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- W116084821 abstract "Chlorogenic acid (1), a cancer chemopreventive agent widely found in fruits, tea and coffee, undergoes efficient conjugation with glutathione (GSH), in the presence of horseradish peroxidase/H(2)O(2) or tyrosinase at pH 7.4, to yield three main adducts that have been isolated and identified as 2-S-glutathionylchlorogenic acid (3), 2,5-di-S-glutathionylchlorogenic acid (4) and 2,5,6-tri-S-glutathionylchlorogenic acid (5) by extensive NMR analysis. The same pattern of products could be obtained by reaction of 1 with GSH in the presence of nitrite ions in acetate buffer at pH 4. Mechanistic experiments suggested that oxidative conjugation reactions proceed by sequential nucleophilic attack of GSH on ortho-quinone intermediates. Overall, these results provide the first complete spectral characterization of the adducts generated by biomimetic oxidation of 1 in the presence of GSH, and disclose a new possible nitrite-mediated conjugation pathway of 1 with GSH at acidic pH of physiological relevance." @default.
- W116084821 created "2016-06-24" @default.
- W116084821 creator A5030585327 @default.
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- W116084821 date "2003-11-01" @default.
- W116084821 modified "2023-09-27" @default.
- W116084821 title "Oxidative conjugation of chlorogenic acid with glutathione" @default.
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- W116084821 doi "https://doi.org/10.1016/s0968-0896(03)00460-7" @default.
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