Microbiological 1α-hydroxylation of norethisterone

Ambrus, Gábor; Szarka, Eszter; Barta, I.; Horváth, Gy.; Radics, L.; Kajtár, M.

doi:10.1016/s0039-128x(75)80010-9

Cited by 7 publications

(6 citation statements)

References 6 publications

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“…Hydroxylation in various positions of esterane and pregnane-based steroids using A. kiliense [16] and A. potronii [17], respectively, has been reported in some studies. A. alabamensis and A. roseum were found to carry out the side chain cleavage of 3 -hydroxy-24-ethylcholest-5-ene, cholest-5-en-3 -ol, 3 -hydroxy-24-ethylcholest-5,22-diene [18] and pregn-4-en-3,20-dione [19], respectively.…”

Section: Introductionmentioning

confidence: 99%

“…A. alabamensis and A. roseum were found to carry out the side chain cleavage of 3 -hydroxy-24-ethylcholest-5-ene, cholest-5-en-3 -ol, 3 -hydroxy-24-ethylcholest-5,22-diene [18] and pregn-4-en-3,20-dione [19], respectively. The potential of the strains belonging to Acremonium strictum for the biotransformation of some steroid substances such as 19-norethisterone [16], androstendione [20], hydrocortisone [21] and progesterone [22,23] was also studied in some limited publications. However, to date no research has been carried out on the microbial transformation of androst-1,4-dien-3,17-dione (ADD) by this fungus.…”

Section: Introductionmentioning

confidence: 99%

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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: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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“…Microbial conversion may be a contributing factor, as the presence of a C 11 hydroxyl group in the β-configuration results in steric interactions favoring this unique α-configuration at C-1 (1, 3). Microbial hydroxylation of C 19 steroids at positions C-1 and C-2, as well as microbial 1α-hydroxylation, have been demonstrated elsewhere (4, 5). In this view, we have recently isolated bacteria of the genus Rhodococcus from the renal/interrenal tissue of the winter skate Leucoraja ocellata (J. Wiens, R. Ho, A. K. C. Brassinga, C. A. Deck, P. J. Walsh, R. N. Ben, K. McClymont, A. N. Evans, and W. G. Anderson, unpublished data).…”

Section: Genome Announcementmentioning

confidence: 74%

Complete Genome Sequence of a Rhodococcus Species Isolated from the Winter Skate Leucoraja ocellata

Wiens

Fernando

et al. 2016

Genome Announc

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“…() had demonstrated microbial hydroxylation of C19 steroids at positions C1 and C2 with additional evidence for microbial 1α‐hydroxylation provided by Ambrus et al . (). At the time of publication, Kime () suggested that the observation of 1α‐hydroxylation (Dodson et al ., ) was inapplicable to C21‐steroids.…”

Section: Introductionmentioning

confidence: 97%

“…Owing to 1 -OH-B's C11 hydroxyl group in the -configuration, however, the close steric proximity of C1 and C11 favours this unique C1 -configuration (Schwarz et al, 1964). Referenced by Kime (1975) himself in his paper on the steroid's original chemical synthesis was the fact that Dodson et al (1957) had demonstrated microbial hydroxylation of C19 steroids at positions C1 and C2 with additional evidence for microbial 1 -hydroxylation provided by Ambrus et al (1975). At the time of publication, Kime (1975) suggested that the observation of 1 -hydroxylation (Dodson et al, 1957) was inapplicable to C21-steroids.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of 1α‐hydroxycorticosterone in the winter skate Leucoraja ocellata: evidence to suggest a novel steroidogenic route

Wiens

Brassinga

et al. 2017

Journal of Fish Biology

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The present study explores the ability of intracellular bacteria within the renal-inter-renal tissue of the winter skate Leucoraja ocellata to metabolize steroids and contribute to the synthesis of the novel elasmobranch corticosteroid, 1α-hydroxycorticosterone (1α-OH-B). Despite the rarity of C1 hydroxylation noted in the original identification of 1α-OH-B, literature provides evidence for steroid C1 hydroxylation by micro-organisms. Eight ureolytic bacterial isolates were identified in the renal-inter-renal tissue of L. ocellata, the latter being the site of 1α-OH-B synthesis. From incubations of bacterial isolates with known amounts of potential 1α-OH-B precursors, one isolate UM008 of the genus Rhodococcus was seen to metabolize corticosteroids and produce novel products via HPLC analysis. Cations Zn and Fe altered metabolism of certain steroid precursors, suggesting inhibition of Rhodococcus steroid catabolism. Genome sequencing of UM008 identified strong sequence and structural homology to that of Rhodococcus erythropolis PR4. A complete enzymatic pathway for steroid-ring oxidation as documented within other Actinobacteria was identified within the UM008 genome. This study highlights the potential role of Rhodococcus bacteria in steroid metabolism and proposes a novel alternative pathway for 1α-OH-B synthesis, suggesting a unique form of mutualism between intracellular bacteria and their elasmobranch host.

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Microbiological 1α-hydroxylation of norethisterone

Cited by 7 publications

References 6 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

Complete Genome Sequence of a Rhodococcus Species Isolated from the Winter Skate Leucoraja ocellata

Biosynthesis of 1α‐hydroxycorticosterone in the winter skate Leucoraja ocellata: evidence to suggest a novel steroidogenic route

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