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Biocatalyzed transformation of progesterone by Geobacillus gargensis DSM 15378

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Abstract

The formation of secosteroids, 9,10-seco-4-pregnene-3,9,20-trione and 9,10-seco-4-pregnene-20α-hydroxy-3,9-dione, catalyzed by thermophilic bacterium Geobacillus gargensis DSM 15378 from progesterone is being reported for the first time. In addition, seven other hydroxy/keto progesterone derivatives, 7-ketoprogesterone, 11-ketoprogesterone, 20α-hydroxyprogesterone, 6β-hydroxyprogesterone, 6α-hydroxyprogesterone, 5α-pregnane-3,6,20-trione and 3β-hydroxy-5α-pregnane-6,20-dione, were identified through their spectral data. The influence of SDS, as a surfactant, on progesterone biotransformation products was investigated.

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References

  1. Graf, M.R., Jia, W., Lewbart, M.L., and Loria, R.M., Chem. Biol. Drug Des., 2009, vol. 74, no. 6, pp. 625–629.

    Article  CAS  PubMed  Google Scholar 

  2. Appukuttan, A., Kasseckert, S.A., Kumar, S., Reusch, H.P., and Ladilov, Y., Cardiovasc. Res., 2013, vol. 99, no. 4, pp. 734–742.

    Article  CAS  PubMed  Google Scholar 

  3. Schaffer, S., Tandon, R., Zipse, H., Siess, W., Schmidt, A., Jamasbi, J., et al., Biochem. Pharmacol., 2013, vol. 86, no. 2, pp. 279–285.

    Article  CAS  PubMed  Google Scholar 

  4. Buttari, B., Segoni, L., Profumo, E., D’Arcangelo, D., Rossi, S., Facchiano, F., et al., Biochem. Pharmacol., 2013, vol. 86, no. 1, pp. 130–137.

    Article  CAS  PubMed  Google Scholar 

  5. Marumudi, E., Khadgawat, R., Surana, V., Shabir, I., Joseph, A., and Ammini, A.C., Steroids, 2013, vol. 78, no. 8, pp. 741–746.

    Article  CAS  PubMed  Google Scholar 

  6. Afzal, M., Al-Awadi, S., and Oommen, S., Methods Mol. Biol., 2010, vol. 594, pp. 349–356. DOI: 10.1007/978-1-60761-411-1-25.

    Article  CAS  PubMed  Google Scholar 

  7. Franceschini, S., van Beek, H.L., Pennetta, A., Martinoli, C., Fraaije, M.W., and Mattevi, A., J. Biol. Chem., 2012, vol. 287, no. 27, pp. 22626–22634.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  8. Habibi, Z., Yousefi, M., Ghanian, S., Mohammadi, M., and Ghasemi, S., Steroids, 2012, vol. 77, no. 13, pp. 1446–1449.

    Article  CAS  PubMed  Google Scholar 

  9. Gong, W., Xiong, G., and Maser, E., Appl. Environ. Microbiol., 2012, vol. 78, no. 4, pp. 941–950.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  10. Bezsudnova, E.Y., Boyko, K.M., Polyakov, K.M., Dorovatovskiy, P.V., Stekhanova, T.N., Gumerov, V.M., et al., Biochim, 2012, vol. 94, no. 12, pp. 2628–2638.

    Article  CAS  Google Scholar 

  11. Liu, B., Zhang, N., Zhao, C., Lin, B., Xie, L., and Huang, Y., J. Microbiol. Biotechnol., 2012, vol. 22, no. 10, pp. 1388–1394.

    Article  CAS  PubMed  Google Scholar 

  12. Repo, H., Oeemig, J.S., Djupsjobacka, J., Iwai, H., and Heikinheimo, P., Acta Crystallogr. Sec. D. Biol. Crystallogr., 2012, vol. 68, no.11, pp.1479–1487.

    Article  CAS  Google Scholar 

  13. Glebocka, A., Sicinski, R.R., Plum, L.A., and Deluca, H.F., J. Steroid Biochem. Mol. Biol., 2013, vol. 136, pp. 39–43. DOI: 10.1016/j.jsbmb.2012.09.030.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  14. Guan, Y.Z., Shan, S.M., Zhang, W., Luo, J.G., and Kong, L.Y., Steroids, 2014, vol. 82. DOI: 10.1016/j.steroids.2014.01.004

  15. Nazina, T.N., Lebedeva, E.V., Poltaraus, A.B., Tourova, T.P., Grigoryan, A.A., Sokolova, D., et al., Inter. J. Syst. Evol. Microbiol., 2004, vol. 54, no. 6, pp. 2019–2024.

    Article  CAS  Google Scholar 

  16. Ramaley, R.F. and Hixson, J., J. Bacteriol., 1970, vol. 103, no. 2, pp. 527–528.

    PubMed Central  CAS  PubMed  Google Scholar 

  17. Garcia-Pichel, F., Mechling, M., and Castenholz, R.W., Appl. Environ. Microbiol., 1994, vol. 60, no. 5, pp. 211–215.

    Google Scholar 

  18. Al-Awadi, S., Afzal, M., and Oommen, S., Steroid Biochem. Mol. Biol., 2001, vol. 78, no. 5, pp. 493–498.

    Article  CAS  Google Scholar 

  19. Wang, P.H., Leu, Y.L., Ismail, W., Tang, S.L., Tsai, C.Y., Chen, H.J., et al., J. Lipid Res., 2013, vol. 54, no. 5, pp. 1493–1504.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  20. Lai, D., Yu, S., van Ofwegen, L., Totzke, F., Proksch, P., and Lin, W., Bioorg. Med. Chem., 2011, vol. 19, no. 22, pp. 6873–6880.

    Article  CAS  PubMed  Google Scholar 

  21. Zheng, Q.C., Chen, G.D., Kong, M.Z., Li, G.Q., Cui, J.Y., Li, X.X., et al., Steroids, 2013, vol. 78, no. 9, pp. 896–901.

    Article  CAS  PubMed  Google Scholar 

  22. Migliuolo, A., Piccialli, V., and Sica, D., Steroids, 1992, vol. 57, no. 7, pp. 344–347.

    Article  CAS  PubMed  Google Scholar 

  23. Crossley, N.S. and Dowell, R., J. Chem. Soc., [Perkin1], 1971, vol. 13, pp. 2499–2502.

    CAS  Google Scholar 

  24. Meira, C.S., Guimaraes, E.T., Bastos, T.M., Moreira, D.R., Tomassini, T.C., Ribeiro, I.M., et al., Parasitol., 2013, vol. 140, no. 14, pp. 1811–1821.

    Article  CAS  Google Scholar 

  25. Yadav, M.R., Sabale, P.M., Giridhar, R., Zimmer, C., and Hartmann, R.W., Steroids, 2012, vol. 77, nos. 8–9, pp. 850–857.

    Article  CAS  PubMed  Google Scholar 

  26. Manire, C.A., Rasmussen, L.E., and Gross, T.S., J. Exp. Zool., 1999, vol. 284, no. 5, pp. 595–603.

    Article  CAS  PubMed  Google Scholar 

  27. Yamada, A., Yamada, M., Fujita, Y., Nishigami, T., Nakasho, K., and Uematsu, K., J. Biol. Chem., 2001, vol. 276, no. 7, pp. 4604–4610.

    Article  CAS  PubMed  Google Scholar 

  28. Hall, P.E. and Fotherby, K., Biochem. J., 1967, vol. 104, no. 2, p. 23.

    Google Scholar 

  29. Lee, Y.E., Choi, Y.H., Jeong, S.H., Kim, H.S., Lee, S.H., and Song, K.B., Curr. Microbiol., 2009, vol. 58, no. 4, pp. 332–337.

    Article  CAS  PubMed  Google Scholar 

  30. Sanai, Y., Suzuki, T., Yanaihara, T., and Nakayama, T., Nihon Sanka Fujinka Gakkai zasshi, 1984, vol. 36, no. 2, pp. 195–201.

    CAS  PubMed  Google Scholar 

  31. Huang, D.Y., Kominami, S., and Takemori, S., Science in China Ser., B Chem. Life Sci. Earth Sci., 1993, vol. 36, no. 4, pp.411–419.

    CAS  Google Scholar 

  32. Jayasekara, W.S., Yonezawa, T., Ishida, M., Yamanouchi, K., and Nishihara, M., J. Reprod. Dev., 2005, vol. 51, no. 2, pp. 265–272.

    Article  CAS  PubMed  Google Scholar 

  33. Miura, R., Shiota, K., Noda, K., Yagi, S., Ogawa, T., and Takahashi, M., Biochem. J., 1994, vol. 299, no. 2, pp. 561–567.

    PubMed Central  CAS  PubMed  Google Scholar 

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Correspondence to M. Afzal.

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Al-Beloshei, N.E., Al-Awadhi, H.A., Al-Khalaf, R.A.R. et al. Biocatalyzed transformation of progesterone by Geobacillus gargensis DSM 15378. Appl Biochem Microbiol 51, 321–328 (2015). https://doi.org/10.1134/S0003683815030023

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  • DOI: https://doi.org/10.1134/S0003683815030023

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