Novel pyrazine metabolites found in polymyxin biosynthesis byPaenibacillus polymyxa

Abstract

A complex mixture of methyl-branched alkyl-substituted pyrazines was found in the growth medium of the polymyxin-producing bacterium Paenibacillus polymyxa, and of these, seven are new natural compounds. A total of 19 pyrazine metabolites were identified. The dominant metabolite was 2,5-diisopropylpyrazine as identified using a combination of high-resolution mass spectrometry, (1)H- and (13)C-nuclear magnetic resonance, gas chromatography-mass spectrometry as well as co-elution with an authentic standard. Its biosynthesis was correlated with growth and production was strongly stimulated by valine supplementation. The other pyrazine metabolites, all related pyrazines with either one, two or three alkyl substituents, were identified by means of their mass spectral data and/or co-elution with authentic standards.

Ecology and biotechnological potential of Paenibacillus polymyxa: a minireview

“…Co-production of polymyxin E1 and a lantibiotic from P. polymyxa strain OSY-DF are potentially useful in food and medical applications [17]. P. polymyxa also produces pyrazine metabolites which was stimulated by valine supplementation [48]. In 2005, Stern et al [49] evaluated anti-Campylobacter activity of three P. polymyxa strains from poultry production environments.…”

Production of tripropeptins in media supplemented with precursors based on the biosynthetic pathway

“…The improved productions of other cyclic lipopeptide antibiotics with acyl side chains have previously been achieved by supplement of these amino acids or fatty acids. 5,6,7 Here, we report an improvement in the production ratio of TPPs by addition of the postulated precursors such as branched chain amino acids, short-chain carboxylic acids or 3-hydroxy fatty acids. Under the standard culture conditions, TPPs were produced in the ratio of TPPA (8.4%), TPPB (8.9%), TPPC (71.3%) and TPPD (11.4%).…”

Mining into interspecific bacterial interactions

“…The performed bioassays with the volatile compound 2,5-bis(1-methylethyl)-pyrazine revealed significant antibacterial and antifungal Exploring bacterial interspecific interactions for discovery of novel antimicrobial compounds 132 activity against the used microbial strains. Previous studies have already shown that pyrazine compounds can exhibit antimicrobial activities (Beck et al, 2003;Kucerova-Chlupacova et al, 2015). The detected pyrazine is most probably produced by the Burkholderia isolate, as small amounts of this compound were detected in the monoculture of these bacteria but not in monocultures of Paenibacillus.…”

“…The detected pyrazine is most probably produced by the Burkholderia isolate, as small amounts of this compound were detected in the monoculture of these bacteria but not in monocultures of Paenibacillus. The bacterial production of the volatile 2,5-bis(1-methylethyl)-pyrazine was ,so far, only reported for few bacteria (Beck et al, 2003;Dickschat et al, 2005;Rajini et al, 2011).…”

“…The interaction increased the production of specific antimicrobial compounds such as 2,5-bis(1-methylethyl)-pyrazine and as well of a unknown soluble pederin like compound (C25H45NO9, m/z= 504.316) [M + H + ]. The production of 2,5-bis(1-methylethyl)-pyrazine was so far only reported for a few bacteria (Beck et al, 2003;Dickschat et al, 2005;Rajini et al, 2011).…”