Total Syntheses of Coronatines by Exo-selective Diels-Alder Reaction and Their Biological Activities on Stomatal Opening
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- Okada Masahiro
- Department of Chemistry, Tohoku University
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- Egoshi Syusuke
- Department of Chemistry, Tohoku University
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- Ito Satoko
- Department of Chemistry, Tohoku University
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- Matsubara Akira
- Department of Chemistry, Tohoku University
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- Ueda Minoru
- Department of Chemistry, Tohoku University
Bibliographic Information
- Other Title
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- 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)
Abstract
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.
Journal
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- Symposium on the Chemistry of Natural Products, symposium papers
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Symposium on the Chemistry of Natural Products, symposium papers 51 (0), 455-460, 2009
Symposium on the Chemistry of Natural Products Steering Committee
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Details 詳細情報について
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- CRID
- 1390282681054680192
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- NII Article ID
- 110009757684
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- ISSN
- 24331856
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed