A novel pathway for the photooxidation of catechin in relation to its prooxidative activity

Scientific Reports
Shunichi ShishidoYoshimi Niwano

Abstract

In the present study, we evaluated the prooxidative mode of action of photoirradiated (+)-catechin at 400 nm in relation to reactive oxygen species generation and its possible application to disinfection. Photoirradiation of (+)-catechin at a concentration of 1 mg/mL yielded not only hydrogen peroxide (H2O2) but hydroxyl radical (·OH) in a total amount of approximately 20 μM in 10 min. As a result, photoirradiated catechin killed Staphylococcus aureus, and a > 5-log reduction in viable bacteria counts was observed within 20 min. Liquid chromatography-high-resolution-electrospray ionization-mass spectrometry showed that photoirradiation decreased the (+)-catechin peak (molecular formula C15H14O6) whilst it increased two peaks of a substance with the molecular formula C15H12O6 with increasing irradiation time. Nuclear magnetic resonance analysis revealed that the two C15H12O6 peaks were allocated to intramolecular cyclization products that are enantiomers of each other. These results suggest that photoirradiation induces oxidation of (+)-catechin resulting in the reduction of oxygen to generate H2O2. This H2O2 is then homolytically cleaved to ·OH, and alongside this process, (+)-catechin is finally converted to two intramolecular...Continue Reading

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Citations

Aug 18, 2020·Food Science and Biotechnology·Eunok Choe
Mar 25, 2020·International Journal of Molecular Sciences·Elda ChiainoMaria Frosini
Jun 3, 2021·Pathogens·Meishan Wu, Angela C Brown
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ying GaoYong-Quan Xu

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Methods Mentioned

BETA
electron spin resonance
ESR
nuclear magnetic resonance
NMR
X-ray

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