Differential effects of theasinensins and epigallocatechin-3-O-gallate on phospholipid bilayer structure and liposomal aggregation

(−)-Epigallocatechin-3-O-gallate (EGCg), the major catechin responsible for the health-enhancing and disease-preventive effects of green tea, is susceptible to auto-oxidation at physiological pH levels. However, whether the oxidized EGCg resulting from its oral consumption possesses any bioactive functions remains unclear. This study presents a differential analysis of intact and oxidized EGCg regarding their interactions with phosphatidylcholine liposomes, serving as a simple biomembrane model. In the presence of ascorbic acid, pre-oxidized EGCg induced liposomal aggregation in a dose-dependent manner, whereas intact EGCg did not. Toxicity evaluation using calcein-loaded liposomes revealed that liposomal aggregation is associated with minimal membrane damage. Through fractionation of the oxidized EGCg sample, the fraction containing theasinensins showed high liposomal aggregation activity. Overall, these results suggest that oxidatively condensed EGCg dimers may stimulate various cells by altering the plasma membrane in a manner different from that of EGCg monomers.