A new acylated oleanane triterpenoid from Couepia polyandra that inhibits the lyase activity of DNA polymerase beta

J Nat Prod. 2003 Nov;66(11):1463-5. doi: 10.1021/np0301893.

Abstract

Bioassay-directed fractionation of a n-hexane extract of Couepia polyandra using an assay to detect inhibitors of the lyase activity of DNA polymerase beta resulted in the isolation of the new triterpene 3beta,16beta,23-triacetoxyolean-12-en-28-oic acid (1) and four known compounds, oleanolic acid, betulinic acid, stigmasterol, and beta-sitosterol. The structure of the new compound was established on the basis of extensive 1D and 2D NMR spectroscopic interpretation. All five compounds inhibited DNA polymerase beta lyase activity.

Publication types

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

MeSH terms

  • Base Sequence
  • Betulinic Acid
  • Chrysobalanaceae / chemistry*
  • DNA Polymerase beta / antagonists & inhibitors*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology*
  • Lyases / antagonists & inhibitors
  • Mexico
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification*
  • Oleanolic Acid / pharmacology*
  • Pentacyclic Triterpenes
  • Plant Bark / chemistry
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*

Substances

  • 3beta,16beta,23-triacetoxyolean-12-en-28-oic acid
  • Enzyme Inhibitors
  • Pentacyclic Triterpenes
  • Triterpenes
  • oleanane
  • Oleanolic Acid
  • DNA Polymerase beta
  • Lyases
  • Betulinic Acid