Biocatalytic modifications of pregnenolone by selected filamentous fungi

Kollerov, Vyacheslav; Шутов, А. А.; Kazantsev, A. V.; Donova, Marina V.

doi:10.1080/10242422.2018.1549237

Cited by 12 publications

(11 citation statements)

References 39 publications

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“…The same oxidation and isomerisation pathway can be observed in fungal transformation [34,53,54]. Kollerov and others tested 75 selected fungal strains of Ascomycota and Zygomycota divisions to transform pregnenolone, especially into 11αhydroxyprogesterone [54]. In total, 60 strains converted pregnenolone, but only 21 fungal strains were able to form 7α-hydroxypregnenolone, thus evidencing the presence of 7α-hydroxylase activity.…”

Section: Discussionmentioning

confidence: 84%

“…In the human body, the isaria fumoso 3-hydroxy-5-ene moiety of pregnenolone (and 17β-hydroxypregnenolone) is transformed to 3-oxo-4-ene of progesterones. The same oxidation and isomerisation pathway can be observed in fungal transformation [34,53,54]. Kollerov and others tested 75 selected fungal strains of Ascomycota and Zygomycota divisions to transform pregnenolone, especially into 11αhydroxyprogesterone [54].…”

Section: Discussionmentioning

confidence: 86%

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

Kozłowska

Sycz

Janeczko

2022

IJMS

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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.

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Section: Discussionmentioning

confidence: 84%

Section: Discussionmentioning

confidence: 86%

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

Kozłowska

Sycz

Janeczko

2022

IJMS

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“…In a number of other cases, a fungal steroid hydroxylase may have more than one activity, such as the P-450 lun steroid 11β-/14α-hydroxylase from Cochliobolus lunatus [ 53 ]. In this regard, the study of steroid transformation in fungi (and other organisms) has two levels: (i) primary screening of steroid transforming activity (current study is devoted to this) [ 20 , 21 , 22 , 34 ]; and (ii) the establishment of the molecular basis of these activities associated with the cloning of individual genes, obtaining recombinant strains and proteins, allowing unambiguous determination of their activity [ 53 , 54 , 55 , 56 ].…”

Section: Discussionmentioning

confidence: 99%

“…However, for the overwhelming majority of molds, the “capacity” of steroid biotransformation has not been characterized [ 2 , 19 ]. In this regard, among various groups of filamentous fungi, active screening for the ability to transform pharmaceutically significant steroids is being carried out [ 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Androstenedione by Filamentous Fungi Isolated from Cultural Heritage Sites in the State Tretyakov Gallery

Zhgun

Потапов

Avdanina

et al. 2022

Biology

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The transformation of steroids by microorganisms is widely used in medical biotechnology. A huge group of filamentous fungi is one of the most promising taxa for screening new biocatalytic reactions in order to obtain pharmaceutically significant steroids. In this work, we screened 10 filamentous fungi-destructors of egg tempera for the ability to biotransform androst-4-en-3,17-dione (AD) during cultivation in a liquid nutrient medium or in a buffer solution. These taxonomically unrelated strains, belonging to the classes Eurotiomycetes, Dothideomycetes and Sordariomycetes, are dominant representatives of the microbiome from halls where works of tempera painting are stored in the State Tretyakov Gallery (STG, Moscow, Russia). Since the binder of tempera paints, egg yolk, contains about 2% cholesterol, these degrading fungi appear to be a promising group for screening for steroid converting activity. It turned out that all the studied fungi-destructors are able to transform AD. Some strains showed transformation efficiency close to the industrial strain Curvularia lunata RNCIM F-981. In total, 33 steroids formed during the transformation of AD were characterized, for 19 of them the structure was established by gas chromatography/mass spectrometry analysis. In this work, we have shown for the first time that fungi-destructors of tempera paintings can efficiently transform steroids.

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“…The standards of pregnenolone were purchased from TIC (TOKYO Chemical Industry, Japan). For HMR analysis, pregnenolone samples were purified according to Kollerov et al 41 Purified pregnenolone was dissolved in MeOD for 1 H-and 13 C-NMR analysis. Spectra were acquired using a Bruker Avance III-600 with a 5 mm TXI probe.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Pregnenolone Overproduction in Yarrowia lipolytica by Integrative Components Pairing of the Cytochrome P450scc System

et al. 2019

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Microbial production of steroid drugs exhibits great potentials in much greener and more sustainable manners, in which engineering multiple cytochrome P450s is the prerequisite requirement. The pairing of multicomponents of P450 systems is a tremendous challenge. Herein, biosynthesis of pregnenolone (a common precursor of steroid drugs) in Yarrowia lipolytica was taken as a typical instance to explore the engineering strategy of the cytochrome P450 side-chain cleavage enzyme (P450scc) system. The mature forms of the components belonging to P450scc system, CYP11A1, adrenodoxin (Adx), and adrenodoxin reductase (AdR), were coexpressed in a former constructed campesterol producing strain. To maximize pregnenolone production, an integrative components pairing strategy was proposed for pairing the component sources and balancing the expression levels of CYP11A1, Adx, and AdR. Led by the above approaches, a 2344-fold improvement of pregnenolone titer was achieved at the shake flask level. Consequently, a highest reported pregnenolone titer of 78.0 mg/L in microbes was obtained in a 5 L bioreactor. Our study not only highlights the integrative components pairing of cytochrome P450scc as a general strategy for engineering other cytochrome P450s, but also provides a feasible and efficient platform of Y. lipolytica for other steroids production.

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Biocatalytic modifications of pregnenolone by selected filamentous fungi

Cited by 12 publications

References 39 publications

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

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

Biotransformation of Androstenedione by Filamentous Fungi Isolated from Cultural Heritage Sites in the State Tretyakov Gallery

Pregnenolone Overproduction in Yarrowia lipolytica by Integrative Components Pairing of the Cytochrome P450scc System

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