Skip to main content
Log in

Microbiologic oxidation of isosafrole into piperonal

  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

The biotransformation of isosafrole by Cladosporium sphaerospermum yielded piperonal, which is a compound of great commercial importance in the flavor and fragrance industries. The experiments were performed in 500-mL conical flasks containing 100 mL of Czapek-modified medium in an orbital shaker with controlled agitation and temperature. Spores of C. sphaerospermum were used as inocula, and after 96 h of incubation the substrate was added to the culture. Samples of 2 mL were withdrawn at 24-h intervals and analyzed by gas chromatography, (GC) and/or GC/MS spectroscopy.

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.

Similar content being viewed by others

References

  1. Roberts, S. M. (2000), J. Chem. Soc. (Perkin Trans. 1) 611–633.

  2. Moro-oka, Y, and Akita, M. (1998), Catalysis Today 41, 327–338.

    Article  CAS  Google Scholar 

  3. DeMontellano, P. R. O. (1995), Cytochrome P-450 Structure, Mechanism and Biochemistry, 2nd ed., Plenum, New York.

    Google Scholar 

  4. Archelas, A. and Furstoss, R. (1997), Annu. Rev. Microbiol. 51, 491–525.

  5. Groves, J. T. and Neumann, R. (1989) J. Am. Chem. Soc. 111, 2900–2909.

    Article  CAS  Google Scholar 

  6. Mansuy, D. (1994), Pure Appl. Chem. 66(4), 737–744.

    CAS  Google Scholar 

  7. Narimatsu, S; Kobayashi, N.; Masubuchi, Y., Horie, T., Kakegawa, T., Kobayashi, H., et al. (2000), Chem. Biol. Int. 127, 73–90.

    Article  CAS  Google Scholar 

  8. Faber, K. (1995), Biotransformations in Organic Chemistry, 2nd ed., Springer-Verlag, Berlin, Germany.

    Google Scholar 

  9. Prelog, V. (1964), Pure Appl. Chem. 9, 119–130.

    Article  CAS  Google Scholar 

  10. Seebach, D., Sutter, M. A., Weber, R. H., and Zuger, M. F. (1984), Org. Synth. 63, 1–10.

    Google Scholar 

  11. Welsh, F. W., Murray, W. D., and Williams, R. E. (1989), Crit. Rev. Biotech. 9(2), 105–169.

    CAS  Google Scholar 

  12. Costas, M., Chem, K., and Que, L. Jr. (2000), Coord. Chem. Rev. 200–202, 517–544.

    Article  Google Scholar 

  13. Gonsalves, A. M. d’A. R., and Pereira, M. M. (1996), J. Mol. Catal. A: Chem. 113, 209–211.

    Article  Google Scholar 

  14. Kato, Y. and Asono, Y. (2001), J. Mol. Catal. B: Enzymat. 13, 27–36.

    Article  CAS  Google Scholar 

  15. Conesa, A., Punt, P. J., and van den Hondel, C. A. M. J. J. (2002), J. Biotechnol. 93, 143–158.

    Article  CAS  Google Scholar 

  16. Delaforge, M., Jaouen, M., and Bouille, G. (1999), Envir. Toxicol. Pharm. 7, 153–158.

    Article  CAS  Google Scholar 

  17. Keseru, G. M., Balogh, G. T., Arvai, G., and Bertók, B. (1999), Tetrahedron 55, 4457–4466.

    Article  CAS  Google Scholar 

  18. Shimoni, E.; Ravid, U., and Shoham, Y. (2000), J. Biotechnol. 78, 1–9.

    Article  CAS  Google Scholar 

  19. Kakko, I., Toimela, T., and Tahti, H. (2000), Chemosphere 40, 301–305.

    Article  CAS  Google Scholar 

  20. Cappuccino, J. G. and Scherman, N. (1992), Microbiology: A Laboratory Manual, 3rd ed., Beijamings Curmmings, New York, NY.

    Google Scholar 

  21. Demain, A. L. and Solomon, N. A. (1986), in Manual of Industrial Microbiology and Biotechnology, John Wiley & Sons, New York, NY, 97–121.

    Google Scholar 

  22. Adams, R. P. (1995), Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy, Allured Publishing, Carol Stream, IL.

    Google Scholar 

  23. Barreiro, E. J. and Fraga, C. A. M. (2001), in Química Médica: As Bases Moleculares da Ação dos Fármacos, Artmed Editora, Porto Alegre, Brazil, pp. 182–185.

    Google Scholar 

  24. Adam, W., Lazarus, M., Saha-Möller, C. R., Weichold, O., Hoch, U., Häring, D., and Schreier, P. (1999), Adv. Biochem. Eng. Biotechnol. 63, 73–108.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Octavio A. C. Antunes.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Santos, A.S., Pereira, N., da Silva, I.I. et al. Microbiologic oxidation of isosafrole into piperonal. Appl Biochem Biotechnol 107, 649–657 (2003). https://doi.org/10.1385/ABAB:107:1-3:649

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1385/ABAB:107:1-3:649

Index Entries

Navigation