13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates

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DOIResolve DOI: http://doi.org/10.1007/s11746-010-1638-2
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TypeArticle
Journal titleJournal of the American Oil Chemists' Society
Volume87
Issue12
Pages14251433; # of pages: 9
Subject13C NMR; Anchovy; DHA; EPA; Fish oil concentrate; Regio-isomeric distribution; Regioselectivity; Sardine; Triacylglycerol
AbstractThe regio-isomeric distribution of the omega-3 polyunsaturated fatty acids (PUFA) cis-5,8,11,14,17-eicosapentaenoic acid (EPA) and cis-4,7,10,13,16,19- docosahexaenoic acid (DHA) in the triacylglycerols (TAG) of anchovy/sardine fish oil was determined by 13C nuclear magnetic resonance (NMR) analysis under quantitative conditions. From the measurements of sn-1,3 and sn-2 carbonyl peak areas it was established that EPA was mainly located in the sn-1,3 positions, whereas DHA primarily occupied the sn-2 position. Reconstituted TAG prepared by Candida antarctica lipase-B (CALB) glycerolysis of the ethyl ester (EE) or the free fatty acid (FFA) forms of anchovy/sardine fish oil, displayed a different pattern: EPA was equally distributed, while DHA was preferentially attached to the sn-1,3 positions. TAG concentrates of varying EPA and DHA molar fractions were prepared by CALB-catalyzed glycerolysis of the corresponding EE and FFA. 13C-NMR analysis of the purified products revealed a lack of CALB regioselectivity for EPA and a slight sn-1,3 regioselectivity for DHA. Since this pattern was observed in all cases of this study, it was concluded that the lipase regioselectivity during TAG synthesis is independent of both the acyl donor type (carboxylic acid or ester) and the fatty acid content of the oil substrate. © 2010 AOCS.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Institute for Marine Biosciences
Peer reviewedYes
NRC number55609
NPARC number17676090
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Record identifier07a42bb9-70d3-41ff-8f96-8a8ed6142200
Record created2011-04-02
Record modified2016-05-09
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