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

Cited 25 time in Web of Science Cited 37 time in Scopus
Authors
Surh, Young-Joon; Ahn, Seung Ho; Kim, Kee-Cheon; Park, Jeong-Bae; Sohn, Yeo Won; Lee, Sang Sup
Issue Date
1995-03
Citation
Life Sciences, Vol.56 No.16, pp.PL305-PL311
Keywords
CAPSAICINALIPHATIC HYDROXYLATIONMETABOLIC OXIDATION PATHWAY
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 hepatic 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 metabolism of capsaicinoids via hydroxylation of their side chains plays an important role in the detoxification of these pharmacologically active substances.
ISSN
0024-3205
URI
https://hdl.handle.net/10371/172812
DOI
https://doi.org/10.1016/0024-3205(95)00091-7
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Graduate School of Convergence Science and Technology (융합과학기술대학원)Dept. of Molecular and Biopharmaceutical Sciences (분자의학 및 바이오제약학과)Journal Papers (저널논문_분자의학 및 바이오제약학과)
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