P-23 タイ薬用植物Mitragyna speciosaに含有されるインドールアルカロイド類の構造と化学合成及び薬理学的研究(ポスター発表の部)

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The leaves of Mitragyna speciosa Korth. have been known as an opium substitute in traditional use by Thai and Malay natives. With the object to clarify pharmacological profiles of this plant species as well as to utilize this plant resource as a medicinal development, the following chemical and pharmacological studies were carried out. I: Alkaloids in the leaves of Mitragyna speciosa growing in Thailand. Reinvestigation of the alkaloidal constituents in the leaves of the plant resulted in the isolation of a major indole alkaloid, mitragynine (1), and three minor alkaloids. Furthermore, a new alkaloid (5) was obtained. The structure of 5 was initially deduced by spectroscopic analysis and finally determined to be 7α-hydroxy-7H-mitragynine by chemical transformation from 1. II: Chiral synthesis of mitragynine and its pseudoindoxyl derivative. Starting from an optically pure alcohol (8), an enantioselective total synthesis of mitragynine (1), a major alkaloidal component of this plant, was attained for the first time. Furthermore, 1 was converted into the pseudoindoxyl derivative (18), which had stronger analgesic activity than that of 1. The stereochemistry of the C2, C3 positions in pseudoindoxyls was also investigated. III. Synthetic studies of new Mitragyna alkaloids. To establish the synthetic route of the new skeletal type of indole alkaloids (25, 26) isolated from Malaysian Mitragyna speciosa, we examined the synthesis of a simple alkaloid, nauclefidine (27). As a results, the structure of nauclefidine was revised as formula (31) based on the total synthesis and biomimetic transformation from the vincoside lactam (36). IV: Pharmacological evaluation of the Mitragyna alkaloids. The crude alkaloid mixture and mitragynine showed non-narcotic antinociceptive activities in mice and inhibited contraction of smooth muscle of Guinea-pig ileum. The mechanism of these action will be reported.
天然有機化合物討論会の論文
1995-09-01

P-23 タイ薬用植物Mitragyna speciosaに含有されるインドールアルカロイド類の構造と化学合成及び薬理学的研究(ポスター発表の部)

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