62. インダノファンの光学活性体の超長鎖脂肪酸伸長阻害活性に及ぼす影響

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Indanofan, 2-[2-(3-chloro phenyl) oxiran-2-ylmethyl]-2-ethylindan-1,3-dione, having oxirane moiety strongly inhibits germination of grass weeds, e.g. Echinochloa oryzicola, and some dicotyledonous weeds, Elatine triandra and Lindernia pyxidaria. Although its accurate herbicidal mode of action has not elucidated yet, the primary site of action of indanofan has been considered to be on the elongation step(s) in very-long-chain fatty acid (VLCFA) biosynthesis. Indanofan is a racemate due to one chiral carbon at 2 position of the oxirane moiety. S-Enantiomer of indanofan was reported to be two times more herbicidally active against barnyardgrass in pot test than the racemic mixture, although the Renantiomer did not exhibit any herbicidal activity. In this study, influence of enantiomers and a racemate of indanofan on VLCFA elongation was assayed using leek (Allium porrum) microsomal preparation and inhibitory action of the enantiomers were compared to confirm the relation between their absolute configurations and VLCFA elongation inhibition in cell-free level. The I_<50>-values of S-, R-forms and the racemate for elongation of C18 : 0-acid were 1.7×10^<-8>, >10^<-3> and 3.0×10^<-8>M, respectively. While the I_<50>-values of those for elongation of C20 : 0-acid were 2.5×10^<-8>, 10^<-3> and 7.0×10^<-8>M, respectively. These findings indicated that the S-enantiomer inhibited elongation of both C18 : 0- and C20 : 0-acid ca. 2-3 times more strongly than the racemate, yielding almost no inhibition of the R-enantiomer. It was concluded that S-enantiomer was responsible for the inhibition of the elongation of both C18 : 0- and C20 : 0-acid.
植物化学調節学会の論文
2003-10-10

62. インダノファンの光学活性体の超長鎖脂肪酸伸長阻害活性に及ぼす影響

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