RESUMEN
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-ß 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.
Asunto(s)
Alcoholes Bencílicos/química , Ácidos Docosahexaenoicos/química , Ésteres/metabolismo , Oxidorreductasas/química , Animales , Encéfalo/efectos de los fármacos , Encéfalo/metabolismo , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Dieta , Ácidos Docosahexaenoicos/metabolismo , Enzimas Inmovilizadas/metabolismo , Eritrocitos/efectos de los fármacos , Eritrocitos/metabolismo , Proteínas Fúngicas/metabolismo , Lipasa/metabolismo , Masculino , Ratones , Ratones Endogámicos C57BL , Neuronas/citología , Neuronas/efectos de los fármacos , Neuronas/metabolismo , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/metabolismo , Fármacos Neuroprotectores/farmacología , Oxidorreductasas/biosíntesis , Oxidorreductasas/farmacología , Ratas , Ratas WistarRESUMEN
Docosahexaenoic acid vanillyl ester (DHA-VE) was synthesized from docosahexaenoic acid ethyl ester (DHA-EE) and vanillyl alcohol by a solvent-free alcoholysis process catalysed by Candida antarctica lipase B. Oxidative stability of pure DHA-VE and the crude reaction medium consisting of 45% DHA-VE and 55% DHA-EE were compared with that of DHA-EE under various storage conditions. Oxidation progress was followed by determination of conjugated dienes and FTIR measurements. Analyses showed that DHA-EE was rapidly oxidised under all storage conditions in comparison with DHA-VE and crude reaction medium, whatever the temperature and the storage time. The grafting of vanillyl alcohol appeared as a powerful way to stabilize DHA against oxidation. Thanks to their stability, both DHA-VE and the crude reaction medium, allowing the production of the ester, offer huge potential as functional ingredients.
