COMPARISONS OF VARIOUS BIOLOGICAL-ACTIVITIES OF STEREOISOMERS OF METHYL JASMONATE

Stereoisomers of methyl jasmonate (JA-Me) showed different biological activities in four bioassay systems. Growth of soybean callus was inhibited strongly by (1R,2S)- and (1R,2R)-JA-Me. By contrast, (1S,2R)- and (1S,2S)-JA-Me had very low inhibitory effect on it, suggesting that the activity is dependent largely on the (1R)-configuration. With regard to potato tuber-induction and the senescence-promotion of oat leaves, although the highest activities were found in (1R,2S)-JA-Me, isomers which have the (1S)-configuration showed considerable activities. (1R,2S)- and (1S,2R)-JA-Me equally inhibited straight growth of oat coleoptiles. These results suggest that requirements of the absolute configurations of the two side chains with respect to the plane of the cyclopentanone ring for each activity are different, and that there are different receptors which trigger reactions leading to the individual activity.