Benzyl benzoates: New phlorizin analogs as mushroom tyrosinase inhibitors

Bioorg Med Chem. 2011 Feb 1;19(3):1167-71. doi: 10.1016/j.bmc.2010.12.051. Epub 2010 Dec 30.

Abstract

In our research, 14 benzyl benzoates with hydroxyl(s) (3-16) were synthesized and their inhibitory activity on mushroom tyrosinase was tested. Results indicated that among these compounds, 4-hydroxybenzyl 3,5-dihydroxybenzoate (3), 4-hydroxybenzyl 2,4-dihydroxybenzoate (5), 4-hydroxybenzyl 2,4,6-dihydroxybenzoate (7), 3-hydroxybenzyl 3,5-dihydroxybenzoate (8), 3-hydroxybenzyl 2,4-dihydroxybenzoate (10) exhibited inhibitory activity with their IC(50) less than 10μM. Further studies showed these five compounds were competitive inhibitors of tyrosinase and their structure-activity relationships were investigated in this article.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / enzymology
  • Cosmetics
  • Drug Discovery*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Food Preservation
  • Inhibitory Concentration 50
  • Kinetics
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Phlorhizin / analogs & derivatives*
  • Salicylates / chemical synthesis*
  • Salicylates / chemistry
  • Salicylates / pharmacology*
  • Structure-Activity Relationship

Substances

  • 4-hydroxybenzyl 2,4-dihydroxybenzoate
  • Cosmetics
  • Enzyme Inhibitors
  • Salicylates
  • Phlorhizin
  • Monophenol Monooxygenase