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Trans Fatty Acids

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Trans Fatty Acids Copyright! Reproduction and dissemination – also partial – applicable to all media only with written permission of Umschau Zeitschriftenverlag GmbH, Wiesbaden. Science & Research | Overview Peer-reviewed | Manuscript received: April 09, 2018 | Revision accepted: : July 09, 2018 Trans fatty acids Origin, metabolism, health risks Maria Pfeuffer, Gerhard Jahreis the 1960s partially hydrogenated Abstract fats were a preferred alternative for Trans fatty acids (TFA) are generated both during partial industrial hydrogenation saturated fats in the food industry. of oils and by incomplete microbial hydrogenation of polyunsaturated fatty acids A high TFA content improves the in the rumen. Elaidic acid (t9-18:1), the trans isomer of oleic acid, is the major functionality of a fat, i.e. texture isomer in industrial sources of TFA. Some trans isomers of linoleic acid and of and structure, thermal and oxi- α-linolenic acid may also arise, depending on the vegetable oil used for hydro- dation stability and extends shelf genation and processing conditions. Vaccenic acid (t11-18:1) is the major trans life. There are also natural sources isomer in ruminant fats. Elaidic acid and vaccenic acid differ in various biochemi- of TFA in fat from ruminants, i.e. cal activities. TFA show adverse effects on blood lipids, inflammation parameters milk fat and meat and products and endothelial function. Epidemiological studies observed an increased risk of made from them, as enzymes of the coronary heart diseases and total mortality with increasing intake of industrially rumen bacteria incompletely hydro- generated TFA. Particularly fats for baking, roasting and deep-frying have or had genate polyunsaturated fatty acids a high content of TFA. Originally, margarine was an important source. Due to of the feed. Depending on the feeding mandatory regulations and voluntary measures the TFA content of foods and regimen fat in cow’s milk contains thus TFA intake decreased markedly in many countries. This probably decreased 2–8% TFA [1, 2]. health risks. Vaccenic acid (trans11-18:1), occa- Keywords: elaidic acid, vaccenic acid, metabolism, health risks, intake, sionally also called trans vaccenic (governmental) regulations acid, predominates in the ruminant TFA (R-TFA, rumen-derived), ac- counting for up to 70% of R-TFA, with the trans double bond in po- sition n-7 (shorthand notation t11- 18:1, t-18:1n-7 or (old delta-no- Origin and nomenclature tation) C18:1 ∆11t). A minor fatty of trans fatty acids acid is trans palmitoleic acid (short- hand notation t9-16:1, t-16:1n-7 or Unsaturated fatty acids have double t-16:1n7) [1, 2]. Monounsaturated bonds mostly in cis-configuration, TFA generated through partial in- leading to a kink in the hydrocarbon dustrial hydrogenation (I-TFA, in- chain. Trans fatty acids (TFA) on the dustrially produced) with a chain contrary are unsaturated carboxylic length of 18 carbon atoms (C18) acids with at least one double bond have trans double bonds in position in trans configuration. In contrast C4 to C16. The most important ones to the cis isomer the hydrocarbon are t9-18:1 and t10-18:1. Their per- chain of a monounsaturated trans centage of total t-18:1 amounts to fatty acid is almost straight (♦ Fig- about 28% and 23% respectively [3]. ure 1). Structure, melting point and Elaidic acid (shorthand notation t9- Citation: other physical properties shift TFA 18:1, t-18:1n-9 or C18:1 ∆9t) is the Pfeuffer M, Jahreis G (2018) Trans in the direction of saturated fatty trans isomer of oleic acid. But also fatty acids. Origin, metabolism, acids. For one TFA are generated t11-18:1 is found in I-TFA, with ap- health risks. Ernahrungs Um- during partial industrial hydro- proximately 1% of total t-18:1 [3]. schau 65(12): 196–203 genation of vegetable oils and, to a Thus I-TFA and R-TFA contain ba- This article is available online: small extent, during oil refining [1]. sically the same trans isomers, but DOI: 10.4455/eu.2018.047 This process turns liquid oils into in very different proportions. The t9 semi-solid spreadable fats. Since to t11 ratio (so-called t9/t11 index) 196 Ernaehrungs Umschau international | 12/2018 Copyright! Reproduction and dissemination – also partial – applicable to all media only with written permission of Umschau Zeitschriftenverlag GmbH, Wiesbaden. gives an indication of the origin of TFA in foods. For R-TFA it is usually < 1.0 [2]. TFA are largely monounsaturated c9-18:1 (t-18:1). Depending on the vegeta- oleic acid ble oil used for hydrogenation and processing conditions also poly- unsaturated TFA (t-18:2, t-18:3 and others) may arise, normally in t9-18:1 low concentrations, in particular elaidic acid trans isomers of linolenic acid (e.g. c9,t12-18:2) and of α-linolenic acid (e.g. c9,c12,t15-18:3). If TFA have t11-18:1 two or more double bonds a dis- vaccenic acid tinction needs to be made between those with isolated and conjugated double bonds, both for physiologi- cal and legal reasons. According to the Food and Drug Administration (FDA) and the Codex Alimentarius Commission only fatty acids with non-conjugated trans double bonds Fig. 1: Structure of oleic acid, various trans fatty acids (TFA), and of conju- are defined as TFA, whereby at least gated linoleic acid (CLA) one of these double bonds must be The position of the double bonds is usually indicated by the carbon atom coun- ting from the carboxylic end of the carbon chain (delta-notation), different from in trans configuration. According the cis unsaturated fatty acids. One exception, for example, is t9-16:1, also called to this definition conjugated linoleic t-16:1n-7. acid (CLA) c9,t11-CLA is not a TFA. Metabolism sented on average 2.52% of plasma vert t-18:3 isomers to trans isomers phospholipids including an average of eicosapentaenoic acid [11] and Incorporation into lipids of 0.25% t-16:1, 2.01% t-18:1, and docosahexaenoic acid [12]. Trans of various tissues 0.27% t-18:2 isomers [6]. docosahexaenoic acid was detected Among men with an average TFA in- TFA were found in triglycerides, in brain [12], but not t9-18:1 [8]. take of 2.6 g/d (range 0.7–8.6 g/d), phospholipids and cholesterol es- High intake of α-linolenic acid as equal to 1.5 energy percent (En%) ters of various tissues [5, 7]. Their compared to linoleic acid decreased and 5.5% of total fat intake, the mean incorporation relative to total lipid the incorporation of TFA into rat concentration of TFA in adipose tis- differed depending both on the tissue liver and adipose tissue [7]. sue (upper buttock subcutaneous and trans isomer [8]. TFA incorpo- fat) was 4.9% (1.7–7.7%) [4]. TFA ration decreases the fluidity of mem- Fatty acid metabolic pathways intake and concentration in adipose branes. Therefore, incorporation into tissue were somewhat lower among phospholipids, membrane lipids as Concerning absorption, transport, women. Subjects consuming a diet well as functional lipids, is of special and oxidation TFA undergo a fate high in soft margarine from partially importance. This incorporation was similar to that of the corresponding hydrogenated soybean oil and pro- isomer-dependent, too. Isomers of cis isomers. TFA can inhibit ∆6-de- viding 4.15 En% TFA had increased t-18:1 were mainly esterified at the saturase, the first step enzyme of plasma TFA concentrations, 3.8% in sn1-position of glycerol in glycero- the elongation-desaturation system. phospholipids, 7.1% in triglycerides phospholipids [9]. Among t-18:2 Trans isomers differ in their inhib- and 4.4% in cholesterol esters. The isomers c9,t12-18:2 was preferred itory effect, with t,t-18:2 being a t-18:2 isomers (CLA not included) for incorporation, predominantly more potent inhibitor than t9-18:1 accounted for 26, 37 and 57% of at the sn2-position [10]. Among [9]. Thus TFA can impair the syn- total TFA [5]. Ten different TFA iso- t-18:3 isomers c9,c12,t15-18:3 was thesis of the long-chain fatty acids mers were identified in plasma phos- the major one, also at the sn2-po- arachidonic acid (20:4n-6), eicosa- pholipids in an US cohort (samples sition [11]. Enzymes of the elonga- pentaenoic acid (20:5n-3) and doco- taken in 1992). Total TFAs repre- tion-desaturation system may con- sahexaenoic acid (22:6n-3) and their Ernaehrungs Umschau international | 12/2018 197 Copyright! Reproduction and dissemination – also partial – applicable to all media only with written permission of Umschau Zeitschriftenverlag GmbH, Wiesbaden. Science & Research | Overview through … additional double bond chain shortening study supplementation with t11- from… (∆9-desaturase) (partial ß-oxidation) 18:1 changed neither immune cell t9-18:1 no t7-16:1 function nor plasma biomarkers of also t-18:1n-9 also t-16:1n-9, t-16:1n9 immune function and inflamma- (elaidic acid) tion [20]. Different from t11-18:1 t10-18:1 no not known neither t9-18:1 nor t10-18:1 are t11-18:1 c9,t11-CLA t9-16:1 ∆9-desaturated (♦ Table 1). This also t-18:1n-7 also t-16:1n-7, t-16:1n7 may be an explanation for their (vaccenic acid) more unfavorable pathobiochemical Tab. 1: Possible metabolites of major t-18:1 isomers [15, 17] effect. They were more cytotoxic to liver cells and increased, different to t11-18:1, the expression of lipogenic incorporation into tissues. Higher triglycerides, the ∆9-desaturation genes (fatty acid synthase, ∆9-de- content of trans eicosapentaenoic products were selectively incorpo- saturase) and transcriptional regu- acid [11] and trans docosahexaenoic rated into phospholipids [15].
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