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Regioselective lipase-catalyzed synthesis of 3-O-acyl-derivatives of resveratrol and study of their antioxidant properties

AuthorsTorres, Pamela ; Poveda, Ana; Jiménez-Barbero, Jesús ; Ballesteros Olmo, Antonio ; Plou Gasca, Francisco José
Immobilized Enzymes
Vinyl Esters
Issue Date2010
SeriesJournal of Agricultural and Food Chemistry, 58, 807-813 (2010)
AbstractOne of the approaches to increase 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, the lipase B from Candida 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 position 3-OH caused a higher loss of activity compared with the 4’-OH.
Publisher version (URL)DOI: 10.1021/jf903210q
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