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.
Highlights
The pyrazinone ring is a non-aromatic heterocyclic ring with two nitrogens that are situated para- to each other
In vitro studies demonstrated that PsoF, a single polypeptide containing a methyl transferase (MT) and a FAD-dependent monooxygenase (FMO), can act as a trans C-methylation of the backbone of the growing polyketide chain and catalyze the stereospecific epoxidation in the late stage of the biosynthesis [15]
K51G recovered from a sediment collected from the Butre River, which is situated in the western region mangroves of Ghana
Summary
The pyrazinone ring is a non-aromatic heterocyclic ring with two nitrogens that are situated para- to each other They are derived from the aromatic pyrazine ring by single oxidation of one of the carbon atoms as opposed to double oxidation, which gives the diketopiperazine ring common in the structures of many drugs in current use. C-5 of the pyrazinone ring is understandable, based on the current literature available, there exists another group of pyrazinone compounds that possess substituents on both the C-5 and C-6 carbons of the pyrazinone skeleton (Figure 1). C-5 and C-6 positions rendering its biosynthesis difficult to understand completely In this communication, we describe the taxonomy and large-scale fermentation of the producing strain and the extraction, isolation, physico-chemical characterization, antimicrobial screening and the structure determination of butrepyrazinone (10)
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