Testosterone as biotransformation product in steroid conversion byMycobacterium sp.

Hung, Blanca Rosa; Falero, Alina; Llanes, Nury; Pérez, Celso; Ramirez, Maria A.

doi:10.1007/bf01023332

Cited by 21 publications

(12 citation statements)

References 6 publications

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“…Some of the 17b-HSD activities described in the conventional mutants appears to have different catalytic properties. In fact, in some mycobacterial strains, the double reduction of ADD [both of 17-keto group and 1(2)-double bound] was more effective for TS formation than a single reduction of 17-keto group of AD (Hung et al, 1994;Egorova et al, 2009). This work represents a proof of concept of the possibilities of using this model bacteria and metabolic engineering approaches for the production of pharmaceutical steroids.…”

Section: Discussionmentioning

confidence: 78%

“…Moreover, a singlestep microbial transformation process has been reported for the production of TS from sterols using several Mycobacterium sp. mutants (Wang et al, 1982;Hung et al, 1994;Liu et al, 1994;Llanes et al, 1995;Liu and Lo, 1997;Borrego et al, 2000;Lo et al, 2002;Mei et al, 2005;Egorova et al, 2009). During the course of this work, Dlugovitzky et al (2015) have shown that Mycobacterium smegmatis PTCC 1307 was able to produce TS and other estrogens from tritiated precursors.…”

Section: Introductionmentioning

confidence: 87%

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Engineering Mycobacterium smegmatis for testosterone production

Fernández-Cabezón

Galán

2016

Microbial Biotechnology

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SummaryA new biotechnological process for the production of testosterone (TS) has been developed to turn the model strain Mycobacterium smegmatis suitable for TS production to compete with the current chemical synthesis procedures. We have cloned and overexpressed two genes encoding microbial 17β‐hydroxysteroid: NADP 17‐oxidoreductase, from the bacterium Comamonas testosteroni and from the fungus Cochliobolus lunatus. The host strains were M. smegmatis wild type and a genetic engineered androst‐4‐ene‐3,17‐dione (AD) producing mutant. The performances of the four recombinant bacterial strains have been tested both in growing and resting‐cell conditions using natural sterols and AD as substrates respectively. These strains were able to produce TS from sterols or AD with high yields. This work represents a proof of concept of the possibilities that offers this model bacterium for the production of pharmaceutical steroids using metabolic engineering approaches.

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Section: Discussionmentioning

confidence: 78%

Section: Introductionmentioning

confidence: 87%

Engineering Mycobacterium smegmatis for testosterone production

Fernández-Cabezón

Galán

2016

Microbial Biotechnology

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“…On the other hand, the steroid 1,2-dehydrogenase activity of parental strains and mutants (Table 2) must be associated with a higher ADD yield [8]. Both M2 and M10 exhibited a higher specific activity than parental strains, which is partially in agreement with control biotransformation experiments.…”

Section: Add Sensitivity Test and Characterization Of Resistant Mutantsmentioning

confidence: 56%

Resistance to androstanes as an approach for androstandienedione yield enhancement in industrial mycobacteria

Pérez¹,

Falero²,

Llanes³

et al. 2003

Journal of Industrial Microbiology and Biotechnology

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The resistance to androstandienedione (ADD) of industrial mycobacteria was demonstrated as a valuable approach to increasing ADD yield in sterol fermentations. Colonies growing at 1 mg/ml ADD in culture medium after nitrosoguanidine mutagenesis showed a differential behavior in respect to parentals in cholesterol biotransformation. In the presence of exogenous ADD, a substantial depletion of ADD production was observed in parental strains B3683 and Ex4, whereas it was unaffected, and even increased, in resistant colonies. An apparent reduction from ADD to androstandione and testosterone was also noticed. Furthermore, the ADD resistance phenotype may be related to the increase in steroid 1,2 dehydrogenase activity.

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“…5 shows that most Rhodococcus strains under study convert BSS to stigmast-4-ene-3-one in the presence of n-hexadecane, and the proportion of the target product in the mixture of biodegradation products in most active cultures ranges from 40.0 to 98.0%. have been reported to convert sterols to testosterone in one stage [18,19]. The cells of R. erythropolis IEGM 487 convert 25% of BSS to stigmast-4-ene-3-one in the presence of n-hexadecane and intensively produce cholesterol esterase and cholesterol oxidase in the presence of β-sitosterol palmitate (Fig.…”

Section: Resultsmentioning

confidence: 98%

Bioconversion of β-Sitosterol and Its Esters by Actinobacteria of the Genus Rhodococcus

Ившина

Гришко

Ноговицина

et al. 2005

Appl Biochem Microbiol

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The ability of pure cultures of Rhodococcus actinobacteria from the Ural Specialized Collection of Alkanotrophic Microorganisms (World Federation for Culture Collections accession number 768; http://www.ecology.psu.ru/iegmcol) to convert β -sitosterol (BSS) and its 3 β -acylated derivatives was studied. Rhodococcus strains with pronounced cholesterol oxidase activity, capable of converting BSS to stigmat-4-ene-3-one in the reaction of cooxidation with n -hexadecane, were selected. The dependence of the activity of cholesterol oxidase of rhodococci on the length of the acyl group in BSS esters was studied. Conditions under which Rhodococcus cells convert BSS to 17 β -hydroxyandrost-4-ene-3-one (testosterone), commonly used in pharmacology, were determined.

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Testosterone as biotransformation product in steroid conversion byMycobacterium sp.

Cited by 21 publications

References 6 publications

Engineering Mycobacterium smegmatis for testosterone production

Engineering Mycobacterium smegmatis for testosterone production

Resistance to androstanes as an approach for androstandienedione yield enhancement in industrial mycobacteria

Bioconversion of β-Sitosterol and Its Esters by Actinobacteria of the Genus Rhodococcus

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