Tyrosinase inhibition studies of cycloartane and cucurbitane glycosides and their structure-activity relationships

Bioorg Med Chem. 2006 Sep 1;14(17):6085-8. doi: 10.1016/j.bmc.2006.05.002. Epub 2006 May 23.

Abstract

In the present paper, tyrosinase inhibition studies and structure-activity relationship of eight cycloartane glycosides and one cucurbitane glycoside and its genin, which were isolated from Astragalus (Leguminoseae) and Bryonia (Cucurbitaceae) plants, have been discussed. The activities are compared with two reference tyrosinase inhibitors, kojic acid and l-mimosine. These studies and the SAR showed that the askendoside B which exhibited highly potent (IC50 =13.95 microM) tyrosinase inhibition could be a possible lead molecule for the development of new medications of several skin diseases related with the over-expression of the enzyme tyrosinase, like hyperpigmentation. The molecule also may be interesting for the cosmetic industries as a skin whitening agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Astragalus Plant / chemistry
  • Cucurbitaceae / chemistry
  • Glycosides / chemistry*
  • Glycosides / metabolism
  • Mimosine / chemistry
  • Mimosine / metabolism
  • Molecular Structure
  • Monophenol Monooxygenase / metabolism*
  • Peptides / chemistry*
  • Peptides / metabolism
  • Pyrones / chemistry
  • Pyrones / metabolism
  • Structure-Activity Relationship
  • Triterpenes / chemistry*
  • Triterpenes / metabolism*

Substances

  • Glycosides
  • Peptides
  • Pyrones
  • Triterpenes
  • cucurbitane
  • Mimosine
  • cycloartane
  • kojic acid
  • Monophenol Monooxygenase