13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates
The 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...
Published in: | Journal of the American Oil Chemists' Society |
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ftnrccanada:oai:cisti-icist.nrc-cnrc.ca:cistinparc:17676090 2023-05-15T13:54:10+02:00 13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates Reyes Suárez, Erick Mugford, Paul F. Rolle, Alfred J. Burton, Ian W. Walter, John A. Kralovec, Jaroslav A. 2010-12-01 text https://doi.org/10.1007/s11746-010-1638-2 https://nrc-publications.canada.ca/eng/view/object/?id=07a42bb9-70d3-41ff-8f96-8a8ed6142200 https://nrc-publications.canada.ca/fra/voir/objet/?id=07a42bb9-70d3-41ff-8f96-8a8ed6142200 eng eng Journal of the American Oil Chemists' Society, Volume: 87, Issue: 12, Publication date: 2010-12-01, Pages: 1425–1433 doi:10.1007/s11746-010-1638-2 13C NMR Anchovy DHA EPA Fish oil concentrate Regio-isomeric distribution Regioselectivity Sardine Triacylglycerol article 2010 ftnrccanada https://doi.org/10.1007/s11746-010-1638-2 2021-09-01T06:24:32Z The 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. Peer reviewed: Yes NRC publication: Yes Article in Journal/Newspaper Antarc* Antarctica National Research Council Canada: NRC Publications Archive Journal of the American Oil Chemists' Society 87 12 1425 1433 |
institution |
Open Polar |
collection |
National Research Council Canada: NRC Publications Archive |
op_collection_id |
ftnrccanada |
language |
English |
topic |
13C NMR Anchovy DHA EPA Fish oil concentrate Regio-isomeric distribution Regioselectivity Sardine Triacylglycerol |
spellingShingle |
13C NMR Anchovy DHA EPA Fish oil concentrate Regio-isomeric distribution Regioselectivity Sardine Triacylglycerol Reyes Suárez, Erick Mugford, Paul F. Rolle, Alfred J. Burton, Ian W. Walter, John A. Kralovec, Jaroslav A. 13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates |
topic_facet |
13C NMR Anchovy DHA EPA Fish oil concentrate Regio-isomeric distribution Regioselectivity Sardine Triacylglycerol |
description |
The 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. Peer reviewed: Yes NRC publication: Yes |
format |
Article in Journal/Newspaper |
author |
Reyes Suárez, Erick Mugford, Paul F. Rolle, Alfred J. Burton, Ian W. Walter, John A. Kralovec, Jaroslav A. |
author_facet |
Reyes Suárez, Erick Mugford, Paul F. Rolle, Alfred J. Burton, Ian W. Walter, John A. Kralovec, Jaroslav A. |
author_sort |
Reyes Suárez, Erick |
title |
13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates |
title_short |
13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates |
title_full |
13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates |
title_fullStr |
13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates |
title_full_unstemmed |
13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates |
title_sort |
13c-nmr regioisomeric analysis of epa and dha in fish oil derived triacylglycerol concentrates |
publishDate |
2010 |
url |
https://doi.org/10.1007/s11746-010-1638-2 https://nrc-publications.canada.ca/eng/view/object/?id=07a42bb9-70d3-41ff-8f96-8a8ed6142200 https://nrc-publications.canada.ca/fra/voir/objet/?id=07a42bb9-70d3-41ff-8f96-8a8ed6142200 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
Journal of the American Oil Chemists' Society, Volume: 87, Issue: 12, Publication date: 2010-12-01, Pages: 1425–1433 doi:10.1007/s11746-010-1638-2 |
op_doi |
https://doi.org/10.1007/s11746-010-1638-2 |
container_title |
Journal of the American Oil Chemists' Society |
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87 |
container_issue |
12 |
container_start_page |
1425 |
op_container_end_page |
1433 |
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1766259831644094464 |