33526-41-9Relevant articles and documents
Steroids' transformations in Penicillium notatum culture
Bartmanska, Agnieszka,Dmochowska-Gladysz, Jadwiga,Huszcza, Ewa
, p. 193 - 198 (2005)
The application of Penicillium notatum genus for biotransformations of steroids has been investigated. The reactions observed include insertion of an oxygen atom into D-ring of steroids, 15α-hydroxylation of 17α-methyl testosterone derivatives, ester bond hydrolysis, and degradation of a testosterone derivatives side chain. Microbial production of testolactones, the biologically active compounds, was also achieved using this strain in up to 98% yield.
Biotransformation of dianabol with the filamentous fungi and β-glucuronidase inhibitory activity of resulting metabolites
Khan, Naik T.,Zafar, Salman,Noreen, Shagufta,Al Majid, Abdullah M.,Al Othman, Zeid A.,Al-Resayes, Saud Ibrahim,Atta-Ur-Rahman,Choudhary, M. Iqbal
, p. 65 - 72 (2014/05/20)
Biotransformation of the anabolic steroid dianabol (1) by suspended-cell cultures of the filamentous fungi Cunninghamella elegans and Macrophomina phaseolina was studied. Incubation of 1 with C. elegans yielded five hydroxylated metabolites 2-6, while M. phaseolina transformed compound 1 into polar metabolites 7-11. These metabolites were identified as 6β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (2), 15α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (3), 11α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (4), 6β,12β,17β-trihydroxy-17α-methylandrost-1,4-dien-3-one (5), 6β,15α,17β-trihydroxy-17α-methylandrost-1,4-dien-3-one (6), 17β-hydroxy-17α-methylandrost-1,4-dien-3,6-dione (7), 7β,17β,-dihydroxy-17α-methylandrost-1,4-dien-3-one (8), 15β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (9), 17β-hydroxy-17α-methylandrost-1,4-dien-3,11-dione (10), and 11β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (11). Metabolite 3 was also transformed chemically into diketone 12 and oximes 13, and 14. Compounds 6 and 12-14 were identified as new derivatives of dianabol (1). The structures of all transformed products were deduced on the basis of spectral analyses. Compounds 1-14 were evaluated for β-glucuronidase enzyme inhibitory activity. Compounds 7, 13, and 14 showed a strong inhibition of β-glucuronidase enzyme, with IC50 values between 49.0 and 84.9 μM.
Metabolism of anabolic steroids in humans: Synthesis of 6β-hydroxy metabolites of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and metandienone
Schaenzer, Willi
, p. 353 - 366 (2007/10/02)
Hydroxylation at position 6β of testosterone I (17β-hydroxyandrost-4- en-3-one) and the anabolic steroids 17α-methyltestosterone II (17β-hydroxy- 17α-methylandrost-4-en-3-one), metandienone III (17β-hydroxy-17α- methylandrosta-1,4-dien-3-one), 4-chloro-1,2-dehydro-17α-methyltestosterone IV (4-chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one), and fluoxymesterone V (9-fluoro-11β, 17β-dihydroxy-17a-methylandrost-4-en-3- one) was achieved via light-induced autooxidation of the corresponding trimethylsilyl 3,5-dienol ethers dissolved in isopropanol or ethanol. The reaction further yielded the 6α-hydroxy isomer in low amounts. The 6β- hydroxy isomers of I-V and the 6α-hydroxy isomers of I, III, and IV were isolated and characterized by 1H and 13C NMR, high-performance liquid chromatography, gas chromatography, and mass spectrometry. Human excretion studies with single administered doses of boldenone (17β-hydroxyandrosta- 1,4-dien-3-one), 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, metandienone, 17α-methyltestosterone, and [16,16,17- 2H3]testosterone showed that 6β-hydroxylation is the major metabolic pathway in the metabolism of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and metandienone, whereas for boldenone, 17α- methyltestosterone, and testosterone, 6β hydroxylation is negligable.
