New Sesquiterpenes from Litsea verticillata

J Nat Prod. 2003 May;66(5):609-15. doi: 10.1021/np020508a.

Abstract

Seven new sesquiterpenes, named litseagermacrane (1), 7-epi-eudesm-4(15)-ene-1alpha,6alpha-diol (2), 5-epi-eudesm-4(15)-ene-1beta,6beta-diol (4), litseahumulanes A (6) and B (7), and litseachromolaevanes A (11) and B (12), as well as the known compounds 7-epi-eudesm-4(15)-ene-1beta,6beta-diol (3), eudesm-4(15)-ene-1beta,6alpha-diol (5), octahydro-4-hydroxy-3alpha-methyl-7-methylene-alpha-(1-methylethyl)-1H-indene-1-methanol (8), 10-hydroxyl-15-oxo-alpha-cadinol (9), and aphanamol II (10), were isolated from an anti-HIV fraction of the leaves and twigs of Litsea verticillata Hance (Figure 1). Isolates 1, 4, and 12 were found to inhibit HIV-1 replication in a green fluorescent protein (GFP)-based reporter cell line (HOG.R5) with IC(50) values of 6.5 (27.5), 17.4 (73.1), and 28.0 (119.7) microg/mL (microM), respectively. The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra. Compound 11 was confirmed by X-ray crystallographic analysis.

Publication types

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

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology
  • Crystallography, X-Ray
  • Green Fluorescent Proteins
  • Inhibitory Concentration 50
  • Litsea / chemistry*
  • Luminescent Proteins
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Stereoisomerism
  • Vietnam

Substances

  • Anti-HIV Agents
  • Luminescent Proteins
  • Sesquiterpenes
  • Green Fluorescent Proteins