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Biotransformation of androst-4-ene-3,17-dione and nandrolone decanoate by genera of Aspergillus and Fusarium

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Abstract

The ability of five fungal species belonging to two genera of Aspergillus and Fusarium has been examined in the microbial transformation of androst-4-ene-3, 17-dione (AD). Furthermore, the biotransformation of nandrolone decanoate (2) by F. fujikuroi has been studied. AD (1) was converted by cultures of Aspergillus sp. PTCC 5266 to form 11α-hydroxy-AD (3) as the only product, with a yield of 86% in 3 days. Moreover, two hydroxylated metabolites 11α-hydroxy-AD (3, 65%) and 7β-hydroxy-AD (4; 18%) were isolated in biotransformation of AD by A. nidulans. On the other hand, it was metabolized by F. oxysporum to produce 14α-hydroxy-AD (5; 38%) and testosterone (6; 12%). Microbial transformation of AD by F. solani led to the production of 11α-hydroxy-AD (3; 54%) and testosterone (6; 14%). AD was reduced at the 17-position by F. fujikuroi to produce testosterone in the yield of 42%. Finally, nandrolone decanoate was transformed by F. fujikuroi via hydrolysis and oxidation at the 17-position to produce two metabolites namely 17β-hydroxyestr-4-en-3-one (7, 25.4%) and estr-4-en-3,17-dione (8, 33%), respectively. The all metabolites were purified and subsequently identified based on their spectra data analysis and comparing them to the literature data.

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Acknowledgements

This work was supported by a Research Council of Shahid Beheshti University, Tehran, Iran and Islamic Azad University of Ilam, Iran for which the authors are thankful.

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Authors and Affiliations

  1. Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C, Tehran, Iran

    Marjan Heidary, Zohreh Habibi & Fatemeh Ansari

  2. Department of Chemistry, Ilam Branch, Islamic Azad University, Ilam, Iran

    Saba Ghasemi

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  1. Marjan Heidary
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  2. Saba Ghasemi
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  3. Zohreh Habibi
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  4. Fatemeh Ansari
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Correspondence to Saba Ghasemi or Zohreh Habibi.

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Heidary, M., Ghasemi, S., Habibi, Z. et al. Biotransformation of androst-4-ene-3,17-dione and nandrolone decanoate by genera of Aspergillus and Fusarium. Biotechnol Lett 42, 1767–1775 (2020). https://doi.org/10.1007/s10529-020-02902-4

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  • DOI: https://doi.org/10.1007/s10529-020-02902-4

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