Ultraviolet B (UVB) photosensitivities of tea catechins and the relevant chemical conversions

Abstract

Ultraviolet B (UVB) photosensitivities of eight catechins were screened. In both water and ethanol, epicatechin (EC, 575 μM) and catechin (C, 575M) exhibited low photostabilities under 6 h UVB radiation with the generation of yellow photoproducts, while other catechins (epigallocatechin gallate, epigallocatechin, epicatechin gallate, gallocatechingallate, gallocatechin, catechin gallate) were relatively UVB-insensitive. Photoisomerization and photolysis were two important UVB-induced reactions to EC whereas photolysis was the dominant reaction for C. The influencing factors of time (2-10 h), solvent (water, ethanol) and substrate concentration (71.875-1150μM) on UVB-induced chemical conversions of EC and C were investigated, and eight photoproducts were identified through ultra performance liquid chromatography-diode array detection-Tandem mass spectrometry (UPLC-DAD-MS/MS) and 1H nuclear magnetic resonance (1H-NMR analysis). Photolysis reaction involved two pathways, including radical reaction and photo-induced electron transfer reaction. The 2,2-diphenylpicrylhydrazyl (DPPH) scavenging abilities of eight catechins did not change upon 6 h UVB irradiation. EC and C are photosensitive catechins among eight catechins causing deep color.