Sesquiterpenes and butenolides, natural anti-HIV constituents from Litsea verticillata

Planta Med. 2005 May;71(5):452-7. doi: 10.1055/s-2005-864142.

Abstract

In a continuing investigation, six sesquiterpenes, as well as five butenolides were isolated from the leaves and twigs of Litsea verticillata Hance (Lauraceae). Among the isolates, three were determined to be new sesquiterpenes: isolitseanes A (1), B (2) and C (3); three known sesquiterpenes were identified as oxyphyllenodiol B (4), 1,2,3,4-tetrahydro-2,5-dimethyl-8-(1-methylethyl)-1,2-naphthalenediol (5), and chromolaevanedione (6). The butenolides include the novel litseabutenolide (9) and four known compounds: 3- epi-litsenolide D2 (7), cis-listenolide D1 (8), 4-hydroxy-2-methylbut-2-enolide (10), and hydroxydihydrobovolide (11). Isolates 2, 4, 5, 7, 9, 10 and 11 were found to inhibit HIV-1 replication in a green fluorescent protein (GFP)-based reporter cell line (HOG.R5) with IC50 values of 38.1, 54.6, 91.0, 9.9, 40.3, 129.8, and 122.7 microM, respectively. Structure elucidation and identification were based on spectroscopic means including 1D and 2D NMR analyses.

Publication types

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

MeSH terms

  • 4-Butyrolactone / administration & dosage
  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / pharmacology
  • 4-Butyrolactone / therapeutic use
  • Anti-HIV Agents / administration & dosage
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Anti-HIV Agents / therapeutic use
  • HIV-1 / drug effects*
  • Humans
  • Inhibitory Concentration 50
  • Litsea*
  • Phytotherapy*
  • Plant Extracts / administration & dosage
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Extracts / therapeutic use
  • Sesquiterpenes / administration & dosage
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes / therapeutic use

Substances

  • Anti-HIV Agents
  • Plant Extracts
  • Sesquiterpenes
  • butenolide
  • 4-Butyrolactone