Microbial transformation of androst-4-ene-3,17-dione by Beauveria bassiana

Xiong, Zhigang; Qi, Wei; Chen, Hanmei; Chen, Shouwen; Xu, Wenjin; Qiu, Guofu; Liang, Shucai; Hu, Xianming

doi:10.1016/j.steroids.2006.07.007

Cited by 41 publications

(22 citation statements)

References 17 publications

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“…6␤ or 7␤) stereochemical configuration was the predominant respective steroidal transformation for the 4-ene and 5-ene molecules however; in two cases (2,14) it was non-stereospecific giving rise to both ␣,␤-epimers. Similar fungal metabolic handling of the tested substrates has been observed in a wide range of non-thermophilic fungi with 4-ene [22][23][24] and 5-ene containing steroids [20,21,23,[25][26][27][28][29]. Interestingly, allylic oxidation of progesterone (1) at C-6 has been observed in two species of thermophilic Bacilli [5,30], however, side-chain degradation and reductive transformation observed in both thermophilic Bacilli and non-thermophilic fungi [5,31,32] were not detected.…”

Section: Discussionsupporting

confidence: 63%

Predominant allylic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by the thermophilic fungus Rhizomucor tauricus IMI23312

Hunter

Mills

Dedi

et al. 2008

The Journal of Steroid Biochemistry and Molecular Biology

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Section: Discussionsupporting

confidence: 63%

Predominant allylic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by the thermophilic fungus Rhizomucor tauricus IMI23312

Hunter

Mills

Dedi

et al. 2008

The Journal of Steroid Biochemistry and Molecular Biology

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“…Microbiological transformations of steroids include hydroxylation, Baeyer-Villiger oxidation, reduction, and isomerization. Among them, 11a-, 11b-, and 17a-hydroxylation reactions carried out by filamentous fungi are the key reactions to obtain molecules with high biological activity (Xiong et al 2006;Gonzalez et al 2017;Kozłowska et al 2019). Many filamentous fungi are used in steroid transformations, and EPF can also be efficiently used for transformations.…”

Section: Steroid Biotransformationmentioning

confidence: 99%

Entomopathogenic fungi: unconventional applications

Litwin

Nowak

Różalska

2020

Rev Environ Sci Biotechnol

158

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Entomopathogenic fungi (EPF) are microorganisms that cause fatal diseases of arthropods. The infection process involves several stages that consist of direct contact of the fungus with the surface of the cuticle of the attacked insect. The factors that determine the effectiveness of the infection process include lytic enzymes, secondary metabolites, and adhesins produced by EPF. Because of their high insecticidal effectiveness, these fungi are commonly used as biopesticides in organic farming. As the environment and farmlands are contaminated with many compounds of anthropogenic origin (e.g., pesticides), the effects of these toxic compounds on EPF and the mechanisms that affect their survival in such a toxic environment have been studied in recent years. This review presents information on the capacity of EPF to remove toxic contaminants, including alkylphenols, organotin compounds, synthetic estrogens, pesticides and hydrocarbons. Moreover, these fungi produce numerous secondary metabolites that can be potentially used in medicine or as antimicrobial agents. Despite their huge potential in biocontrol processes, the use of EPF has been underestimated due to a lack of knowledge on their abilities. In our work, we have presented the available data on the possibilities of the additional and unconventional use of these microorganisms.

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“…The microbial transformation of steroids has long prevailed in the pharmaceutical industry since the 1950s [2,3]. Degradation of steroids can yield much valuable steroidal derivatives, such as 4-androstene-3,17-dione (AD), androst-1,4-diene-3,17-dione (ADD), 9α-OH-AD, and 9α-OH-ADD [4,5,6,7,8]. ADD has been (FAD)-binding site was coincided with the sequence G-S-G-(A/G)-(A/ G)-(A/G)-X 17 -E [18,19].…”

Section: Introductionmentioning

confidence: 99%

Over-expression of Mycobacterium neoaurum 3-ketosteroid-Δ1-dehydrogenase in Corynebacterium crenatum for efficient bioconversion of 4-androstene-3,17-dione to androst-1,4-diene-3,17-dione

Zhang

Yang

et al. 2016

Electronic Journal of Biotechnology

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a b s t r a c tBackground: 3-Ketosteroid-Δ 1 -dehydrogenase (KSDD), a flavoprotein enzyme, catalyzes the bioconversion of 4-androstene-3,17-dione (AD) to androst-1,4-diene-3,17-dione (ADD). To date, there has been no report about characterization of KSDD from Mycobacterium neoaurum strains, which were usually employed to produce AD or ADD by fermentation. Results: In this work, Corynebacterium crenatum was chosen as a new host for heterologous expression of KSDD from M. neoaurum JC-12 after codon optimization of the KSDD gene. SDS-PAGE and western blotting results indicated that the recombinant C. crenatum harboring the optimized ksdd (ksdd II ) gene showed significantly improved ability to express KSDD. The expression level of KSDD was about 1.6-fold increased C. crenatum after codon optimization. After purification of the protein, we first characterized KSDD from M. neoaurum JC-12, and the results showed that the optimum temperature and pH for KSDD activity were 30°C and pH 7.0, respectively. The K m and V max values of purified KSDD were 8.91 μM and 6.43 mM/min. In this work, C. crenatum as a novel whole-cell catalyst was also employed and validated for bioconversion of AD to ADD. The highest transformation rate of AD to ADD by recombinant C. crenatum was about 83.87% after 10 h reaction time, which was more efficient than M. neoaurum JC-12 (only 3.56% at 10 h). Conclusions: In this work, basing on the codon optimization, overexpression, purification and characterization of KSDD, we constructed a novel system, the recombinant C. crenatum SYPA 5-5 expressing KSDD, to accumulate ADD from AD efficiently. This work provided new insights into strengthening sterol catabolism by overexpressing the key enzyme KSDD, for efficient ADD production.

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Microbial transformation of androst-4-ene-3,17-dione by Beauveria bassiana

Cited by 41 publications

References 17 publications

Predominant allylic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by the thermophilic fungus Rhizomucor tauricus IMI23312

Predominant allylic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by the thermophilic fungus Rhizomucor tauricus IMI23312

Entomopathogenic fungi: unconventional applications

Over-expression of Mycobacterium neoaurum 3-ketosteroid-Δ1-dehydrogenase in Corynebacterium crenatum for efficient bioconversion of 4-androstene-3,17-dione to androst-1,4-diene-3,17-dione

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