Chemistry of Natural Compounds

, Volume 49, Issue 4, pp 665–670 | Cite as

Fungal transformation of methyltestosterone by the soil ascomycete Acremonium strictum to some hydroxy derivatives of 17-methylsteroid

  • N. Nassiri-Koopaei
  • M. Mogharabi
  • M. Amini
  • A. Shafiee
  • M. A. Faramarzi
Article

The ascomycete Acremonium strictum was used for the biotransformation of methyltestosterone (1), a pharmaceutical steroid substance, into some steroid derivatives (6β-hydroxy-17α-methyltestosterone (2), 6β,12β-dihydroxy-17α-methyltestosterone (3), 7β-hydroxy-17α-methyltestosterone (4), 6β,17β-dihydroxy-17α-methylandrosta-1,4-dien-3-one (5), and 3,17β-dihydroxy-17α-methylestra-1,3,5(10)-triene (6). The fermentation was carried out in Sabouraud-dextrose broth (SDB) supplemented with 1 mM of the substrate, and the temperature and aeration rate were adjusted to 30°C and 150 rpm, respectively. The biotransformation characteristics observed were hydoxylations at C-6β, C-7β, and C-12β, 1,2-dehydrogenation, and ring A aromatization. The best fermentation conditions, such as temperature, substrate concentration, pH, incubation period, and aeration, were found to be 25°C, 1 mM, pH 6.5, 6 days, and 150 rpm, respectively, for maximum biotransformation of 1.

Keywords

Acremonium strictum biotransformation methyltestosterone steroid fungus ascomycete 

References

  1. 1.
    M. I. Choudhary, S. Erum, M. Atif, R. Malik, N. T. Khan, and Atta-ur-Rahman, Steroids, 76, 1288 (2011).Google Scholar
  2. 2.
    L. H. Huang, J. Li, G. Xu, X. H. Zhang, Y. G. Wang, Y. L. Yin, and H. M. Liu, Steroids, 75, 1039 (2010).PubMedCrossRefGoogle Scholar
  3. 3.
    T. J. Novicki, K. LaFe, L. Bui, U. Bui, R. Geise, K. Marr, and B. T. Cookson, J. Clin. Microbiol., 41, 2623 (2003).PubMedCrossRefGoogle Scholar
  4. 4.
    M. S. Ali-Shtayeh, T. K. Khaleel, and R. M. Jamous, Mycopathology, 156, 193 (2002).CrossRefGoogle Scholar
  5. 5.
    K. J. Kwon-Chung and J. E. Bennett, Medical Mycology, Philadelphia, Lea & Febiger, 1992.Google Scholar
  6. 6.
    A. M. Tagne, E. Neergaard, H. J. Hansen, and C. The, Eur. J. Plant Pathol., 108, 93 (2002).CrossRefGoogle Scholar
  7. 7.
    X. H. Kang, X. S. He, and N. Zhang, Southwest China J. Agric. Sci., 15, 73 (2002).Google Scholar
  8. 8.
    M. A. Faramarzi, M. Tabatabaei Yazdi, G. Zarrini, and A. Shafiee, Steroids, 67, 869 (2002).PubMedCrossRefGoogle Scholar
  9. 9.
    M. A. Faramarzi, M. T. Tabatabaei Yazdi, M. Amini, G. Zarrini, and A. Shafiee, FEMS Microbiol. Lett., 222, 183 (2003).PubMedCrossRefGoogle Scholar
  10. 10.
    M. A. Faramarzi, M. Tabatabaei Yazdi, H. Jahandar, M. Amini, and H. R. Monsef-Esfahani, J. Ind. Microbiol. Biotechnol., 33, 725 (2006).PubMedCrossRefGoogle Scholar
  11. 11.
    M. Tabatabaei Yazdi, S. M. Zanjanian, M. A. Faramarzi, M. Amini, A. Amani, and K. Abdi, Arch. Pharm. Chem. Life Sci., 339, 473 (2006).CrossRefGoogle Scholar
  12. 12.
    M. A. Faramarzi, M. Tabatabaei Yazdi, M. Amini, and A. Shafiee, Biotechnology, 7, 343 (2008).CrossRefGoogle Scholar
  13. 13.
    D. N. Kirk, H. C. Toms, C. Douglas, K. A. White, K. E. Smith, S. Latif, and R. W. P. Habbard, J. Chem. Soc. Perkin Trans. 2, 1567 (1990).Google Scholar
  14. 14.
    J. R. Hanson, H. Nasir, and A. Parvez, Phytochemistry, 42, 411 (1996).CrossRefGoogle Scholar
  15. 15.
    E. Huszcza and J. Dmochowska-Gladysz, J. Basic Microbiol., 43, 113 (2003).PubMedCrossRefGoogle Scholar
  16. 16.
    M. A. Faramarzi, M. Torshabi, M. Badiee, H. Rastegar, H. Forootanfar, and E. Mohit, Chem. Nat. Compd., 47, 59 (2011).CrossRefGoogle Scholar
  17. 17.
    W. Schanzer and S. Horning, Steroids, 60, 353 (1995).PubMedCrossRefGoogle Scholar
  18. 18.
    R. P. Boivin, V. Lu-The, R. Lachance, F. Labrie, and D. Poirier, J. Med. Chem., 43, 4465 (2000).PubMedCrossRefGoogle Scholar
  19. 19.
    E. Vischer, Ch. Meystre, and A. Wettstein, Helv. Chim. Acta, 38, 1502 (1955).CrossRefGoogle Scholar
  20. 20.
    E. L. Rongone and A. Segaloff, Steroids, 1, 179 (1963).CrossRefGoogle Scholar
  21. 21.
    D. J. Abraham, Burger’s Medicinal Chemistry and Drug Discovery, 6th Ed., New York, John Wiley and Sons, 2006.Google Scholar
  22. 22.
    M. Numazawa, Y. Watari, S. Komatsu, K. Yamashita, and M. Nagaoka, Steroids, 73, 1262 (2008).PubMedCrossRefGoogle Scholar
  23. 23.
    M. W. Hornung, K. M. Jensen, J. J. Korte, M. D. Kahl, E. J. Durhan, J. S. Denny, T. R. Henry, and G. T. Ankley, Aquat. Toxicol., 66, 15 (2004).PubMedCrossRefGoogle Scholar
  24. 24.
    R. Maltais and D. Poirier, Steroids, 76, 929 (2011).PubMedCrossRefGoogle Scholar
  25. 25.
    A.-S. Clouet-Dumas, B. Le Bizec, M.-A. Le Pape, D. Maume, F. Monteau, and F. Andre, J. Steroid Biochem. Mol. Biol., 74, 57 (2000).PubMedCrossRefGoogle Scholar
  26. 26.
    F. Naghibi, M. Tabatabaei Yazdi, and S. Shahhosseini, Daru J. Pharm. Sci., 10, 70 (2002).Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • N. Nassiri-Koopaei
    • 1
  • M. Mogharabi
    • 1
  • M. Amini
    • 2
  • A. Shafiee
    • 2
  • M. A. Faramarzi
    • 1
    • 2
  1. 1.Department of Pharmaceutical BiotechnologyFaculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical SciencesTehranIran
  2. 2.Pharmaceutical Sciences Research CenterTehran University of Medical SciencesTehranIran

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