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

Kyeremeh K, Acquah KS, Camas M, Tabudravu J, Houssen W, Deng H, Jaspars M - Mar Drugs (2014)

Bottom Line: K51G recovered from Ghanaian mangrove river sediment.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.

View Article: PubMed Central - PubMed

Affiliation: Marine and Plant Laboratory of Ghana, Department of Chemistry, University of Ghana, Accra, P.O. Box LG 56, Ghana. kkyeremeh@ug.edu.gh.

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.

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The best candidate structure calculated by the Structure Elucidator with 13C chemical shift deviations between experimental and predicted of the HOSE-code (dA) Incremental Method (dI) and Artificial Neural Net (dN).
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marinedrugs-12-05197-f004: The best candidate structure calculated by the Structure Elucidator with 13C chemical shift deviations between experimental and predicted of the HOSE-code (dA) Incremental Method (dI) and Artificial Neural Net (dN).

Mentions: Further confirmation of the structure was performed by calculating all possible structures using the ACD/LABS Structure Elucidator [11] software as follows: The proton NMR and 2D NMR data including Edited-gHSQCAD, gCOSY, gHMBCAD and ROESY, the molecular formula plus a predetermined mono-substituted benzene ring were entered into the software. Non-standard correlations [12] were detected notably in the gCOSY correlation between H-7 and H-12, and in the HMBC correlations between C-3 and H-12, and C-8 and H-12. These were automatically resolved by the software and calculations resulted in 14 possible structures (Figures S8) of which the proposed structure was placed as the best possible candidate (Figure 3 and Figure 4). The low number of the chemical shift deviations of the HOSE-code (dA) [13], Incremental Method (dI) [14], and Artificial Neural Net (dN) [14] 13C chemical shifts indicate that the proposed structure is correct.


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

Kyeremeh K, Acquah KS, Camas M, Tabudravu J, Houssen W, Deng H, Jaspars M - Mar Drugs (2014)

The best candidate structure calculated by the Structure Elucidator with 13C chemical shift deviations between experimental and predicted of the HOSE-code (dA) Incremental Method (dI) and Artificial Neural Net (dN).
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4210894&req=5

marinedrugs-12-05197-f004: The best candidate structure calculated by the Structure Elucidator with 13C chemical shift deviations between experimental and predicted of the HOSE-code (dA) Incremental Method (dI) and Artificial Neural Net (dN).
Mentions: Further confirmation of the structure was performed by calculating all possible structures using the ACD/LABS Structure Elucidator [11] software as follows: The proton NMR and 2D NMR data including Edited-gHSQCAD, gCOSY, gHMBCAD and ROESY, the molecular formula plus a predetermined mono-substituted benzene ring were entered into the software. Non-standard correlations [12] were detected notably in the gCOSY correlation between H-7 and H-12, and in the HMBC correlations between C-3 and H-12, and C-8 and H-12. These were automatically resolved by the software and calculations resulted in 14 possible structures (Figures S8) of which the proposed structure was placed as the best possible candidate (Figure 3 and Figure 4). The low number of the chemical shift deviations of the HOSE-code (dA) [13], Incremental Method (dI) [14], and Artificial Neural Net (dN) [14] 13C chemical shifts indicate that the proposed structure is correct.

Bottom Line: K51G recovered from Ghanaian mangrove river sediment.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.

View Article: PubMed Central - PubMed

Affiliation: Marine and Plant Laboratory of Ghana, Department of Chemistry, University of Ghana, Accra, P.O. Box LG 56, Ghana. kkyeremeh@ug.edu.gh.

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.

Show MeSH
Related in: MedlinePlus