Biotransformation of Testosterone by Ulocladium Chartarum Mrc 72584

Abstract

The incubation of testosterone 1 with Ulocladium chartarum MRC 72584 has been reported. U. chartarum MRC 72584 hydroxylated testosterone 1 at C-7β, C-6β, C-14α and C-12β, accompanied by a 5α-reduction and oxidations at C-6 and at C-17.

Latent Functions and Applications of Cytochrome P450 Monooxygenases from Thamnidium elegans: A Novel Biocatalyst for 14α-Hydroxylation of Testosterone

“…Based on this NMR analysis, we identified the product as 14α-hydroxytestosterone. As shown in Figure 2, the 13 C NMR spectrum of the product was identical to literature data (Table S1), 22,25,26 and 1 H NMR, distortionless enhancement by polarization transfer, 13 C NMR, and two-dimensional NMR spectra (Figures S6−S10) consistently agreed with the production of 14α-hydroxytestosterone by CYP5312A4. Although it is possible that several structural isomers of hydroxytestosterone (molecular weight: 304) concomitantly appeared as minor products (Figure S11), CYP5312A4 showed high specificity in converting testosterone to the 14α-hydroxylated derivative.…”

“…The functional identification of CYP5312A4 complements earlier notions that several fungi can convert testosterone to 14α-hydroxytestosterone even though metabolic systems involved in the reaction have not been identified. 22 , 25 , 26 Thus, functionomic studies may highlight latent potentials of fungal P450s hidden behind fungal biology.…”

“…The functional identification of CYP5312A4 complements earlier notions that several fungi can convert testosterone to 14α-hydroxytestosterone even though metabolic systems involved in the reaction have not been identified. 22,25,26 Thus, functionomic studies may highlight latent potentials of fungal P450s hidden behind fungal biology. Besides studying steroid conversion, functional screening also revealed interesting insights into the catalytic potentials of TeCYPs (Table 3; see also Figure S13).…”

“… 7 , 20 , 21 Steroidal drugs are used widely in treating people because of their medicinal properties, including antitumor, anti-inflammatory, antidiabetic, antimicrobial, and anticonvulsant properties. 22 The properties of steroids are differentiated based on the side chain at C17 and the level of oxygenation of the four rings of the steroidal core. 4 In addition, the hydroxyl groups in steroids affect their physiological functions.…”

“…24 Therefore, developing synthetic strategies for producing a wide variety of steroidal compounds is of significant interest. Microbial biotransformation can provide a powerful tool to achieve site-/regioselective modification of steroids; for example, several fungi such as Cephalosporium aphidicola, 25 Aspergillus sydowii, 26 and Ulocladium chartarum 22 have been shown to metabolize exogenous steroids to their hydroxylated derivatives. The fungal kingdom consists of a wide variety of eukaryotic microorganisms with an estimated size of 1.5 million species.…”