Enzymic oxidation of capsaicin

The oxidation of capsaicin (8-methyl-N-vanillyl-6-nonenamide) has been investigated by means of electrochemical, enzymic and chemical procedures. Capsaicin appears to form a fluorescent dimer comparable with those known to be formed from some other compounds bearing the vanillyl(4-hydroxy-3-methoxyb...

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Bibliographic Details
Published inBiochemical pharmacology Vol. 41; no. 12; p. 1863
Main Authors Boersch, A, Callingham, B A, Lembeck, F, Sharman, D F
Format Journal Article
LanguageEnglish
Published England 15.06.1991
Subjects
Capsaicin - chemistry
Capsaicin - metabolism
Cresols - metabolism
Electrochemistry - methods
Ferricyanides - metabolism
Fluorescence
Homovanillic Acid - metabolism
Oxidation-Reduction
Peroxidases - metabolism
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Summary:The oxidation of capsaicin (8-methyl-N-vanillyl-6-nonenamide) has been investigated by means of electrochemical, enzymic and chemical procedures. Capsaicin appears to form a fluorescent dimer comparable with those known to be formed from some other compounds bearing the vanillyl(4-hydroxy-3-methoxybenzyl-) group. If such a dimer of capsaicin were to be formed in tissues, it would bind tightly to lipid structures and its formation would prove difficult to follow. Tests on other substances bearing the vanillyl group that might be used to investigate the dimerization reaction in tissues and tissue extracts showed that 4-hydroxy-3-methoxyphenylacetic acid is a poor second substrate for peroxidase reactions. It was found that 2-methoxy-4-methylphenol (creosol) was more suitable. These results support the suggestion that the oxidation of capsaicin may be involved in some of its biological actions.
ISSN:0006-2952
DOI:10.1016/0006-2952(91)90125-O