Tyrosinase inhibitory effects of 1,3-diphenylpropanes from Broussonetia kazinoki

Bioorg Med Chem. 2009 Jan 1;17(1):35-41. doi: 10.1016/j.bmc.2008.11.022. Epub 2008 Nov 18.

Abstract

Six 1,3-diphenylpropanes exhibiting inhibitory activities against both the monophenolase and diphenolase actions of tyrosinase were isolated from the methanol (95%) extract of Broussonetia kazinoki. These compounds, 1-6, were identified as kazinol C (1), D (2), F (3), broussonin C (4), kazinol S (5) and kazinol T (6). The latter two species (5 and 6) emerged to be new 1,3-diphenylpropanes which we fully spectroscopically characterized. The IC(50) values of compounds (1, 3-5) for monophenolase inhibition were determined to range between 0.43 and 17.9 microM. Compounds 1 and 3-5 also inhibited diphenolase significantly with IC(50) values of 22.8, 1.7, 0.57, and 26.9 microM, respectively. All four active tyrosinase inhibitors (1, 3-5) were competitive inhibitors. Interestigly they all mainfested simple reversible slow-binding inhibition against diphenolase. The most potent inhibitor, compound 4 diplayed the following kinetic parameters k(3)=0.0993 microM(-1)min(-1), k(4)=0.0048 min(-1), and K(i)(app)=0.0485 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / pharmacology*
  • Binding, Competitive
  • Broussonetia / chemistry*
  • Hemiterpenes / pharmacology*
  • Inhibitory Concentration 50
  • Kinetics
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Plant Extracts
  • Propane / pharmacology*
  • Resorcinols / pharmacology*

Substances

  • Benzene Derivatives
  • Hemiterpenes
  • Plant Extracts
  • Resorcinols
  • kazinol C
  • Monophenol Monooxygenase
  • Propane