Michael-Type Addition of Illudin S, a Toxic Substance from Lampteromyces japonicus, with Cysteine and Cysteine-Containing Peptides in Vitro

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概要

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• Reactions of illudin S with cysteine derivatives (cysteine methyl ester, glutathione and a peptide, Cys-Asp-Pro-Gly-Tyr-Ile-Gly-Ser-Arg) were investigated. In the reaction with cysteine methyl ester, four products (P1,P2,P3,P4) were obtained and their structures were determined, on the basis of MS and NMR data, to be adducts of the mercapto group of cysteine methyl ester with the α, β-unsaturated carbonyl group of illudin S. In the reactions with glutathione and the peptide, two addition products in each case were identified by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and NMR analyses. The structures of these adducts also indicated that the α, β-unsaturated carbonyl group in illudin S behaves as a Michael acceptor for the mercapto group in cysteine.

• 公益社団法人日本薬学会の論文
• 1996-02-15

著者

• 井上 哲也

  Faculty Of Pharmaceutical Sciences Osaka University

• TANAKA Ken

  National Police Agency

• TEZUKA Yasuhiro

  Research Institute for Wakan-Yaku, Toyama Medical and Pharmaceutical University

• Tanaka K

  Department Of Molecular Engineering Graduate School Of Engineering Kyoto University

• 井上 勗

  Ohmiya Research Laboratory Fuji Yakuhin Co. Ltd.

• Inoue T

  Ohmiya Research Laboratory Fuji Yakuhin Co. Ltd

• Tanaka Ken-ichiro

  Faculty Of Pharmaceutical Sciences Okayama University

• Tezuka Yasuhiro

  Research Institute For Wakan-yaku (oriental Medicines) Toyama Medical And Pharmaceutical University

• Tezuka Yasuhiro

  Research Institute For Wakan-yaku (oriental Medicines) Toyama Medical Pharmaceutical University

• KIKUCHi Tohru

  Research Institute for Wakan-Yaku (Oriental Medicines), Toyama Medical and Pharmaceutical University

• Kikuchi T

  Research Institute For Wakan-yaku (oriental Medicines) Toyama Medical And Pharmaceutical University

• Tanaka Katsuyuki

  Dept. Biol. Sci. Fac. Sci. Hiroshima Univ.

• INOUE Takako

  National Research Institute of Police Science

• Tanaka K

  Dept. Biol. Sci. Fac. Sci. Hiroshima Univ.

• Inoue T

  Osaka University Of Pharmaceutical Sciences

• 井上 輝比古

  Pharmaceutical Research Department Ube Laboratory Corporate Research & Development Ube Industrie

• Kikuchi Tohru

  Research Institute For Wakan-yaku (oriental Medicines) Toyama Medical And Pharmaceutical University

• Inoue Takao

  Faculty Of Pharmaceutical Sciences Hoshi University

• KIKUCHI Tohru

  Research Institute for Wakan-Yaku (Oriental Medicine), Toyama Medical and Pharmaceutical University

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