Antioxidation and tyrosinase inhibition of polyphenolic curcumin analogs

Zhi Yun Du, Yong Fu Jiang, Zhi Kai Tang, Rong Qing Mo, Gui Hua Xue, Yu Jing Lu, Xi Zheng, Chang Zhi Dong, Kun Zhang

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

A series of polyphenolic curcumin analogs were synthesized and their inhibitory effects on mushroom tyrosinase and the inhibition of 1,1-diphenyl-2-picrylhydrazyl (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.

Original languageEnglish (US)
Pages (from-to)2351-2358
Number of pages8
JournalBioscience, Biotechnology and Biochemistry
Volume75
Issue number12
DOIs
StatePublished - 2011
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Keywords

  • Antioxidation
  • Inhibition kinetics
  • Polyphenolic curcumin analogs
  • Tyrosinase inhibition

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