Tyrosinase inhibitory activity of a glucosylated hydroxystilbene in mouse melan-a melanocytes

J Nat Prod. 2014 Jun 27;77(6):1270-4. doi: 10.1021/np4008798. Epub 2014 Jun 16.

Abstract

2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucopyranoside (1), isolated from Polygonum multiflorum, is a noncompetitive inhibitor of tyrosinase in cell-free kinetics; it reduced the Vmax values in a dose-dependent manner. Compound 1 inhibited PKA-induced melanogenesis, reduced the protein expression of tyrosinase and its transcription factor, the microphthalmia-associated transcription factor, and lowered the complex formation between tyrosinase and tyrosinase-related protein 1 (TRP-1). Immunofluorescence microscopy revealed no association of tyrosinase with the endoplasmic reticulum or lysosomes, implying the absence of a direct effect of 1 on the maturation process of the enzyme. The antimelanogenic activity of 1 is likely mediated through a noncompetitive inhibition on tyrosinase, down-regulation of the expression of melanogenic proteins, and reduction of tyrosinase/TRP-1 complex formation.

MeSH terms

  • Animals
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology*
  • Melanins / metabolism
  • Membrane Glycoproteins / metabolism
  • Mice
  • Microscopy, Fluorescence
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Oxidoreductases / metabolism
  • Stilbenes / chemistry
  • Stilbenes / isolation & purification*
  • Stilbenes / pharmacology*

Substances

  • 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucopyranoside
  • Glucosides
  • Melanins
  • Membrane Glycoproteins
  • Stilbenes
  • Oxidoreductases
  • TYRP1 protein, human
  • Monophenol Monooxygenase

Grants and funding

National Institutes of Health, United States