Novel pyrazine metabolites found in polymyxin biosynthesis by Paenibacillus polymyxa

Corresponding Author

Hans C Beck

CelCom, Department of Biochemistry and Molecular Biology, University of Southern Denmark-Odense, DK-5230 Odense M, Denmark

Biotechnological Institute, Holbergsvej 10, DK-6000 Kolding, Denmark

*Corresponding author. Tel.: +45 75520433; Fax: +45 75529989, E-mail address: [email protected]Search for more papers by this author

Anne M Hansen,

Anne M Hansen

Biotechnological Institute, Holbergsvej 10, DK-6000 Kolding, Denmark

Search for more papers by this author

Frants R Lauritsen,

Frants R Lauritsen

CelCom, Department of Biochemistry and Molecular Biology, University of Southern Denmark-Odense, DK-5230 Odense M, Denmark

Search for more papers by this author

Hans C Beck,

Corresponding Author

Hans C Beck

CelCom, Department of Biochemistry and Molecular Biology, University of Southern Denmark-Odense, DK-5230 Odense M, Denmark

Biotechnological Institute, Holbergsvej 10, DK-6000 Kolding, Denmark

*Corresponding author. Tel.: +45 75520433; Fax: +45 75529989, E-mail address: [email protected]Search for more papers by this author

Anne M Hansen,

Anne M Hansen

Biotechnological Institute, Holbergsvej 10, DK-6000 Kolding, Denmark

Search for more papers by this author

Frants R Lauritsen,

Frants R Lauritsen

CelCom, Department of Biochemistry and Molecular Biology, University of Southern Denmark-Odense, DK-5230 Odense M, Denmark

Search for more papers by this author

First published: 09 January 2006

https://doi.org/10.1016/S0378-1097(03)00054-5

Citations: 14

Share a link

Email
Wechat
Bluesky

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, ¹H- and ¹³C-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.

References

[1] Murray, K.E., Shipton, J., Whitfield, F.B. (1970) 2-Methoxypyrazines and the flavour of green peas (Pisum sativum). Chem. Ind. 4, 897–898.
Google Scholar
[2] Murray, K.E., Whitfield, F.B. (1975) The occurrence of 3-alkyl-2-methoxypyrazines in raw vegetables. J. Sci. Food Agric. 26, 973–986.
10.1002/jsfa.2740260714
CAS Web of Science® Google Scholar
[3] Yamaguchi, N., Toda, T., Teramoto, T., Okuhira, T., Sugawara, E., Ito, T. (1993) Effect of sugars on microbiological pyrazine formation by Bacillus natto in synthetic liquid medium. Nippon Shokuhin Kogyo Gakkaishi 40, 841–848.
10.3136/nskkk1962.40.841
CAS Web of Science® Google Scholar
[4] Besson, I., Creuly, C., Gros, J.B., Larroche, C. (1997) Pyrazine production by Bacillus subtilis in solid-state fermentation on soyabeans. Appl. Microbiol. Biotechnol. 47, 489–495.
10.1007/s002530050961
CAS Web of Science® Google Scholar
[5] MacDonald, J.C. (1973) Toxicity, analyses, and production of aspergillic acid and its analogues. Can. J. Biochem. 51, 1311–1315.
10.1139/o73-172
CAS PubMed Web of Science® Google Scholar
[6] Kim, N.D., Kwak, M.K., Kim, S.G. (1997) Inhibition of cytochrome P450 2E1 expression by 2-(allylthio)pyrazine, a potential chemoprotective agent: Hepatoprotective effects. Biochem. Pharmacol. 53, 261–269.
10.1016/S0006-2952(96)00647-8
CAS PubMed Web of Science® Google Scholar
[7] Seitz, E.W. (1994) Fermentation production of pyrazines and terpenoids for flavors and fragrances. In: Bioprocess Production of Flavour, Fragrance, and Color ingredients (Gabelman, A., Ed.), pp. 95–134. Wiley, New York.
Google Scholar
[8] Chen, T-B., Reineccius, G.A., Bjorklund, J.A., Leete, E. (1991) Biosynthesis of 2-methoxy-3-isopropylpyrazine in Pseudomonas perolens. J. Agric. Food Chem. 39, 1009–1012.
10.1021/jf00005a042
Web of Science® Google Scholar
[9] Gallois, A., Kergomard, A., Adda, J. (1988) Study of the biosynthesis of 3-isopropyl-2-methoxypyrazine produced by Pseudomonas taetrolens. Food Chem. 28, 299–309.
10.1016/0308-8146(88)90105-7
CAS Web of Science® Google Scholar
[10] McIver, R.C. and Reineccius, G.A. (1986) Synthesis of 2-methoxy-3-isopropylpyrazine by Pseudomonas perolens. In: Biogeneration of Aromas (Palimnet, T.H. and Croteau, R., Eds.), pp. 266–274. ACS Symposium Series 317; American Chemical Society, Washington, DC.
Google Scholar
[11] Leejeerajumnean, A., Duckham, S.C., Owens, J.D., Ames, J.M. (2001) Volatile compounds in Bacillus-fermented soyabeans. J. Sci. Food Agric. 81, 525–529.
10.1002/jsfa.843
CAS Web of Science® Google Scholar
[12] Owens, J.D., Allagheny, N., Kipping, G., Ames, J.M. (1997) Formation of volatile compounds during Bacillus subtilis fermentation of soya beans. J. Sci. Food Agric. 74, 132–140.
10.1002/(SICI)1097-0010(199705)74:1<132::AID-JSFA779>3.0.CO;2-8
CAS Web of Science® Google Scholar
[13] MacDonald, J.C. (1965) Biosynthesis of pulcherriminic acid. Biochem. J. 96, 533–538.
10.1042/bj0960533
CAS PubMed Web of Science® Google Scholar
[14] MacDonald, J.C. (1962) Biosynthesis of hydroxyaspergillic acid. J. Biol. Chem. 237, 1977–1981.
CAS PubMed Web of Science® Google Scholar
[15] Kuo, M.C., Zhang, Y., Hartman, T.G., Rosen, R.T., Ho, C.T. (1989) Selective purge and trap method for the analysis of volatile pyrazines. J. Agric. Food Chem. 37, 1020–1022.
10.1021/jf00088a045
CAS Web of Science® Google Scholar
[16] Kotiaho, T., Lauritsen, F.R. (2002) Membrane inlet mass spectrometry. Comp. Anal. Chem. XXXVII, 531–557.
10.1016/S0166-526X(02)80053-8
Google Scholar
[17] Lauritsen, F.R., Lunding, A. (1998) A study of the bioconversion potential of the fungus Bjerkandera adusta with respect to a production of chlorinated aromatic compounds. Enzyme Microb. Technol. 22, 459–465.
10.1016/S0141-0229(97)00237-8
CAS Web of Science® Google Scholar
[18] Beck, H.C. (1997) Biosynthetic pathway for halogenated methoxybenzaldehydes in the white rot fungus Bjerkandera adusta. FEMS Microbiol. Lett. 149, 233–238.
10.1111/j.1574-6968.1997.tb10334.x
CAS Web of Science® Google Scholar
[19] Zilkowski, B.W., Bartelt, R.J., Blumberg, D., James, D.G., Weaver, D.K. (1999) Identification of host-related volatiles attractive to pineapple beetle. J. Chem. Ecol. 25, 229–251.
10.1023/A:1020857721010
CAS Web of Science® Google Scholar
[20] Jetz, W., Rowe, C., Guilford, T. (2001) Non-warning odors trigger innate color aversions - as long as they are novel. Behav. Ecol. 12, 134–139.
10.1093/beheco/12.2.134
Web of Science® Google Scholar

Citing Literature

Volume220, Issue1

March 2003

Pages 67-73

Novel pyrazine metabolites found in polymyxin biosynthesis by Paenibacillus polymyxa

Abstract

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Novel pyrazine metabolites found in polymyxin biosynthesis by Paenibacillus polymyxa

Abstract

References

Citing Literature

References

Related

Information