Enzymatic production of bioactive docosahexaenoic acid phenolic ester

• Published in: Food Chemistry
• Main Authors: 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
• Other Authors: 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
• Language: English
• Published: HAL CCSD 2015
• Subjects: 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; Antarc*; Antarctica
• Online Access: https://hal.univ-lorraine.fr/hal-01267210; https://doi.org/10.1016/j.foodchem.2014.09.028

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.