N-benzylideneaniline and N-benzylaniline are potent inhibitors of lignostilbene-alpha,beta-dioxygenase, a key enzyme in oxidative cleavage of the central double bond of lignostilbene.
Lignostilbene-alpha,beta-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 beta-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 microM and N-(4-hydroxybenzyl)-3-methoxyaniline was also active with IC50 = 10 microM. The information obtained from the structure-activity relationships study here can aid in discovering inhibitors of both abscisic acid and vitamin A biosynthesis.
D000040:Abscisic Acid / Q000037:antagonists & inhibitors; D000814:Aniline Compounds / Q000494:pharmacology*; D001597:Benzylidene Compounds / Q000494:pharmacology*; D049308:Dioxygenases; D020128:Inhibitory Concentration 50; D007700:Kinetics; D008956:Models, Chemical; D010100:Oxygen / Q000378:metabolism*; D010105:Oxygenases / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D014801:Vitamin A / Q000037:antagonists & inhibitors
D000814:Aniline Compounds; D001597:Benzylidene Compounds; D014801:Vitamin A; D000040:Abscisic Acid; D010105:Oxygenases; D049308:Dioxygenases; C069684:lignostilbene-alpha,beta-dioxygenase; D010100:Oxygen