N-Benzylideneaniline and N-Benzylaniline are Potent Inhibitors of Lignostilbene-α,β-dioxygenase, a Key Enzyme in Oxidative Cleavage of the Central Double Bond of Lignostilbene

Abstract

Lignostilbene-α,β-dioxygenase (LSD, EC 1.13.11.43) is involved in oxidative cleavage of the central double bond of lignostilbene to form the corresponding aldehydes by a mechanism similar to those of 9-cis-epoxycarotenoid dioxygenase and β-carotene 15,15′-dioxygenase, key enzymes in abscisic acid biosynthesis and vitamin A biosynthesis, respectively. In this study, several N-benzylideneanilines and amine were synthesized and examined for their efficacy as inhibitors of LSD. N-(4-Hydroxybenzylidene)-3-methoxyaniline was found to be a potent inhibitor with IC₅₀ = 0.3 µM and N-(4-hydroxybenzyl)-3-methoxyaniline was also active with IC₅₀ = 10 µM. The information obtained from the structure-activity relationships study here can aid in discovering inhibitors of both abscisic acid and vitamin A biosynthesis.

Keywords::

• 9-cis-epoxycarotenoid dioxygenase
• Lignostilbene-α,β-dioxygenase
• Lignostilbene