Catechin exhibits numerous physiological characteristics. In this study, we determined the photosensitivity of catechin to various lights under alkaline conditions, and the mechanisms by which catechin generates free radical species and polymerizes via a photoreaction. In addition to this, the application of catechin photolysis was investigated. A solution of catechin is transparent, but turns yellowish under blue light illumination (BLI) in neutral or weak alkaline solutions. When catechin is subjected to BLI, a dimeric catechin (proanthocyanidin) and a superoxide anion radical (${\mathrm{O}}_2^{•-}$) are generated in a photolytic reaction. When ascorbic acid or gallic acid is added to catechin and the mixture is subjected to BLI at alkaline pH, fewer catechin dimers and less ${\mathrm{O}}_2^{•-}$ are produced, because both acids inhibit the photosensitive oxidation of catechin. When AlCl₃ is added to catechin and the mixture is subjected to BLI at pH 8, a photolytic reaction is suppressed by AlCl₃, and AlCl₃ acts as a catalyst for the disconnection of proanthocyanidin during photolysis. Under alkaline conditions, catechin generates ${\mathrm{O}}_2^{•-}$ via photosensitive oxidation, which suppresses the growth of Acinetobacter baumannii (A. baumannii) by at least 4 logs, and deactivates its multi-drug-resistant strain. This study shows that catechin photolysis is a process of oxidation, and that it can be safely applied as a tool for environmental applications.

Catechins belonging to polyhydroxylated polyphenols are the primary compounds found in green tea. They are associated with many physiological properties. Epicatechin (EC) is a non-gallate-type catechin with four phenolic hydroxyl groups attached. The changes in EC treated with color light illumination in an alkaline condition were investigated by chromatographic and mass analyses in this study. In particular, the superoxide anion radical (O2•−) was investigated during the EC photolytic process. EC is unstable under blue light illumination in an alkaline solution. When EC was treated with blue light illumination in an alkaline solution, O2•− was found to occur via a photosensitive redox reaction. In addition, the generation of monomeric, dimeric, and trimeric compounds is investigated. On the other hand, epigallocatechin gallate (EGCG), which is a gallate-type catechin, is stable under blue light illumination in an alkaline solution. Adding EGCG, during the blue light illumination treatment of EC decreased photolytic formation, suggesting that gallate-type catechins can suppress the photosensitive oxidation of EC. Gallate-type catechins are formed via the esterification of non-gallate-type catechins and gallic acid (GA). The carbonyl group on the gallate moiety of gallate-type catechins appears to exhibit its effect on the stability against the photosensitive oxidation caused by blue light illumination.

Catechin is a flavan-3-ol, a derivative of flavans, with four phenolic hydroxyl groups, which exhibits a wide range of physiological properties. Chromatographic analyses were employed to examine the effects of blue light irradiation on the changes of catechin hydrate in an alkaline condition. In particular, the detection of a superoxide anion radical (O₂•⁻), a reactive oxygen species (ROS), and the inactivation of Acinetobacter baumannii (A. baumannii)—including a carbapenem-resistant A. baumannii (CRAB)—was investigated during the photoreaction of catechin hydrate. Following basification with blue light irradiation, the transparent solution of catechin hydrate turned yellowish, and a chromogenic catechin dimer was separated and identified as a proanthocyanidin. Adding ascorbic acid during the photolytic treatment of catechin hydrate decreased the dimer formation, suggesting that ascorbic acid can suppress the photosensitive oxidation of catechin. When catechin hydrate was irradiated by blue light in an alkaline solution, O₂•⁻ was produced via photosensitized oxidation, enhancing the inactivation of A. baumannii and CRAB. The present findings on the photon-induced oxidation of catechin hydrate provides a safe practice for the inactivation of environmental microorganisms.

Tetracycline (TC) is a broad-spectrum antibiotic compound. Wastewater with TC may have an adverse effect on ecosystems. Riboflavin-5′-phosphate (FMN or flavin mononucleotide) is a non-toxic product of the phosphorylation of vitamin B₂ and is required for the proper functioning of the humans. FMN is sensitized to ultraviolet (UV) and blue light radiation, as evidenced by the generation of reactive oxygen species (ROS). This study inspects feasible applications of blue light on FMN so as to develop a valid way of degrading TC by FMN photolysis. We used the increased rate of bacterial survival as a practical indicator of antibiotic degradation. TC in the presence of FMN solution decomposed completely after 20 W/m² of blue light irradiation (TCF treatment), and the degradation of TC (D-TCF) occurred after the photolytic process. After TCF treatment, colony-forming units (CFUs) of Escherichia coli (E. coli) were determined for the D-TCF solution. The CFU of E. coli preservation was 93.2% of the D-TCF solution (50 μg/mL of TC in the presence of 114 μg/mL of FMN solution treated with 20 W/m² of blue light irradiation at 25 °C for 1 h) cultivation. The mass spectrum of D-TCF showed diagnostic ion signals at m/z 431.0 and 414.0 Da. The molecular formula of D-TCF was C₂₁H₂₂N₂O₈, and the exact mass was 430.44 g/mol. TC degradation by FMN photolysis can significantly decrease the antimicrobial ability of TC. The results expressed here regarding the influence of FMN photolysis on TC degradation offer an environmentally sound wastewater treatment method.

Tea is rich in catechins and aluminum. In this study, the process of catechin photolysis was applied as a model for examining the effects of aluminum chloride (AlCl₃) on the structural changes of catechin and the alteration of aluminum complexes under blue light irradiation (BLI) at pH 8 using liquid chromatography and mass spectrometry techniques. Additionally, the effects of anions on catechin upon the addition of AlCl₃ and treatment with BLI were also studied. In this study, when 1 mM catechin was treated with BLI, a superoxide anion radical (${\mathrm{O}}_2^{•-}$) was generated in an air-saturated aqueous solution, in addition to forming a dimeric catechin (proanthocyanidin) via a photon-induced redox reaction. The relative percentage of catechin was found to be 59.0 and 95.7 for catechin treated with BLI and catechin upon the addition of 1 mM AlCl₃ treated with BLI, respectively. It suggested that catechin treated with BLI could be suppressed by AlCl₃, while AlCl₃ did not form a complex with catechin in the photolytic system. However, under the same conditions, it was also found that the addition of AlCl₃ inhibited the photolytic formation of ${\mathrm{O}}_2^{•-},$ and reduced the generation of proanthocyanidin, suggesting that the disconnection of proanthocyanidin was achieved by AlCl₃ acting as a catalyst under treatment with BLI. The influence of 1 mM fluoride (${\mathrm{F}}^{-}$) and 1 mM oxalate (${\mathrm{C}}_2{\mathrm{O}}_4^{2-}$) ions on the photolysis of 1 mM catechin upon the addition of 1 mM AlCl₃ and treatment with BLI was found to be insignificant, implying that, during the photolysis of catechin, the Al species were either neutral or negatively charged and the aluminum species did not form a complex with anions in the photolytic system. Therefore, aluminum, which is an amphoteric species, has an inherent potential to stabilize the photolysis of catechin in an alkaline conditions, while suppressing the ${\mathrm{O}}_2^{•-}$ and proanthocyanidin generation via aluminum ion catalysis in the catechin/Al system under treatment with BLI.