Inhibitory effect of methyl jasmonate and its related compounds on kinetin-induced retardation of oat leaf senescence [structure-activity relationships, Avena sativa]
1981
Ueda, J. | Kato, J. (Osaka Prefectural Univ., Sakai (Japan). Coll. of Integrated Arts and Sciences) | Yamane, H. | Takahashi, N.
The senescence-promoting activities of methyl jasmonate and its related compounds were compared with respect to structure-activity relationships. The activities were assayed by using oat (Avena sativa L. cv. Victory) leaf segments in the presence of 2 mu-g/ml kinetin. Dextrorotatory methyl jasmonate prepared from an authentic sample of the racemate mixture was less active than the naturally occurring levorotatory form especially at its low concentrations (0.1 to 2.5 mu-g/ml). The activity of jasmonic acid, the free acid form of methyl jasmonate, was much less than the methyl ester, and this relationship was true for the other compounds tested. The reduction of the unsaturated bond in the substituent at the C-2 position and the keto group at the C-3 position greatly reduced the activity. The length of the n-alkyl substituents at the C-2 position had also a significant effect on the activity. From these results, it is concluded that the important functional groups for the high senescence-promoting activity of the methyl jasmonate related compounds are the methyl acetate substituent at the C-1 position, the 2'-cis-pentenyl or n-pentyl group at the C-2 position and the keto group at the C-3 position in methyl jasmonate.
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