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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Graf, M.R., Jia, W., Lewbart, M.L., and Loria, R.M., Chem. Biol. Drug Des., 2009, vol. 74, no. 6, pp. 625–629.
Appukuttan, A., Kasseckert, S.A., Kumar, S., Reusch, H.P., and Ladilov, Y., Cardiovasc. Res., 2013, vol. 99, no. 4, pp. 734–742.
Schaffer, S., Tandon, R., Zipse, H., Siess, W., Schmidt, A., Jamasbi, J., et al., Biochem. Pharmacol., 2013, vol. 86, no. 2, pp. 279–285.
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.
Marumudi, E., Khadgawat, R., Surana, V., Shabir, I., Joseph, A., and Ammini, A.C., Steroids, 2013, vol. 78, no. 8, pp. 741–746.
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.
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.
Habibi, Z., Yousefi, M., Ghanian, S., Mohammadi, M., and Ghasemi, S., Steroids, 2012, vol. 77, no. 13, pp. 1446–1449.
Gong, W., Xiong, G., and Maser, E., Appl. Environ. Microbiol., 2012, vol. 78, no. 4, pp. 941–950.
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.
Liu, B., Zhang, N., Zhao, C., Lin, B., Xie, L., and Huang, Y., J. Microbiol. Biotechnol., 2012, vol. 22, no. 10, pp. 1388–1394.
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.
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.
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
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.
Ramaley, R.F. and Hixson, J., J. Bacteriol., 1970, vol. 103, no. 2, pp. 527–528.
Garcia-Pichel, F., Mechling, M., and Castenholz, R.W., Appl. Environ. Microbiol., 1994, vol. 60, no. 5, pp. 211–215.
Al-Awadi, S., Afzal, M., and Oommen, S., Steroid Biochem. Mol. Biol., 2001, vol. 78, no. 5, pp. 493–498.
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.
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.
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.
Migliuolo, A., Piccialli, V., and Sica, D., Steroids, 1992, vol. 57, no. 7, pp. 344–347.
Crossley, N.S. and Dowell, R., J. Chem. Soc., [Perkin1], 1971, vol. 13, pp. 2499–2502.
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.
Yadav, M.R., Sabale, P.M., Giridhar, R., Zimmer, C., and Hartmann, R.W., Steroids, 2012, vol. 77, nos. 8–9, pp. 850–857.
Manire, C.A., Rasmussen, L.E., and Gross, T.S., J. Exp. Zool., 1999, vol. 284, no. 5, pp. 595–603.
Yamada, A., Yamada, M., Fujita, Y., Nishigami, T., Nakasho, K., and Uematsu, K., J. Biol. Chem., 2001, vol. 276, no. 7, pp. 4604–4610.
Hall, P.E. and Fotherby, K., Biochem. J., 1967, vol. 104, no. 2, p. 23.
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.
Sanai, Y., Suzuki, T., Yanaihara, T., and Nakayama, T., Nihon Sanka Fujinka Gakkai zasshi, 1984, vol. 36, no. 2, pp. 195–201.
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.
Jayasekara, W.S., Yonezawa, T., Ishida, M., Yamanouchi, K., and Nishihara, M., J. Reprod. Dev., 2005, vol. 51, no. 2, pp. 265–272.
Miura, R., Shiota, K., Noda, K., Yagi, S., Ogawa, T., and Takahashi, M., Biochem. J., 1994, vol. 299, no. 2, pp. 561–567.
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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