphingomyelin of ram spermatozoa, as well as in bull spermatozoa [7,8,14]. In the normal human brain, the presence of VLC n-3 hexaenoic acids (36:6) was also found, but in smaller amounts than omega-6 fatty acids [122]. Tetratriaconta-19,22,25,28,31-pentaenoic acid (34:5) has been described in Marine Sponge (Petrosia pellasarca)[120]. There are numerous modifications of omega-3 fatty acids, and many of them play the role of hormones or compounds produced in stressful situations in plants. We only mention a few examples that occur in dietary sources. The most important seem to be the previously mentioned 2-hydroxylinolenic acid and two hydroxy acids occurring in plants of the genus Lesquerella—densipolic and auricolic acid [130,163–166]. One of them, densipolic acid, was found in Linum usitatissimum [132]. Another example is (9Z)-12-hydroxy-9-dodecenoic acid (HDA), which is one of the main products of the lipoxygenase pathway, widespread among plants [126–128]. Additionally, oxo fatty acids are prevalent in the plant world. For instance, 12-oxo-cis-9-dodecenoic acid is one of the reaction products catalyzed by the fatty acid hydroperoxide lyase, present in many plants, in large quantities, inter alia, in mature soybeans [124,125]. Table1 lists the acids belonging to all of the groups discussed above.

3. Bioavailability Bioavailability is a relative term, which can refer to both the speed of absorption and the quantity of the substance absorbed. The speed can be understood as the rate at which the substance is absorbed from the gastrointestinal tract and reaches the portal system. Absorption of the substance occurs in the gastrointestinal tract only to a certain extent, depending on many factors. The extent of absorption and the speed of substance transport to the portal circulation describe the bioavailability in the narrower sense. Traditionally, bioavailability can also be considered in a broader context, taking into account the amount of substance that reaches the systemic circulation or the place of physiological destiny (activity) [167]. This broader approach is particularly important when considering the effect of metabolic processes and excretion on the transport of substances from the portal circulation. Not all of the absorbed substance reaches the systemic circulation or tissue compartment consistent with the physiological destination. This difference in amount is very important from the point of view of pharmacokinetics and dietary planning. Fatty acids may be present in the body as free fatty acids, bound to glycerol, to form triacylglycerol (TG), diacylglycerol (DAG) or monoacylglycerol (MAG), or to form a composition of membrane phospholipids. In naturally occurring TG molecules, LC PUFA occupies the second position [167]. In the phospholipids of cell membranes the latter position is competed by EPA and DHA with arachidonic acid, and if necessary, they are released by the enzyme phospholipase A2 and are used to synthesise eicosanoids [136]. Otherwise, in the human brain, VLCFAs (C34–38) are attached to the skeleton of glycerol (glycerol moiety), which in phospholipids are located in the sn-1 position [122]. In fish and fish oils, LC omega-3 PUFAs are mainly found as triacylglycerides and free fatty acids [167,168]. In Krill oil phospholipids are also an important fraction of these fatty acids (30–65% of EPA and DHA), mainly phosphatidylcholine [167,169–171]. EPA and DHA represent approximately Nutrients 2018, 10, 1662 15 of 33

18% and 12%, respectively, of the content of naturally occurring fish oils [167]. However, due to the transesterification process, oil blends often contain much more of both EPA and DHA. This process is related to the substitution of the removed glycerol backbone with ethanol, resulting in the formation of ethylesters (EE), which can then be converted to re-esterified TG (rTG)-ethanol is enzymatically removed, resulting in free fatty acids being released, then attached by enzymes back to the glycerol backbone [167,168]. An example of a drug in which the content of EPA (DHA) is increased as a result of transesterification is Lovaza [168,172]. Another method to increase the content of EPA and DHA has been used in Epanova. Glycerol is removed and replaced with a hydrogen atom, which, in combination with the released fatty acid, forms a carboxylic acid. Ethylesters (of which Lovaza is composed) require the hydrolysis of the ester bond by pancreatic lipase before they release the free fatty acids that can be absorbed in the small intestine. This step is not required by the carboxylic acids. Interestingly, EPA and DHA-EE are also absorbed unchanged. However, this form accounts for < 1% of the total pool of EPA and DHA in circulation after ingestion of omega-3 acids EE [168]. In rTG, LC PUFAs take up not mainly the sn-2 position (which takes place in natural TG), but can also (simultaneously) be bound in the position of sn-1 or sn-3 with equal paradigmicity. rTG particles frequently contain two LC PUFAs—then the probability of binding EPA and DHA in the sn-1 or sn-3 position is higher than in the sn-2 position [167]. According to Schuchardt, [167] binding of LC omega-3 PUFA to glycerol in the sn-1/3 position facilitates the lipase hydrolysis of the bond, thus increasing bioavailability. According to Dyerberg, [173] the presence of MAG and DAG in rTG mixtures increases the absorption of LC PUFAs in the intestine due to the easier formation of micelles. Bandarra [174], in turn, based on the results of his research on hamsters, proves that the location of DHA in the sn-2 position increases the absorption of this acid in the intestine and its incorporation into tissues. However, a certain limitation of Bandarra’s study is that the author used a commercially available fish oil, which is known only to be rich in DHA with an unspecified binding site with the glycerol backbone—we do not know what part of DHA is associated in positions other than sn-2.

3.1. Methods of Measuring the Bioavailability of Omega-3 Fatty Acids We can measure omega-3 FAs concentration in plasma, serum, blood cells and lymph. The content of FAs in the plasma reflects the short to medium-long supply of fatty acids in the diet, while the concentration of fatty acids in the blood cells is usually a good indicator of long-term bioavailability [167,175]. As far as the long-chain omega-3 fatty acids are concerned, it is possible to measure many markers that indicate the presence of DHA in a specific form, but only one (the level of phospholipid EPA in plasma) that is useful for determining the level of EPA [167,176]. Admittedly, erythrocyte EPA is a weak dose-dependent indicator of LC omega-3 PUFAs substitution at normal dietary levels, however (sum of), erythrocyte EPA and DHA concentration seems to be, as will be mentioned below, a relatively good indicator of long-term bioavailability and also reflects the content of LC omega-3 PUFAs in non-blood tissues [167,177]. In Browning’s study, [177] EPA + DHA-PC (in the case of sudden changes in intake) and platelet/mononuclear cells EPA + DHA (in the case of long-term consumption assessment) were considered biomarkers that best represent the intake of fish with high fat content in a typical UK population (1–4 servings a week).

3.2. Chemical Binding The bioavailability of omega-3 fatty acids can also be expressed by calculating different coefficients, the most important of which seem to be omega-3 index, Cmax and AUCt (area under the (concentration-time) curve), the modification of which is the incremental area under the curve (iAUCt)[169]. The omega-3 index is defined as the proportion of the sum of EPA and DHA content in the total fatty acid content in the erythrocyte (erythrocyte membrane), and is expressed as a percentage [167,178,179]. It is a good indicator of long-term bioavailability (from the last 80–120 days [179]) due to the long lifetime of erythrocytes and their high number in the blood. Nutrients 2018, 10, 1662 16 of 33

Plasma content of EPA and DHA, as well as many other fatty acids, weakly correlates or does not correlate at all with the levels of these acids in the erythrocyte membrane [179]. The omega-3 index is also a good indicator of the incorporation of fatty acids into tissues, and this applies not only to gastrointestinal tissues, but also to the myocardium, liver, and kidney [167,180]. It was established that the supply of long-chain omega-3 fatty acids at the level of 1 g/d may result in an increase in the omega-3 index by two percentage points over eight weeks [181]. The omega-3 index is influenced by many factors, such as smoking, physical activity (the intensity of which decreases the omega-3 index), and genes [178]. The maximum levels of EPA and DHA in plasma (Cmax) can be determined five–nine h after administration, while the persistent levels of EPA and DHA in plasma are achieved within two weeks of daily supplementation. The half-life of EPA and DHA after repeated administration is 37 h and 48 h, respectively [170]. The bioavailability of omega-3 fatty acids varies depending on the type of chemical binding (lipid structure), and can be ranked as follows: PL > rTG > TG > FFA > EE [167,178,179,182,183]. Both EE and rTG are not natural components of dietary oils, but they are created in the process of their chemical modification, which is called transesterification. As a result, highly concentrated oils containing up to 90% of EPA and DHA can be obtained [167]. The hierarchical order presented above does not, however, reflect reality to the extent that some authors would like it to. In their trial Kohler et al. [178] proved that the bioavailability of EPA and DHA in the form of phospholipids does not have to be greater than the bioavailability of these acids in the form of triglycerides—the bioavailability of EPA and DHA in krill meal was comparable to their bioavailability in fish oil, despite a slightly higher total fat content in krill meal. Yurko-Mauro et al. [184] achieved similar results—krill oil containing almost 44% of phospholipids showed bioavailability similar to the bioavailability of fish oil, both in the form of triglycerides and ethyl esters. This indicates the (great) share of non-chemical binding (and total fat content) factors in shaping the bioavailability of omega-3 fatty acids [169,178,185]. One explanation may be the observation of Nordoy, Reference [186], who noticed similarly good absorption of omega-3 fatty acids (including EPA and DHA) in the form of TG and EE if they are administered as a component of fish oil in equivalent amounts. Both krill oil, and to a lesser extent, krill meal and fish oil, which are rich in fat. Many studies, however, maintain that krill oil, especially when very rich in phospholipids, is characterized by extremely high bioavailability, significantly higher than triglyceride-rich fish oil [170,187–189]. Those also find an understandable explanation. Between the omega-3 PUFAs bound to phospholipids and those linked to triglycerides, there is some difference associated with predestination to a specific type of blood transport and metabolism in the liver. DHA-TG is preferentially assigned to LDL-PL, while DHA-PL is preferentially assigned to HDL-PL. It was also found that omega-3 PUFAs, including DHA, in the form associated with phospholipids, are more intensely embedded in tissues. This is probably due to the better availability of LC n-3 PUFA-PL acids contained in krill oil than those present in fish oil LC n-3 PUFA-TG for liver beta-oxidation pathways [189]. Krill oil inhibits de novo lipogenesis, but enhances fatty oxidation [170].

3.3. Brain Transport Omega-3 acids are incorporated into the cell membrane of many organs and tissues, above all the heart, nervous tissue and retina [167]. Oral supplementation with omega-3 PUFAs increases the content of these acids in the cerebrospinal fluid [190]. Efficient passage of the blood-brain barrier, however, requires carrier particles—in the case of DHA, it is 1-lyso, 2-docosahexaenoyl-glycerophosphocholine (LysoPC-DHA), which increases intracerebral DHA transport up to 10-fold. It is a brain-specific particle and does not facilitate the transport of DHA to the heart, liver or kidney, although detailed studies are required in humans. Carriers (transporting DHA to the brain) with potentially better properties are synthesized, an example of which is obtaining of AceDoPC (1-acetyl,2-docosahexaenoyl-glycerophosphocholine) [191]. Nutrients 2018, 10, 1662 17 of 33

3.4. Parenteral Administration Most of the studies, especially those based on humans, which serve to determine the bioavailability of omega-3 acids, apply to their oral administration. It is difficult to fully validate the parenteral administration of omega-3 fatty acids in relation to the healthy population, because this method of supply is reserved mainly for patients undergoing intensive therapy, both adults and preterm infants [142,192,193]. In addition, it is worth noting that parenteral administration of mixtures based on fish oil may lead to biochemical liver damage and even the progression of fibrosis in this organ [194]. Al-Taan et al. [195] conducted a study on 20 patients awaiting the surgical removal of colorectal metastases from liver cancer. These individuals had normal liver function tests and plasma lipid levels within the reference range. The aim of the study was to assess the content of fatty acids in plasma phosphatidylcholine and erythrocytes during and after intravenous infusion of oil emulsion. Phosphatidylcholine (PC) is the main phospholipid that can be found in the circulation (blood) and erythrocyte (membrane) during and shortly after intravenous infusion of the oil emulsion. Parenteral administration of DHA and EPA lipid emulsion allowed a rapid and significant increase in their blood levels (EPA/DHA in plasma PC and EPA in erythrocytes). However, EPA levels returned to their initial values five–12 days after the end of the infusion. Not only Al-Taan, but also Browning [177], suggested a quicker turnover of EPA than DHA in cells, and thus this effect occurs with both oral and intravenous supply, with a different time of administration. The fact of a relatively short infusion of oil emulsion is also significant.

3.5. Matrix Effect and Emulsification Many authors emphasize the key role of the fat content in food in the absorption of omega-3 acids (‘the matrix effect’ [167,179]) and suggest the necessity of introducing a recommendation to consume formulations containing omega-3 fatty acids with high-fat food [167,178,196]. Schuchardt underscores the lack of the expected cardioprotective effect in the German population supplementing omega-3 PUFAs during breakfast due to the relatively low-fat typical German breakfast [167]. Similarly, American society is in the habit of eating a low-fat breakfast, which in their case contains only 16% of the fat consumed during the day [197]. In addition, the fat content of food is sometimes inversely proportional to the amount of omega-3 fatty acids it contains. For example, high-fat plants may have few omega-3 fatty acids—Entandrophragma angolense—a potential health benefit food source has fat estimated as 59.43% of fresh weight. However, 33.29 weight % of Entandrophragma seed oil contains oleic acid and only 0.2 weight % is alpha-linolenic acid [139,198]. Chia, on the other hand, contains oil in the amount of 27 g per 100 g of seeds, of which 64.04% is ALA and only 14.98% are saturated fatty acids [68]. Soybean contains slightly less fat. However, the high content of linoleic acid and the unfavourable omega-6/omega-3 ratio make it a food of dubious health value, especially because it has been shown that induction of obesity in mice with soybean oil is possible [95,139,199]. The fat contained in the diet stimulates the pancreas to secrete fat-digesting enzymes and the gallbladder to eject bile that contains bile salts, which emulsify fats and activate pancreatic lipase [196]. However, it is recommended that persons with a high cardiovascular risk should reduce the supply of animal fat. On the other hand, substituting animal fat with vegetable fat is not necessarily a good solution, taking into account eating habits, ubiquitous overweight and often low content of omega-3 fatty acids in rich-fat plants. These people benefit from the achievements of nanotechnology, among which Cavazos-Garduno [200] mentions nanoparticles, nanospheres, nanocapsules, solid lipid nanoparticles (SLN), self-emulsifying drug delivery systems (SEDDS) and nanoemulsions, which significantly improve the absorption of fatty acids in a low-fat environment. Research indicates that particles smaller than 0.2 micrometers are absorbed better. The self-microemulsifying delivery system (SMEDS) contains LC n-3 FA-EE and a number of compounds that are emulsified in the stomach without the need for a high-fat meal [196]. It has been known for many years that emulsified omega-3 acids are characterized by equally good bioavailability Nutrients 2018, 10, 1662 18 of 33 in poor and high fat environments [196,201]. Qin analysis [196] indicates that the absorption of DHA + EPA EE contained in SMEDS preparations is 6 times higher than DHA + EPA EE alone. To confirm the effectiveness of SMEDS technology, long-term studies are needed to analyze the embedding process of the above-mentioned fatty acids in the structure of cell membranes, especially erythrocytes. The benefits of emulsification were also described by Puri, [138]. He used similar self-nanoemulsifying drug delivery systems (SNEDDS). Absorption of omega-3 fatty acid ethylesters can also be enhanced through the use of Advanced Lipid Technologies (ALT). ALT is, according to the manufacturer, a special lipophilic system that, regardless of the supply of food and the fat content thereof, increases the bioavailability of lipid-based compounds, including omega-3 fatty acid ethyl esters, generating the spontaneous formation of micelles. An example of a preparation equipped with this component is SC401 (DHA and EPA ethylesters + Advanced Lipid Technologies). In the supply of low-fat food, the intake of SC401 was associated with significantly higher values demonstrating the bioavailability of DHA and EPA than Lovaza (nearly 2-fold higher Cmax and 3-fold higher AUC(0-last)). Free fatty acids are another example of a formula well absorbed with a low fat content in the diet. Epanova bioavailability in conditions of low fat supply is much greater than with Lovaza (AUC(0−t) for Epanova is four times higher than for Lovaza), which in turn, consumed with high-fat food, has similar bioavailability as SC401 accepted in conditions of low food supply [201]. Vegetarians and vegans will also be able to use the emulsification technique in line with their own lifestyle, as the results of the latest research indicate the possibility of using vegetable proteins from pea, lentil, and faba bean as emulsifiers [202]. Moreover, oil-in-water nanoemulsions are constructed using vegetarian oils (algae and flaxseed oil) [202,203]. A very common method of the incorporation of nanoemulsion into food is its transformation, most often into the form of powder, using microencapsulation [204]. Microencapsulation stabilizes the oil mixture, protects it against oxidation, and eliminates the phase difference often present when mixed with food [181]. Microencapsulation of fish oil increases the bioavailability of omega-3 PUFAs to a value very close to the bioavailability of these acids in meals rich in fish oil in liquid form [205]. Emulsification increases the bioavailability of LC omega-3 PUFAs by increasing the efficiency of incorporation into triacylgliceryde-rich lipoproteins [206]. Emulsifiers also modify the expression of genes responsible for the transport of fatty acids in enterocytes [143]. Emulsification (pre-emulsification) increases the absorption of LC PUFAs, including DHA, EPA, and ALA, but does not have the effect on the absorption of fatty acids having shorter chain length and fewer unsaturated bonds [143,207,208]. Of course, emulsification elevates not only the bioavailability of omega-3 acids in the blood, but also in the lymph. Emulsifiers used in food are part of this mechanism. For example, soya lecithin added to flaxseed oil increases the number and size of ALA-rich chylomicrons produced by enterocytes. However, another emulsifier, sodium caseinate, significantly reduces the absorption of ALA in the intestine. This is probably related to the effect on the expression of the FABP2 gene, which is involved in the transport of fatty acids in enterocytes. It was noted that the presence of soy lecithin in the emulsion was accompanied by high expression of this gene, whereas the use of sodium caseinate was associated with a decrease in FABP2 gene expression [143]. This process requires careful research on humans, because it is likely that the effect of emulsifiers on gene expression should be considered during food production, especially when we expect a specific healing effect.

4. Interactions between Long-Chain Polyunsaturated Fatty Acids Linoleic acid (LA), which is omega-6 fatty acid, competes with ALA for enzymes converting alpha-linolenic acid to EPA, DPA, and DHA. LA is (similarly to arachidonic acid), inter alia, the precursor of eicozanoids, while DHA, DPA, and EPA can be transformed into anti-inflammatory agents. [25,26,209]. Changes in the supply of omega-6 PUFAs affect the plasma concentration of omega-3 fatty acids. This applies to both non-esterified omega-3 fatty acids and those associated with Nutrients 2018, 10, 1662 19 of 33 phospholipids, triglycerides, and cholesteryl esters. Taha et al. [209] showed that reducing the supply of omega-6 PUFAs for 12 weeks increases the concentration of omega-3 PUFAs in the plasma. In addition, the simultaneous increase in the supply of omega-3 PUFAs for a dozen weeks further elevates the concentration of these acids in the plasma and lowers the level of arachidonic acid. An important interaction of omega-6 PUFAs with omega-3 PUFAs is the production of non-native thromboxanes and leukotrienes [170]. This probably results, among others, from the substrate competition for the catalytic center of desaturases and elongases, and the reduction of arachidonic acid production with a sufficiently high supply of n-3 PUFAs. Based on Wood’s critical analysis, [185], it can be concluded that an increase in EPA level and also in a certain degree of DHA can probably be achieved by reducing the supply of linoleic acid and/or increasing the intake of alpha-linolenic acid, although the extent of the change is small. It is suggested to maintain the ratio of omega-6/omega-3 consumption in the range from 1/5 to 1/10, and ideally, as in Japanese society, from 1/2 to 1/4 [141,210]. In turn, for breastfeeding mothers, this ratio should not exceed 10 [211]. Meanwhile, the diets of Western societies are characterized by a clear advantage of the supply of omega-6 fatty acids and the ratio of n-6/n-3 shaping in the range of 15/1 to 16.7/1 [212]. The discussion about the preferred ratio of consumption of omega-6 to omega-3 fatty acids has been going on for many years and still has not produced convincing results. Researchers are wondering about the legitimacy of returning to an “ancestral diet”, which is attributed to the balanced consumption of both groups of fatty acids at the level of 1:1 [213–216]. Attention is also paid to certain health benefits that may result from a strictly defined omega-6 to omega-3 ratio, as exemplified by the postulated beneficial effect of the 4:1 ratio on the functioning of the nervous system or reduction of tumor cell proliferation in patients with colorectal cancer who they were nourishing themselves, keeping the ratio 2.5:1 in the diet [212,217–219]. The above authors indicate the desirability of consuming up to four times more omega-6 fatty acids than omega-3 and this value depends on the disease under consideration. Regardless of the symptoms or lack thereof, most researchers postulated not exceeded intakes omega6/omega-3 at 10 [211,213]. In light of eating habits of the societies of many highly developed countries, a certain compromise seems to be current recommendations for the consumption of omega-6 and omega-3 fatty acids, which shape the omega-6/omega-3 index in the range from 7:1 to 11:1 [220]. Kohler et al. [178] studied the bioavailability of DHA and EPA added in the form of ethyl esters to sausages with similar ALA content. Both the Omega-3 index and the percentage of EPA and DHA in erythrocytes increased significantly more in the verum group than in the control (placebo) group, in which they remained almost unchanged. The content of DPA similarly increased in both groups. The absence of a significant increase in EPA and DHA in the control group, despite ALA supplementation in both groups, is not surprising, as ALA is converted to EPA and DHA to a very small extent [136,140,141]. The difference in the increase in EPA, DHA and DPA levels in the control group may be due to the different conversion efficiency of ALA to the above-mentioned acids, although this is not the only reason, because these acids may also be converted into each other. Interestingly, the ALA level increased slightly in the control group (p = 0.038), while in the treatment group it decreased slightly (p = 0.141). Despite the small difference in these ALA levels and the lack of statistical significance of ALA decrease in the treatment group, the explanation of large differences in ALA levels after supplementation between individual participants requires careful research on the metabolic interactions of individual omega-3 fatty acids.

5. Lipid Oxidation LC omega-3 PUFAs are sensitive to oxidation [206,221]. Some studies report increased levels of peroxidized lipids in fish oil capsules, and as their regular consumption may adversely affect health, this problem needs to be considered [206]. One of the ways of protecting omega-3 acids against oxidation is the microencapsulation of oils using WPI-GA complex coacervates and spray dried microcapsules [221]. One of the less expensive alternative methods is ionic gelation using Nutrients 2018, 10, 1662 20 of 33

Salvia hispanica mucus in combination with sodium alginate and calcium [222]. The effect of oxidation on the bioavailability of omega-3 fatty acids is not clear. According to Staprans and Naruszewicz [223,224], the consumption of peroxidized vegetable oils increases the number of peroxidized lipids in chylomicrons. Ottestad [206], on the other hand, reports that consumption of oxidised cod liver oil has no effect on the incorporation of omega-3 PUFAs into lipoproteins rich in triacylglycerides.

6. Conclusions Over recent years, there has been significant progress in research on the bioavailability of omega-3 fatty acids. We know more and more of their sources and we understand better the importance of their chemical structure and the form of supplementation. People consume omega-3 fatty acids mainly with fish, and to a lesser extent with cereal products and meat. Some of them, however, do not appear in the abovementioned products, or their presence is unexplored. In addition, the content of individual acids in plants depends on the place of their occurrence, and in animals on the type of diet. Despite the high availability of seafood, which is rich in many omega-3 acids, the authors recognize the need to constantly search for new sources of omega-3 fatty acids due to the risk of excessive exposure to mercury methyl and other toxic compounds present in fishing areas. In addition, some acids, such as coniferonic or juniperonic acid, occur mainly in plants that are not widely used in consumption, or are even poisonous, but can be used in the pharmaceutical industry and medicinal chemistry. This is important because of the many reasons for finding omega-3 fatty acids and their derivatives, valuable active substances that may be important in the development of new drugs and therapeutic regimens. Opinions about the bioavailability of omega-3 fatty acids are divided. Some believe that phospholipid-bound acids are absorbed better, as well as more intensely incorporated into tissues than those associated in triglyceride form, due to the specificity of blood transport and better accessibility of beta-oxidation pathways. Others, however, are of the opinion that factors unrelated to the type of chemical binding play a key role, and the fat content in food is decisive. In addition, promising effects seem to result from the use of special lipophilic systems and nano(micro)emulsions. However, the type of emulsifier used should be taken into account, as some influence the expression of the gene involved in the transport of fatty acids in enterocytes in various ways. Fatty acids affect each other’s metabolism in the body, which is of dietary importance. Several times higher consumption of omega-6 than omega-3 fatty acids is recommended by most researchers. Omega-3 fatty acids, like all fatty acids, are highly susceptible to oxidation. There are methods that disrupt this process and may be used in the production of supplements, but the significance of the process itself for bioavailability is unclear. It is hoped that reading the above review encourages scientists to carry out further research, which will dispel these and many other doubts.

Funding: This research received no external funding Conflicts of Interest: The authors declare no conflict of interest, financial or otherwise.

Abbreviations The following abbreviations are used in this manuscript:

13-LnHPO (9Z,11E,15Z)-13-Hydroperoxyoctadeca-9,11,15-trienoic acid ALA alpha-Linoleic acid ALT Advanced Lipid Technologies ARA Arachidonic acid AUCt Area under the (concentration-time) curve CFA Conjugated fatty acid Cmax Maximum concentration Nutrients 2018, 10, 1662 21 of 33

DAG Diacylglycerol DHA (4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid (cervonic acid) DPA (7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid (clupanodonic acid) DTrE (13Z,16Z,19Z)-Docosa-13,16,19-trienoic acid EE Ethyl esters EFA Essential fatty acid EPA (5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid (timnodonic acid) ETA (8Z,11Z,14Z,17Z)-Icosa-8,11,14,17-tetraenoic acid ETE (11Z,14Z,17Z)-Icosa-11,14,17-trienoic acid (homo-alpha-linolenic acid) FA Fatty acid FFA Free fatty acid FMLP N-Formylmethionyl-leucyl-phenylalanine HDA (9Z)-12-Hydroxydodec-9-enoic acid HDL High-density lipoprotein HFA Hydroxy fatty acid HPA (6Z,9Z,12Z,15Z,18Z)-Henicosa-6,9,12,15,18-pentaenoic acid iAUCt Incremental area under the (concentration-time) curve LA Linoleic acid LC Long-chain LDL Low-density lipoprotein MAG Monoacylglycerol MCFA Medium-chain fatty acid MUFA Monounsaturated fatty acid PA Phosphatidic acid PC Phosphatidylcholine PE Phosphatidylethanolamine PG Phosphatidylglycerol PKC Protein kinase C PL Phospholipids PUFA Polyunsaturated fatty acid rTG Re-esterified TG SC401 DHA and EPA ethylesters + Advanced Lipid Technologies SCFA Short-chain fatty acid SDA Stearidonic acid SEDDS Self-emulsifying drug delivery system SLN Solid lipid nanoparticles SMEDS Self-microemulsifying delivery system SNEDDS Self-nanoemulsifying drug delivery system TG Triacylglycerol (Triacylglyceride, Triglyceride) VFA Volatile fatty acid VLCFA Very long-chain fatty acid WPI-GA Whey protein isolate-gum arabic (complex)

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