In vitro inhibition studies of phytoene desaturase by bleaching ketomorpholine derivatives.
The herbicidal activities of homochiral steroisomeric 5-methy1-2-(3-trifluoromethybenzyl)-3-keto- morpholine derivatives were investigated in vitro as inhibitors of phytoene desaturase, a key enzyme in carotenoid biosynthesis. It was demonstrated that ketomorpholines are classical bleaching compounds which directly inhibit phytoene desaturase, accumulating phytoene at the expense of colored carotenoids. Ketomorpholines interact with phytoene desaturase in a noncompetitive manner with respect to phytoene. A structure-activity investigation for in vitro inhibition of phtoene desaturase activity revealed that the relative and absolute stereochemistry is important for optimum inhibition for the 5-methyl derivatives, and that the distance of the phenyl group from the ketomorpholine ring is critical for the inhibitory potential. The average herbicidal score on 7 weeds and the in vitro I(50) values related very well with the exception of two compounds. It was postulated that the discrepancies may possibly occur through modification in plants to compounds that are either more or less active herbicides.
Sandmann
G
G
Botanisches Institut, Goethe Universität, Frankfurt, Germany. sandmann@em.uni-frankfurt.de
Mitchell
G
G
D002338:Carotenoids / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D006540:Herbicides / Q000494:pharmacology*; D009025:Morpholines / Q000737:chemistry* / Q000494:pharmacology*; D010088:Oxidoreductases / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D004791:Enzyme Inhibitors; D006540:Herbicides; D009025:Morpholines; D002338:Carotenoids; C100185:(all-E) phytoene; D010088:Oxidoreductases; C022398:phytoene dehydrogenase