Antioxidation and Tyrosinase Inhibition of Polyphenolic Curcumin Analogs

• Published in: Bioscience, biotechnology, and biochemistry Vol. 75; no. 12; pp. 2351 - 2358
• Main Authors: DU, Zhi-Yun, JIANG, Yong-Fu, TANG, Zhi-Kai, MO, Rong-Qing, XUE, Gui-Hua, LU, Yu-Jing, ZHENG, Xi, DONG, Chang-Zhi, ZHANG, Kun
• Format: Journal Article
• Language: English
• Published: Tokyo Japan Society for Bioscience, Biotechnology, and Agrochemistry 2011; Japan Society for Bioscience Biotechnology and Agrochemistry; Oxford University Press
• Subjects: Agaricales - enzymology; Animals; antioxidation; Biological and medical sciences; Biphenyl Compounds - chemistry; Catalytic Domain; Curcumin - analogs & derivatives; Drug Discovery; Enzyme Inhibitors - adverse effects; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - metabolism; Enzyme Inhibitors - pharmacology; Female; Free Radical Scavengers - adverse effects; Free Radical Scavengers - chemistry; Free Radical Scavengers - metabolism; Free Radical Scavengers - pharmacology; Fundamental and applied biological sciences. Psychology; Hydroxides - chemistry; inhibition kinetics; Inhibitory Concentration 50; Male; Mice; Models, Molecular; Monophenol Monooxygenase - antagonists & inhibitors; Monophenol Monooxygenase - chemistry; Monophenol Monooxygenase - metabolism; Picrates - chemistry; polyphenolic curcumin analogs; Polyphenols - adverse effects; Polyphenols - chemistry; Polyphenols - metabolism; Polyphenols - pharmacology; tyrosinase inhibition; Enzyme; Analog; tyrosinase inhibition; polyphenolic curcumin analogs; Oxidoreductases; Kinetics; Inhibition; Monophenol monooxygenase; antioxidation; inhibition kinetics
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.110547

A series of polyphenolic curcumin analogs were synthesized and their inhibitory effects on mushroom tyrosinase and the inhibition of 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical formation were evaluated. The results indictated that the analogs possessing m-diphenols and o-diphenols exhibited more potent inhibitory activity on tyrosinase than reference compound rojic acid, and that the analogs with o-diphenols exhibited more potent inhibitory activity of DPPH free-radical formation than reference compound vitamin C. The inhibition kinetics, analyzed by Lineweaver-Burk plots, revealed that compounds B 2 and C 2 bearing o-diphenols were non-competitive inhibitors, while compounds B 11 and C 11 bearing m-diphenols were competitive inhibitors. In particular, representative compounds C 2 and B 11 showed no side effects at a dose of 2,000 mg/kg in a preliminary evaluation of acute toxicity in mice. These results suggest that such polyphenolic curcumin analogs might serve as lead compounds for further design of new potential tyrosinase inhibitors.