NMR analytical approach to clarify the antioxidative molecular mechanism of catechins using 1,1-diphenyl-2-picrylhydrazyl

Each tea catechin was reacted with 1,1-diphenyl-2-picrylhydrazyl (DPPH), and the reaction mixture was subjected to NMR analysis. The antioxidation mechanism of (+)-catechin [(+)-C] is considered to be due to the change of the B-ring to an o-quinone structure at first because of the appearance of two carbonyl signals. This is substantiated by trapping the compound as an adduct of a 1,2-phenylenediamine to an o-quinone. (-)-Epicatechin [(-)-EC] was also confirmed to give a similar result, but in the case of (-)-epigallocatechin [(-)-EGC] and ethyl gallate (EG) no carbonyl signals were observed. The antioxidation mechanisms of(-)-EGC and EG are different from those of(+)-C and (-)-EC. This may be one of the reasons for the differences of the antioxidative activities between the two types of catechins.