Butrepyrazinone, a new pyrazinone with an unusual methylation pattern from a Ghanaian Verrucosispora sp. K51G

Mar Drugs. 2014 Oct 16;12(10):5197-208. doi: 10.3390/md12105197.

Abstract

We report the structural characterization of a new pyrazinone analogue; butrepyrazinone, which was isolated from a new actinomycete strain Verrucosispora sp. K51G recovered from Ghanaian mangrove river sediment. Spectroscopy-guided fractionation led to the isolation of a compound from the fermentation culture and a combination of NMR spectroscopy, high-resolution mass spectrometry and computer-aided calculations revealed that butrepyrazinone (10) possesses an unusual methylation pattern on the pyrazinone ring. Butrepyrazinone (10), however, displayed no antibacterial activity against Gram-positive S. aureus ATCC 25923, the Gram-negative E. coli ATCC 25922 and a panel of clinical isolates of methicillin-resistant S. aureus (MRSA) strains, suggesting that 10 may act as a signal molecule for this strain. Although the same molecule has been synthesized previously, this is the first report to disclose the discovery of butrepyrazinone (10) from nature.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinobacteria / chemistry*
  • Actinomycetales / chemistry*
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Escherichia coli / drug effects
  • Geologic Sediments / microbiology
  • Ghana
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Methylation / drug effects*
  • Microbial Sensitivity Tests
  • Pyrazines / chemistry*
  • Rivers / microbiology

Substances

  • Anti-Bacterial Agents
  • Pyrazines