66.植物毒素コロナチンの合成と植物気孔開口誘導活性(口頭発表)

概要

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The phytotoxin coronatine 1 showed not only jasomonic acid mimetic biological activity, but also stomatal opening activity. In order to elucidate the chemical characteristics of stomatal opening, we synthesized 1 and their derivatives, and studied structure-activity relationships. Employing the Diels-Alder reaction of hydroxypyrone derivative 2 with cyclopentendione 3 as a key reaction in the formation of multifunctionalized intermediate 4, coronafacic acid 5 was synthesized in 6 steps. After condensation of 5 and coronamic acid benzyl ester 6, the resulting mixture was purified by HPLC to give 1. We investigated stomatal opening activities of 5 and 1, as well as jasmonic acid and isoleucine jasmonate. Coronatine 1 and isoleicine jasmonate showed stomatal opening activities, while 5 and jasmonic acid had no activity. The result indicated that coronatine 1 played the role for a molecular mimic of isoleucine jasmonate rather than jasmonic acid. Additionally, enantiomer of 1 did not showed stomatal opening activity. This result suggested that our enantiodifferential approach would be applicable for studies on the target protein of 1 using synthetic coronatine probe and enantiomer of 1.
植物化学調節学会の論文
2008-10-06