Effect of Active Groups and Oxidative Dimerization on the Antimelanogenic Activity of Catechins and Their Dimeric Oxidation Products

• Published in: Journal of agricultural and food chemistry Vol. 70; no. 4; pp. 1304 - 1315
• Main Authors: Wang, Wei, Chen, Lin, Wang, Weiwei, Zhang, Jianyong, Engelhardt, Ulrich H, Jiang, Heyuan
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 02.02.2022
• Subjects: Catechin - pharmacology; Dimerization; Functional Structure/Activity Relationships; Oxidation-Reduction; Oxidative Stress; Structure-Activity Relationship; dimeric oxidation products; structure−activity relationship; antimelanogenic activity; catechins; oxidative dimerization
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.1c07028

Some catechins and their dimeric oxidation products are well known to possess antimelanogenic activity, which could be influenced by their structures and oxidative dimerization. This study compared the antimelanogenic activity of different catechins and dimeric oxidation products and clarified the mechanism using an α-MSH-stimulated B16F10 cell model. It was found that 100 μg/mL (−)-gallocatechin gallate, (−)-epigallocatechin gallate, theasinensin A, and theaflavine-3,3′-digallate could significantly inhibit melanin synthesis without cytotoxicity. The tyrosinase (TYR) activities were 26.24 ± 4.97, 31.57 ± 5.37, 66.10 ± 9.62, and 78.19 ± 5.14%, respectively, and the melanin contents were 38.29 ± 3.50, 41.21 ± 7.62, 62.13 ± 9.80, and 68.82 ± 11.62%, respectively. These compounds inhibit melanin production by attenuating the mRNA levels of TYR, TRP1, and TRP2 gene. The structure–activity relationship showed that geometrical isomerism was not the key factor affecting catechins’ antimelanogenic activity. Compared with the catechol, catechins with B-ring pyrogallol inhibited melanin synthesis more effectively. The number of galloyl groups was positively correlated with antimelanogenic activity. Compared with 3-galloyl, 3′-galloyl was a stronger active group in antimelanogenesis. Interestingly, the contribution of B-ring pyrogallol to the antimelanogenic activity was significantly stronger than that of 3-galloyl in catechins. Additionally, the antimelanogenic activity of the dimeric oxidation product at 100 μM was more than or equal to that of individual substrate–catechin, while being significantly less than that of the substrate–catechin mixture. Results indicated that pyrogallol and galloyl were the active groups inhibiting melanin synthesis. The oxidative dimerization weakened the antimelanogenic activity of the substrate–catechin mixture.