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

被引:68
|
作者
Torres, Pamela
Poveda, Ana [2 ]
Jimenez-Barbero, Jesus [2 ]
Ballesteros, Antonio
Plou, Francisco J. [1 ]
机构
[1] CSIC, Inst Catalisis & Petr Quim, Dept Biocatalisis, Madrid 28049, Spain
[2] CSIC, Ctr Invest Biol, Madrid 28040, Spain
关键词
Antioxidants; acylation; lipases; regioselectivity; polyphenols; vinyl esters; Trolox equivalent antioxidant activity; TEAC; ENVIRONMENTAL BIOCATALYSIS; BIOLOGICAL EVALUATION; TRANS-RESVERATROL; GREEN PROCESSES; ANALOGS; ENZYMES; MODEL; ACIDS; REMEDIATION; ACYLATION;
D O I
10.1021/jf903210q
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
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.
引用
收藏
页码:807 / 813
页数:7
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