P-73 Exo選択的Diels-Alder反応を用いた植物毒素コロナチン両鏡像体の合成と植物気孔開口活性(ポスター発表の部)

DOI

書誌事項

タイトル別名
  • Total Syntheses of Coronatines by Exo-selective Diels-Alder Reaction and Their Biological Activities on Stomatal Opening

抄録

The natural phytotoxin coronatine, which is composed of two individual parts, coronafacic acid and coronamic acid, exhibits various promising biological activities similar to jasmonic acid, which is noe of the phytohormones. Interstingly, coronatine induces stomatal opening involving the swelling of guard cells in which jasmonic acid is not involved as an endogenous regulator. In order to apply the enantiodifferential approach for the identification of its target protein, we established syntheses of four stereoisomers of coronatine employing the exo-selectie Diels-Alder reaction as a key step. It will be advantageous to go through versatile intermediate for the preparation of various derivatives. Remarkable differences in a stomatal opening activity were observed between enantiomers of coronatine. This result strongly suggests that the stereostructure of coronatine is so important for its stomatal opening activity. In addition, structure-activity relationship studies suggested that coronatine operates as a molecular mimic of jasmonyl-L-isoleucine in plant guard celld. We also synthesized coronatine azide according to our synthetic strategy of coronatine, which possessed potent stomatal opening activity.

収録刊行物

詳細情報 詳細情報について

  • CRID
    1390282681054680192
  • NII論文ID
    110009757684
  • DOI
    10.24496/tennenyuki.51.0_455
  • ISSN
    24331856
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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