title: Antioxidation and tyrosinase inhibition of polyphenolic curcumin analogs.
abstract: 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.
authors.affiliation: Laboratory of Natural Medicine and Green Chemistry, School of Light Industry and Chemical Engineering, Guandgong University of Technology, Guangzhou, China.
authors.forename: Zhi-Yun
authors.initials: ZY
authors.lastname: Du
authors.forename: Yong-Fu
authors.initials: YF
authors.lastname: Jiang
authors.forename: Zhi-Kai
authors.initials: ZK
authors.lastname: Tang
authors.forename: Rong-Qing
authors.initials: RQ
authors.lastname: Mo
authors.forename: Gui-Hua
authors.initials: GH
authors.lastname: Xue
authors.forename: Yu-Jing
authors.initials: YJ
authors.lastname: Lu
authors.forename: Xi
authors.initials: X
authors.lastname: Zheng
authors.forename: Chang-Zhi
authors.initials: CZ
authors.lastname: Dong
authors.forename: Kun
authors.initials: K
authors.lastname: Zhang
mesh_terms: D000363:Agaricales / Q000201:enzymology; D000818:Animals; D001713:Biphenyl Compounds / Q000737:chemistry; D020134:Catalytic Domain; D003474:Curcumin / Q000031:analogs & derivatives*; D055808:Drug Discovery; D004791:Enzyme Inhibitors / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D005260:Female; D016166:Free Radical Scavengers / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D006878:Hydroxides / Q000737:chemistry; D020128:Inhibitory Concentration 50; D008297:Male; D051379:Mice; D008958:Models, Molecular; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D010851:Picrates / Q000737:chemistry; D059808:Polyphenols / Q000009:adverse effects / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*
chemical_list: D001713:Biphenyl Compounds; D004791:Enzyme Inhibitors; D016166:Free Radical Scavengers; D006878:Hydroxides; D010851:Picrates; D059808:Polyphenols; C031356:hydroxide ion; C004931:1,1-diphenyl-2-picrylhydrazyl; D014442:Monophenol Monooxygenase; D003474:Curcumin