Skip to main content
Log in

Biotransformation of methyltestosterone by the filamentous fungus Mucor racemosus

  • Published:
Chemistry of Natural Compounds Aims and scope

Fungi have proved to be powerful biocatalysts in steroid biotransformations. In the present study, the soil isolate filamentous fungus Mucor racemosus was applied for bioconversion of methyltestosterone (1), an anabolic steroid, in a five-day fermentation. Microbial metabolites were purified chromatographically and identified on the basis of their spectral data as 7α-hydroxymethyltestosterone (2), 15α-hydroxymethyltestosterone (3), and 12,15α-dihydroxymethyltestosterone (4). Observed modifications were hydroxylations at C-7α, C-12, and 15α-positions. Best fermentation condition for production of hydroxylated derivatives was found to be 25°C at 150 rpm for 5 days with a substrate concentration of 1 mg/mL.

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

Similar content being viewed by others

References

  1. P. Fernandes, A. Cruz, B. Angelova, H. M. Pinheiro, and J. M. C. Cabral, Enzyme Microb. Technol., 32, 688 (2003).

    Article  CAS  Google Scholar 

  2. M. A. Faramarzi, S. Adrangi, and M. Tabatabaei Yazdi, J. Phycol., 44, 27 (2008).

    Article  CAS  Google Scholar 

  3. L. Hilterhaus and A. Liese, in: White Biotechnology. Advances in Biochemical Engineering/Biotechnology, Vol. 105, D. Sell and R. Ulber, eds., Berlin, Springer, 2007, p. 133.

    Google Scholar 

  4. E. J. Lenardao, R. A. Freitag, M. J. Dabdoub, A. C. Ferreira Batista, and C. Da Cruz Silveira, Quim. Nova, 26, 123 (2003).

    Article  CAS  Google Scholar 

  5. M. J. Carlile, S. C. Watkinson, and G. W. Gooday, The Fungi, 2nd Edn., California, Academic Press, 2001.

    Google Scholar 

  6. K. H. Domsch, W. Gams, and T. H. Anderson, Compendium of Soil Fungi, Vol. 1, London, Academic Press, 1980.

    Google Scholar 

  7. S. B. Mahato and I. Majumdar, Phytochemistry, 43, 883 (1993).

    Article  Google Scholar 

  8. W. Charney, Microbial Transformation of Steroids: Handbook, 1st Edn., London, Academic Press, 1967.

    Google Scholar 

  9. K. M. Madyastha and T. Joseph, Appl. Microbiol. Biotechnol., 44, 339 (1995).

    Article  CAS  Google Scholar 

  10. W. Ge, S. Wang, L. Shan, N. Li, and H.-M. Liu, J. Mol. Catal. B: Enzym., 55, 37 (2008).

    Article  CAS  Google Scholar 

  11. H. Li, H. M. Liu, W. Ge, L. Huang, and L. Shan, Steroids, 70, 970 (2005).

    Article  PubMed  CAS  Google Scholar 

  12. M. A. Faramarzi, M. Badiee, M. Tabatabaei Yazdi, M. Amini, and M. Torshabi, J. Mol. Catal. B: Enzym., 50, 7 (2008).

    Article  CAS  Google Scholar 

  13. M. A. Faramarzi, N. Zolfaghary, M. Tabatabaei Yazdi, S. Adrangi, H. Rastegar, M. Amini, and M. Badiee, J. Chem. Technol. Biotechnol., 84, 1021 (2009).

    Article  CAS  Google Scholar 

  14. H. L. Holland and E. M. Thomas, Can. J. Chem., 60, 160 (1982).

    Article  CAS  Google Scholar 

  15. Y. M. Alvarez-Ginarte, R. Crespo, L. A. Montero-Cabrera, J. A. Ruiz-Garcia, Y. Marrero Ponce, R. Santana, E. Pardillo-Fontdevila, and E. Alonso-Becerra, QSAR Comb. Sci., 24, 218 (2005).

    Article  CAS  Google Scholar 

  16. E. Huszcza and J. Dmochowska-Gladysz, Phytochemistry, 62, 155 (2003).

    Article  PubMed  CAS  Google Scholar 

  17. A. Bartmanska, J. Dmochowska-Gladysz, and E. Huszcza, Steroids, 70, 193 (2005).

    Article  PubMed  CAS  Google Scholar 

  18. J. R. Hanson, H. Nasir, and A. Parvez, Phytochemistry, 42, 411 (1996).

    Article  CAS  Google Scholar 

  19. M. Zakelj-Mavric and I. Belic, J. Steroid Biochem., 28, 197 (1987).

    Article  PubMed  CAS  Google Scholar 

  20. W. J. Marsheck, J. Jia, and P. T. Wang, U. S. Pat., 4397947 (1983).

  21. E. Huszcza and J. Dmochowska-Gladysz, J. Basic Microb., 43, 113 (2003).

    Article  CAS  Google Scholar 

  22. K. Tachibana, I. Imaoka, H. Yoshino, N. Kato, M. Nakamura, M. Ohta, H. Kawata, K. Taniguchi, N. Ishikura, M. Nagamuta, E. Onuma, and H. Sato, Bioorg. Med. Chem. Lett., 17, 5573 (2007).

    Article  PubMed  CAS  Google Scholar 

  23. A. G. Fragkaki, Y. S. Angelis, M. Koupparis, A. Tsantili-Kakoulidou, G. Kokotos, and C. Georgakopoulos, Steroids, 74, 172 (2009).

    Article  PubMed  CAS  Google Scholar 

  24. A. Swizdor and T. Kolek, Steroids, 70, 817 (2005).

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgment

This work was supported financially by a grant (No. 89-04-33-12044) from Tehran University of Medical Sciences, Tehran, Iran. The helpful advice of Dr. Sina Adrangi (Tehran University of Medical Sciences, Tehran, Iran) is also acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. A. Faramarzi.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 55–58, January–February, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Torshabi, M., Badiee, M., Faramarzi, M.A. et al. Biotransformation of methyltestosterone by the filamentous fungus Mucor racemosus . Chem Nat Compd 47, 59–63 (2011). https://doi.org/10.1007/s10600-011-9830-7

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-011-9830-7

Keywords

Navigation