Transforamtion of Grayanotoxin III to 10-epi-Grayanotoxin III. Its X-Ray Crystallographic Analysis and Acute Toxicity in Mice

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概要

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• Grayanotoxin(GTX) III, a tetracyclic diterpenoid, is the main toxic component obtained from the leaves of Leucothoe grayama MAX. In this paper, we report the correlation between toxicity and C_<10> stereostructure of GTX-III. 10-epi-GTX-III was derived from GTX-III in four steps. Oxidation of the GTX-II-3,6,14,16-tetraacetate with formic acid/hydrogen peroxide in chloroform gave 10,20-epoxy derivative in high yield. Reduction of the 10,20-epoxyacetate with LiAlH_4 in tetrahydrofuran gave the two products, 10-epi-GTX-III and 10,20-epoxy-GTX-II. The absolute structure of the 10-epi-GTX-III was deduced from the results of X-ray crystallographic analysis. Dosage level of acute toxicity of 10-epi-GTX, III in mice was estimated at about half of natural GTX-III.

• 公益社団法人日本薬学会の論文
• 1996-06-15

著者

• Narama Isao

  Institute For Protein Research Osaka University

• Sato M

  Graduate School Of Integrated Science Yokohama City University

• Matsuura T

  Institute For Protein Research Osaka University

• Sakurai Masahiro

  Department Of Life Science Faculty Of Biocscience And Bioctechnology Tokyo Institute Of Technology

• SATO Mamoru

  Institute for Protein Research, Osaka University

• TERAI Tadamasa

  Department of Applied Chemistry, Osaka Institute of Technology

• NARAMA Isao

  Faculty of Pharmaceutical Science, Setsunan University

• MATUURA Tetsuro

  Faculty of Pharmaceutical Sciences, Setsunan University

• TETSUMI Masahiro

  Faculty of Pharmaceutical Sciences, Setsunan University

• Terai Tadamasa

  Dep. Of Applied Chemistry Osaka Inst. Of Technol.

• MATSUURA Teruro

  Research Institute of Drug Safety, Setsunan University

• Sato M

  Graduate School Of Pharmaceutical Sciences Hokkaido University

• Terai Tadamasa

  Department Of Applied Chemistry Osaka Institute Of Technology

• Matsuura T

  Research Institute Of Drug Safety Setsunan University

• Narama I

  Setsunan Univ. Osaka Jpn

• Terai T

  Dep. Of Applied Chemistry Osaka Inst. Of Technol.

• Sato Mamoru

  Institute for Protein Research

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