Biotransformation of cholesterol to 1,4-androstadiene-3,17-dione (ADD) by Nocardia species

Sharma, Preeti; Slathia, Parvez Singh; Somal, Priti; Mehta, Pardeep

doi:10.1007/s13213-012-0422-y

Cited by 13 publications

(8 citation statements)

References 23 publications

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“…It was reported that the ADD production by Nocardia sp. was hampered in the presence of glucose, which interfering with substrate mass transfer [ 19 ]. However, in this study, it was found that feeding glucose as carbon source could enhance the ADD production by M .…”

Section: Resultsmentioning

confidence: 99%

“…neoaurum , which was different from the effect in Nocardia sp. [ 19 ]. Besides, in this study, we found that the ADD production was hampered in the presence of fructose, which was in accordance with the effect of glucose in Nocardia sp.…”

Section: Resultsmentioning

confidence: 99%

“…Besides, in this study, we found that the ADD production was hampered in the presence of fructose, which was in accordance with the effect of glucose in Nocardia sp. [ 19 ]. These results mainly due to the different carbon sources induce different metabolic activities or lead to different cell envelope characteristics [ 4 , 30 ].…”

Section: Resultsmentioning

confidence: 99%

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Enhanced Production of Androst-1,4-Diene-3,17-Dione by Mycobacterium neoaurum JC-12 Using Three-Stage Fermentation Strategy

et al. 2015

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To improve the androst-1,4-diene-3,17-dione (ADD) production from phytosterol by Mycobacterium neoaurum JC-12, fructose was firstly found favorable as the initial carbon source to increase the biomass and eliminate the lag phase of M. neoaurum JC-12 in the phytosterol transformation process. Based on this phenomenon, two-stage fermentation by using fructose as the initial carbon source and feeding glucose to maintain strain metabolism was designed. By applying this strategy, the fermentation duration was decreased from 168 h to 120 h with the ADD productivity increased from 0.071 g/(L·h) to 0.108 g/(L·h). Further, three-stage fermentation by adding phytosterol to improve ADD production at the end of the two-stage fermentation was carried out and the final ADD production reached 18.6 g/L, which is the highest reported ADD production using phytosterol as substrate. Thus, this strategy provides a possible way in enhancing the ADD production in pharmaceutical industry.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Enhanced Production of Androst-1,4-Diene-3,17-Dione by Mycobacterium neoaurum JC-12 Using Three-Stage Fermentation Strategy

et al. 2015

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“…In these two genera, cholesterol C17 side-chain degradation proceeds via a process resembling β-oxidation of fatty acids. Many strains from the genera Mycobacterium, Rhodococcus, Nocardia, and Arthrobacter have been demonstrated to cleave the C17 side chain of cholesterol via this pathway [15,[20][21][22]. Pathway 2, which comprises three enzymes (AcmA, AcmB, and C25DH) for the activation of cholesterol, is an oxygen-independent degradation pathway identified in the denitrifying beta-proteobacterium Sterolibacterium denitrificans [16].…”

Section: Cholesterol C17 Side-chain Degradation Pathwaysmentioning

confidence: 99%

Structures and molecular mechanisms of action of the cholesterol C17 side-chain-degrading enzymes

Kong

Zhang

et al. 2022

Syst Microbiol and Biomanuf

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Cholesterol, an essential lipid for mammalian cells, can be used as a carbon source by bacteria and as a precursor for steroid hormones in animal cells. The cholesterol C17 side-chain-cleavage pathways are the committed and rate-limiting steps in the biosynthesis of steroid drugs. Three cholesterol C17 side-chain degradation pathways have been identified in nature: the β-oxidation pathways in actinobacteria, the oxygen-independent degradation pathway in Sterolibacterium denitrificans, and the cholesterol side-chain degradation pathway in mammals. An in-depth understanding of the structures and molecular mechanisms of enzymes in these degradation processes will facilitate the creation of enzyme mutants with better catalytic capabilities. The introduction of the engineered enzymes into the microbial cell factories may contribute to the industrial production of steroid drugs.

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“…AD and ADD, belonging to the family of 17 ketosteroids, have served as potential substrates for the production of sex hormones, anticoncipients, and antiphlogistics as well as blood pressure regulating agents [88][89][90][91]. AD has been the starting material for the preparation of androgens and anabolic drugs and more recently for the production of spironolactone [91][92]. ADD has served as a precursor for estrogens and other contraceptive agents.…”

Section: Biotransformation Of Cholesterolmentioning

confidence: 99%

Cholesterol oxidase: Role in biotransformation of cholesterol

2015

J App Biol Biotech

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Cholesterol oxidase (COX, E.C.1.1.3.6) catalyses the oxidation of cholesterol to 4 -cholestene-3-one with the reduction of oxygen to hydrogen peroxides. COXs are secreted bacterial enzymes that catalyze the first step in the degradation of cholesterol. Some bacteria, such as Mycobacterium, Rhodococcus and Nocardia sp. produce an intracellular form of the enzyme that is membrane bound, while the enzyme from Arthrobacter, Schizopyllum, Streptoverticillium, Brevibacterium and Streptomyces is found in the extracellular fraction. These organisms play important roles in biotransformation and bioconversion of organic compounds. Bioconversion reactions are the subject of increasing interest in the pharmaceutical industry because of the demand for enantiomerically pure compounds. Bioconversion processes that involve enzymatic or microbial biocatalysts, when compared to their chemical counterparts, offer the advantages of high selectivity and mild operating conditions. Bioconversions may involve isolated and purified enzymes directly in free or immobilized form in order to enhance process stability. Medium engineering attempts to enhance the solubility of substrate and remove(s) the inhibition of product simultaneously by adding an inherently biocompatible and non-biodegradable ingredient to bioconversion medium. The extremely poor solubility of cholesterol as a substrate or steroids in aqueous media lowers the transformation rate and increase costs. The methods of enhancing steroid solubility in bioconversion media include substrate derivatization or micronization, ultrasonication or the use of detergents, water miscible co-solvents, cyclodextrins, polymers and liposomal aqueous biphasic media. Steroids like cholesterol are completely soluble in some organic solvents like benzene, toluene and butanol. Biphasic systems where in the microbial cells are present in the aqueous phase and steroids dissolved in the organic phase is considered an ideal system. In the present review article we try to discuss on the solvent tolerant properties and biotransformation capability of cholesterol oxidase producing different organisms of different species and their applications in different fields.

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Biotransformation of cholesterol to 1,4-androstadiene-3,17-dione (ADD) by Nocardia species

Cited by 13 publications

References 23 publications

Enhanced Production of Androst-1,4-Diene-3,17-Dione by Mycobacterium neoaurum JC-12 Using Three-Stage Fermentation Strategy

Enhanced Production of Androst-1,4-Diene-3,17-Dione by Mycobacterium neoaurum JC-12 Using Three-Stage Fermentation Strategy

Structures and molecular mechanisms of action of the cholesterol C17 side-chain-degrading enzymes

Cholesterol oxidase: Role in biotransformation of cholesterol

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