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

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.

Glycosylation of Quercetin by Selected Entomopathogenic Filamentous Fungi and Prediction of Its Products’ Bioactivity

“…Based on the previously described results regarding the biotransformations of flavonoid compounds in entomopathogenic strains, especially quercetin biotransformation conducted by those micro-organisms, we decided to use five strains of the Beauveria bassiana species, two of the Beauveria caledonica species and the Isaria farinosa KCh KW1.1 as biocatalysts. Among entomopathogenic filamentous fungi, B. bassiana strains are most commonly used in biotransformation (including flavonoid compounds) [47][48][49][50]. Our previous publications described differences in the biotransformation of methoxyflavones and dehydroepiandrosterone (DHEA) in the cultures of various strains belonging to this species [51,52].…”

Biotransformation of Δ1-Progesterone Using Selected Entomopathogenic Filamentous Fungi and Prediction of Its Products’ Bioactivity

“…In our previous manuscripts, we described the ability of the Isaria farinosa KCh KW 1.1 strain to hydroxylate progesterone and its derivatives effectively, leading to 6β,11α-dihydroxy derivatives [ 17 , 33 ]. These metabolites were obtained during the transformation of progesterone, 11α-hydroxyprogesterone, and 16α,17α-epoxyprogesterone [ 17 , 33 ].…”

“…In our previous manuscripts, we described the ability of the Isaria farinosa KCh KW 1.1 strain to hydroxylate progesterone and its derivatives effectively, leading to 6β,11α-dihydroxy derivatives [ 17 , 33 ]. These metabolites were obtained during the transformation of progesterone, 11α-hydroxyprogesterone, and 16α,17α-epoxyprogesterone [ 17 , 33 ]. However, during the transformation of 17α-hydroxyprogesterone, we isolated three hydroxy derivatives: 6β,17α-dihydroxyprogesterone, 12β,17α-dihydroxyprogesta-1,4-diene-3-one, and 6β,12β,17α-trihydroxyprogesterone [ 17 ].…”

“…Over the course of more than 70 years of research, it has been observed that the biotransformation of progesterone by filamentous fungi can proceed in two main directions: hydroxylation or Baeyer–Villiger oxidation, and rarely does a combination of these processes occur [ 17 , 18 , 19 ]. Hydroxylation predominantly occurs at the 6β and/or 11α positions; however, fungal cultures have also demonstrated the capability for hydroxylation at the 14α, 7α, 7β, 11β, 17α, 9α, 8β, 16α, 15α, 15β, 21, and 12β positions [ 20 , 21 , 22 ].…”

“…Further, biocatalysts of hydroxylation were used including strains of entomopathogenic filamentous fungi. The Isaria farinosa KCh KW 1.1 strain possesses the ability to effectively dihydroxylate progesterone and its derivatives [ 17 , 33 ]. Isaria fumosorosea KCh J2 is known for its ability to carry out multienzymatic transformations of steroid compounds [ 34 , 35 ].…”