Studies on Bacillus stearothermophilus. Part 1. Transformation of progesterone to a new metabolite 9,10-seco-4-pregnene-3,9,20-trione

Al-Awadi, Sameera; Afzal, Muhammad; Oommen, Sosama

doi:10.1016/s0960-0760(01)00115-7

Cited by 25 publications

(25 citation statements)

References 23 publications

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“…Chemical structures of progesterone (I) and its metabolites produced by M. tenera: 20β-hydroxypregn-4-en-3-one (II), 20α-hydroxypregn-4-en-3-one (III), 6β-hydroxypregn-4-en-3,20-dione (IV), and 6α-hydroxypregn-4-en-3,20-dione (V) . The structure of compound IV was proved depend on its spectral data (not shown) with those of the literature(Al-Awadi et al 2001). 6α-Hydroxypregn-4-en-3,20-dione (V) This compound was crystallized from chloroform; yield, 4.2%; m.p., 208-210°C, [a] D +176°(CHCl 3 ); lit(Hill et al 1991); m.p., 211-213°C, [a] D +179.6°(CHCl 3 ); Rf (hexane/ ethyl acetate, 6:4 (v/v)): 0.22; retention time (methanol/ water, 63:37 (v/v)): 8.98 min.…”

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confidence: 86%

“…Currently, steroids and their derivatives have been found extensive applications, such as anabolic, hormone replacement, progestational, antitumor agents, and oral contraceptives as well as sedatives. Research in the field of microbial biotransformation is being continued for developing of newer and more useful steroid analogues that are synthesized with great difficulty through chemical reactions (Al-Awadi et al 2001;Bigdeli and Ahmadi 1991;Faramarzi et al 2006).…”

Section: Introductionmentioning

confidence: 99%

“…Chemical structure of compound III was elucidated based on comparing the obtained spectral analyses (not shown) with those of published data(Al-Awadi et al 2001). Chemical structures of progesterone (I) and its metabolites produced by M. tenera: 20β-hydroxypregn-4-en-3-one (II), 20α-hydroxypregn-4-en-3-one (III), 6β-hydroxypregn-4-en-3,20-dione (IV), and 6α-hydroxypregn-4-en-3,20-dione (V) .…”

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Microalgal transformation of progesterone by the terrestrial-isolated cyanobacterium Microchaete tenera

et al. 2011

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A large number of microorganisms including various microalgal strains are able to convert steroid compounds into useful metabolites. In the present study, the ability of Microchaete tenera, a rice paddy field-isolated microalga, was investigated for biotransformation of progesterone. The incubation was carried out at 25°C under continuous illumination in the present of 0.25 gL −1 of progesterone. After 5 days incubation of the microalga in BG-11 liquid medium, the broth was extracted and the products were purified by the aid of chromatographic methods. Structure elucidation of the metabolites was performed by spectral data ( 13 C NMR, 1 H NMR, FTIR, and MS) and physical constants (melting points and optical rotations). Eventually, four major steroids including 20β-hydroxypregn-4-en-3-one, 20α-hydroxypregn-4-en-3-one, 6β-hydroxypregn-4-en-3,20-dione and 6α-hydroxypregn-4-en-3,20-dione were the results of this biotransformation. The study also showed that the best concentration of starting material, temperature, photoregime, and the influence of CO 2 partial pressure on the production of bioconverted metabolites were 0.25 gL −1 , 25°C, continuous light and 2.0±0.1% (v/v), respectively. Highest concentrations of all biotransformed metabolites were obtained in the 5th day.

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confidence: 86%

Section: Introductionmentioning

confidence: 99%

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Microalgal transformation of progesterone by the terrestrial-isolated cyanobacterium Microchaete tenera

et al. 2011

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“…In our earlier studies, we applied thermophilic Geobacillus stearothermophilus for the transformation of steroids, amino acids, and aromatic compounds [15], [18], [19]. In this study, we report transformation of chenodeoxycholic acid (CDCA) by thermophilic G. stearothermophilus.…”

Section: Introductionmentioning

confidence: 98%

“…Secosteroids with novel molecular structures have also been obtained after the ring cleavage [14], [15]. Thus, microbial cleavage of steroid rings A-D has been reported to give unusual products that could not be synthesized by conventional chemical syntheses [16].…”

Section: Introductionmentioning

confidence: 99%

Transformation of chenodeoxycholic acid by thermophilic Geobacillus stearothermophilus

Afzal

Oommen

Al-Awadi

2011

Biotech and App Biochem

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We performed a series of experiments with Geobacillus stearothermophilus, a thermophile isolated from oil-contaminated soil in the Kuwaiti desert. The organism has a good potential for the transformation of a broad spectrum of organic molecules such as steroids, amino acids, and aromatic hydrocarbons. In the present study, we tested its potential for the transformation of a bile component, chenodeoxycholic acid (CDCA). Five transformed products, namely, cholic acid, methylcholate, methylchenodeoxycholate, 3α-hydroxy-7-oxo-5β-cholanic acid, and 7α-hydroxy-3-oxo-5β-cholanic acid, were the major transformation products catalyzed by G. stearothermophilus. Under aerobic conditions, no evidence of side chain degradation, ring cleavage, or dehydrogenation was found among the metabolites of CDCA. CDCA transformation by a thermophile is reported for the first time.

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Steroid Bioconversion

Fernandes¹,

Cabral²

2010

Encyclopedia of Industrial Biotechnology

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Steroids constitute a particular class of lipids characterized by a typical tetracyclic skeleton, composed of one five‐member ring and three fused six‐member rings. Steroids are widely used as therapeutic agents and since their inception in the market, research efforts have been made in order to improve production processes as well as to develop novel synthetic molecules, with enhanced efficiency and reduced side effects. Given the complexity of the steroid skeleton, total chemical synthesis of given steroid molecules is hardly an effective approach; hence, steroid production processes rely on chemical modifications of educts that structurally resemble the targeted product. Still, steroid molecules present multiple chiral centers, a feature that makes particularly appealing the use of the selective microbial catalysts to provide a pathway that does not require protection, and additional deprotection steps. Furthermore, bioconversions are performed in a milder, greener environment, as compared to the purely chemical approach. The present work aims to provide an overview of steroid bioconversions. The potential of biologic agents (microbial cells/enzymes) to catalyze the conversion of a wide array of steroid educts will be presented, with particular emphasis on those that have achieved particular relevance, as well as on key aspects within the field. The chapter ends with the perspective trends in the field of steroid bioconversions

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Studies on Bacillus stearothermophilus. Part 1. Transformation of progesterone to a new metabolite 9,10-seco-4-pregnene-3,9,20-trione

Cited by 25 publications

References 23 publications

Microalgal transformation of progesterone by the terrestrial-isolated cyanobacterium Microchaete tenera

Microalgal transformation of progesterone by the terrestrial-isolated cyanobacterium Microchaete tenera

Transformation of chenodeoxycholic acid by thermophilic Geobacillus stearothermophilus

Steroid Bioconversion

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