PMID: 11325537Apr 28, 2001Paper

Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants

Biochimica Et Biophysica Acta
Hiroki HottaYoshio Tsujino

Abstract

Reaction mechanisms of polyphenolic antioxidants were studied using electrochemical methods (flow column electrolysis and cyclic voltammetry). In flow column electrolysis, the numbers (ns) of electrons involved in the oxidation of catechols (chlorogenic acid and caffeic acid) became larger than two (i.e. the number of -OH moieties) at pH > 7; the n-values finally reached ca. 4 at pH 10. Other polyphenols including catechin, ellagic acid, and curcumin exhibited higher n-values than the numbers of -OH moieties in the whole pH range studied (4 < pH < 10). Such unusually large n-values for polyphenols were found to correlate to their irreversible behavior in cyclic voltammetry. A digital simulation analysis of the voltammograms of chlorogenic acid clearly showed that the electrode reaction at higher pHs can be elucidated in terms of a quasi-reversible electron transfer followed by a chemical reaction and also suggested that the chemical reaction is of second order to the concentration of chlorogenic acid, i.e. a dimerization reaction. In a similar manner, polyphenolic antioxidants generally undergo certain chemical reactions on the occasion of their oxidation. As a result, some oxidizable, phenolic -OH moieties are reproduced in th...Continue Reading

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