Skip to main content
Log in

Formation and identification of trimethylimidazole during tetramethylpyrazine production from glucose by Bacillus strains

  • Original Research Paper
  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Abstract

During 2,3,5,6-tetramethylpyrazine production from glucose by Bacillus strains, a novel product was detected and identified as 2,4,5-trimethylimidazole (TMI) by GC/MS. TMI appeared in the culture medium only after glucose had been depleted and then increased to 0.25–0.31 g l−1 in 90–120 h. When the ammonium source was changed from (NH4)2SO4 to (NH4)2HPO4, only about one tenth of TMI was detected. Although the mechanistic events largely remain unclear, both microbial strains tested demonstrated similar dynamic processes of TMI production, suggesting that TMI formation is a genuine feature of Bacillus species.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Besson I, Creuly C, Gros JB, Larroche C (1997) Pyrazine production by Bacillus subtilis in solid-state fermentation on soybeans. Appl Microbiol Biotechnol 47:489–495

    Article  CAS  Google Scholar 

  • Cui B, Zheng BL, He K, Zheng QY (2003) Imidazole alkaloids from Lepidium meyenii. J Nat Prod 66:1101–1103

    Article  PubMed  CAS  Google Scholar 

  • Harper JL, Smith RAJ, Bedford JJ, Leader JP (1997) Synthesis, acidity and 19F NMR characteristics of imidazoles bearing 1-fluorinated substituents with potential application as probes for intracellular pH determination. Tetrahedron 53:8211–8224

    Article  CAS  Google Scholar 

  • Hashim P, Selamat J, Ali A, Kharidah S (1997) Pyrazines formation in cocoa beans: changes during fermentation. J Food Sci Technol 34:483–487

    CAS  Google Scholar 

  • Kim KS, Lee HJ, Shon DH, Chung DK (1994) Optimum condition for the production of tetramethylpyrazine flavor compound by aerobic fed-batch culture of Lactococcus lactis subsp. lactis biovar diacetylactis FC1. J Microbiol Biotechnol 4:327–332

    CAS  Google Scholar 

  • Kosuge T, Zenda H, Tsuji K, Yamamoto T, Narita H (1971) Studies on flavor components of foodstuffs. Part 1. Distribution of tetramethylpyrazine in fermented foodstuffs. Agric Biol Chem 35:693–696

    Google Scholar 

  • Larroche C, Besson I, Gros JB (1999) High pyrazine production by Bacillus subtilis in solid substrate fermentation on ground soybeans. Process Biochem 34:667–674

    Article  CAS  Google Scholar 

  • Miller A, Scanlan RA, Lee JS, Libbey LM, Morgan ME (1973) Volatile compounds produced in sterile fish muscle (Sebastes melanops) by Pseudomonas perolens. Appl Microbiol 25:257–261

    PubMed  CAS  Google Scholar 

  • Wolkenberg SE, Wisnoski DD, Leister WH, Wang Y, Zhao Z, Lindsley CW (2004) Efficient synthesis of imidazoles from aldehydes and 1, 2-diketones using microwave irradiation. Org Lett 6:1453–1456

    Article  PubMed  CAS  Google Scholar 

  • Xiao Z, Xu P (2007) Acetoin metabolism in bacteria. Crit Rev Microbiol 33:127–140

    Article  PubMed  CAS  Google Scholar 

  • Xiao ZJ, Xie NZ, Liu PH, Hua DL, Xu P (2006) Tetramethylpyrazine production from glucose by a newly isolated Bacillus mutant. Appl Microbiol Biotechnol 73:512–518

    Article  PubMed  CAS  Google Scholar 

  • Xiao ZJ, Liu PH, Qin JY, Xu P (2007) Statistical optimization of medium components for enhanced acetoin production from molasses and soybean meal hydrolysate. Appl Microbiol Biotechnol 74:61–68

    Article  PubMed  CAS  Google Scholar 

  • Zak DL, Ostovar K, Keeney PG (1972) Implication of Bacillus subtilis in the synthesis of tetramethylpyrazine during fermentation of cocoa beans. J Food Sci 37:967–968

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Project for Young Scientists’ Fund of National Natural Science Foundation of China under Grant No. 30800012.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jian R. Lu.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 14 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xiao, Z., Lu, J.R., Ma, C. et al. Formation and identification of trimethylimidazole during tetramethylpyrazine production from glucose by Bacillus strains. Biotechnol Lett 31, 1421–1425 (2009). https://doi.org/10.1007/s10529-009-0012-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10529-009-0012-7

Keywords

Navigation