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Production of Omega- 3 Fatty Acid Concentrates from Fish and Algal Oils and Their Structural Assessment by Nmr

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Production of Omega- 3 Fatty Acid Concentrates from Fish and Algal Oils and Their Structural Assessment by Nmr PRODUCTION OF OMEGA- 3 FATTY ACID CONCENTRATES FROM FISH AND ALGAL OILS AND THEIR STRUCTURAL ASSESSMENT BY NMR Kralovec, JA 1, Weijie W 1, Barrow CJ 2 and Reyes-Suarez E 1 1Ocean Nutrition Canada Ltd. Dartmouth, Nova Scotia, B2Y 4T6, Canada; 2School of Life and Environmental Science, Faculty of Science and Technology, 1 Pigdons Road, Geelong, Victoria 2127, Australia 1 LC-PUFA, OMEGA-3 vs. OMEGA-6 H3C COOH ααα-linolenic acid (ALA, C18:3, n-3) H C 3 COOH linoleic acid (C18:2, n-6) H C 3 COOH arachindonic acid (ARA, C18:4, n-6) H3C COOH eicosapentaenoic acid (EPA, C20:5, n-3) COOH H3C docosahexaenoicoic acid (DHA, C22:6, n-3) LC-PUFAs are categorized by the position of the 1 st double bond counting from the CH 3-terminal Location of the 1 st double bond dictates biological activity All double bonds are CH 2-interruped Omega-3 series starts with α-linolenic acid (ALA,18:3n-3) Omega-6 series starts with linoleic acid (LA,18:2n-6) Calder. Schweiz. Zeit. Ernährungmedizin 2009 , 5, 14-19 The most studied omega-3 FA are EPA and DHA 2 PRODUCTION OF EPA/DHA CONCENTRATES STARTING OMEGA-3 OIL SELECTION The richest and the cheapest source of EPA/DHA is fish oil Starting oils with right FA profiles and EPA/DHA content ~30%! anchovy/sardine (18/12TG, for high level EPA concentrates) tuna (05/25TG, for high level DHA concentrates) CORE OMEGA-3 CONCENTRATION OCOR 1 TECHNOLOGIES Fish oils are in the form of triglycerides →→→ OCOR 2 Winterization OCOR Cold Solvent Precipitation 3 Urea Clathration Ethanolysis + Fractional Distillation ⇒ Ethyl Ester (EE) Concentrates Enzyme-assisted Concentration ⇒⇒⇒ Triglyceride (TG) Concentrates 3 EE CONCENTRATES ETHANOLYSIS AND DISTILLATION Ethanolysis Distillation TG EE EE 30% 30% 60% Ethanolysis Distillation - TG EE EE Medium chain or medium Splitting TG molecules lowers the boiling points ! chain EE DHA-TG bp ~ 910 oC, vs. DHA-EE bp ~ 450 oC) DHA residues or DHA-EE EPA residues or EPA-EE Glycerol backbone or glycerol Popular technology towering over the other options O = CI 1.67 O, output CI, capital investment Economic advantage of large throughput! 4 CONCENTRATION STRATEGY A ETHANOLYSIS / DISTILLATION / GLYCEROLYSIS Ethanolysis Distillation - TG EE EE TG GLYCEROLYSIS EE TG HO FFA RCOO i RCOOR1 + HO RCOO - R1OH HO RCOO CALB R, a mixture of C14-C24 hydrocarbon residues,, primarily those of EPA and/or DHA R1, H or Et; i, CALB, 60-85 C, vacuum Immobilized Candida antarctica lipase B (CALB) in Packed Bed Reactor The reaction is driven forward by EtOH or water removal under vacuum 5 PACKED BED REACTOR Trap (condenser) Evaporation tank Heated stirred tank Vacuum pump Distributor Reactor Pump Pump 6 MANUFACTURING OF TG CONCENTRATES Green technologies (free or immobilized lipases) Packed bed reactors Reaction mixture cycling trough PBR First to introduce food grade immobilized lipase for EE –TG conversion ! i ii EE FFA TG o i: CALB-L, EtOH/H 2O, 50 C, vacuum ii: CALB-FPX66, glycerol, 70 oC, vacuum ~ 80 reactions on 1 batch of immobilized. enzyme! 7 CONCENTRATION STRATEGY B HYDROLYSIS AND EPA (DHA) INSERTION Hydrolysis EPA/DHA Insertion - TG DG TG Hydrolysis: Lipo-JD, P buffer pH7.5, 40 oC, 42 h; EPA/DHA insertion: CALB, EPA/DHA source, 70 oC, 24h TIME COURSE OF 18/12TG HYDROLYSIS 35 DHA in glyceride EPA in glyceride 30 DHA in FFA EPA in FFA 25 20 15 EPA/DHA Content (%) (%) EPA/DHA Content 10 Candida rugosa lipase 5 0 0 10 20 30 40 50 60 8 Total FFA in reaction mixture (%) POSITIONAL DISTRIBUTION (PD) OF EPA/DHA IN TG OILS It is very likely that the oxidative stability and thus also sensory qualities of EPA/DHA rich TG oils and their TG concentrates correlate with the positional distribution of fatty acid residues, primarily EPA and DHA in TG molecules. FACTS AND STRATEGY OCOR1 Complexity Fish oil contains 30 to 60 different fatty acids Assuming 30 and taking into account positional distribution, OCOR2 theoretically 27000 different TGs Chromatography Complex mixtures, need for non-aqueous conditions OCOR3 If R 1≠R2, C 2 is chiral Mass spectrometry Neutral compounds - poor ionization, difficulty adding reagents to mobile phase for adduct formation NMR 9 Complex mixtures, limited data in the literature SYNTHESIS OF STANDARDS O O SYMMETRIC (CH2)14CH3 (CH2)14CH3 O O DHA EDCl, DMAP HO DHA O CH2Cl2 O O (CH2)14CH3 (CH2)14CH3 O O 1,3-dipalmitate O O ASYMMETRIC (CH ) CH (CH ) CH 2 14 3 2 14 3 O O O O DHA H C(H C) Method A H C(H C) 3 2 14 3 2 14 EDCl, DMAP O O CH Cl 2 2 DHA O HO 1,2-dipalmitate Palmitic acid EDCl, DMAP CH2Cl2 HO Method B O DHA O Amberlyst O EDCl, DMAP O HO MeOH, CH2Cl2 CH2Cl2 HO DHA O DHA O 10 Wijesundera et. al. J. Amer. Oil Chem. Soc . 2007 , 84 , 11-21 POSITIONAL DISTRIBUTION OF EPA AND DHA BY NMR 13 C NMR (preferred) Better resolution (larger spectral range) than 1H NMR, although lower sensitivity CARBONYL (C-1) CARBONS (preferred) Carbonyls from sn-1,3- and sn-2 chains form clusters of peaks Within each cluster, chemical shifts differences between acyl chains occur as a result of the proximity to a neighboring double bond Unable to discriminate between sn -1 and sn -3 positions 11 POSITIONAL DISTRIBUTION OF EPA AND DHA BY NMR Carbonyl region of the 125 MHz 13 C NMR spectrum of a mixture of TG standards of seven fatty acids BASIC FACTS EPA Carbonyls from sn -1,3 chains resonate at (sn -1,3) higher chemical shifts than sn -2 chains EPA DHA (sn -2) (sn -1,3) Within each cluster carbonyls from saturated DHA (sn -2) chains resonate at a higher chemical shift Chemical shifts are in a direct correlation with the distance of the carbonyl carbon to sn -1,3 sn -2 the first double bond 173.4 173.2 173.0 172.8 172.6 172.4 ppm Unsaturation on the γ-position ( ∆4, DHA) Carbonyl chemical shifts of acyl chains that differ in double bond induces a greater shift on carbonyl chemical group shifts; DHA carbonyls resonate in a unique 173.40 γ to an olefinic 173.20 carbon position, which allows a straightforward 173.00 172.80 assignment 172.60 172.40 Chemical shift (ppm) shift Chemical C-1 (sn-1,3) 172.20 C-1 (sn-2) 172.00 Sat Δ9 Δ8 Δ7 Δ6 Δ5 Δ4 DHA Position of the first double bond relative to the carbonyl carbon 12 POSITIONAL DISTRIBUTION OF EPA AND DHA BY NMR INVESTIGATED FISH OILS QUANTITATIVE 13 C NMR 18/12TG (sardine oil) Under full-decoupling conditions nOe Re-esterified 18/12TG build up may differ for carbonyls of sn -1,3 and sn -2 chains 05/25TG (tuna oil) Sn -1,3/ sn -2 area ratios were measured for EPA and DHA carbonyls as a function of the relaxation delay for 18/12TG (100mg/0.7mL CDCl 3) Variation of the carbonyl areas ratio: A(sn-1,3)/A(sn-2) for EPA and A(sn-2)/A(sn- 1,3) for DHA as a function of the relxation delay in a full-decoupled sequence Area ratios for both EPA and 5 4.5 DHA carbonyls remain 4 3.5 DHA (C=O) constant after 12s delay Areas ratio Areas 3 EPA (C=O) 2.5 (working range) 2 1.5 1 1.5 3 4.5 6 7.5 9 10.5 12 13.5 15 16.5 18 19.5 21 22.5 Relaxation delay (s) 13 POSITIONAL DISTRIBUTION OF EPA AND DHA BY NMR Carbonyl region of the 125 MHz 13 C NMR spectrum of Carbonyl region of the 125 MHz 13 C NMR spectrum of 18/12TG oil (100 mg/ 0.7 mL CDCl 3) Re-esterified 18/12TG oil (100 mg/ 0.7 mL CDCl 3) Monounsat Sat Monounsat Sat (sn -2) Sat Sat (sn -1,3) (sn -1,3) (sn -1,3) (sn -1,3) (sn -2) Monounsat DHA Monounsat DHA EPA (sn -2) (sn -2) EPA (sn -2) (sn -2) (sn -1,3) EPA (sn -1,3) EPA (sn -2) DHA (sn -2) DHA STA STA (sn -1,3) STA STA (sn -1,3) (sn -1,3) (sn -2) (sn -1,3) (sn -2) 173.4 173.2 173.0 172.8 172.6 172.4 172.2 ppm 173.4 173.2 173.0 172.8 172.6 172.4 172.2 ppm Carbonyl region of the 125 MHz 13 C NMR spectrum of 0525TG tuna oil (100 mg/ 0.7 mL CDCl 3) Sat (sn -1,3) Monounsat Sat DHA (sn -1,3) (sn -2) (sn -2) DHA (sn -1,3) Monounsat (sn -2) EPA (sn -1,3) EPA (sn -2) 173.6 173.4 173.2 173.0 172.8 172.6 172.4 172.2 ppm 14 POSITIONAL DISTRIBUTION OF EPA AND DHA BY NMR Molar percentages of individual chains in sn -1,3 an sn -2 glycerol RE-ESTERIFICATION OF 18/12TG positions (fish oil TG 18/12) Sat Ethanolysis % 30 Mono STA - 25 EPA 20 DHA (No concentration of EPA or DHA) 15 10 The distribution of saturated and mono- 5 unsaturated chains as well stearidonic 0 % (sn-1,3)/Total % (sn-2)/Total acid (STA) remains unaffected Molar percentages of individual chains in sn -1,3 and sn -2 glycerol positions The distribution of EPA and DHA chains (TG 18-12 re-esterified) is affected % Sat 30 Mono STA 25 EPA that was mostly in sn -1,3 is EPA 20 DHA randomized on re-esterification 15 10 DHA that was mostly in sn -2 is 5 located mostly in sn -1,3 on re- 0 % (sn-1,3)/Total % (sn-2)/Total esterification 15 POSITIONAL DISTRIBUTION OF EPA AND DHA BY NMR 05/25TG TUNA OIL Molar percentages of individual chains in sn -1,3 and sn -2 glycerol positions (tuna oil) Saturated and monounsaturated Sat % 40 Mono chains are preferably located in 35 EPA sn -1,3 positions 30 DHA 25 20 15 EPA is present in equal amounts 10 in both sn -1,3 and sn -2 positions 5 0 % (sn-1,3)/Total % (sn-2)/Total DHA shows a slight preference for the sn -2 position 16 SUMMARY The evidence for the beneficial effects of omega-3 fatty acids FA, particularly EPA and DHA is undisputable.
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