P-32 多量体型pyrrolidinoindolineアルカロイドの探索と合成研究(ポスター発表の部)
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概要
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Poly-pyrrolidinoindoline alkaloids, such as (-)-chimonanthine and hodgkinsine, have been isolated from the plants belonging to Calycanthaceae, Idiospermaceae, and Rubiaceae, as well as from the dendrobatid frog. Recent pharmacological study revealed this type of alkaloids has the potent antinociceptive activities that interact with opioid receptors. To discover the new poly-pyrrolidinoindoline alkaloids, we carried out the chemical investigation of the constituents in Psychotria rostrata (Rubiaceae), Chimonanthus praecox (Calycanthaceae), and Chimonanthus praecox f. concolor (Calycanthaceae), and the synthetic studies on polymeric pyrrolidinoindoline alkaloids isolated from these plants. 1) New type of poly-pyrrolidinoindoline alkaloids from P. rostrata (Rubiaceae) The leaves of Psychotria rostrata Bl. were used as folk medicine for the treatment of constipation in Malaysia. We succeeded in isolation of two new alkaloids, psychotrimine (1) and psychopentamine (2), from the MeOH extract of P. rostrata leaves. These alkaloids are the first example that contains the tryptamine and pyrrolidinoindoline unit in the same molecule. Attempts at the total synthesis of 1 are under investigation in our laboratory. 2) New Chimonanthus alkaloids from C. praecox and C. praecox f. concolor We isolated two new alkaloids, (-)-chimonanthidine (3) and chimonamidine (4), from the MeOH extract of C. praecox seeds, as well as two new alkaloids, CPC-1 (12) and CPC-2 (13), from the MeOH extract of C. praecox f. concolor seeds. The structures of 3, 4, and 13 were elucidated by means of spectroscopic analysis and biomimetic total synthesis. Interestingly, it was found that natural chimonamidine (4) comprises a mixture slightly enriched with the (R)-(-)-enantiomer. 3) Total synthesis of chimonanthidine and structure reinvestigation of isochimonanthine Recently, we have developed a new synthetic method for the dimerization of indole derivatives using hypervalent idodine(III) reagent. We utilized this method for the synthesis of rac-chimonanthidine (rac-3) and rac-isochimonanthine (rac-22), the later of which was isolated from an Indonesian rubiaceous Argostemma yappii. The data for the proposed structure of isochimonanthine were not identical with those of the natural product. Careful structure reinvestigation led us to the conclusion that so-called isochimonanthine was the mixture of (+)-chimonanthine (25) and meso-chimonanthine (26) in the ratio of 1: 1.
- 天然有機化合物討論会の論文
- 2005-09-15
著者
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高山 廣光
千葉大院薬
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北島 満里子
千葉大院薬
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松田 洋平
千葉大院薬
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森 郁江
千葉大院薬
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増渕 恭平
千葉大院薬
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小暮 紀行
千葉大院薬
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Lajis Nordin
Universiti Putra Malaysia
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Takayama H
Faculty Of Pharmaceutical Sciences Teikyo University
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Takayama Hiroaki
帝京大学 薬
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Takayama Hiroaki
Faculty Of Pharmaceutical Sciences Teikyo University
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高山 廣光
Graduate School Of Pharmaceutical Sciences Chiba Univ.
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Takayama Hiromitsu
Laboratory Of Molecular Structure And Biological Function Graduate School Of Pharmaceutical Sciences
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高山 広光
Faculty Of Pharmaceutical Sciences Chiba University
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