Studies on Bacillus stearothermophilus. Part III. Transformation of testosterone

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

doi:10.1007/s00253-003-1269-8

Cited by 33 publications

(23 citation statements)

References 21 publications

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“…No change was observed in the biotransformation pattern among the diVerent pH values; the concentrations of all the produced metabolites were high in a neutral pH value (pH 7). The same result was reported by Al-Awadi et al [36] on the biotransformation of progesterone by Bacillus stearothermophilus and by Sallam et al [37] on the bioconversion of 19-nortestosterone by Rhodococcus sp. They also found the optimum pH as 7.…”

Section: Discussionsupporting

confidence: 84%

Studies on the microbial transformation of androst-1,4-dien-3,17-dione with Acremonium strictum

Faramarzi

Yazdi

Jahandar

et al. 2006

J IND MICROBIOL BIOTECHNOL

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The strain of Acremonium strictum PTCC 5282 was applied to investigate the biotransformation of androst-1,4-dien-3,17-dione (I; ADD). Microbial products obtained were purified by preparative TLC and the pure metabolites were characterized on the basis of their spectroscopic features (13C NMR, 1H NMR, FTIR, MS) and physical constants (melting points and optical rotations). The 15 alpha-Hydroxyandrost-1,4-dien-3,17-dione (II), 17 beta-hydroxyandrost-1,4-dien-3-one (III), androst-4-en-3,17-dione (IV; AD), 15 alpha-hydroxyandrost-4-en-3,17-dione (V), 15 alpha,17 beta-dihydroxyandrost-1,4-dien-3-one (VI) and testosterone (VII) were produced during this fermentation. Formation of the 15 alpha,17 beta-dihydroxy derivative of ADD is reported for the first time during steroid biotransformation. The bioconversion reactions observed were 1,2-hydrogenation, 15 alpha-hydroxylation and 17-ketone reduction. From the time course profile of this biotransformation, ketone reduction and 1,2-hydrogenation were observed from the first day of fermentation while 15 alpha-hydroxylation occurred from the third day. Optimum concentration of the substrate, which gave the maximum bioconversion efficiency, was 0.5 mg ml(-1) in one batch. The highest yield of the microbial products recorded in this work was achieved within the pH range 6.5-7.3 and at the temperature of 27 degrees C.

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Section: Discussionsupporting

confidence: 84%

Studies on the microbial transformation of androst-1,4-dien-3,17-dione with Acremonium strictum

Faramarzi

Yazdi

Jahandar

et al. 2006

J IND MICROBIOL BIOTECHNOL

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“…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: Discussionmentioning

confidence: 67%

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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“…Geobacillus stearothermophilus assisted metabolism of progesterone, testosterone, androst-4-ene-3,17-dione and 11a-hydroxyprogesterone resulted in a number of metabolites as reported in our previous studies (Al-Awadi et al 2001, 2002, 2003, 2006. The present study reports the possible sequence of hydroxylation of 17a-hydroxyprogesterone and 21a-hydroxyprogesterone by G. stearothermophilus.…”

Section: Introductionmentioning

confidence: 58%

Studies onGeobacillus stearothermophilus-Part V1: Transformation of 17α-hydroxyprogesterone and 21-hydroxyprogesterone

Al-Awadi

Afzal

Oommen

2007

Biocatalysis and Biotransformation

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Side chain cleavage by biotransformation of 17a-hydroxyprogesterone 1 and 21-hydroxyprogesterone 2 by the thermophile, Geobacillus stearothermophilus was investigated. The side chain cleavage product, androst-4-ene-3,17-dione 1a & 2a, was a common product formed from both substrates. 17a-hydroxy-5a-pregnane-3,6,20-trione 1b and 17a-20a-dihydroxyprogesterone 1c were formed from 1. A rare 17-carboxylic acid analogue of androstene 2b, a transformation product of 2, was also identified. G. stearothermophilus also facilitated hydroxylation of 17a-hydroxyprogesterone at 6a-and 6b-positions resulting in 6b,17a-dihydroxyprogesterone 1d, 6a,17a-dihydroxyprogesterone 1e, 6b,21-dihydroxyprogesterone 2c and 6a,21-dihydroxyprogesterone 2d. All transformation products were identified through their spectral data and comparison with reference compounds.

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Studies on Bacillus stearothermophilus. Part III. Transformation of testosterone

Cited by 33 publications

References 21 publications

Studies on the microbial transformation of androst-1,4-dien-3,17-dione with Acremonium strictum

Studies on the microbial transformation of androst-1,4-dien-3,17-dione with Acremonium strictum

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

Studies onGeobacillus stearothermophilus-Part V1: Transformation of 17α-hydroxyprogesterone and 21-hydroxyprogesterone

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