96(P-26) タイ産植物Pueraria mirificaを起原とする健康食品"プエラリア"の品質管理 : 指標イソフラボンKwakhurinの全合成及び簡易HPLC検査法の開発(ポスター発表の部)
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概要
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Pueraria mirifica (Leguminosae) has been used in folk medicine as "kwao keur" for rejuvenating purpose in Thailand and Burma. We present the total synthesis of kwakhurin (3), a characterictic isoflavone component of P. mirifica, as an index of quality standard for commercial "kwao keur." Furthermore, we examine the convenient HPLC analysis for P. mirifica and commercial supplements. 1) Total Synthesis of Kwakhurin (3) Route A. Via deoxybenzoin: Doxybenzoin derivative 14 was prepared by Friedel-Crafts acylation of resorsin 8 and phenylacetic acid 13 after protection of the phenolic function with a triisopropyl group. Construction of isolfavone skeleton followed by chemical modifications afforded kwakhurin triisopropyl ether 25; however deprotection of the isopropyl groups in 25 was failed. Route B. Convergent synthesis: Isoflavone skeleton 36, which was protected with MEM groups, was constructed by Suzuki-Miyaura coupling of 3-bromochromone 31 (AC-ring) and aryl boronic acid 35 (B-ring) in the presence of TBAB as an additive. No improvement was observed in microwave-assisted coupling reaction. After chemical modifications Claisen rearrangement of 1,1-dimethylallyl ether 42 in PhNEt_2 gave 6'-prenylisoflavone 39 in high yield. Successive methylation and deprotection of 39 yielded a target kwakhurin (3) in good yield. The total yield was 12% from 32. 2) Convenient HPLC Analysis for P. mirifica Independently, analysis of miroestrol (1), one of active principles of P. mirifica, by HPLC was examined under several conditions.
- 天然有機化合物討論会の論文
- 2004-10-01
著者
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石川 勉
千葉大薬
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熊本 卓哉
千葉大学大学院薬学研究院
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熊本 卓哉
千葉大院薬
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石川 勉
千葉大院薬
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伊藤 文博
千葉大院薬
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岩崎 美砂子
千葉大院薬
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下川 聡子
千葉大院薬
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渡辺 敏子
千葉大院薬
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樋口 義洋
白鳥製薬
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高師 美穂
白鳥製薬
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熊本 卓哉
千葉大学薬学部
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熊本 卓哉
千葉大 大学院薬学研究院
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