Inhibitory Effects of (2'R)-2',3'-dihydro-2'-(1-hydroxy-1-methylethyl)-2,6'-bibenzofuran-6,4'-diol on Mushroom Tyrosinase and Melanogenesis in B16-F10 Melanoma Cells

Phytother Res. 2015 Jul;29(7):1040-5. doi: 10.1002/ptr.5344. Epub 2015 Mar 31.

Abstract

(2'R)-2',3'-Dihydro-2'-(1-hydroxy-1-methylethyl)-2,6'-bibenzofuran-6,4'-diol (DHMB) is a natural compound extracted from Morus notabilis. It was found that DHMB acts as a competitive inhibitor against mushroom tyrosinase with a Ki value of 14.77 μM. Docking results further indicated that it could form strong interactions with one copper ion with a distance of 2.7 Å, suggesting the mechanism of inhibition might be due to chelating copper ions in the active site. Furthermore, melanin production in B16-F10 murine melanoma cells was significantly inhibited by DHMB in a concentration-dependent manner without cytotoxicity. The results of western blotting also showed that DHMB decreased 3-isobuty-1-methxlzanthine-induced mature tyrosinase expression. Taken together, these findings indicated that DHMB may be a new promising pigmentation-altering agent for agriculture, cosmetic, and therapeutic applications.

Keywords: (2′R)-2′,3′-dihydro-2′-(1-hydroxy-1-methylethyl)-2,6′-bibenzofuran-6,4′-diol; Moraceae; Morus notabilis; inhibitor; melanogenesis; tyrosinase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / enzymology*
  • Animals
  • Benzofurans / chemistry*
  • Cell Line, Tumor
  • Cyclic AMP / metabolism
  • Enzyme Inhibitors / chemistry
  • Melanins / biosynthesis*
  • Melanoma, Experimental / metabolism*
  • Mice
  • Molecular Docking Simulation
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Morus / chemistry

Substances

  • (2'R)-2',3'-dihydro-2'-(1-hydroxy-1-methylethyl)-2,6'-bibenzofuran-6,4'-diol
  • Benzofurans
  • Enzyme Inhibitors
  • Melanins
  • Cyclic AMP
  • Monophenol Monooxygenase