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

• KOBATA Kenji

  Graduate School of Nutritional and Environmental Sciences and COE program in the 21st century, University of Shizuoka

• IWASAWA Takahito

  Graduate School of Nutritional and Environmental Sciences and COE program in the 21st century, University of Shizuoka

• IWASAKI Yusaku

  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

• KIKUZAKI Hiroe

  Graduate School of Human Life Science, Osaka City University

• NAKATANI Nobuji

  Graduate School of Human Life Science, Osaka City University

• 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)₂) resulted in the formation of (±)-capsaicinol acetate at a 7.2% yield in a single step. The effectiveness of (±)-capsaicinol in TRPV1 activation (EC₅₀=1.1 μM) was found to be weaker than that of capsaicin (EC₅₀=0.017 μM), 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

  公益社団法人 日本農芸化学会

キーワード

• capsaicinol
• allylic oxidation
• transient receptor potential vanilloid 1 (TRPV1)
• adrenaline secretion
• pungency

詳細情報

• CRID: 1390001206479481088
• NII論文ID: 10018528146
• NII書誌ID: AA10824164
• DOI: 10.1271/bbb.60064
• ISSN: 13476947
• ISSN: 09168451
• NDL書誌ID: 8040360
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I8040360
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.60064
• Web Site: https://search.jamas.or.jp/link/ui/2007057506
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可