Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea

J Nat Prod. 2003 Feb;66(2):263-8. doi: 10.1021/np020379y.

Abstract

In a continuing search for anti-HIV compounds from plants of Vietnam, 19 compounds, including a new triterpene, were isolated from an extract of the leaves and stem of Vatica cinerea. The new triterpene was determined to be a cycloartane triterpenoid with 29 skeletal carbons and was assigned the name vaticinone (1). The known triterpenes included three cycloartanes, a lanostane, two dammaranes, three lupanes, an ursane, and an oleanane. A chlorophyll isolate was identified as pheophorbide a (13). The majority of the triterpenes, the sesquiterpene, 1-hydroxycyclocolorenone, and pheophorbide a showed anti-HIV activity, with the chlorophyll being the most active, demonstrating an IC(50) value of 1.5 microgram/mL (2.5 microM), while being completely devoid of toxicity up to a concentration of 20 microgram/mL (33.8 microM). Vaticinone (1) was found to inhibit the replication of HIV-1, with an IC(50) value of 6.5 microgram/mL (15.3 microM; selective index = 1.4). The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra.

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
  • Chlorophyll / chemistry
  • Chlorophyll / isolation & purification
  • Chlorophyll / pharmacology
  • Ericales / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Osteosarcoma
  • Plant Leaves
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Stereoisomerism
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology
  • Tumor Cells, Cultured / drug effects
  • Vietnam

Substances

  • Anti-HIV Agents
  • Sesquiterpenes
  • Triterpenes
  • vaticinone
  • Chlorophyll