A sphingolipid and tyrosinase inhibitors from the fruiting body of Phellinus linteus

Arch Pharm Res. 2004 Jul;27(7):742-50. doi: 10.1007/BF02980143.

Abstract

This paper for the first time reports the isolation of 5 compounds from Phellinus linteus. A sphingolipid (1) and two tyrosinase inhibitory compounds (2, 3) along with two carboxylic acids (4, 5), were isolated from the fruiting body of Phellinus linteus (Berk & Curt) Aoshima. The structure of compound 1 was identified as 1-omicron-beta-D-glucopyranosyl-(2S, 3R, 4E, 8E)-2-[(2R)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol, known as cerebroside B, based on spectroscopic methods such as 1 D and 2D NMR as well as by acid hydrolysis. Compounds 2 -5 were identified as protocatechualdehyde (2), 5-hydroxymethyl-2-furaldehyde (HMF) (3), succinic acid (4), and fumaric acid (5) based on the spectroscopic evidence. Compounds 2 and 3 inhibited the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with an IC50 of 0.40 and 90.8 microg/mL, respectively. The inhibitory kinetics, which were analyzed by the Lineweaver-Burk plots, were found to be competitive and noncompetitive inhibitors with a Ki of 1.1 microM and 1.4 mM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Basidiomycota / chemistry*
  • Benzaldehydes / analysis
  • Benzaldehydes / pharmacology
  • Catechols / analysis
  • Catechols / pharmacology
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / isolation & purification
  • Fumarates / analysis
  • Fumarates / pharmacology
  • Gas Chromatography-Mass Spectrometry
  • Kinetics
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Sphingolipids / pharmacology*
  • Succinic Acid / analysis
  • Succinic Acid / pharmacology

Substances

  • Benzaldehydes
  • Catechols
  • Enzyme Inhibitors
  • Fumarates
  • Sphingolipids
  • protocatechualdehyde
  • fumaric acid
  • Succinic Acid
  • Monophenol Monooxygenase