Effect of Active Groups and Oxidative Dimerization on the Antimelanogenic Activity of Catechins and Their Dimeric Oxidation Products
| العنوان: | Effect of Active Groups and Oxidative Dimerization on the Antimelanogenic Activity of Catechins and Their Dimeric Oxidation Products |
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| المؤلفون: | Wei Wang, Lin Chen, Weiwei Wang, Jianyong Zhang, Ulrich H. Engelhardt, Heyuan Jiang |
| المصدر: | Journal of Agricultural and Food Chemistry. 70:1304-1315 |
| بيانات النشر: | American Chemical Society (ACS), 2022. |
| سنة النشر: | 2022 |
| مصطلحات موضوعية: | Oxidative Stress, Structure-Activity Relationship, General Chemistry, General Agricultural and Biological Sciences, Dimerization, Oxidation-Reduction, Catechin |
| الوصف: | 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. |
| تدمد: | 1520-5118 0021-8561 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1e7b20aaa6a170a60cf882ed896d79ae https://doi.org/10.1021/acs.jafc.1c07028 |
| حقوق: | CLOSED |
| رقم الأكسشن: | edsair.doi.dedup.....1e7b20aaa6a170a60cf882ed896d79ae |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 15205118 00218561 |
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