Capsaicinol: Synthesis by allylic oxidation and its effect on TRPV1-expressing cells and adrenaline secretion in rats
2006
Kobata, K.(Shizuoka Univ. (Japan)) | Iwasawa, T. | Iwasaki, Y. | Morita, A. | Suzuki, Y. | Kikuzaki, H. | Nakatani, N. | Watanabe, T.
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)) resulted in the formation of (+-)-capsaicinol acetate at a 7.2% yield in a single step. The effectiveness of (+-)-capsaicinol in TRPV1 activation (ECsub(50)=1.1microM) was found to be weaker than that of capsaicin (ECsub(50)=0.017 microM), whereas the efficacy of (+-)-capsaicinol reached 75% of that of capsaicin. Intravenous administration of (+-)-capsaicinol in anesthetized rats dosedependently 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.
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