In vitro Inhibition Studies of Phytoene Desaturase by Bleaching Ketomorpholine Derivatives

The herbicidal activities of homochiral steroisomeric 5-methyl-2-(3-trifluoromethylbenzyl)-3-ketomorpholine 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...

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Veröffentlicht in:Journal of agricultural and food chemistry 2001-01, Vol.49 (1), p.138-141
Hauptverfasser: Sandmann, Gerhard, Mitchell, Glynn
Format: Artikel
Sprache:eng
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Zusammenfassung:The herbicidal activities of homochiral steroisomeric 5-methyl-2-(3-trifluoromethylbenzyl)-3-ketomorpholine 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 phytoene 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 I50 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. Keywords: Phytoene desaturase inhibition; bleaching; herbicidal activity; ketomorpholine; carotenoid biosynthesis
ISSN:0021-8561
1520-5118
DOI:10.1021/jf0010432