Enzymatic production of bioactive docosahexaenoic acid phenolic ester
International audience Docosahexaenoic acid (DHA) is increasingly considered for its health benefits. However, its use as functional food ingredient is still limited by its instability. In this work, we developed an efficient and solvent-free bioprocess for the synthesis of a phenolic ester of DHA....
Published in: | Food Chemistry |
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Online Access: | https://hal.univ-lorraine.fr/hal-01267210 https://doi.org/10.1016/j.foodchem.2014.09.028 |
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ftinserm:oai:HAL:hal-01267210v1 2024-05-12T07:53:32+00:00 Enzymatic production of bioactive docosahexaenoic acid phenolic ester Roby, Mohamed H. Allouche, Ahmad Dahdou, Layal de Castro, Vanessa C. Silva, Paulo H. Alves, Da Targino, Brenda N. Huguet, Marion Paris, Cedric Chrétien, Francoise Gueant, Rosa-Maria Desobry, Stéphane Oster, Thierry Humeau, Catherine Laboratoire d'Ingénierie des Biomolécules (LIBio) Université de Lorraine (UL) Fayoum University Unité de Recherches Animal et Fonctionnalités des Produits Animaux (URAFPA) Institut National de la Recherche Agronomique (INRA)-Université de Lorraine (UL) Universidade Federal de Viçosa = Federal University of Viçosa (UFV) Université de Lorraine (UL)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE) Structure et Réactivité des Systèmes Moléculaires Complexes (SRSMC) Institut de Chimie - CNRS Chimie (INC-CNRS)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS) Nutrition-Génétique et Exposition aux Risques Environnementaux (NGERE) Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lorraine (UL) French Ministry of Research and Higher Education Lorraine Region European Commission for Erasmus Mundus Grant University of Damascus (Syria) CAPES/MEC-Brazilian Ministry of Education 2015-03 https://hal.univ-lorraine.fr/hal-01267210 https://doi.org/10.1016/j.foodchem.2014.09.028 en eng HAL CCSD Elsevier info:eu-repo/semantics/altIdentifier/doi/10.1016/j.foodchem.2014.09.028 hal-01267210 https://hal.univ-lorraine.fr/hal-01267210 doi:10.1016/j.foodchem.2014.09.028 PRODINRA: 294627 WOS: 000343952300053 ISSN: 0308-8146 EISSN: 1873-7072 Food Chemistry https://hal.univ-lorraine.fr/hal-01267210 Food Chemistry, 2015, 171, pp.397-404. ⟨10.1016/j.foodchem.2014.09.028⟩ http://www.journals.elsevier.com/food-chemistry/ fish-oil polyunsaturated fatty-acid transesterification learning-ability gallate egcg derivative antioxidant activity alzheimers-disease vanillyl alcohol lipase-catalyzed synthesis Antioxidant DHA Enzymatic esterification Neuroprotection plant phenolic [CHIM]Chemical Sciences info:eu-repo/semantics/article Journal articles 2015 ftinserm https://doi.org/10.1016/j.foodchem.2014.09.028 2024-04-18T00:30:19Z International audience Docosahexaenoic acid (DHA) is increasingly considered for its health benefits. However, its use as functional food ingredient is still limited by its instability. In this work, we developed an efficient and solvent-free bioprocess for the synthesis of a phenolic ester of DHA. A fed-batch process catalyzed by Candida antarctica lipase B was optimised, leading to the production of 440 g/L vanillyl ester (DHA-VE). Structural characterisation of the purified product indicated acylation of the primary OH group of vanillyl alcohol. DHA-VE exhibited a high radical scavenging activity in acellular systems. In vivo experiments showed increased DHA levels in erythrocytes and brain tissues of mice fed DHA-VE-supplemented diet. Moreover, in vitro neuroprotective properties of DHA-VE were demonstrated in rat primary neurons exposed to amyloid-beta oligomers. In conclusion, DHA-VE synergized the main beneficial effects of two common natural biomolecules and therefore appears a promising functional ingredient for food applications. Article in Journal/Newspaper Antarc* Antarctica Inserm: HAL (Institut national de la santé et de la recherche médicale) Food Chemistry 171 397 404 |
institution |
Open Polar |
collection |
Inserm: HAL (Institut national de la santé et de la recherche médicale) |
op_collection_id |
ftinserm |
language |
English |
topic |
fish-oil polyunsaturated fatty-acid transesterification learning-ability gallate egcg derivative antioxidant activity alzheimers-disease vanillyl alcohol lipase-catalyzed synthesis Antioxidant DHA Enzymatic esterification Neuroprotection plant phenolic [CHIM]Chemical Sciences |
spellingShingle |
fish-oil polyunsaturated fatty-acid transesterification learning-ability gallate egcg derivative antioxidant activity alzheimers-disease vanillyl alcohol lipase-catalyzed synthesis Antioxidant DHA Enzymatic esterification Neuroprotection plant phenolic [CHIM]Chemical Sciences Roby, Mohamed H. Allouche, Ahmad Dahdou, Layal de Castro, Vanessa C. Silva, Paulo H. Alves, Da Targino, Brenda N. Huguet, Marion Paris, Cedric Chrétien, Francoise Gueant, Rosa-Maria Desobry, Stéphane Oster, Thierry Humeau, Catherine Enzymatic production of bioactive docosahexaenoic acid phenolic ester |
topic_facet |
fish-oil polyunsaturated fatty-acid transesterification learning-ability gallate egcg derivative antioxidant activity alzheimers-disease vanillyl alcohol lipase-catalyzed synthesis Antioxidant DHA Enzymatic esterification Neuroprotection plant phenolic [CHIM]Chemical Sciences |
description |
International audience Docosahexaenoic acid (DHA) is increasingly considered for its health benefits. However, its use as functional food ingredient is still limited by its instability. In this work, we developed an efficient and solvent-free bioprocess for the synthesis of a phenolic ester of DHA. A fed-batch process catalyzed by Candida antarctica lipase B was optimised, leading to the production of 440 g/L vanillyl ester (DHA-VE). Structural characterisation of the purified product indicated acylation of the primary OH group of vanillyl alcohol. DHA-VE exhibited a high radical scavenging activity in acellular systems. In vivo experiments showed increased DHA levels in erythrocytes and brain tissues of mice fed DHA-VE-supplemented diet. Moreover, in vitro neuroprotective properties of DHA-VE were demonstrated in rat primary neurons exposed to amyloid-beta oligomers. In conclusion, DHA-VE synergized the main beneficial effects of two common natural biomolecules and therefore appears a promising functional ingredient for food applications. |
author2 |
Laboratoire d'Ingénierie des Biomolécules (LIBio) Université de Lorraine (UL) Fayoum University Unité de Recherches Animal et Fonctionnalités des Produits Animaux (URAFPA) Institut National de la Recherche Agronomique (INRA)-Université de Lorraine (UL) Universidade Federal de Viçosa = Federal University of Viçosa (UFV) Université de Lorraine (UL)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE) Structure et Réactivité des Systèmes Moléculaires Complexes (SRSMC) Institut de Chimie - CNRS Chimie (INC-CNRS)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS) Nutrition-Génétique et Exposition aux Risques Environnementaux (NGERE) Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lorraine (UL) French Ministry of Research and Higher Education Lorraine Region European Commission for Erasmus Mundus Grant University of Damascus (Syria) CAPES/MEC-Brazilian Ministry of Education |
format |
Article in Journal/Newspaper |
author |
Roby, Mohamed H. Allouche, Ahmad Dahdou, Layal de Castro, Vanessa C. Silva, Paulo H. Alves, Da Targino, Brenda N. Huguet, Marion Paris, Cedric Chrétien, Francoise Gueant, Rosa-Maria Desobry, Stéphane Oster, Thierry Humeau, Catherine |
author_facet |
Roby, Mohamed H. Allouche, Ahmad Dahdou, Layal de Castro, Vanessa C. Silva, Paulo H. Alves, Da Targino, Brenda N. Huguet, Marion Paris, Cedric Chrétien, Francoise Gueant, Rosa-Maria Desobry, Stéphane Oster, Thierry Humeau, Catherine |
author_sort |
Roby, Mohamed H. |
title |
Enzymatic production of bioactive docosahexaenoic acid phenolic ester |
title_short |
Enzymatic production of bioactive docosahexaenoic acid phenolic ester |
title_full |
Enzymatic production of bioactive docosahexaenoic acid phenolic ester |
title_fullStr |
Enzymatic production of bioactive docosahexaenoic acid phenolic ester |
title_full_unstemmed |
Enzymatic production of bioactive docosahexaenoic acid phenolic ester |
title_sort |
enzymatic production of bioactive docosahexaenoic acid phenolic ester |
publisher |
HAL CCSD |
publishDate |
2015 |
url |
https://hal.univ-lorraine.fr/hal-01267210 https://doi.org/10.1016/j.foodchem.2014.09.028 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 0308-8146 EISSN: 1873-7072 Food Chemistry https://hal.univ-lorraine.fr/hal-01267210 Food Chemistry, 2015, 171, pp.397-404. ⟨10.1016/j.foodchem.2014.09.028⟩ http://www.journals.elsevier.com/food-chemistry/ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.foodchem.2014.09.028 hal-01267210 https://hal.univ-lorraine.fr/hal-01267210 doi:10.1016/j.foodchem.2014.09.028 PRODINRA: 294627 WOS: 000343952300053 |
op_doi |
https://doi.org/10.1016/j.foodchem.2014.09.028 |
container_title |
Food Chemistry |
container_volume |
171 |
container_start_page |
397 |
op_container_end_page |
404 |
_version_ |
1798843113644490752 |