Hydroxylative activity of Aspergillus niger towards androst-4-ene and androst-5-ene steroids

Świzdor, Alina; Panek, Anna; Milecka-Tronina, Natalia

doi:10.1016/j.steroids.2017.08.009

Cited by 14 publications

(10 citation statements)

References 26 publications

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“…When compared to the literature, the change in the characteristic multiplicity of 17α-H resonance suggested the presence of a 16β-hydroxyl group. 5 The NMR data and melting point of 5 were comparable with the literature. 5,6 The fourth metabolite was identified as 16β,17αdihydroxyandrost-4-ene-3-one 6.…”

supporting

confidence: 79%

“…5 The NMR data and melting point of 5 were comparable with the literature. 5,6 The fourth metabolite was identified as 16β,17αdihydroxyandrost-4-ene-3-one 6. The 13 C NMR-spectrum of 6 had new resonances at δ C 86.54 ppm and δ C 80.83 ppm, which were assigned to two hydroxyl groups.…”

supporting

confidence: 79%

“…The hydroxylation of androst-4-en-3-ones at C-16β by Aspergillus niger, 5,6,10,11 Whetzelinia sclerotiorum, 6 Corticium centrifugum 12 and Wojnowicia graminis 13 has been previously reported. The biotransformation of testosterone 1 by A. niger KCH910, 5 A. niger ATCC 9142 (NRRL 599), 6,10 W. sclerotiorum, 6 A. niger TCCC 41650, 11 C. centrifugum 12 and W. graminis 13 gave some 16β-hydroxylated metabolites. 16β,17α-Dihydroxyandrost-4-ene-3-one 6, which was isolated from the incubation of 1 with C. cladosporioides MRC 70282, had only been isolated from the incubation of 1 with A. niger ATCC 9142.…”

mentioning

confidence: 87%

“…The NMR data of 2 were comparable with the literature. 5 The second metabolite was identified as 17β-hydroxyandrost-4-ene-3,16-dione 4. The 13 C NMR spectrum of 4 had a new carbon atom resonance at δ C 216.61 ppm, indicating the presence of a carbonyl group in ring D. The metabolite retained the 17α-H resonance of 1 as a broad singlet at δ H 3.77 ppm, suggesting that an oxidation had taken place at C-16.…”

mentioning

confidence: 99%

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Microbial Transformation of Some Steroids by Cladosporium Cladosporioides Mrc 70282

Yildirim¹,

Kuru

Yılmaz

2018

Journal of Chemical Research

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Incubation of testosterone, androstenedione and progesterone with Cladosporium cladosporioides MRC 70282 for 5 days is reported. Testosterone was hydroxylated at C-16β and then oxidised at C-16. This was accompanied by a minor independent oxidation at C-17 and epimerisation at C-17. Androstenedione was reduced at C-17 and hydroxylated at C-16β, and this was then oxidised to a ketone at C-16. This was accompanied by a minor epimerisation at C-17. Progesterone was hydroxylated at C-21, and this was accompanied by a minor independent 5α-reduction.

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supporting

confidence: 79%

supporting

confidence: 79%

mentioning

confidence: 87%

mentioning

confidence: 99%

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Microbial Transformation of Some Steroids by Cladosporium Cladosporioides Mrc 70282

Yildirim¹,

Kuru

Yılmaz

2018

Journal of Chemical Research

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“…Progesterone ( 1 ), pregnenolone ( 5 ), 16α,17α-epoxy-pregnenolone ( 9 ), 16α,17α-epoxy-progesterone ( 14 ), and 16-dehydropregnenolone acetate ( 20 ) were purchased from Sigma-Aldrich Chemical Co. Testosterone ( 2 ), androstenedione ( 3 ), DHEA (dehydroepiandrosterone) ( 6 ) were purchased from Steraloids Inc. 16α-Hydroxyandrostenedione ( 15 ) was obtained in our previous work by transformation of testosterone using Aspergillus niger KCH910 [ 38 ]. The last four of the aforementioned compounds and 14 were used as analytical standards for the time course experiments.…”

Section: Methodsmentioning

confidence: 99%

Metabolic fate of pregnene-based steroids in the lactonization pathway of multifunctional strain Penicillium lanosocoeruleum

2018

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BackgroundMetabolic activities of microorganisms to modify the chemical structures of organic compounds became an effective tool for the production of high-valued steroidal drugs or their precursors. Currently research efforts in production of steroids of pharmaceutical interest are focused on either optimization of existing processes or identification of novel potentially useful bioconversions. Previous studies demonstrated that P. lanosocoeruleum KCH 3012 metabolizes androstanes to the corresponding lactones with high yield. In order to explore more thoroughly the factors determining steroid metabolism by this organism, the current study was initiated to delineate the specificity of this fungus with respect to the cleavage of steroid side chain of progesterone and pregnenolone The effect of substituents at C-16 in 16-dehydropregnenolone, 16α,17α-epoxy-pregnenolone and 16α-methoxy-pregnenolone on the pattern of metabolic processing of these steroids was also investigated.Results and discussionAll of the analogues tested (except the last of the listed) in multi-step transformations underwent the Baeyer–Villiger oxidation to their δ-d-lactones. The activity of 3β-HSD was a factor affecting the composition of the product mixtures. 16α,17α-epoxy-pregnenolone underwent a rare epoxide opening with retention stereochemistry to give four 16α-hydroxy-lactones. Apart from oxidative transformations, a reductive pathway was revealed with the unique hydrogenation of 5-ene double bond leading to the formation of 3β,16α-dihydroxy-17a-oxa-d-homo-5α-androstan-17-one. 16α-Methoxy-pregnenolone was transformed to the 20(R)-alcohol with no further conversion.ConclusionsThis work clearly demonstrated that P. lanosocoeruleum KCH 3012 has great multi-functional catalytic properties towards the pregnane-type steroids. Studies have highlighted that a slight modification of the d-ring of substrates may control metabolic fate either into the lactonization or reductive and oxidative pathways. Possibility of epoxide opening by enzymes from this microorganism affords a unique opportunity for generation of novel bioactive steroids.Electronic supplementary materialThe online version of this article (10.1186/s12934-018-0948-1) contains supplementary material, which is available to authorized users.

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Biotransformation of testosterone by the filamentous fungus Penicillium pinophilum

Mehmannavaz

Nickavar

2022

Arch Microbiol

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The microbial biotransformation is a robust procedure in developing steroids and fungi are practical tools in this process therefore, the fungal modi cation of testosterone by Penicillium pinophilum was investigated. The three prominent metabolites, including 14α-hydroxyandrost-4-en-3,17-dione (II), 14αhydroxytestosterone (III), and 11α-hydroxytestosterone (IV), were isolated and characterized by chromatographic and spectroscopic methods. The time course pro le showed that the content of the metabolites II and III began to decrease after 24 h and 96 h, respectively. In comparison, the content of the metabolite IV remained stable after 24 h. In-silico studies showed that the probability of binding to the androgen receptor remains high for all three metabolites. However, the probability of binding to the estrogen receptors α and β increased for metabolite IV but decreased for metabolite III. Penicillium pinophilum as a potentially viable biocatalyst could hydroxylate C-11α and C-14α positions and oxidize the C-17β hydroxyl group to 17-ketone in testosterone molecule.

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Hydroxylative activity of Aspergillus niger towards androst-4-ene and androst-5-ene steroids

Cited by 14 publications

References 26 publications

Microbial Transformation of Some Steroids by Cladosporium Cladosporioides Mrc 70282

Microbial Transformation of Some Steroids by Cladosporium Cladosporioides Mrc 70282

Metabolic fate of pregnene-based steroids in the lactonization pathway of multifunctional strain Penicillium lanosocoeruleum

Biotransformation of testosterone by the filamentous fungus Penicillium pinophilum

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