Five Unprecedented Secondary Metabolites from the Spider Parasitic Fungus Akanthomyces novoguineensis

Molecules. 2017 Jun 14;22(6):991. doi: 10.3390/molecules22060991.

Abstract

Five new compounds including the glycosylated β-naphthol (1, akanthol), a glycosylated pyrazine (2, akanthozine), and three amide derivatives including a hydroxamic acid derivative (3-5) were isolated from the spider-associated fungus Akanthomyces novoguineensis (Cordycipitaceae, Ascomycota). Their structures were elucidated by using high resolution mass spectrometry (HRMS) and NMR spectroscopy. In this study, the antimicrobial, cytotoxic, anti-biofilm, and nematicidal activities of the new compounds were evaluated. The distribution pattern of secondary metabolites in the species was also revealed in which more isolates of A. novoguineensis were encountered and their secondary metabolite profiles were examined using analytical HPLC with diode array and mass spectrometric detection (HPLC-DAD/MS). Remarkably, all isolated compounds are specifically produced by A. novoguineensis.

Keywords: Akanthomyces novoguineensis; akanthol; akanthozine; chemotaxonomy; hydroxamic acid.

MeSH terms

  • Amides / chemistry
  • Amides / isolation & purification
  • Amides / metabolism
  • Animals
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / isolation & purification*
  • Antinematodal Agents / metabolism
  • Chromatography, High Pressure Liquid
  • Hypocreales / chemistry
  • Hypocreales / metabolism*
  • Magnetic Resonance Spectroscopy
  • Naphthols / chemistry
  • Naphthols / isolation & purification
  • Naphthols / metabolism
  • Pyrazines / chemistry
  • Pyrazines / isolation & purification
  • Pyrazines / metabolism
  • Secondary Metabolism / genetics*
  • Spiders / microbiology*

Substances

  • Amides
  • Antinematodal Agents
  • Naphthols
  • Pyrazines
  • 2-naphthol