| Project/Area Number |
06680553
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Bioorganic chemistry
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| Research Institution | Chiba University |
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Principal Investigator |
TAKAYAMA Hiromitsu Chiba University, Fac. Pharm. Sciences, Associate Professor, 薬学部, 助教授 (90171561)
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| Co-Investigator(Kenkyū-buntansha) |
SAKAI Shin-ichiro Chiba University Emenritus Professor, 名誉教授 (20009161)
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| Project Period (FY) |
1994 – 1995
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| Project Status |
Completed (Fiscal Year 1995)
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| Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1995: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1994: ¥1,400,000 (Direct Cost: ¥1,400,000)
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| Keywords | Thai Traditional Medicine / Analgesic Alkaloid / Mitragyna speciosa / Chemical Constituent / Indole Alaloid / Mitragynine / Chemical Synthesis / アルカロイド合成 / 化学変換反応 / インドールアルカロイドの化学構造 / インドールアルカロイドの合成 |
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| Research Abstract |
The leaves of Mitragyna speciosa Korth. have been known as an opium substitute in traditional use by Thai and Malay natives. Reinvestigation of the alkaloidal constituents in the leaves of the plant resulted in the isolation of a major indole alkaloid, mitragynine, and a new minor alkaloid 7alpha-hydroxy-7H-mitragynine. Starting from an optically pure alcohol, an enantioselective total synthesis of mitragynine was attained. Mitragynine was converted into the pseudoindoxyl derivative and its stereochemistry of C2, C3 was elucidated. The structure of nauclefidine, having a basic skeleton in the new type of Mitragyne alkaloids, was revised based on the total synthesis and biomimetic transformation from the vincoside lactam. The crude alkaloid mixture and mitragynine showed non-narcotic antinociceptive activities and inhibited contraction of smooth muscle.
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