New 3-O-acyl betulinic acids from Strychnos vanprukii Craib

J Nat Prod. 2004 Jun;67(6):994-8. doi: 10.1021/np030469i.

Abstract

Three new betulinic acid derivatives, 3beta-O-trans-feruloylbetulinic acid (1), 3beta-O-cis-feruloylbetulinic acid (2), and 3beta-O-cis-coumaroylbetulinic acid (4), along with two known triterpenes, 3beta-O-trans-coumaroylbetulinic acid (3) and ursolic acid (6) were isolated from the leaves and twigs of Strychnos vanprukiiCraib. All isolates showed moderate anti-HIV activity with IC50 values ranging from 3 to 7 microg/mL (5 to 15 microM) in an indicator cell line for HIV infectivity. The structures of the new isolates were elucidated by spectroscopic techniques including 1D and 2D NMR spectroscopy. In addition, the structure of 1 was confirmed by X-ray crystallography.

Publication types

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

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Betulinic Acid
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Pentacyclic Triterpenes
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Strychnos / chemistry*
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology
  • Tumor Cells, Cultured

Substances

  • Anti-HIV Agents
  • Antineoplastic Agents, Phytogenic
  • Pentacyclic Triterpenes
  • Triterpenes
  • Betulinic Acid