著者

チャンサカオ スニー 石川 勉 関 宏子 関根 啓子 岡田 峯明 樋口 義洋 チャイチャンティピュース チャイヨー

出版者

天然有機化合物討論会実行委員会

雑誌

天然有機化合物討論会講演要旨集

巻号頁・発行日

vol.42, pp.49-54, 2000

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"Kwao Keur." which had been identified as Puraria mirifica (Leguminosae), has long been used in Thailand and Burma as a rejuvenating folk medicine and has a fascinating history. A potent estrogenic principle has been known to be an unusual phenol miroestrol (1). Although the possible presence of an alternative active component was suggested, there has been no isolation of any other powerful phytoestrogens. with further studies leading instead to the isolation of isoflavonoids. These situation made us re-investigate the estrogenic principles of P. mirifica. The bioassay-guided separation of the ethyl acetate extract of the tuberous roots of P. mirifica by chromatographic techniques resulted in the successful isolation of a new phytoestrogen. (+)-deoxymiroestrol (4). together with (+)-1 and (+)-isomiroestrol (7). The structure of (+)-1 had been determined by X-ray crystallographic analysis and its enantioselective total synthesis was recently reported. Thus. the structure of (+)-deoxymiroestrol (4) was established by comparison of its NMR data with those of (+)-1. The growth-promoting effect of them on MCF-7 human breast cancer cells showed the strongest activity with 4. Interestingly. 4 was easily converted into 1 and 7 by aerial oxidation. suggesting that 4 may be the actual phytoestrogen of P. mirifica. On the other hand daidzein (2), genistein (3), and coumestrol (6) belong to isoflavonoids were isolated as phytoestrogens with lower activity. In addition, it was found that kwakhurin (5). a characteristic isoflavonoid in this plant. also showed the same activity as 2.

著者

チャンサカオ スニー 石川 勉 関 宏子 関根 啓子 岡田 峯明 樋口 義洋 チャイチャンティピュース チャイヨー

出版者

天然有機化合物討論会実行委員会

雑誌

天然有機化合物討論会講演要旨集 42 (ISSN:24331856)

巻号頁・発行日

pp.49-54, 2000-10-01 (Released:2017-08-18)

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"Kwao Keur." which had been identified as Puraria mirifica (Leguminosae), has long been used in Thailand and Burma as a rejuvenating folk medicine and has a fascinating history. A potent estrogenic principle has been known to be an unusual phenol miroestrol (1). Although the possible presence of an alternative active component was suggested, there has been no isolation of any other powerful phytoestrogens. with further studies leading instead to the isolation of isoflavonoids. These situation made us re-investigate the estrogenic principles of P. mirifica. The bioassay-guided separation of the ethyl acetate extract of the tuberous roots of P. mirifica by chromatographic techniques resulted in the successful isolation of a new phytoestrogen. (+)-deoxymiroestrol (4). together with (+)-1 and (+)-isomiroestrol (7). The structure of (+)-1 had been determined by X-ray crystallographic analysis and its enantioselective total synthesis was recently reported. Thus. the structure of (+)-deoxymiroestrol (4) was established by comparison of its NMR data with those of (+)-1. The growth-promoting effect of them on MCF-7 human breast cancer cells showed the strongest activity with 4. Interestingly. 4 was easily converted into 1 and 7 by aerial oxidation. suggesting that 4 may be the actual phytoestrogen of P. mirifica. On the other hand daidzein (2), genistein (3), and coumestrol (6) belong to isoflavonoids were isolated as phytoestrogens with lower activity. In addition, it was found that kwakhurin (5). a characteristic isoflavonoid in this plant. also showed the same activity as 2.