Regioselective Lipase-Catalyzed Synthesis of 3-O-Acyl Derivatives of Resveratrol and Study of Their Antioxidant Properties
Regioselective Lipase-Catalyzed Synthesis of 3-O-Acyl Derivatives of Resveratrol and Study of Their Antioxidant Properties
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DOI：
10.1021/jf903210q
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发表时间：
2010-01-27
影响因子：
6.1
通讯作者：
Plou, Francisco J.
中科院分区：
文献类型：
--
作者：
Torres, Pamela;Poveda, Ana;Plou, Francisco J.
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 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 3-OH position caused a higher loss of activity compared with that at the 4'-OH.
