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

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Chemistry of Natural Compounds Aims and scope

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.

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Acknowledgment

This work was supported by Grant No. 91-02-90-18474 awarded to M.A.F. by the Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran.

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Authors and Affiliations

  1. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, P. O. Box 14155-6451, 14176, Tehran, Iran

    N. Nassiri-Koopaei, M. Mogharabi & M. A. Faramarzi

  2. Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, 14176, Tehran, Iran

    M. Amini, A. Shafiee & M. A. Faramarzi

Authors
  1. N. Nassiri-Koopaei
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  2. M. Mogharabi
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  3. M. Amini
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  4. A. Shafiee
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  5. M. A. Faramarzi
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Corresponding author

Correspondence to M. A. Faramarzi.

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Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2013, pp. 571–575.

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Nassiri-Koopaei, N., Mogharabi, M., Amini, M. et al. Fungal transformation of methyltestosterone by the soil ascomycete Acremonium strictum to some hydroxy derivatives of 17-methylsteroid. Chem Nat Compd 49, 665–670 (2013). https://doi.org/10.1007/s10600-013-0703-0

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  • DOI: https://doi.org/10.1007/s10600-013-0703-0

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