Reducing Activity of Polyphenols with Stable Radicals of the TTM Series. Electron Transfer versus H-Abstraction Reactions in Flavan-3-ols

Abstract
A new method to test the antioxidant activity of polyphenols by electron transfer reactions to a stable organic free radical, tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl radical (HNTTM), is reported. Therefore, the activity of the natural flavanols, (−)-epicatechin, and two synthetic derivatives, 4β-(S-cysteinyl)epicatechin and 4β-(2-aminoethylthio)epicatechin, can be differentiated by their capacity to transfer hydrogen atoms to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and to transfer electrons to HNTTM.