Inhibitory effect of 2,4,2',4'-tetrahydroxy-3-(3-methyl-2-butenyl)-chalcone on tyrosinase activity and melanin biosynthesis

Biological & Pharmaceutical Bulletin
Xiaodong ZhangHeyao Wang

Abstract

2,4,2',4'-Tetrahydroxy-3-(3-methyl-2-butenyl)-chalcone (TMBC), a naturally occurring compound from Morus nigra, modulated melanogenesis by inhibiting tyrosinase. TMBC inhibited the L-dopa oxidase activity of mushroom tyrosinase with an IC(50) value of 0.95+/-0.04 microM, which was more potent than kojic acid (IC(50)=24.88+/-1.13 microM), a well-known tyrosinase inhibitor. The kinetic studies of tyrosinase inhibition revealed that TMBC acts as a competitive inhibitor of mushroom tyrosinase with L-dopa as the substrate. Furthermore, TMBC effectively inhibited both cellular tyrosinase activity and melanin biosynthesis in B16 melanoma cells without significant cytotoxicity. The inhibitory effect of TMBC on melanogenesis was attributed to the direct inhibition of tyrosinase activity, rather than the suppression of tyrosinase gene expression. These results indicated that TMBC may be a new promising pigmentation-altering agent for cosmetic or therapeutic applications.

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Citations

Jul 8, 2009·International Journal of Molecular Sciences·Te-Sheng Chang
Jan 8, 2010·International Journal of Molecular Sciences·Nico SmitStan Pavel
Oct 24, 2012·Journal of Asian Natural Products Research·Xiao HuAi-Jun Hou
Feb 17, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Sang Yeul LeeTae-gyu Nam
Mar 24, 2012·Journal of Cellular Biochemistry·Xiaodong ZhangHeyao Wang
Feb 18, 2015·Natural Product Research·Zhuya YangZhihong Zhou
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Aug 17, 2016·Evidence-based Complementary and Alternative Medicine : ECAM·Nadia TabassumDarren R Williams
Mar 20, 2010·Journal of Agricultural and Food Chemistry·Zong-Ping ZhengMingfu Wang
Apr 20, 2011·Journal of Natural Products·Ling-Ling YuMyeong-Hyeon Wang
Dec 15, 2011·Journal of Natural Products·Xiao HuAi-Jun Hou

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