2006年3月
Synthesis of 26,27-bisnorcastasterone analogs and analysis of conformation-activity relationship for brassinolide-like activity
BIOORGANIC & MEDICINAL CHEMISTRY
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- 巻
- 14
- 号
- 6
- 開始ページ
- 1761
- 終了ページ
- 1770
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1016/j.bmc.2005.10.024
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
Three castasterone (CS) derivatives with varied side-chain moieties, 26,27-bisnorcastasterone (20S-bisilorCS), 20-epi-26,27-bisnorcastastcrone (20R-bisnorCS), and 21,26,27-trisnorcastasterone (trisnorCS), were synthesized stereoselectively from either stigmasterol or dehydroisoandrosterone. The 50% effective doses (ED50, nmol/plant) in the concentration-response Curve for brassinolide-like activity in the rice lamina inclination assay were determined to be 0.020 nmol (pED(50) = 10.7) for 20S-bisnorCS, 3.2 nmol (pED50 = 8.5) for 20R-bisnorCS, and 2.0 nmol (pED50 = 8.7) for trisnorCS. An analog containing an ester linkage between the steroid and the side-chain moiety of 20S-bisnorCS was also synthesized and its activity was evaluated to be 3.2 nmol (pED50 = 8.5), being equipotent to 20R-bisnorCS and trisnorCS. The activity of 20S-bisnorCS was 1/40 that of CS. The conformation analysis was conducted using a systematic search, showing that the activity decreases with an increase in the degree of freedom of the side chain of the steroidal skeleton. (c) 2005 Elsevier Ltd. All rights reserved.
- リンク情報
- ID情報
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- DOI : 10.1016/j.bmc.2005.10.024
- ISSN : 0968-0896
- PubMed ID : 16288879
- Web of Science ID : WOS:000235579900010