Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system
The enzymatic transesterification of docosahexaenoic acid (DHA) ethyl ester with glycerol was performed with several lipases in a solvent-free system and it involves the initial formation of sn-2 docosahexaenyl monoacylglyceride. This DHA derivative is highly relevant for improving the bioavailabili...
Published in: | Cogent Food & Agriculture |
---|---|
Main Authors: | , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Taylor & Francis Group
2016
|
Subjects: | |
Online Access: | https://doi.org/10.1080/23311932.2016.1164569 https://doaj.org/article/f04879d741044e50ae580c7369034640 |
id |
ftdoajarticles:oai:doaj.org/article:f04879d741044e50ae580c7369034640 |
---|---|
record_format |
openpolar |
spelling |
ftdoajarticles:oai:doaj.org/article:f04879d741044e50ae580c7369034640 2023-05-15T13:47:42+02:00 Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system Sonia Moreno-Perez Pilar Luna Javier Señorans Jose M. Guisan Gloria Fernandez-Lorente 2016-12-01T00:00:00Z https://doi.org/10.1080/23311932.2016.1164569 https://doaj.org/article/f04879d741044e50ae580c7369034640 EN eng Taylor & Francis Group http://dx.doi.org/10.1080/23311932.2016.1164569 https://doaj.org/toc/2331-1932 2331-1932 doi:10.1080/23311932.2016.1164569 https://doaj.org/article/f04879d741044e50ae580c7369034640 Cogent Food & Agriculture, Vol 2, Iss 1 (2016) immobilized lipases in solvent-free systems sn-2 regioselective transesterification of dha-ee with glycerol novel dha derivatives Agriculture S Food processing and manufacture TP368-456 article 2016 ftdoajarticles https://doi.org/10.1080/23311932.2016.1164569 2022-12-31T06:37:48Z The enzymatic transesterification of docosahexaenoic acid (DHA) ethyl ester with glycerol was performed with several lipases in a solvent-free system and it involves the initial formation of sn-2 docosahexaenyl monoacylglyceride. This DHA derivative is highly relevant for improving the bioavailability of DHA and it has received increasing interest in the field of nutrition. Three commercial lipases, from Rhizomucor miehei (RML), Alcaligenes sp (QL), and Candida antarctica-fraction B (CALB) were tested. In certain cases (CALB), using an excess of DHA ethyl ester and high temperatures the transesterification reaction continues to the formation of triacylglycerides, but in other cases, sn-2 monoacylglyceride (2-MG) is the unique synthetic product even in the presence of high concentrations of DHA ethyl ester. At low temperatures (e.g. 37°C), RML derivatives synthesize only 2-MG in 15 min. These very mild conditions are very interesting for the thermal oxidative stability of the omega-3 fatty acid and for the thermal stability of the biocatalyst. Using Normal Phase HPLC-ELSD and accurate markers, the formation of the 2-MG was confirmed. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Cogent Food & Agriculture 2 1 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
immobilized lipases in solvent-free systems sn-2 regioselective transesterification of dha-ee with glycerol novel dha derivatives Agriculture S Food processing and manufacture TP368-456 |
spellingShingle |
immobilized lipases in solvent-free systems sn-2 regioselective transesterification of dha-ee with glycerol novel dha derivatives Agriculture S Food processing and manufacture TP368-456 Sonia Moreno-Perez Pilar Luna Javier Señorans Jose M. Guisan Gloria Fernandez-Lorente Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system |
topic_facet |
immobilized lipases in solvent-free systems sn-2 regioselective transesterification of dha-ee with glycerol novel dha derivatives Agriculture S Food processing and manufacture TP368-456 |
description |
The enzymatic transesterification of docosahexaenoic acid (DHA) ethyl ester with glycerol was performed with several lipases in a solvent-free system and it involves the initial formation of sn-2 docosahexaenyl monoacylglyceride. This DHA derivative is highly relevant for improving the bioavailability of DHA and it has received increasing interest in the field of nutrition. Three commercial lipases, from Rhizomucor miehei (RML), Alcaligenes sp (QL), and Candida antarctica-fraction B (CALB) were tested. In certain cases (CALB), using an excess of DHA ethyl ester and high temperatures the transesterification reaction continues to the formation of triacylglycerides, but in other cases, sn-2 monoacylglyceride (2-MG) is the unique synthetic product even in the presence of high concentrations of DHA ethyl ester. At low temperatures (e.g. 37°C), RML derivatives synthesize only 2-MG in 15 min. These very mild conditions are very interesting for the thermal oxidative stability of the omega-3 fatty acid and for the thermal stability of the biocatalyst. Using Normal Phase HPLC-ELSD and accurate markers, the formation of the 2-MG was confirmed. |
format |
Article in Journal/Newspaper |
author |
Sonia Moreno-Perez Pilar Luna Javier Señorans Jose M. Guisan Gloria Fernandez-Lorente |
author_facet |
Sonia Moreno-Perez Pilar Luna Javier Señorans Jose M. Guisan Gloria Fernandez-Lorente |
author_sort |
Sonia Moreno-Perez |
title |
Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system |
title_short |
Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system |
title_full |
Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system |
title_fullStr |
Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system |
title_full_unstemmed |
Synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system |
title_sort |
synthesis of sn-2 docosahexaenoyl monoacylglycerol by mild enzymatic transesterification of docosahexaenoic acid ethyl ester and glycerol in a solvent-free system |
publisher |
Taylor & Francis Group |
publishDate |
2016 |
url |
https://doi.org/10.1080/23311932.2016.1164569 https://doaj.org/article/f04879d741044e50ae580c7369034640 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Cogent Food & Agriculture, Vol 2, Iss 1 (2016) |
op_relation |
http://dx.doi.org/10.1080/23311932.2016.1164569 https://doaj.org/toc/2331-1932 2331-1932 doi:10.1080/23311932.2016.1164569 https://doaj.org/article/f04879d741044e50ae580c7369034640 |
op_doi |
https://doi.org/10.1080/23311932.2016.1164569 |
container_title |
Cogent Food & Agriculture |
container_volume |
2 |
container_issue |
1 |
_version_ |
1766247741644603392 |