2005
DOI: 10.1248/cpb.53.1455
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Microbial Hydroxylation of Pregnenolone Derivatives

Abstract: yielded four known oxidative metabolites, 1, androsta-1,4-diene-3,17-dione (8), 6b b,15b b-dihydroxyandrost-4-ene-3,17-dione (9) and 11a a,15b b-dihydroxypreg-4-ene-3,20-dione (10). Fermentation of 2 with R. stolonifer yielded two known metabolites, 11a a-hydroxypreg-4-ene-3,20-dione (11) and 7. Compounds 1-11 were screened for their cholinesterase inhibitory activity in a mechanism-based assay.

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Cited by 28 publications
(17 citation statements)
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“…6␤ or 7␤) stereochemical configuration was the predominant respective steroidal transformation for the 4-ene and 5-ene molecules however; in two cases (2,14) it was non-stereospecific giving rise to both ␣,␤-epimers. 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: Discussionsupporting
confidence: 61%
“…6␤ or 7␤) stereochemical configuration was the predominant respective steroidal transformation for the 4-ene and 5-ene molecules however; in two cases (2,14) it was non-stereospecific giving rise to both ␣,␤-epimers. 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: Discussionsupporting
confidence: 61%
“…1 H NMR (CDCl 3 , 400 MHz,δ in ppm, multi., J in Hz): 6.09 (1H, s, H-4), 7.06 (1H, d, H-1 4 . It is in accordance with the literature data for 6β,11α-dihydroxypregesterone [13]. …”
Section: Resultssupporting
confidence: 93%
“…All of them are more polar than the substrate itself. 13 CNMR data of the substrate as well as the conversion products are listed in Table 1 It is in accordance with the literature data for 15α-hydroxyl pregesterone [11].…”
Section: Isolation Of Transformed Productssupporting
confidence: 86%
See 1 more Smart Citation
“…Selective 7β-hydroxylation of pregnenolones is possible with organic methods, but syntheses that favor 7α-hydroxylation do not appear possible 24 . While microbial pregnenolone 7α-hydroxylation has been described, the organisms make a mixture of products and the enzymes have not been identified [25][26][27] . Thus our method for selective 7-hydroxylation fills a gap in steroid synthetic methods.…”
Section: Cc-by-nc-ndmentioning
confidence: 99%