Biotransformation of testosterone and testosterone heptanoate by four filamentous fungi

• Published in: Steroids 2014-12, Vol.92, p.7-12
• Main Authors: Ghasemi, Sabrieh, Mohajeri, Maryam, Habibi, Zohreh
• Format: Article
• Language: English
• Subjects: 14α-Hydroxy testosterone; 6β-Hydroxy testosterone; Absidia - metabolism; Biotransformation; Filamentous fungi; Fusarium - metabolism; Hydroxytestosterones - metabolism; Testosterone - analogs & derivatives; Testosterone - metabolism; Testosterone heptanoate
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/j.steroids.2014.09.002

[Display omitted] •Biotransformation of testosterone and testosterone heptanoate was investigated.•Four filamentous fungi were used for the biotransformation.•6β and 14α-hydroxytestosterone were obtained in biotransformation of testosterone heptanoate.•Androst-4-ene-3,17-dione was the major product in the biotransformation of testosterone.•Time course study was also carried out with four fungal species. 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.