Butrepyrazinone, a New Pyrazinone with an Unusual Methylation Pattern from a Ghanaian Verrucosispora sp. K51G

Kwaku Kyeremeh (Corresponding Author), Kojo Acquah, Mustafa Camas, Jioji Tabudravu, Wael E Houssen, Hai Deng, Marcel Jaspars (Corresponding Author)

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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.
Original languageEnglish
Pages (from-to)5197-5208
Number of pages12
JournalMarine Drugs
Volume12
Issue number10
DOIs
Publication statusPublished - 16 Oct 2014

Keywords

  • micromonosporaceae
  • mangrove
  • actinomycete
  • pyrazinone

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