Antifungal metabolites from fungal endophytes of Pinus strobus

Phytochemistry. 2011 Oct;72(14-15):1833-7. doi: 10.1016/j.phytochem.2011.05.003. Epub 2011 May 31.

Abstract

The extracts of five foliar fungal endophytes isolated from Pinus strobus (eastern white pine) that showed antifungal activity in disc diffusion assays were selected for further study. From these strains, the aliphatic polyketide compound 1 and three related sesquiterpenes 2-4 were isolated and characterized. Compound 2 is reported for the first time as a natural product and the E/Z conformational isomers 3 and 4 were hitherto unknown. Additionally, the three known macrolides; pyrenophorol (5), dihydropyrenophorin (6), and pyrenophorin (7) were isolated and identified. Their structures were elucidated by spectroscopic analyses including 2D NMR, HRMS and by comparison to literature data where available. The isolated compounds 1, 2, and 5 were antifungal against both the rust Microbotryum violaceum and Saccharomyces cerevisae.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Ascomycota / chemistry*
  • Base Sequence
  • Basidiomycota / drug effects
  • Endophytes / chemistry
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / isolation & purification
  • Heterocyclic Compounds / pharmacology
  • Ketones / chemistry
  • Ketones / isolation & purification
  • Ketones / pharmacology
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Macrolides / chemistry*
  • Macrolides / isolation & purification
  • Macrolides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Sequence Data
  • Pinus / microbiology*
  • Plant Leaves / chemistry
  • Polyketides / chemistry*
  • Polyketides / isolation & purification
  • Polyketides / pharmacology
  • Saccharomyces / drug effects
  • Sequence Analysis, DNA
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology

Substances

  • 5-(hydroxymethyl)-2-(2',6',6'-trimethyltetrahydro-2H-pyran-2-yl)phenol
  • Antifungal Agents
  • Heterocyclic Compounds
  • Ketones
  • Lactones
  • Macrolides
  • Polyketides
  • Sesquiterpenes
  • methyl 6-(acetyloxy)-5-formyl-7-oxoocta-2,4-dienoate
  • pyrenophorol
  • pyrenophorin

Associated data

  • GENBANK/JF706648
  • GENBANK/JF706649
  • GENBANK/JF706650
  • GENBANK/JF706651
  • GENBANK/JF706652