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PublicationJournal of Agricultural and Food Chemistry
Year2010
Volume58
Pages807-813
International

Regioselective Lipase-Catalyzed Synthesis of 3-O-Acyl Derivatives of Resveratrol and Study of Their Antioxidant Properties

Authors:Pamela Torres Salas, Ana Poveda , Jesus Jimenez-Barbero , Antonio Ballesteros Olmo, Francisco José Plou Gasca
Groups of research:Applied Biocatalysis

One of the approaches to increasing the bioavailability of resveratrol is to protect its 3-OH phenolic group. In this work, regioselective acylation of resveratrol at 3-OH was achieved by transesterification with vinyl acetate catalyzed by immobilized lipase from Alcaligenes sp. (lipase QLG). The maximum yield of 3-O-acetylresveratrol was approximately 75%, as the lipase also catalyzes its further acetylation affording the diester 3,4′-di-O-acetylresveratrol and finally the peracetylated derivative. Long saturated and unsaturated fatty acid vinyl esters were also effective as acyl donors with similar regioselectivity. In contrast, lipase B fromCandida antarctica catalyzes the acylation of the phenolic group 4′-OH with 80% yield and negligible formation of higher esters. The analysis of the antioxidant properties showed that the Trolox equivalent antioxidant capability (TEAC) values for the acetyl and stearoyl derivatives at 3-OH were, respectively, 40% and 25% referred to resveratrol. The addition of an acyl chain in the 3-OH position caused a higher loss of activity compared with that at the 4′-OH.

Keywords:Antioxidants; acylation; lipases; regioselectivity; polyphenols; vinyl esters; Trolox equivalent antioxidant activity; TEAC
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