Depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities

Bioorg Med Chem Lett. 2012 Jun 15;22(12):4159-62. doi: 10.1016/j.bmcl.2012.04.046. Epub 2012 Apr 16.

Abstract

We synthesized benzoate ester derivatives of kojic acid with and without adamantane moiety. Benzoate derivatives 2a-e that did not contain an adamantane moiety showed potent tyrosinase inhibitory activities. However, depigmenting activity was not noted in a cell-based assay. Contrasting results were obtained for benzoate derivatives (3a-e) containing an adamantane moiety. Compounds 3a-e showed potent depigmenting activities without tyrosinase inhibitory activities. To the best of our knowledge, this is the first study showing the depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities.

MeSH terms

  • Adamantane / chemistry*
  • Agaricales / enzymology
  • Animals
  • Biological Assay
  • Cell Survival / drug effects
  • Esters
  • Melanins / antagonists & inhibitors*
  • Melanins / biosynthesis
  • Melanocytes / cytology
  • Melanocytes / drug effects*
  • Melanocytes / metabolism
  • Mice
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Monophenol Monooxygenase / metabolism
  • Pigmentation / drug effects*
  • Pyrones / chemistry*
  • Pyrones / pharmacology
  • Structure-Activity Relationship
  • Tyrosine / metabolism

Substances

  • Esters
  • Melanins
  • Pyrones
  • Tyrosine
  • kojic acid
  • Monophenol Monooxygenase
  • Adamantane