66. Synthesis and stomatal opening activity of coronatine
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- Okada Masahiro
- Grad. School. Sci., Tohoku Univ.
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- Ito Satoko
- Grad. School. Sci., Tohoku Univ.
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- Matsubara Akira
- Grad. School. Sci., Tohoku Univ.
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- Ueda Minoru
- Grad. School. Sci., Tohoku Univ.
Bibliographic Information
- Other Title
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- 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)
Abstract
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.
Journal
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- The Janapese Society for Chemical Regulation of Plants, Abstract
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The Janapese Society for Chemical Regulation of Plants, Abstract 43 (0), 80-, 2008
The Janapese Society for Chemical Regulation of Plants
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Details 詳細情報について
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- CRID
- 1390282679399581056
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- NII Article ID
- 110007468240
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- ISSN
- 21896313
- 09191887
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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