- Microbial transformation of androstenedione by Cladosporium sphaerospermum and Ulocladium chartarum
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In this work, incubations of androstenedione 1 with Cladosporium sphaerospermum MRC 70266 and Ulocladium chartarum MRC 72584 have been reported. C. sphaerospermum MRC 70266 mainly hydroxylated 1 at C-6β, accompanied by a hydroxylation at C-15α, a reduction at C-17, a 5α-reduction and oxidations at C-6 and C-16 following hydroxylations. U. chartarum MRC 72584 hydroxylated 1 at C-6β, C-7α, C-7β and C-14α, accompanied by an oxidation at C-6 following its hydroxylation, a reduction at C-17 and a 5α-reduction. 6β,17β-Dihydroxyandrost-4-en-3,16-dione 8, one of the metabolites from the incubation of 1 with C. sphaerospermum MRC 70266, was determined as a new compound.
- Yildirim, Kudret,Kuru, Ali,Kü?ükba?ol, Eda
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- Biotransformation of androst-4-ene-3,17-dione by some fungi
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The incubations of androst-4-ene-3,17-dione with Aspergillus candidus MRC 200634, Aspergillus tamarii MRC 72400, Aspergillus wentii MRC 200316 and Mucor hiemalis MRC 70325 for 5 days are reported. A. candidus MRC 200634 mainly hydroxylated androst-4-ene-3,17-dione at C-11α, C-15α and C-15β whilst A. wentii MRC 200316 hydroxylated it mainly at C-6β. A. tamarii MRC 72400 showed predominately a Baeyer–Villiger monooxygenase activity. M. hiemalis MRC 70325 hydroxylated the substrate at C-14α and reduced most of it at C-17.
- Yildirim, Kudret,Kuru, Ali,Keskin, Ece,Salihoglu, Aylin,Bukum, Neslihan
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p. 594 - 597
(2017/11/14)
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- Microbial transformation of androst-4-ene-3,17-dione by three fungal species Absidia griseolla var. igachii, Circinella muscae and Trichoderma virens
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Microbial transformation of androst-4-ene-3,17-dione (AD;I) by three fungal species including Absidia griseolla var. igachii, Circinella muscae and Trichoderma virens was investigated for the first time. While A. griseolla and C. muscae carried out hydroxylation reactions, the third fungi performed reduction of the 17-carbonyl group in a chemoselective manner. Incubation of AD by A. griseolla yielded four metabolites 6β- (II), 7α- (III), 7β- (VI) and 14α-hydroxy-AD (V), among which 6β-hydroxy-AD (II) was identified as the major product. Furthermore, the metabolites produced during AD biotransformation by C. muscae were 6β- (II), 7β- (III) and 14α-hydroxy-AD (V). On the other hand, T. virens remarkably reduced AD into testosterone (VI) as the only product with 60% yield. These metabolites were purified by TLC and identified by 1H NMR, 13C NMR and other spectroscopic data.
- Heidary, Marjan,Habibi, Zohreh
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- Biotransformation of some steroids by Mucor hiemalis MRC 70325
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In this work, incubations of testosterone, dehydroepiandrosterone and pregnenolone with Mucor hiemalis MRC 70325 have been reported. Incubation of testosterone afforded androst-4-en-3,17-dione (3%), 14a-hydroxyandrost- 4-en-3,17-dione (9%), 6β-hydroxyandrost-4-en-3,17-dione (2%) and 14a,17β-dihydroxyandrost-4-en-3-one (62%). Incubation of dehy droepiandrosterone afforded 3β,17β-dihydroxyandrost-5-ene (6%) and 3β,7α-dihydroxyandrost-5- en-17-one (72%). Incubation of pregnenolone afforded 3β,14a-dihydroxypregn-5-en-7,20-dione (3%), 3β,7α- dihydroxypregn- 5-en-20-one (64%) and 3β,7α,11α- trihydroxypregn-5-en-20-one (11%). 3β,14a-Dihydroxypregn-5-en-7,20-dione was identified as a new metabolite. Website
- Yildirim, Kudret,Saran, Hilal,Dolu, Omer Faruk,Kuru, Ali
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p. 566 - 569
(2013/10/22)
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- Biotransformations of steroid compounds by Chaetomium sp. KCH 6651
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Biotransformations of steroid compounds: androstenedione, testosterone, progesterone, pregnenolone and DHEA using Chaetomium sp. 1 KCH 6651 strain as a biocatalyst were investigated. The microorganism proved capable of selective hydroxylation of the steroid substrates. Androstenedione was converted to 14α-hydroxyandrost-4-en-3,17-dione (in over 75% yield) and 6β-hydroxyandrost-4-en-3,17-dione (in low yield), while testosterone underwent regioselective hydroxylation at 6β position. Progesterone was transformed to a single product-6β,14α-dihydroxypregnan-4-en-3,20-dione in high yield, whereas biotransformation of DHEA resulted in the formation of 7α-hydroxy derivative, which was subsequently converted to 7α-hydroxyandrost-4-en-3,17-dione.
- Janeczko, Tomasz,Dmochowska-Gladysz, Jadwiga,Kostrzewa-Suslow, Edyta,Bialonska, Agata,Ciunik, Zbigniew
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experimental part
p. 657 - 661
(2009/07/19)
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- The hydroxylation of testosterone and some relatives by Cephalosporium aphidicola
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The fungus Cephalosporium aphidicola has been shown to hydroxylate testosterone, 19-nortestosterone, 1-dehydrotestosterone, 1α-methyltestosterone, androst-4-en-3-one, androst-4-en-3,17-dione and 17α-methyltestosterone predominantly at the C-6β position with a minor hydroxylation occurring at the C-14α position. 19-Nortestosterone was also hydroxylated at the C-10β position. In contrast to the hydroxylation of progesterone by this organism, hydroxylation at C-11α was a minor pathway.
- Hanson, James R.,Nasir, Habib,Parvez, Aslam
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p. 411 - 415
(2007/10/03)
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- Microbial transformation of steroids: Contribution to 14α-hydroxylations
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The regioselective and stereoselective hydroxylation of steroids by fungal strains previously known for their hydroxylation capabilities, such as Thamnostylum (= Helicostylum) piriforme ATCC 8992, Mucor griseocyanus ATCC 1207a, Actinomucor elegans (= Mucor parasiticus) MMP 3122 (Mucorales), and Zygodesmus sp. ATCC 14716, was investigated with special interest for the 14α-hydroxylation reaction. A preliminary screening had shown that some of these microorganisms were adequate for the production of 14α-hydroxylated derivatives of the following steroids: progesterone, 5β-pregnane-3,20- dione, 3β-hydroxy-5β-pregnane-20-one, 3β-hydroxy-5β-17(αH)-etianic acid methyl ester, androst-4-ene-3,17-dione, and testosterone. About 20 metabolites have been isolated and purified by silicagel chromatography and semi-preparative reverse-phase HPLC. These metabolites have been fully characterized by 1H, 13C NMR and mass spectrometry. All the identified metabolites were hydroxylated at some distinct positions, such as 6β-, 7α- , 9α-, 14α-, 15β-, or dihydroxylated at 6β, 14α-, 7α, 14α-, 9α, 14α- , 14α, 15α-, 14α, 15β-positions; nine of these metabolites have not been reported previously. The relationship between the structural features of the investigated steroids and the site-specific hydroxylation has been delineated, and progesterone was found to be the best substrate for the production of 14α-hydroxylated derivative, using T. piriforme.
- Azerad, Robert
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p. 337 - 352
(2007/10/02)
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- METABOLISM OF PROGESTERONE AND TESTOSTERONE BY A BACILLUS SP.
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Microbial transformations by a Bacillus sp. were employed as a means of preparing potentially important derivatives of progesterone and testosterone.Each microbial metabolite was subjected to structure elucidation employing 1H and 13C nmr, mass spectral and cd analysis.HPLC was used for the determination of the percentages of the metabolites formed.The progesterone metabolites were characterised as 14-hydroxy-4-pregnene-3,20-dione (II), 14-hydroxy-5α-pregnane-3,6,20-trione (III), 11α-hydroxy-5α-pregnane-3,6,20-trione (IV) and 11α,14-dihydroxy-4-pregnene-3,20-dione (V).The testosterone analogs were identified as 4-androstene-3,17-dione (VII), 17β-hydroxy-5α-androstane-3,6-dione (VIII), 14-hydroxy-4-androstene-3,17-dione (IX) and 14,17β-dihydroxy-4-androsten-3-one (X).The availability of the metabolites enabled complete elucidation of their 13C nmr spectra.
- Mahato, Shashi B.,Banerjee, Sukdeb,Sahu, Niranjan P.
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p. 545 - 558
(2007/10/02)
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- Novel Microbial Transformations of Androst-4-ene-3,17-dione by a Mucor sp.
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An efficient reduction of the 17-carbonyl group in a steroid skeleton to a methylene group has been observed for the first time during the microbial conversion of androst-4-ene-3,17-dione (1) and 14α-hydroxyandrost-4-ene-3,17-dione (2) into 6,14α-dihydroxyandrost-4-ene-3-one (3).
- Madyastha, Madhava K.,Valli, Khadar
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p. 1030 - 1031
(2007/10/02)
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- Microbiological Transformations. Part 3. The Oxidation of Androstene Derivatives with the Fungus Cunninghamella elegans
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The products obtained from the incubation of some Δ4- and Δ5-androstene derivatives with Cunninghamella elegans are largely those arising from allylic oxidation or epoxidation of the double bond, but some 9-, 12-, 14-, and 16-hydroxylation also occurs.
- Crabb, Trevor A.,Dawson, Philip J.,Williams, Roger O.
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p. 2535 - 2541
(2007/10/02)
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