Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz

J Enzyme Inhib Med Chem. 2008 Dec;23(6):922-30. doi: 10.1080/14756360701810207.

Abstract

Five flavones displaying tyrosinase inhibitory activity were isolated from the stem barks of Morus lhou (S.) Koidz., a cultivated edible plant. The isolated compounds were identified as mormin (1), cyclomorusin (2), morusin (3), kuwanon C (4), and norartocarpetin (5). Mormin (1) was characterized as a new flavone possesing a 3-hydroxymethyl-2-butenyl at C-3. The inhibitory potencies of these flavonoids toward monophenolase activity of mushroom tyrosinase were investigated. The IC50 values of compounds 1-5 for monophenolase activity were determined to be 0.088, 0.092, 0.250, 0.135 mM, and 1.2 microM, respectively. Mormin (1), cyclomorusin (2), kuwanon C (4) and norartocarpetin (5) exhibited competitive inhibition characteristics. Interestingly norartocarpetin (5) showed a time-dependent inhibition against oxidation of L-tyrosine: it also operated under the enzyme isomerization model (k5 = 0.8424 min(-1), k6 = 0.0576 min(-1), K(app)(i) = 1.354 microM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / drug effects*
  • Agaricales / enzymology*
  • Biocatalysis
  • Flavones / chemistry
  • Flavones / pharmacology*
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Morus / chemistry*
  • Plant Bark / chemistry*
  • Plant Stems / chemistry*
  • Structure-Activity Relationship

Substances

  • Flavones
  • Monophenol Monooxygenase