Biotransformation of progesterone by the ascomycete Aspergillus niger N402

Abstract

The ability of the ascomycete Aspergillus niger N402 to transform exogenous progesterone was investigated. We found that this strain has steroid-hydroxylating activity and can introduce a hydroxyl group into the progesterone molecule mainly at positions C11(α) and C21 with predominant formation of 21-hydroxyprogesterone (deoxycortone). In addition, formation of 6β,11α-dihydroxyprogesterone was also observed. Studying the effects of the growth medium composition and temperature on progesterone conversion by A. niger N402 showed that the most intense accumulation of 21-hydroxyprogesterone occurred in minimal synthetic medium at 28°C. Increasing the cultivation temperature to 37°C resulted in almost complete inhibition of the hydroxylase activity in the minimal medium. In the complete medium, a similar increase in temperature inhibited 11α-hydroxylase activity and completely suppressed 6β-hydroxylase activity, but it produced no effect on 21-hydroxylating activity.

Microbial biotransformation of Pericarpium Citri Reticulatae (PCR) by Aspergillus niger and effects on antioxidant activity

“…In this study, microbial biotransformation of PCR by A. niger was an- molecule (Savinova, et al, 2018). Another A. niger JMU-TS528 could transform rutin to isoquercitrin (Li et al, 2020).…”

“…Other previous reports also have suggested that A. niger has the ability to produce different bioactive compounds by different metabolic pathways, and it can also increase the physiological and biochemical activities of biological substrates by modifying their original molecules. Such as A. niger N402 was reported has steroid‐hydroxylating activity and can introduce a hydroxyl group into the progesterone molecule (Savinova, et al., 2018). Another A. niger JMU‐TS528 could transform rutin to isoquercitrin (Li et al, 2020).…”

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

“…The 11α-hydroxylation is the most frequently reported transformation of progesterone and its derivatives during biotransformation in cultures of filamentous fungi [ 20 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ]. However, in the vast majority of cases, apart from the 11α-hydroxy derivative, other products were also identified [ 20 , 45 , 46 , 47 , 48 , 49 , 50 ].…”

“…An analogous cascade course was previously described during the biotransformation of progesterone leading to 6β-hydroxy-11-oxoprogesterone in cultures of Mucor M881 strains [ 51 ] and Isaria farinosa KCh KW1.1 [ 17 , 33 ]. On the other hand, the ability to dihydroxylate progesterone leading to the 6β,11α-dihydroxy derivative was previously observed in cultures of the following strains: Aspergillus nidulans VKPM F-1069 [ 45 ], A. niger N402 [ 43 ], A. ochraceus [ 49 ], Rhizomucor pusillus and Absidia griseolla var. igachii [ 48 ], Rhizomucor tauricus IMI23312 [ 50 ], Cephalosporium aphidicola [ 46 ], and Trichoderma koningii , T. hamatum , T. aureoviride , and T. pseudokoningii [ 20 ].…”

“…The chemical shift and multiplicity of the signal originating from the proton H-11β unambiguously indicate the introduction of the hydroxyl group at the 11α position (Supplementary Materials: Figures S10-S14). The 11α-hydroxylation is the most frequently reported transformation of progesterone and its derivatives during biotransformation in cultures of filamentous fungi [20,[43][44][45][46][47][48][49][50]. However, in the vast majority of cases, apart from the 11α-hydroxy derivative, other products were also identified [20,[45][46][47][48][49][50].…”