Design and synthesis of lignostilbene-α,β-dioxygenase inhibitors

Lignostilbene-α,β-dioxygenase cleaves the olefinic double bond of phenolic stilbenes by a mechanism similar to that of 9-cis-epoxycarotenoid dioxygenase, a key enzyme in abscisic acid biosynthesis. Several analogues of stilbene were designed and synthesized, and their efficacy as inhibitors of lignostilbene-α,β-dioxygenase was examined. The compound (Z)-1-(4-hydroxyphenyl)-1-fluoro-2-phenylethene (2) was found to be a potent inhibitor of this enzyme with an IC50 of 3 μM.