A new ursane triterpene from Monochaetum vulcanicum that inhibits DNA polymerase beta lyase

J Nat Prod. 2004 May;67(5):899-901. doi: 10.1021/np030531b.

Abstract

Bioassay-directed fractionation of a butanone extract of Monochaetum vulcanicum resulted in the isolation of a new triterpene (1) and four known compounds, ursolic acid (2), 2alpha-hydroxyursolic acid (3), 3-(p-coumaroyl)ursolic acid (4), and beta-sitosteryl-beta-d-galactoside (5). The structure of the new compound 1 was established as 3beta-acetoxy-2alpha-hydroxyurs-12-en-28-oic acid on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical derivatization. Compounds 1-3 and 5 exhibited polymerase beta lyase activity.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetylation
  • Costa Rica
  • DNA Polymerase beta / antagonists & inhibitors*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Inhibitory Concentration 50
  • Lyases / antagonists & inhibitors*
  • Melastomataceae / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • 3beta-acetoxy-2alpha-hydroxyurs-12-ene-28-oic acid
  • Enzyme Inhibitors
  • Triterpenes
  • DNA Polymerase beta
  • Lyases
  • ursolic acid