Two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols
Abstract Symmetrically structured triacylglycerols (TG) rich in docosahexaenoic acid (DHA) with caprylic acid (CA) at the outer positions were synthesized enzymatically form bonito oil in a two‐step process: (i) ethanolysis of bonito oil TG to 2‐monoacylglycerols (2‐MG) and fatty acid ethyl esters,...
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crwiley:10.1007/s11746-001-0336-6 2024-09-09T19:07:28+00:00 Two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols Irimescu, Roxana Furihata, Kiyomi Hata, Kazuhiko Iwasaki, Yugo Yamane, Tsuneo 2001 http://dx.doi.org/10.1007/s11746-001-0336-6 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-001-0336-6 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-001-0336-6 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of the American Oil Chemists' Society volume 78, issue 7, page 743-748 ISSN 0003-021X 1558-9331 journal-article 2001 crwiley https://doi.org/10.1007/s11746-001-0336-6 2024-08-09T04:27:05Z Abstract Symmetrically structured triacylglycerols (TG) rich in docosahexaenoic acid (DHA) with caprylic acid (CA) at the outer positions were synthesized enzymatically form bonito oil in a two‐step process: (i) ethanolysis of bonito oil TG to 2‐monoacylglycerols (2‐MG) and fatty acid ethyl esters, and (ii) reesterification of 2‐MG with ethyl caprylate. Ethanolysis catalyzed by immobilized Candida antarctica lipase (Novozym 435) yielded 92.5% 2‐MG with 43.5% DHA content in 2 h. The 2‐MG formed were reesterified with ethyl caprylate by immobilized Rhizomucor miehei lipase (Lipozyme IM) to give structured TG with 44.9% DHA content [based on fatty acid composition with caprylic acid (CA) excluded] in 1 h. The final structured lipids comprised 85.3% TG with two CA residues and one original fatty acid residue, 13% TG with one CA residue and two original fatty acid residues, and 1.7% tricaprylolglycerol (weight percent). The amount of TG with two CA residues and one C 22 residue (22∶6=DHA, 22∶5, and 22∶4) was 51 wt%. The 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol to 1,2(2,3)‐dicapryloyl‐3 (1)‐docosahexaenoylglycerol ratio (based on high‐performance liquid chromatography peak area percentages) was greater than 50∶1. The recovery of TG as structured lipids after silica gel column purification was approximately 71%. Ethyl esters and 2‐MG formed at 2 h of ethanolysis could be used to determine the positional distribution of fatty acids in the intial TG owing to the high 1,3‐regiospecificity of Novozym 435 and the reduced acyl migration in the system. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of the American Oil Chemists' Society 78 7 743 748 |
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Wiley Online Library |
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English |
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Abstract Symmetrically structured triacylglycerols (TG) rich in docosahexaenoic acid (DHA) with caprylic acid (CA) at the outer positions were synthesized enzymatically form bonito oil in a two‐step process: (i) ethanolysis of bonito oil TG to 2‐monoacylglycerols (2‐MG) and fatty acid ethyl esters, and (ii) reesterification of 2‐MG with ethyl caprylate. Ethanolysis catalyzed by immobilized Candida antarctica lipase (Novozym 435) yielded 92.5% 2‐MG with 43.5% DHA content in 2 h. The 2‐MG formed were reesterified with ethyl caprylate by immobilized Rhizomucor miehei lipase (Lipozyme IM) to give structured TG with 44.9% DHA content [based on fatty acid composition with caprylic acid (CA) excluded] in 1 h. The final structured lipids comprised 85.3% TG with two CA residues and one original fatty acid residue, 13% TG with one CA residue and two original fatty acid residues, and 1.7% tricaprylolglycerol (weight percent). The amount of TG with two CA residues and one C 22 residue (22∶6=DHA, 22∶5, and 22∶4) was 51 wt%. The 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol to 1,2(2,3)‐dicapryloyl‐3 (1)‐docosahexaenoylglycerol ratio (based on high‐performance liquid chromatography peak area percentages) was greater than 50∶1. The recovery of TG as structured lipids after silica gel column purification was approximately 71%. Ethyl esters and 2‐MG formed at 2 h of ethanolysis could be used to determine the positional distribution of fatty acids in the intial TG owing to the high 1,3‐regiospecificity of Novozym 435 and the reduced acyl migration in the system. |
format |
Article in Journal/Newspaper |
author |
Irimescu, Roxana Furihata, Kiyomi Hata, Kazuhiko Iwasaki, Yugo Yamane, Tsuneo |
spellingShingle |
Irimescu, Roxana Furihata, Kiyomi Hata, Kazuhiko Iwasaki, Yugo Yamane, Tsuneo Two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols |
author_facet |
Irimescu, Roxana Furihata, Kiyomi Hata, Kazuhiko Iwasaki, Yugo Yamane, Tsuneo |
author_sort |
Irimescu, Roxana |
title |
Two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols |
title_short |
Two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols |
title_full |
Two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols |
title_fullStr |
Two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols |
title_full_unstemmed |
Two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols |
title_sort |
two‐step enzymatic synthesis of docosahexaenoic acid‐rich symmetrically structured triacylglycerols via 2‐monoacylglycerols |
publisher |
Wiley |
publishDate |
2001 |
url |
http://dx.doi.org/10.1007/s11746-001-0336-6 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1007%2Fs11746-001-0336-6 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-001-0336-6 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the American Oil Chemists' Society volume 78, issue 7, page 743-748 ISSN 0003-021X 1558-9331 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11746-001-0336-6 |
container_title |
Journal of the American Oil Chemists' Society |
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78 |
container_issue |
7 |
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743 |
op_container_end_page |
748 |
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1809821517849034752 |