数字农科院2.0

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

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

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

ISSN: 0021-8561

年卷期: 2022 年 70 卷

页码:

收录情况: SCIE(2022版) ; EI(2022版)

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 & PRIME;-digallate could significantly inhibit melanin synthesis without cytotoxicity. The tyrosinase (TYR) activities were 26.24 & PLUSMN; 4.97, 31.57 & PLUSMN; 5.37, 66.10 & PLUSMN; 9.62, and 78.19 & PLUSMN; 5.14%, respectively, and the melanin contents were 38.29 & PLUSMN; 3.50, 41.21 & PLUSMN; 7.62, 62.13 & PLUSMN; 9.80, and 68.82 & PLUSMN; 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 & PRIME;-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 of the substrate-catechin mixture.

分类号:

  • 相关文献

[1]我国苦茶资源主要生化成分的鉴定评价(英文). 王新超,姚明哲,马春雷,陈亮. 2008

[2]Design, synthesis and fungicidal activity of 11-alkoxyimino-5,6-dihydro-dibenzo[b,e] azepine-6-one derivatives. Xu, Yan-jun,Huang, Jia-xing,Liang, Xiao-mei,Zhang, Jian-jun,Wang, Dao-quan,Yan, Xiao-jing,Yuan, Hui-zhu.

[3]Structures and Mechanism of Action for Complex III Inhibiting-Fungicides. Hou Yuxia,Qin Zhaohai,Yuan Huizhu. 2010

[4]Design of novel carbamate acetylcholinesterase inhibitors based on the multiple binding sites of acetylcholinesterase. Mei, Xiangdong,Yuan, Huizhu,Ning, Jun,Zhao, Qianfei.

[5]Design, synthesis and bioactivity of novel phthalimide derivatives as acetylcholinesterase inhibitors. Zhang, Tao,Zhang, Lanxiang,Mei, Xiangdong,Dong, Mengya,Zhang, Kaixin,Ning, Jun.

[6]Synthesis and insecticidal activities of novel oxime ether pyrethroids. Ou, XM,Huang, MZ,Wang, XG,Liu, XP,Wang, YJ,Chen, C,Yao, JR.

[7]Design, synthesis and fungicidal activity of novel 2-substituted aminocycloalkylsulfonamides. Wang, Minlong,Qin, Peiwen,Qi, Zhiqiu,Ji, Mingshan,Li, Xinghai,Liu, Xingyu,Babu, P. Vijaya,Cui, Zi-Ning,Yan, Xiaojing.

[8]Synthesis, Fungicidal Activity and Mode of Action of 4-Phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea. Qi, Zhiqiu,Ji, Mingshan,Li, Xinghai,Cui, Zining,Yan, Xiaojing.

[9]Systematic activity-oriented separation and structure-activity relationship of tobacco cembranoids. Jiao Wang,Kuo Xu,Jianhui Zhang,Guangwei Ren,Xingyou Yang,Zhongfeng Zhang,Yayu Zhang,Yong Xiao,Yongmei Du. 2021

[10]Design, Synthesis And Fungicidal Activity O.f Novel 2-Substituted Aminocycloalkylsulfonamides. Liu, CX,Yan, XJ,Wang, ML,Qin, PW,Qi, ZQ,Ji, MS,Liu, XY,Babu, PV,Li, XH,Cui, ZN. 2017

[11]Systematic activity-oriented separation and structure-activity relationship of tobacco cembranoids. Jiao Wang,Kuo Xu,Jianhui Zhang,Guangwei Ren,Xingyou Yang,Zhongfeng Zhang,Yayu Zhang,Yong Xiao,Yongmei Du. 2021

[12]Synthesis and Biological Profiling of Novel Strigolactone Derivatives for Arabidopsis Growth and Development. Kang, Zhaoyong,Yan, Yujie,Lu, Ruirui,Dong, Xiaoqi,Xu, Jun,Zheng, Dong,Li, Suhua,Gao, Qingzhi,Liu, Shengnan. 2023

[13]Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure-Activity Relationship, Kinetics and Interaction Mechanism. Pan, Junkun,Zhang, Qiang,Zhang, Chunling,Yang, Wenbo,Liu, Hui,Lv, Zhenzhen,Liu, Jiechao,Jiao, Zhonggao. 2022

[14]Insights into inhibitory mechanisms: Unraveling the structure-activity relationship of dietary flavonoids on gut bacterial β-glucuronidase. Jialu Shen,Qingyu Zhao,Kai Zhang,Junmin Zhang,Huiyan Zhang. 2024

[15]Discovery of 3,4-dihydropyrimidine derivatives as novel Anti-PEDV agents targeting viral internalization through a unique calcium homeostasis disruption mechanism. Sai Lv,Rumeng Ma,Qun Tang,Xiaoyang Wang,Chunmei Wang,Keyu Zhang,Houkai Li,Wenchong Ye,Wen Zhou. 2025

[16]Structure-based virtual screening of novel chitin synthase inhibitors for the control of Phytophthora sojae. Liu, Yuansheng,Liu, Jinfeng,Xia, Yeqiang,Chen, Wei,Li, Yingchen,He, Xiao,Yang, Qing. 2024

[17]Mild ultrasound-assisted alkali de-esterification modified pectins: Characterization and structure–activity relationships in immunomodulatory effects. Huan Guo,Dong Li,Baohe Miao,Kanglin Feng,Guijing Chen,Renyou Gan,Zhiliang Kang,Hong Gao. 2025

[18]Structure-activity relationship of ginsenoside derivatives with different glycosides and double bond position on anti-aging bioactivities. Zhang, Juntao,Wang, Weimin,Fan, Daidi,Deng, Jianjun,Yang, Haixia. 2025

[19]Structural basis for the anti-aging effects of hydroxyproline-BCAA dipeptides: An integrated computational and experimental approach. Liu, Linggao,Wu, Ruiyun,Gao, Ziwu,Wang, Haijie,Xu, Anqi,Hou, Xinning,Zhang, Dequan,Wang, Zhenyu. 2025

[20]Comparison of different ginsenosides with C-3 or C-6 sugar moieties on activities in alcohol-induced liver injury mice. Wang, Weimin,Zhou, Kaixuan,Fu, Zengshuai,Huang, Yucheng,Deng, Jianjun,Fan, Daidi,Yang, Haixia. 2025

作者其他论文 更多>>