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Abstract
Prednisolone, a synthetic adrenal corticosteroid drug, is known to have anti-inflammatory and autoimmune activity. Biotransformation of prednisolone was carried out to obtain more bioactive prednisolone derivatives. Among six different fungi, Penicillium aurantiacum proved to be the best prednisolone hydroxylator. As a result of prednisolone biotransformation by P. aurantiacum, whole cells four different prednisolone derivatives were investigated. 20β-Hydroxyprednisolone (1) and 21,21-dimethoxy-11β-hydroxypregn-1,4-dien-3,20-dione (2) were detected as the main metabolites. These metabolites together with other two metabolites, 11β-hydroxyandrost-1,4-dien-3,17-dione (3) and 11β,17β-dihydroxyandrost-1,4-dien-3- one (4), were purified and assigned by an interpretation of their spectral data using mass spectroscopy (MS), proton nuclear magnetic resonance (1H-NMR), carbon nuclear magnetic resonance (13C-NMR) and infrared spectroscopy (IR) analyses. The best fermentation conditions for production of compounds 1–4 were as follows: medium (3) consisting of (g/l): glucose 20; l-asparagine 0.7; MgSO4.7H2O 0.5; KH2PO4 1.52; KCl 0.52; Cu (NO3)2 traces; ZnSO4.7H2O traces, supplemented with prednisolone concentration of 0.3 mg/ml, inoculated by 10% of microorganism and incubated for 72 h. Under these optimized conditions, ∼94.8% of the added prednisolone was converted to aforementioned derivatives, which have the potential to be used in industrial production of important pharmaceutical compounds.
Acknowledgements
The authors would like to thank National Research Centre, Giza, Egypt for financial support of this work.
Disclosure statement
The authors report no conflicts of interest. The authors alone are responsible for the content and writing of this article.