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

Kwaku Kyeremeh; Kojo Acquah; Mustafa Camas; Jioji Tabudravu; Wael E Houssen; Hai Deng; Marcel Jaspars

doi:10.3390/md12105197

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)

^*Corresponding author for this work

Chemistry

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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 language	English
Pages (from-to)	5197-5208
Number of pages	12
Journal	Marine Drugs
Volume	12
Issue number	10
DOIs	https://doi.org/10.3390/md12105197
Publication status	Published - 16 Oct 2014

Keywords

micromonosporaceae
mangrove
actinomycete
pyrazinone

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10.3390/md12105197

marinedrugs-12-05197
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title = "Butrepyrazinone, a New Pyrazinone with an Unusual Methylation Pattern from a Ghanaian Verrucosispora sp. K51G",

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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author = "Kwaku Kyeremeh and Kojo Acquah and Mustafa Camas and Jioji Tabudravu and Houssen, {Wael E} and Hai Deng and Marcel Jaspars",

year = "2014",

month = oct,

day = "16",

doi = "10.3390/md12105197",

language = "English",

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journal = "Marine Drugs",

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T1 - Butrepyrazinone, a New Pyrazinone with an Unusual Methylation Pattern from a Ghanaian Verrucosispora sp. K51G

AU - Kyeremeh, Kwaku

AU - Acquah, Kojo

AU - Camas, Mustafa

AU - Tabudravu, Jioji

AU - Houssen, Wael E

AU - Deng, Hai

AU - Jaspars, Marcel

PY - 2014/10/16

Y1 - 2014/10/16

N2 - 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.

AB - 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.

KW - micromonosporaceae

KW - mangrove

KW - actinomycete

KW - pyrazinone

U2 - 10.3390/md12105197

DO - 10.3390/md12105197

M3 - Article

SN - 1660-3397

VL - 12

SP - 5197

EP - 5208

JO - Marine Drugs

JF - Marine Drugs

IS - 10

ER -

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

Abstract

Keywords

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