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

文献类型： 外文期刊

第一作者： Wang, Wei

作者： Wang, Wei;Wang, Weiwei;Zhang, Jianyong;Jiang, Heyuan;Wang, Wei;Chen, Lin;Engelhardt, Ulrich H.

作者机构：

关键词： antimelanogenic activity; catechins; dimeric oxidation products; structure-activity relationship; oxidative dimerization

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：5.895； 五年影响因子：6.048 ）

ISSN： 0021-8561

年卷期： 2022 年 70 卷 4 期

页码：

收录情况： SCI

摘要： 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 alpha-MSH-stimulated B16F10 cell model. It was found that 100 mu g/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 mu M 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.

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