Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Biotransformation of Hydrocortisone and Nandrolone Decanoate by Three Fungal Species

Document Type : Research Article

Authors
Saba Ghasemi 1
Zohreh Habibi 2
Fatemeh Ansari 2
1 Department of Chemistry, Ilam Branch, Islamic Azad University, Ilam, I.R. IRAN
2 Department of Chemistry, Faculty of Science, Shahid Beheshti University, Tehran, I.R. IRAN
Abstract
The spread of new diseases has elevated the necessity to synthesis novel derivatives from currently used pharmaceutical compounds. Steroid derivatives, especially corticosteroids, are a group of compounds with valuable medicinal properties which have been widely used for the treatment of various diseases such as adrenal gland disorders, inflammatory diseases, hemorrhoids, cerebral edema, anemia, etc. Due to the emergence of new diseases, their market is expected to continue to grow. Therefore, continuous efforts have been made to synthesis of steroidal analogues showing potency and reduced side effects. Since the type, number, and site of functional groups are of high importance in determining physiologic activity of steroids, continuous efforts have been made to synthesis of steroidal analogues showing potency and reduced side effects. Considering the unique characteristics of biocatalysts along with their non-toxic and biodegradable nature, in this study, the biotransformation of wo steroid hormones hydrocortisone (1) and nandrolone decanoate (2) using the fungal species Circinella muscae, Coniothyrium fuckelii, and Fusarium solani were investigated. The biotransformation of hydrocortisone by fungal species of C. fuckelii and C. muscae led to the reduction of the C20-keto group and the production of the 11β,17α,20β,21-Tetrahydroxypregn-4-en-3-one (3) as the only reaction product. Enzymatic reduction of this ketone group is one of the main routes to deactivate corticosteroids. The hydrolysis of the ester group to the metabolite 17β-hydroxyester-4-en-3-one (4, 43%) was done in the biotransformation of nandrolone decanoate by C. fuckelii. However, the incubation of nandrolone decanoate with the fungus F. solani resulted in the production of the ester-4-en-3,17-dione (5) as only product in in the yield of 25%. The structure of the obtained metabolites was determined based on spectroscopic analysis (1H NMR, 13C NMR, and FT-IR) and comparing them to literature data.
Keywords
Steroid
Biotransformation
Hydrocortisone
Nandrolone decanoate
Fungal species

Subjects

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