Dioscin: a synergistic tyrosinase inhibitor from the roots of Smilax china

Food Chem. 2012 Sep 15;134(2):1146-8. doi: 10.1016/j.foodchem.2012.03.003. Epub 2012 Mar 7.

Abstract

In our study, we investigated the inhibition of mushroom tyrosinase in Smilax china. A methanol (MeOH) extract of S. china was partitioned into hexane, ethyl acetate (EtOAc) and water. Of the three fractions, EtOAc extract showed the strongest inhibition of tyrosinase activity with l-tyrosine or l-DOPA as a substrate. Two compounds were isolated from a final active fraction by activity-guided column chromatography. These compounds were identified as dioscin and oxyresveratrol by comparing their mass, (1)H- and (13)C-NMR spectral data with those reported in the literature. Dioscin showed little inhibition activity of tyrosinase, whereas oxyresveratrol, a known tyrosinase inhibitor, showed a strong tyrosinase inhibitory activity. We discovered that a mixture of oxyresveratrol and dioscin (IC(50)=5.1 and 5.7 μg/ml) highly increased the inhibition of tyrosinase activity with l-tyrosine or l-DOPA as the substrate as compared to either oxyresveratrol (IC(50)=7.8 and 10.9 μg/ml) or dioscin (IC(50)>100 and 100 μg/ml) alone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / enzymology*
  • Diosgenin / analogs & derivatives*
  • Diosgenin / chemistry
  • Diosgenin / isolation & purification
  • Diosgenin / pharmacology
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Fungal Proteins / antagonists & inhibitors*
  • Fungal Proteins / metabolism
  • Kinetics
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Plant Roots / chemistry
  • Smilax / chemistry*

Substances

  • Enzyme Inhibitors
  • Fungal Proteins
  • Plant Extracts
  • dioscin
  • Monophenol Monooxygenase
  • Diosgenin