Sesquiterpenes from the wood of Juniperus lucayana

Phytochemistry. 2007 Oct;68(19):2409-14. doi: 10.1016/j.phytochem.2007.05.030. Epub 2007 Jul 2.

Abstract

Bioassay-guided fractionation of ethanolic extract from the wood of Juniperus lucayana afforded three sesquiterpenes named 3-hydroxypseudowiddran-6(7)-en-4-ol (1), 15-hydroxyallo-cedrol (2) and 12-hydroxywiddrol (3) together with six known sesquiterpenes (4-9) and two known flavonoids (10 and 11). Their structures were established on the basis of comprehensive spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry. The structures of compounds were identified as 1alpha,4beta,11alpha,11beta-tetramethylbicyclo[5,4,0]undec-6(7)-en-3alpha, 4alpha-diol (1), 4beta-hydroxymethyl-5,5,9beta-trimethyltricyclo[4.3.0.2(1.4)]undecan-3alpha-ol (2) and 4beta-hydroxymethyl-7alpha,11alpha,11beta-trimethylbicyclo [5.4.0]undec-1-en-4alpha-ol (3). The major compounds isolated were evaluated for their antifungal activity against Botrytis cinerea. Widdrol (7) was the most active, reaching the 71% inhibition level on mycelial growth after 6 days.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Chromatography, High Pressure Liquid
  • Juniperus / chemistry*
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Spectrum Analysis / methods
  • Wood / chemistry*

Substances

  • Antifungal Agents
  • Sesquiterpenes