Antimicrobial sesquiterpenoids from Laurus nobilis L

Nat Prod Res. 2011 Aug;25(14):1295-303. doi: 10.1080/14786419.2010.502532. Epub 2011 Jun 24.

Abstract

Activity-guided fractionations of leaf extracts from Laurus nobilis L. led to the isolation of a known sesquiterpene lactone, deacetyl laurenobiolide (1). Compound 1 showed antimicrobial activity against periopathic pathogens (Actinomyces viscosus, Porphyromonas gingivalis, Prevotella intermedia and Actinobacillus actinomycetemcomitans), opportunistic Gram-positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and fungi (Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus). Furthermore, acetylation and cyclisation of deacetyl laurenobiolide (1) yielded laurenobiolide (2) and a new compound, (5S,6R,7S,8S,10R)-6,8-dihydroxyeudesma-4(15),11(13)-dien-12-oic acid 12,8-lactone (3), respectively. Compounds 2 and 3 also showed antimicrobial activities. All compounds 1-3 demonstrated growth inhibitory effects with minimum inhibitory concentrations ranging from 31 to 1000 µg mL(-1). This is the first report of compounds 1-3 showing antimicrobial activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinomyces viscosus / drug effects
  • Aggregatibacter actinomycetemcomitans / drug effects
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Aspergillus fumigatus / drug effects
  • Candida albicans / drug effects
  • Cryptococcus neoformans / drug effects
  • Laurus / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology*
  • Porphyromonas gingivalis / drug effects
  • Prevotella intermedia / drug effects
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology*
  • Staphylococcus aureus / drug effects
  • Streptococcus mutans / drug effects

Substances

  • Anti-Infective Agents
  • Plant Extracts
  • Sesquiterpenes