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. 2022 Jun 24;23(13):7015.
doi: 10.3390/ijms23137015.

Hydroxylation of Progesterone and Its Derivatives by the Entomopathogenic Strain Isaria farinosa KCh KW1.1

Ewa Kozłowska  1 , Jordan Sycz  1 , Tomasz Janeczko  1
Affiliations

Hydroxylation of Progesterone and Its Derivatives by the Entomopathogenic Strain Isaria farinosa KCh KW1.1

Ewa Kozłowska et al. Int J Mol Sci. .

Abstract

Progesterone biotransformation is worth studying because of the high industrial value of its derivatives. This study investigated the catalytic ability of the entomopathogenic filamentous fungus strain Isaria farinosa KCh KW1.1 to transform progesterone derivatives: 11α-hydroxyprogesterone, 17α-hydroxyprogesterone, 16α,17α-epoxyprogesterone and pregnenolone. In the culture of Isaria farinosa KCh KW1.1, 11α-hydroxyprogesterone was effectively transformed into only one product: 6β,11α-dihydroxyprogesterone. Transformation of 17α-hydroxyprogesterone gave three hydroxy derivatives: 6β,17α-dihydroxyprogesterone, 12β,17α-dihydroxyprogesterone and 6β,12β,17α-trihydroxyprogesterone. Two products: 6β-hydroxy-16α,17α-epoxyprogesterone and 6β,11α-dihydroxy-16α,17α-epoxyprogesterone, were obtained from the 16α,17α-epoxyprogesterone transformation. We isolated two compounds from the biotransformation medium with pregnenolone: 11α-hydroxy-7-oxopregnenolone and 5α,6α-epoxy-3β,11α-dihydroxypregnan-7,20-dione. In this study, we observed only mono- and dihydroxy derivatives of the tested substrates, and the number of obtained products for each biotransformation did not exceed three.

Keywords: Isaria farinosa; biotransformation; entomopathogenic fungi; progesterone derivatives.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Transformation of progesterone (1) in the culture of Isaria farinosa KCh KW1.1.
Figure 2
Figure 2
Hydroxylation of 11α-hydroxyprogesterone (3) by Isaria farinosa KCh KW1.1.
Figure 3
Figure 3
Biotransformation of 17α-hydroxyprogesterone (4) in Isaria frinose KCh KW1.1 culture.
Figure 4
Figure 4
Transformation of 16α,17α-epoxyprogesterone (5) by Isaria farinosa KCh KW1.1.
Figure 5
Figure 5
Pregnenolone (6) modification by Isaria farinosa KCh KW1.1 strain.
Figure 6
Figure 6
Changes in lipophilicity, polarity and insolubility of tested compounds. Lipophilicity is measured as a Log P parameter, polarity as a topological surface area (TPSA) and insolubility as a Log S value.
Figure 7
Figure 7
BOILED-Egg analysis (described in the text).
See this image and copyright information in PMC

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