Oxidation and degradation of (epi)gallocatechin gallate (EGCG/GCG) and (epi)catechin gallate (ECG/CG) in alkali solution

The oxidative decomposition/degradation of two main tea flavanols, EGCG/GCG and ECG/CG, was studied in alkaline solution under ultrasonic-assisted thermal conditions. The study employed HPLC-ESI-ToF-MS to identify the products generated by atmospheric oxygen oxidation and various base-catalyzed reactions. Strong basic condition led to accelerated hydrolysis and oxidation of EGCG/GCG and ECG/CG and yielded gallic acid, de-galloyl flavanols and corresponding o-quinone derivatives. Meanwhile, peroxidation or base-catalyzed cleavage and rearrangement occurred extensively on C- and B-rings of flavanol and generated various simpler aldehydes or acids. Besides, a number of dimers/trimers were produced. This contribution provides empirical proof of oxidative degradation of flavanols under strong alkaline condition. Meanwhile, detailed reaction mechanisms of C-/B-ring degradation and dimerization/polymerization phenomena are proposed to help understand the structural changes of flavanols under strong alkaline conditions.