Capsaicinol : Synthesis by Allylic Oxidation and Its Effect on TRPV1-Expressing Cells and Adrenaline Secretion in Rats

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著者

    • Kobata Kenji KOBATA Kenji
    • Graduate School of Nutritional and Environmental Sciences and COE program in the 21st century, University of Shizuoka
    • MORITA Akihito
    • Graduate School of Nutritional and Environmental Sciences and COE program in the 21st century, University of Shizuoka
    • SUZUKI Yuichi
    • Graduate School of Nutritional and Environmental Sciences and COE program in the 21st century, University of Shizuoka
    • WATANABE Tatsuo
    • Graduate School of Nutritional and Environmental Sciences and COE program in the 21st century, University of Shizuoka

抄録

Capsaicinol is an ingredient of hot red pepper. In this study, we developed a novel method for capsaicinol synthesis and examined capsaicinol's physiological effects on capsaicin receptor (TRPV1)-related actions. Allylic oxidation of capsaicin by palladium acetate (Pd(OAc)<SUB>2</SUB>) resulted in the formation of (±)-capsaicinol acetate at a 7.2% yield in a single step. The effectiveness of (±)-capsaicinol in TRPV1 activation (EC<SUB>50</SUB>=1.1 μ<small>M</small>) was found to be weaker than that of capsaicin (EC<SUB>50</SUB>=0.017 μ<small>M</small>), whereas the efficacy of (±)-capsaicinol reached 75% of that of capsaicin. Intravenous administration of (±)-capsaicinol in anesthetized rats dose-dependently enhanced adrenaline secretion from the adrenal gland. The response to a 5 mg/kg-dose of (±)-capsaicinol was comparable to that of a 0.05 mg/kg-dose of capsaicin. The relative pungency of capsaicinol to capsaicin was coincident with the relative effectiveness in inducing these TRPV1-related actions.

収録刊行物

  • Bioscience, biotechnology, and biochemistry  

    Bioscience, biotechnology, and biochemistry 70(8), 1904-1912, 2006-08-23 

    Japan Society for Bioscience, Biotechnology, and Agrochemistry

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各種コード

  • NII論文ID(NAID)
    10018528146
  • NII書誌ID(NCID)
    AA10824164
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    09168451
  • NDL 記事登録ID
    8040360
  • NDL 雑誌分類
    ZR7(科学技術--農林水産--農産) // ZR2(科学技術--生物学--生化学) // ZP1(科学技術--化学・化学工業)
  • NDL 請求記号
    Z53-G223
  • データ提供元
    CJP書誌  CJP引用  NDL  J-STAGE 
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