title: Enzymatic production of bioactive docosahexaenoic acid phenolic ester.
abstract: 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-β 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.
authors.affiliation: Université de Lorraine, ENSAIA, Laboratoire LIBio, Nancy F-54500, France; Fayoum University, Faculty of Agriculture, Food Science and Technology Dept., 63514 Fayoum, Egypt.
authors.forename: Mohamed H
authors.initials: MH
authors.lastname: Roby
authors.affiliation: Université de Lorraine, ENSAIA, Laboratoire UR AFPA - BFLA (EA 3998, USC INRA 0340), Nancy F-54500, France.
authors.forename: Ahmad
authors.initials: A
authors.lastname: Allouche
authors.affiliation: Université de Lorraine, ENSAIA, Laboratoire LIBio, Nancy F-54500, France.
authors.forename: Layal
authors.initials: L
authors.lastname: Dahdou
authors.affiliation: Laboratório de Biomoléculas e Bioprocessos, Departamento de Tecnologia de Alimentos, Universidade Federal de Viçosa, 36571.000, Viçosa, MG, Brazil.
authors.forename: Vanessa C
authors.initials: VC
authors.lastname: De Castro
authors.affiliation: Laboratório de Biomoléculas e Bioprocessos, Departamento de Tecnologia de Alimentos, Universidade Federal de Viçosa, 36571.000, Viçosa, MG, Brazil.
authors.forename: Paulo H Alves
authors.initials: PH
authors.lastname: da Silva
authors.affiliation: Laboratório de Biomoléculas e Bioprocessos, Departamento de Tecnologia de Alimentos, Universidade Federal de Viçosa, 36571.000, Viçosa, MG, Brazil.
authors.forename: Brenda N
authors.initials: BN
authors.lastname: Targino
authors.affiliation: Université de Lorraine, ENSAIA, Laboratoire UR AFPA - BFLA (EA 3998, USC INRA 0340), Nancy F-54500, France.
authors.forename: Marion
authors.initials: M
authors.lastname: Huguet
authors.affiliation: Université de Lorraine, ENSAIA, Laboratoire LIBio, Nancy F-54500, France.
authors.forename: Cédric
authors.initials: C
authors.lastname: Paris
authors.affiliation: Université de Lorraine, CNRS, UMR 7565, SRSMC, Nancy F-54606, France.
authors.forename: Françoise
authors.initials: F
authors.lastname: Chrétien
authors.affiliation: Université de Lorraine, Faculté de Médecine, Laboratoire NGERE (Inserm U954), Nancy F-54500, France.
authors.forename: Rosa-Maria
authors.initials: RM
authors.lastname: Guéant
authors.affiliation: Université de Lorraine, ENSAIA, Laboratoire LIBio, Nancy F-54500, France.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Desobry
authors.affiliation: Université de Lorraine, ENSAIA, Laboratoire UR AFPA - BFLA (EA 3998, USC INRA 0340), Nancy F-54500, France. Electronic address: thierry.oster@univ-lorraine.fr.
authors.forename: Thierry
authors.initials: T
authors.lastname: Oster
authors.affiliation: Université de Lorraine, ENSAIA, Laboratoire LIBio, Nancy F-54500, France. Electronic address: catherine.humeau@univ-lorraine.fr.
authors.forename: Catherine
authors.initials: C
authors.lastname: Humeau
mesh_terms: D000818:Animals; D001592:Benzyl Alcohols / Q000737:chemistry*; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D004032:Diet; D004281:Docosahexaenoic Acids / Q000737:chemistry* / Q000378:metabolism; D004800:Enzymes, Immobilized / Q000378:metabolism; D004912:Erythrocytes / Q000187:drug effects / Q000378:metabolism; D004952:Esters / Q000378:metabolism*; D005656:Fungal Proteins / Q000378:metabolism; D008049:Lipase / Q000378:metabolism; D008297:Male; D051379:Mice; D008810:Mice, Inbred C57BL; D009474:Neurons / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D018696:Neuroprotective Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D010088:Oxidoreductases / Q000096:biosynthesis / Q000737:chemistry* / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar
chemical_list: D001592:Benzyl Alcohols; D004800:Enzymes, Immobilized; D004952:Esters; D005656:Fungal Proteins; D018696:Neuroprotective Agents; D004281:Docosahexaenoic Acids; D010088:Oxidoreductases; C064258:free radical reductase; D008049:Lipase; C431349:lipase B, Candida antarctica; C024078:vanillyl alcohol
keywords: Antioxidant; DHA; Enzymatic esterification; Neuroprotection; Vanillyl alcohol