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Biotransformation of testosterone and testosterone heptanoate by four filamentous fungi.
Steroids. 2014 Dec; 92:7-12.S

Abstract

The microbial transformations of testosterone and testosterone heptanoate by four fungi: Absidia griseolla var. igachii PTCC 5260, Acremonium chrysogenu PTCC 5271, Fusarium fujikuroi PTCC 5144, and Fusarium solani complex PTCC 5285 were investigated for the first time. Incubation of testosterone heptanoate with F. fujikuroi and F. solani yielded three metabolites, which were isolated and characterized as testosterone, androst-4-ene-3,17-dione, and 6β-hydroxy testosterone. 6β-Hydroxy testosterone was the major metabolite obtained from testosterone heptanoate biotransformation by two fungal species. A. griseolla and A. chrysogenu produced 14α-hydroxy testosterone as major metabolite, together with testosterone and 6β-hydroxy testosterone in lower yields. The biotransformation of testosterone by F. fujikuroi and A. griseolla was also investigated in order to examine the influence of the ester group on the course of transformation. Androst-4-ene-3,17-dione was only identified in the biotransformation of testosterone by F. fujikuroi. The same product was observed in incubation of testosterone by A. griseolla, together with 14α-hydroxy testosterone in very low yield. Furthermore, time course study was also carried out in order to examine the formation of metabolites as a function of time, which was determined by HPLC. The structures of compounds were determined by their comprehensive spectroscopic analysis and comparison with literature data.

Authors+Show Affiliations

Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, Iran.Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, Iran.Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, Iran. Electronic address: z_habibi@sbu.ac.ir.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25223562

Citation

Ghasemi, Sabrieh, et al. "Biotransformation of Testosterone and Testosterone Heptanoate By Four Filamentous Fungi." Steroids, vol. 92, 2014, pp. 7-12.
Ghasemi S, Mohajeri M, Habibi Z. Biotransformation of testosterone and testosterone heptanoate by four filamentous fungi. Steroids. 2014;92:7-12.
Ghasemi, S., Mohajeri, M., & Habibi, Z. (2014). Biotransformation of testosterone and testosterone heptanoate by four filamentous fungi. Steroids, 92, 7-12. https://doi.org/10.1016/j.steroids.2014.09.002
Ghasemi S, Mohajeri M, Habibi Z. Biotransformation of Testosterone and Testosterone Heptanoate By Four Filamentous Fungi. Steroids. 2014;92:7-12. PubMed PMID: 25223562.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biotransformation of testosterone and testosterone heptanoate by four filamentous fungi. AU - Ghasemi,Sabrieh, AU - Mohajeri,Maryam, AU - Habibi,Zohreh, Y1 - 2014/09/16/ PY - 2014/07/16/received PY - 2014/08/22/revised PY - 2014/09/03/accepted PY - 2014/9/17/entrez PY - 2014/9/17/pubmed PY - 2015/9/2/medline KW - 14α-Hydroxy testosterone KW - 6β-Hydroxy testosterone KW - Biotransformation KW - Filamentous fungi KW - Testosterone heptanoate SP - 7 EP - 12 JF - Steroids JO - Steroids VL - 92 N2 - The microbial transformations of testosterone and testosterone heptanoate by four fungi: Absidia griseolla var. igachii PTCC 5260, Acremonium chrysogenu PTCC 5271, Fusarium fujikuroi PTCC 5144, and Fusarium solani complex PTCC 5285 were investigated for the first time. Incubation of testosterone heptanoate with F. fujikuroi and F. solani yielded three metabolites, which were isolated and characterized as testosterone, androst-4-ene-3,17-dione, and 6β-hydroxy testosterone. 6β-Hydroxy testosterone was the major metabolite obtained from testosterone heptanoate biotransformation by two fungal species. A. griseolla and A. chrysogenu produced 14α-hydroxy testosterone as major metabolite, together with testosterone and 6β-hydroxy testosterone in lower yields. The biotransformation of testosterone by F. fujikuroi and A. griseolla was also investigated in order to examine the influence of the ester group on the course of transformation. Androst-4-ene-3,17-dione was only identified in the biotransformation of testosterone by F. fujikuroi. The same product was observed in incubation of testosterone by A. griseolla, together with 14α-hydroxy testosterone in very low yield. Furthermore, time course study was also carried out in order to examine the formation of metabolites as a function of time, which was determined by HPLC. The structures of compounds were determined by their comprehensive spectroscopic analysis and comparison with literature data. SN - 1878-5867 UR - https://www.unboundmedicine.com/medline/citation/25223562/Biotransformation_of_testosterone_and_testosterone_heptanoate_by_four_filamentous_fungi_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0039-128X(14)00234-7 DB - PRIME DP - Unbound Medicine ER -