Isolation of the antibiotic methyl (R,E)-3-(1-hydroxy-4-oxocyclopent-2-en-1-yl)-acrylate EA-2801 from Trichoderma atroviridae

J Antibiot (Tokyo). 2017 Nov;70(11):1053-1056. doi: 10.1038/ja.2017.107. Epub 2017 Sep 20.

Abstract

The endophytic Trichoderma atroviridae UB-LMA was isolated as a symbiont of Taxus baccata and analyzed for its antimicrobial activity. By applying an original approach consisting of solid-state cultivation coupled with solid-phase extraction, a new methyl (R,E)-3-(1-hydroxy-4-oxocyclopent-2-en-1-yl)-acrylate derivative named EA-2801 (1) was isolated together with the previously reported isonitrin A and dermadin methyl ester. The chemical structure of 1 was determined by NMR and MS. Compound 1 showed antimicrobial activity against a panel of Gram-positive and -negative bacteria.

MeSH terms

  • Acrylates / chemistry
  • Acrylates / isolation & purification
  • Acrylates / pharmacology*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Cyclopentanes / chemistry
  • Cyclopentanes / isolation & purification
  • Cyclopentanes / pharmacology*
  • Gram-Negative Bacteria / drug effects*
  • Gram-Positive Bacteria / drug effects*
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Heterocyclic Compounds, 2-Ring / isolation & purification
  • Heterocyclic Compounds, 2-Ring / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Nitriles / chemistry
  • Nitriles / isolation & purification
  • Nitriles / pharmacology*
  • Solid Phase Extraction
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification
  • Spiro Compounds / pharmacology*
  • Trichoderma / chemistry*

Substances

  • Acrylates
  • Anti-Bacterial Agents
  • Cyclopentanes
  • Heterocyclic Compounds, 2-Ring
  • Nitriles
  • Spiro Compounds
  • dermadin methyl ester
  • isonitrin A
  • methyl (R,E)-3-(1-hydroxy-4-oxocyclopent-2-en-1-yl)-acrylate