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

• Published in: Journal of Agricultural and Food Chemistry
• Main Authors: Torres, Pamela, Poveda, Ana, Jiménez-Barbero, Jesús, Ballesteros Olmo, Antonio, Plou Gasca, Francisco José
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2010
• Subjects: Antioxidants; Acylation; Regioselectivity; Polyphenols; Biocatalysis; Immobilized Enzymes; Vinyl Esters; Teac; Trolox; Bioavailability; Martínez; Medina; Morales; Antarc*; Antarctica
• Online Access: http://hdl.handle.net/10261/20714; https://doi.org/10.1021/jf903210q

One 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. We thank Drs. Juan Carlos Espín (CEBAS, CSIC, Murcia, Spain), Juan Carlos Morales (IIQ, CSIC, Sevilla, Spain) and Isabel Medina (IIM, CSIC, Vigo, Spain) for technical information and suggestions. We are grateful to Meito Sangyo Co., Ltd. (Tokyo, Japan) for samples of lipases QLG and PLG. We thank Ramiro Martínez (Novozymes A/S, Madrid, Spain) for supply of lipase samples and suggestions. We are grateful to Comunidad de Madrid for a research contract to P. Torres. This research was supported by the Spanish CSIC (Project 200680F0132). Peer reviewed