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

• Published in: Scientific reports 2018-08, Vol.8 (1), p.12888-11, Article 12888
• Main Authors: Shishido, Shunichi, Miyano, Rei, Nakashima, Takuji, Matsuo, Hirotaka, Iwatsuki, Masato, Nakamura, Keisuke, Kanno, Taro, Egusa, Hiroshi, Niwano, Yoshimi
• Format: Article
• Language: English
• Subjects: 140/131; 631/45/56; 692/699/3017/3018; 82/58; Catechin; Disinfection; Enantiomers; Humanities and Social Sciences; Hydrogen peroxide; Hydroxyl radicals; Ionization; Irradiation; Liquid chromatography; Mass spectrometry; Mass spectroscopy; Mode of action; multidisciplinary; NMR; Nuclear magnetic resonance; Oxidation; Photooxidation; Quinones; Radiation; Reactive oxygen species; Science; Science (multidisciplinary)
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-018-31195-x

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 (H 2 O 2 ) 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 C 15 H 14 O 6 ) whilst it increased two peaks of a substance with the molecular formula C 15 H 12 O 6 with increasing irradiation time. Nuclear magnetic resonance analysis revealed that the two C 15 H 12 O 6 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 H 2 O 2 . This H 2 O 2 is then homolytically cleaved to ·OH, and alongside this process, (+)-catechin is finally converted to two intramolecular cyclization products that are different from the quinone structure of the B ring, as proposed previously for the autoxidation and enzymatic oxidation of catechins.