Antibacterial Radicicol Analogues from Pochonia chlamydosporia and Their Biosynthetic Gene Cluster

J Agric Food Chem. 2019 Jul 3;67(26):7266-7273. doi: 10.1021/acs.jafc.9b01977. Epub 2019 Jun 24.

Abstract

Chemical investigation of fungus Pochonia chlamydosporia strain 170, derived from rice fermentation sediment samples, afforded seven radicicol analogues, including two new compounds, monocillin VI (1) and monocillin VII (2), and five known compounds, monocillin II (3), monorden D (4), monocillin IV (5), monocillin V (6), and pochonin M (7). The structures of compounds 1-7 were established primarily by analysis of nuclear magnetic resonance data, and the absolute configurations of the secondary alcohol in compounds 1 and 2 were assigned by the modified Mosher method. All seven compounds have modest antibacterial activities, with a minimal inhibitory concentration (MIC) of 25.6 μg/mL for compounds 1 and 3-7 and 51.2 μg/mL for compound 2, on inhibition of the growth of the plant pathogen Xanthomonas campestris (the positive control ampicillin showed a MIC value of 12.8 μg/mL), indicating that the fungus has the potential to control bacterial disease. The biosynthetic gene cluster and putative biosynthetic pathways of these radicicol analogues in the P. chlamydosporia genome were proposed. These findings increase our knowledge of the chemical potential of P. chlamydosporia and may allow us to better utilize the fungus as a biological control agent.

Keywords: pv.; antibacterial activity; biosynthetic gene cluster; radicicol analogues.

MeSH terms

  • Anti-Bacterial Agents / biosynthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Biosynthetic Pathways
  • Fungal Proteins / genetics
  • Fungal Proteins / metabolism
  • Hypocreales / chemistry
  • Hypocreales / genetics
  • Hypocreales / metabolism*
  • Macrolides / chemistry*
  • Macrolides / metabolism
  • Macrolides / pharmacology
  • Microbial Sensitivity Tests
  • Multigene Family
  • Xanthomonas campestris / drug effects
  • Xanthomonas campestris / growth & development

Substances

  • Anti-Bacterial Agents
  • Fungal Proteins
  • Macrolides
  • monorden