SOLID PHASE MICROBIAL FERMENTATION OF ANABOLIC STEROID, DIHYDROTESTOSTERONE WITH ASCOMYCETE FUNGUS FUSARIUM OXYSPORUM

Authors

  • Muhammad Atif H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan,
  • Syed Adnan Ali Shah Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
  • Sadia Sultan Universiti Teknologi MARA
  • Muhammad Iqbal Choudhary University of Karachi

Keywords:

Anabolic steroid, Ascomycete, Fusarium oxysporum, Dihydrotestosterone, Solid Phase, Microbial Transformation, Oxidation

Abstract

Objective: Microbial catalysis is used in the commercial production of many bioactive steroids. Solid phase microbial fermentation of anabolic steroid, dihydrotestosterone (DHT, 1), was carried out with ascomycete fungal strain Fusarium oxysporum (NRRL-1392).

Methods: Sabouraud-4% glucose-agar was used to cultivate the fungal cultures as solid phase medium. Substrate 1 was incubated with Fusarium oxysporum (NRRL-1392) for 8 days. Microbial transformed metabolites were purified by using column chromatographic technique.

Results: Ascomycete fungal strain Fusarium oxysporum (NRRL-1392), transformed dihydrotestosterone (1) to four oxidative metabolites 2-5  using solid phase microbial transformation metod. During biotransformation process the hydroxy group was incorporated in inactivated methine carbon atoms at C-7 and C-11 positions. Their structures were elucidated by means of a homo and heteronuclear 2D NMR and by HREI-MS techniques as 17b-hydroxyandrosta-1, 4-dien-3-one 2, androsta-1, 4-diene-3, 17-dione 3, 7a, 17b-dihydroxyandrosta-1, 4-dien-3-one (4), and 11a-hydroxyandrosta-1, 4-diene-3, 17-dione 5. The relative stereochemistry of newly incorporated hydroxy groups were deduced by 2D NOESY experiment.

Conclusion: In conclusion, microbial biocatalysis is an attractive alternative tool for the preparation of new bioactive steroids, which might be difficult to prepare by conventional chemical routes. Furthermore, microbial-catalyzed biotransformations can produce commercially valuable steroidal pharmaceuticals for the pharmaceutical industry.

 

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Published

01-04-2015

How to Cite

Atif, M., S. A. A. Shah, S. Sultan, and M. I. Choudhary. “SOLID PHASE MICROBIAL FERMENTATION OF ANABOLIC STEROID, DIHYDROTESTOSTERONE WITH ASCOMYCETE FUNGUS FUSARIUM OXYSPORUM”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 7, no. 4, Apr. 2015, pp. 104-7, https://mail.innovareacademics.in/journals/index.php/ijpps/article/view/3293.

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