Biotransformation of testosterone by <i>Cladosporium sphaerospermum</i>

Yildirim, Kudret; Kuru, Ali; Yılmaz, Şengül

doi:10.1080/10242422.2019.1583747

Cited by 8 publications

(2 citation statements)

References 23 publications

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“…The fungi are capable of performing controlled enzymatic processes for the biotransformation of steroidal hormones. One such study was conducted by Yildirim et al (2019) , reporting the hydroxylation of testosterone by Cladosporium sphaerospermum MRC 70266, a common endophyte of plants. Incubation of the molecule with Cladosporium sphaerospermum MRC 70266 started a series of reactions in metabolizing this steroid molecule into two new molecules (6b,16b,17b-trihydroxyandrost-4en-3-one6 and 6b,12b,17b-trihydroxyandrost-4-en-3-one7) and four known compounds.…”

Section: Applications Of Endophytic Fungi As Biocatalystmentioning

confidence: 99%

Endophytic Fungi-Mediated Biocatalysis and Biotransformations Paving the Way Toward Green Chemistry

Choudhary

Gupta

Dhar

et al. 2021

Front. Bioeng. Biotechnol.

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Catalysis is a process carried out in the presence of a heterogenous catalyst for accelerating the rate of a chemical reaction. It plays a pivotal role in transition from take, make, and dispose technology to sustainable technology via chemo- and biocatalytic processes. However, chemocatalyzed reactions are usually associated with copious amounts of perilous/hazardous environmental footprints. Therefore, whole-cell biotransformations or enzyme cocktails serve as cleaner biocatalytic alternatives in replacing the classical chemical procedures. These benchmark bioconversion reactions serve as important key technology in achieving the goals of green chemistry by eliminating waste generation at source. For this, nature has always been a driving force in fuelling natural product discovery and related applications. The fungal endophytic community, in particular, has undergone co-evolution with their host plant and has emerged as a powerful tool of genetic diversity. They can serve as a treasure trove of biocatalysts, catalyzing organic transformations of a wide range of substances into enantiopure compounds with biotechnological relevance. Additionally, the biocatalytic potential of endophytic fungi as whole-intact organisms/isolated enzyme systems has been greatly expanded beyond the existing boundaries with the advancement in high-throughput screening, molecular biology techniques, metabolic engineering, and protein engineering. Therefore, the present review illustrates the promising applications of endophytic fungi as biocatalysts for the synthesis of new structural analogs and pharmaceutical intermediates and refinement of existing proteins for novel chemistries.

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Section: Applications Of Endophytic Fungi As Biocatalystmentioning

confidence: 99%

Endophytic Fungi-Mediated Biocatalysis and Biotransformations Paving the Way Toward Green Chemistry

Choudhary

Gupta

Dhar

et al. 2021

Front. Bioeng. Biotechnol.

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“…Microbial biotransformation refers to a metabolic process by which a microorganism changes a compound from one chemical to another. This procedure has been extensively used in the pharmaceutical industry, particularly in producing steroid drugs and hormones (Yildirim et al 2019;Fernandes and Cabral 2006;Faramarzi et al 2008b). Generally, the biological activity of steroids is highly dependent on their proper functionalization.…”

Section: Introductionmentioning

confidence: 99%

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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In Vitro Activation of Paraoxonase 1 by Steroids: An Experimental, Molecular Docking, and Molecular Modelling Study

Deveci,

Çıkrıkcı,

Kuru

et al. 2024

ChemistrySelect

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Paraoxonase 1 (PON1) is an antioxidant enzyme that prevents lipid oxidation by hydrolysing lipid peroxides in the oxidised low‐density lipoprotein (LDL) structure, bound to high‐density lipoprotein (HDL) in serum, and exhibits esterase and lactonase activity. In this work, the hPON1 enzyme was purified from human serum using a hydrophobic gel with Sepharose 4B‐L‐tyrosine‐naphthylamine, and the affinity of some steroid derivatives previously isolated from fungal steroid biotransformations was examined on the pure hPON1 enzyme. The results indicate that all these derivaties activate the hPON1 enzyme to a different extent. Additionally, the binding potential of the most active five steroid derivatives to the PON1 enzyme to form a stable complex was explored through molecular docking and molecular dynamics (MD) simulation. The compounds with the highest potency in the enzymatic assay, S‐8 and S‐20, had the highest binding potential to the enzyme. The stability of the complexes formed by the two compounds was assessed and compared to the stability of the unbound enzyme structure. The enzyme‐compound complexes generally had similar stability to the unbound enzyme structure. Together with this, the MD simulation revealed that compound S‐8 would remain inside the enzyme's binding site during the simulation period, unlike compound S‐20. This situation varies according to the respective derivatives’ functional groups and hydrophobic characteristics.

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Biotransformation of testosterone by Cladosporium sphaerospermum

Cited by 8 publications

References 23 publications

Endophytic Fungi-Mediated Biocatalysis and Biotransformations Paving the Way Toward Green Chemistry

Endophytic Fungi-Mediated Biocatalysis and Biotransformations Paving the Way Toward Green Chemistry

Biotransformation of testosterone by the filamentous fungus Penicillium pinophilum

In Vitro Activation of Paraoxonase 1 by Steroids: An Experimental, Molecular Docking, and Molecular Modelling Study

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