Six Heterocyclic Metabolites from the Myxobacterium Labilithrix luteola

Molecules. 2018 Feb 28;23(3):542. doi: 10.3390/molecules23030542.

Abstract

Two new secondary metabolites, labindole A [2-methyl-3-(2-nitroethyl)-3H-indole] (1) and labindole B [2-methyl-3-(2-nitrovinyl)-3H-indole] (2), were isolated from the myxobacterium Labilithrixluteola (DSM 27648T). Additionally, four metabolites 3, 4, 5 and 6 already known from other sources were obtained. Their structures were elucidated from high resolution electrospray ionisation mass spectrometry (HRESIMS) and 1D and 2D nuclear magnetic resonance (NMR) spectroscopy data and their relative configuration was assigned based on nuclear Overhauser effect (NOE) and vicinal ¹H-NMR coupling data. The compounds where tested for biological activities; labindoles A (1) and B (2) exhibited significant activity against Hepatitis C Virus, 9H-carbazole (3), 3-chloro-9H-carbazole (4) and 4-hydroxymethyl-quinoline (5) showed antifungal activities. Moreover, compound 3 had weak to moderate antibacterial activities, while labindoles A (1) and B (2) were devoid of significant antifungal and antibacterial effects.

Keywords: HCV; antimicrobial activity; antiviral activity; fermentation; natural products; nitroindole.

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Biological Products / chemistry*
  • Biological Products / pharmacology
  • Fermentation
  • Hepacivirus / drug effects
  • Heterocyclic Compounds / chemistry*
  • Heterocyclic Compounds / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Myxococcales / chemistry*
  • Myxococcales / metabolism
  • Secondary Metabolism

Substances

  • Anti-Infective Agents
  • Antiviral Agents
  • Biological Products
  • Heterocyclic Compounds