PMID: 8614248Mar 10, 1995Paper

Metabolism of capsaicinoids: evidence for aliphatic hydroxylation and its pharmacological implications

Life Sciences
Y J SurhS S Lee

Abstract

A new metabolic oxidation pathway of capsaicin (N-[(4-hydroxy-3-methoxyphenyl)-methyl]-8-methyl-(E)-6 -nonenamide), a major pungent and pharmacologically active principle of hot peppers, was investigated. Incubation of capsaicin with phenobarbital-induced rat liver postmitochondrial supernatant enriched with NADPH-generating system produced N-(4,5-dihydroxy-3-methoxybenzyl)-(E)-6 -nonenylamide and a more polar metabolite. The latter metabolite was spectrophotometrically and chromatographically identical to authentic omega-hydroxycapsaicin. This new metabolite was also detected in the urine of rabbits given capsaicin by gastric intubation. Other analogs of capsaicin, such as dihydrocapsaicin and nonivamide, also formed similar metabolites via aliphatic hydroxylation. When tested for antinociceptive activity as well as pungency, the above polar metabolites were found to be inactive while their parent compounds exhibited strong sensory effects. Capsaicin interacted irreversibly with heptic drug metabolizing enzymes, thereby inhibiting their activity as indicated by prolongation of pentobarbital sleeping time in rats. Such inhibition of drug metabolism was not observed with omega-hydroxycapsaicin. These findings suggest that metabo...Continue Reading

Citations

Jan 11, 2005·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Christopher A Reilly, Garold S Yost
Oct 2, 2012·Pharmacological Reviews·Jessica O'NeillAnthony H Dickenson
Jun 1, 2012·Molecular Nutrition & Food Research·Eun Hee HanHye Gwang Jeong
May 9, 2012·Toxicologic Pathology·Keith BleySunita Babbar
May 4, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daisuke SatoNaoji Kubota
Jun 27, 2002·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Rachaneewan KarnkaYuthsak Vaneesorn

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