Natural anti-HIV agents-part I: (+)-demethoxyepiexcelsin and verticillatol from Litsea verticillata

Phytochemistry. 2002 Feb;59(3):325-9. doi: 10.1016/s0031-9422(01)00454-x.

Abstract

The eudesmane sesquiterpenoid, verticillatol (1), as well as the lignan, (+)-5'-demethoxyepiexcelsin (2), and a known lignan, (+)-epiexcelsin (3), were isolated from Litsea verticillata Hance. Lignan 2 showed moderate anti-HIV activity with an IC(50) value of 16.4 microg/ml (42.7 microM), while the known lignan 3 was inactive up to a concentration of 20 microg/ml (48.3 microM). Compound 1 demonstrated weak activity with an IC(50) value of 34.5 microg/ml (144.7 microM) while being devoid of cytotoxicity at 20 microg/ml. The structures were elucidated by 1D and 2D NMR spectroscopy, and the absolute configuration of the new sesquiterpenoid was determined by the generation of Mosher esters.

Publication types

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

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology*
  • Cell Line
  • Furans / chemistry
  • Furans / isolation & purification
  • Furans / pharmacology*
  • HIV-1 / drug effects
  • HIV-1 / pathogenicity
  • Lauraceae / chemistry*
  • Lignans
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • 5'-demethoxyepiexcelsin
  • Anti-HIV Agents
  • Furans
  • Lignans
  • Sesquiterpenes
  • verticillatol