Oxidative dimerisation of 4-hydroxystilbenes in vitro: production of a grapevine phytoalexin mimic

Abstract

Dimerisation of trans-4-hydroxystilbenes with horseradish peroxidase–hydrogen peroxide gives analogous products to those formed from phenylpropenoids; the product (IX) obtained from trans-resveratrol is structurally related to the phytoalexin (I) isolated from grapevines but the coupling orientation is different, and both the natural and synthetic dimers of resveratrol have a similar spectrum of antifungal activity.