Skip to main content
SpringerLink
Log in

7α-Hydroxylation of steroid 5-olefins by mold fungi

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

Abstract

Hydroxylation activity of the mold fungi belonging to the orders Dothideales, Hypocreales, and Mucorales towards Δ5-3β-hydroxysteroids was studied. The fungi Bipolaris sorokiniana, Fusarium sp., and Rhizopus nigricans were able to introduce hydroxy group at position 7α; however, this ability was detected only at a low substrate load and with a low yield. A 7α-hydroxylase activity of the Curvularia lunata VKPM F-981 culture was shown for the first time. It was demonstrated that the studied strain was capable of stereo- and regioselective transformations of androstane 5-olefins at a load not less than 2 g/1. Conversion of pregnane steroids by this culture yielded both 7α- and 11β-hydroxy derivatives. The introduction of 7α-hydroxy group by this strain occurred concurrently with enzymatic hydrolysis of ester groups, which proceeded under mild conditions to give the corresponding alcohols in the cases of both 3-acetate of Δ5-androstenes and mono- and triacetates of Δ5-pregnenes.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Hampl, R., Morfin, R., and Starka, L., Endocrine Regul., 1997, vol. 31, no. 4, pp. 211–218.

    CAS  Google Scholar 

  2. Hampl, R., Lapcic, O., Hill, M., Klak, J., Kasal, A., Novacek, A., Sterzl, I., and Starka, L., Physiol. Res., 2000, vol. 49,Suppl. 1, pp. 107–112.

    Google Scholar 

  3. Fernandes, P., Cruz, A., Angelova, B., Pinheiro, H.M., and Cabral, J.M.S., Enzyme Microb. Technol., 2003, vol. 32, no. 6, pp. 688–705.

    Article  CAS  Google Scholar 

  4. Doostradeh, J., Cotillon, A.C., and Morfin, R., J. Neuroendocrinol., 1997, vol. 9, no. 12, pp. 923–928.

    Article  Google Scholar 

  5. Shi, J., Schulze, S., and Lardy, H.A., Steroids, 2000, vol. 65, no. 3, pp. 124–129.

    Article  CAS  PubMed  Google Scholar 

  6. Lathe, R., Steroids, 2002, vol. 67, no. 12, pp. 967–977.

    Article  CAS  PubMed  Google Scholar 

  7. Weill-Engerer, S., David, J.P., Sardovitch, V., Liere, P., Schumacher, M., Delacurte, A., and Baulieu, E.G., Akwa, Y., Brain Res., 2003, vol. 969,nos. 1–2, pp. 117–125.

    Article  CAS  PubMed  Google Scholar 

  8. Loria, R.M., Steroids, 2002, vol. 67, no. 12, pp. 953–966.

    Article  CAS  PubMed  Google Scholar 

  9. Capek, A., Hanc, O., and Tadra, M.A., Microbial Transformations of Steroids, Prague: Publ. House Czechoslovak Acad. Sci., 1966.

    Google Scholar 

  10. Charney, W. and Herzog, H.L., Microbial Transformation of Steroids, New York: Academic, 1967.

    Google Scholar 

  11. Akhrem, A.A. and Titov, Yu.A., Steroidy i mikroorganizmy (Steroids and Microorganisms), Moscow: Nauka, 1970.

    Google Scholar 

  12. Smith, L.L., in Terpenoids and Steroids, Overton, K.H., Ed., New York: Academic, 1974, pp. 394–530.

    Chapter  Google Scholar 

  13. Mahato, S.B. and Garai, S., Steroids, 1997, vol. 62, no. 4, pp. 332–345.

    Article  CAS  PubMed  Google Scholar 

  14. Bensasson, C.M., Hanson, J.R., and Hunter, A.C., Phytochemistry, 1998, vol. 49, no. 8, pp. 2355–2358.

    Article  CAS  Google Scholar 

  15. Namboori, K., Pereira, L., and Merchant, J.R., Indian J. Biochem. Biophys., 1980, vol. 17, no. 2, pp. 149–152.

    CAS  PubMed  Google Scholar 

  16. Romano, A., Romano, D., Ragg, E., Costantino, F., Lenna, R., Gandolfi, R., and Molinary, F., Steroids, 2006, vol. 71, no. 6, pp. 429–434.

    Article  CAS  PubMed  Google Scholar 

  17. Kolek, T., J. Steroid Biochem. Mol. Biol., 1999, vol. 71,nos. 1–2, pp. 83–90.

    Article  CAS  PubMed  Google Scholar 

  18. Dray, F.J. and Cotillon, A.C., FR Patent No. 2 771 105, 1997.

  19. Wilson, M.R., Gallimore, W.A., and Reese, P.B., Steroids, 1999, vol. 64, no. 12, pp. 834–843.

    Article  CAS  PubMed  Google Scholar 

  20. Madyastha, K.M. and Joseph, T., Appl. Microbiol. Biotechnol., 1995, vol. 44, nos. 3–4, pp. 339–343.

    Article  CAS  Google Scholar 

  21. Lamm, A.S., Chen, A.R.M., Reynolds, W.F., and Reese, P.B., Steroids, 2007, vol. 72, nos. 9–10, pp. 713–722.

    Article  Google Scholar 

  22. Choudhary, M.I., Shah, S.A., Musharraf, S.G., and Shaheen, F., Nat. Prod. Res., 2003, vol. 17, no. 3, pp. 215–220.

    Article  CAS  PubMed  Google Scholar 

  23. Sutton, D.A., Fothergill, A.W., and Rinaldi, M.G., Guide to Clinically Significant Fungi, Baltimore, MD: Williams & Wilkins, 1998. Translated under the title Opredelitel’ patogennykh i uslovno patogennykh gribov, Moscow: Mir, 2001.

    Google Scholar 

  24. Capek, A., Fassatilova, O., and Hanc, O., Folia Microbiol., 1974, vol. 19, no. 5, pp. 378–380.

    Article  CAS  Google Scholar 

  25. Krishnan, R., Madyastha, K.M., and Viswamitra, M., Steroids, 1991, vol. 56, pp. 440–445.

    Article  CAS  PubMed  Google Scholar 

  26. Turuta, A.M., Kamernitskii, A.V., Korobov, A.A., Bogdanov, V.S., Baklashova, T.G., Komarova, G.V., and Koshcheenko, K.A., Khim.-Farm. Zh., 1990, no. 6, pp. 52–55.

Download references

Author information

Authors and Affiliations

  1. Bioengineering Center, Russian Academy of Sciences, Moscow, 117312, Russia

    V. A. Andryushina, A. V. Druzhinina, V. V. Yaderets, T. S. Stytsenko & N. E. Voishvillo

Authors
  1. V. A. Andryushina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Druzhinina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Yaderets
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. S. Stytsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. E. Voishvillo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Druzhinina.

Additional information

Original Russian Text © V.A. Andryushina, A.V. Druzhinina, V.V. Yaderets, T.S. Stytsenko, N.E. Voishvillo, 2010, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2010, Vol. 46, No. 1, pp. 78–83.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Andryushina, V.A., Druzhinina, A.V., Yaderets, V.V. et al. 7α-Hydroxylation of steroid 5-olefins by mold fungi. Appl Biochem Microbiol 46, 69–74 (2010). https://doi.org/10.1134/S0003683810010126

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0003683810010126

Keywords

Search

Navigation