Biotransformation of dehydroepiandrosterone (DHEA) by environmental strains of filamentous fungi

Kozłowska, Ewa; Urbaniak, Monika; Kancelista, Anna; Dymarska, Monika; Kostrzewa-Susłow, Edyta; Stępień, Łukasz; Janeczko, Tomasz

doi:10.1039/c7ra04608a

Cited by 22 publications

(12 citation statements)

References 61 publications

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“…Selecting species for metabolism testing should not be entirely based on literature data. Fusarium acuminatum KCh S1 and Mucor hiemalis KCh W2 provide hydroxylation only at the 7α position, similar to Aspergillus versicolor KCh TJ1, while Penicillium commune KCh W7 and Penicillium chrysogenum KCh S4 do not hydroxylate DHEA at C7, in contrast to literature data 21 , 22 . However, every strain should be treated individually.…”

Section: Introductioncontrasting

confidence: 83%

“…The investigated compound is 3β,11α-dihydroxy-17a-oxa-D-homo-androst-5-en-17-one, and its spectral data are in accordance with the literature 46 . The 13 C NMR data for compound 8 show the appearance of signals, in comparison to compound 5 , at δ 171.73 ppm and at 82.43 ppm, which are characteristic for D-lactone 21 . Further inspection of NMR data revealed that the structure of the A-B ring of compound 5 remained unchanged, which confirms the lactonisation of a D ring.…”

Section: Resultsmentioning

confidence: 96%

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Cascade biotransformation of dehydroepiandrosterone (DHEA) by Beauveria species

Kozłowska

Urbaniak

Hoc

et al. 2018

Sci Rep

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Beauveria bassiana is an entomopathogenic fungus used as a biological control agent. It is a well-known biocatalyst for the transformation of steroid compounds. Hydroxylations at the 7α or 11α position and oxidation to D-homo lactones are described in the literature. In our study, we examined the diversity of metabolism of five different B. bassiana strains and compared them to already known pathways. According to the literature, 7α and 11α-hydroxy derivatives as well as 3β,11α-dihydroxy-17a-oxa-D-homo-androst-5-en-17-one have been observed. Here we describe new DHEA metabolic pathways and two products not described before: 3β-hydroxy-17a-oxa-D-homo-androst-5-en-7,17-dione and 3β,11α-dihydroxyandrost-5-en-7,17-dione. We also used for the first time another species from this genus, Beauveria caledonica, for steroid transformation. DHEA was hydroxylated at the 7α, 7β and 11α positions and then reactions of oxidation and reduction leading to 3β,11α-dihydroxyandrost-5-en-7,17-dione were observed. All tested strains from the Beauveria genus effectively transformed the steroid substrate using several different enzymes, resulting in cascade transformation.

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Section: Introductioncontrasting

confidence: 83%

Section: Resultsmentioning

confidence: 96%

Cascade biotransformation of dehydroepiandrosterone (DHEA) by Beauveria species

Kozłowska

Urbaniak

Hoc

et al. 2018

Sci Rep

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“…The composition of product mixtures was established by 1 HNMR. The crude mixture was separated as described previously by preparative TLC (Silica Gel GF, 500 μm) and chloroform/methanol mixture (9:1, v/v) as an eluent 19–21 . After elution products were detected under UV light (365 nm) then scraped from the plate and eluted with ethyl acetate to give pure fractions.…”

Section: Methodsmentioning

confidence: 99%

Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2

Kozłowska

Dymarska

Kostrzewa-Susłow

et al. 2019

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Estrone, estradiol, ethynylestradiol and estrone 3-methyl ether underwent a biotransformation process in the submerged culture of Isaria fumosorosea KCh J2. Estrone was transformed into seven metabolites, four of which were glycosylated. Estradiol was selectively glycosylated at C-3 and then transformed to D-ring lactone. Ethynylestradiol was coupled with methylglucoside and 6β-hydroxyderivative was obtained. Estrone 3-methyl ether was not transformed indicating that a free hydroxyl group at C-3 is necessary for glycosylation. Baeyer–Villiger oxidation combined with hydroxylation and glycosylation was observed. All glycosides obtained in this study are 3- O -β-methylglucosides.

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“…Steroid compounds are very common in pharmacy and medicine because of their variety of biological activities [ 1 , 2 , 3 ]. Hydroxylation of steroid compounds by microbial monooxygenases, which are similar to mammalian cytochromes P450, is a source of molecules of high biological activity and key intermediates in chemical synthesis [ 4 , 5 , 6 , 7 ]. The first known hydroxylated corticosteroid is cortisol (hydrocortisone), which is produced by the adrenal glands from cortisone by the 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) in response to stress and low blood glucose concentrations.…”

Section: Introductionmentioning

confidence: 99%

“…The first steroid aromatase inhibitor used in treatment was testolactone [ 36 ]. High activity of Baeyer-Villiger monooxygenase are characteristic to strains from the genera Penicillium , e.g., P. simplicissimum, P. lanosocoeruleum, P. commune or P. chrysogenum [ 6 , 37 , 38 ].…”

Section: Introductionmentioning

confidence: 99%

Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations

et al. 2017

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The catalytic activity of enzymes produced by an entomopathogenic filamentous fungus (Isaria fumosorosea KCh J2) towards selected steroid compounds (androstenedione, adrenosterone, progesterone, 17α-methyltestosterone and dehydroepiandrosterone) was investigated. All tested substrates were efficiently transformed. The structure of the substrate has a crucial impact on regio- and stereoselectivity of hydroxylation since it affects binding to the active site of the enzyme. Androstenedione was hydroxylated in the 7α-position to give a key intermediate in the synthesis of the diuretic-7α-hydroxyandrost-4-ene-3,17-dione with 82% conversion. Adrenosterone and 17α-methyltestosterone were hydroxylated in the 6β-position. Hydroxylated derivatives such as 15β-hydroxy-17α-methyltestosterone and 6β,12β-dihydroxy-17α-methyltestosterone were also observed. In the culture of Isaria fumosorosea KCh J2, DHEA was effectively hydroxylated in the C-7 position and then oxidized to give 7-oxo-DHEA, 3β,7α- and 3β,7β-dihydroxy-17a-oxa-d-homo-androst-5-ene-17-one. We obtained 7β-OH-DHEA lactone with 82% yield during 3 days transformation of highly concentrated (5 g/L) DHEA.

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Biotransformation of dehydroepiandrosterone (DHEA) by environmental strains of filamentous fungi

Abstract: Study on the ability of selected filamentous fungus species to transform dehydroepiandrosterone was performed (DHEA) and interesting DHEA derivatives were obtained with high yield.

Cited by 22 publications

References 61 publications

Cascade biotransformation of dehydroepiandrosterone (DHEA) by Beauveria species

Cascade biotransformation of dehydroepiandrosterone (DHEA) by Beauveria species

Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2

Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations

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