Transformations of 4- and 17α-substituted testosterone analogues by Fusarium culmorum

Steroids

Volumn 70, Issue 12, 2005, Pages 817-824

  Świzdor, Alina ^a   Kołek, Teresa ^a  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

Author keywords

Anabolic; Fusarium culmorum; Microbial hydroxylation

Indexed keywords

4 CHLORO 17 METHYLTESTOSTERONE; 4 METHOXYTESTOSTERONE; 4 METHYLTESTOSTERONE; CLOSTEBOL; ESTR 4 ENE 3,17 DIONE; METHYLTESTOSTERONE; NANDROLONE; NORETHANDROLONE; TESTOSTERONE DERIVATIVE; UNCLASSIFIED DRUG; DRUG DERIVATIVE; EPITESTOSTERONE;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; FUSARIUM CULMORUM; HYDROXYLATION; NONHUMAN; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; DRUG EFFECT; FUSARIUM; METABOLISM; PHYSIOLOGY;

FUNGI; FUSARIUM CULMORUM;

BIOTRANSFORMATION; EPITESTOSTERONE; FUSARIUM; HYDROXYLATION;

EID: 24944561092     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.05.005     Document Type: Article

References (41)

1. W. Charney, and H.L. Herzog Microbial transformations of steroids 1967 Academic Press New York/London
2. A.A. Akhrem, and Y.A. Titow Steroids and mikroorganisms 1970 Nauka Press Moscow
3. A. Čapek, and O. Hanč Microbiological transformation of steroids XII. Transformation of steroids by different species and strains of Fusaria Folia Microbiol 5 1960 251 256
4. A. Gluber, Tamm Ch, G. Juchasz, E. Weiss-Berg, and W. Zücher Über die Substratspezifität der Hydroxylierung von Androstan- und Pregnan derivaten durch Fusarium lini Helv Chim Acta 46 1963 889 906
5. G. Defaye, M.J. Luche, and E.M. Chambaz Microbiological 7- and 15-hydroxylations of C-19 steroids J Steroid Biochem 9 1978 331 336
6. A.C. Cotillon, J. Doostzadech, and R. Morfin The inducible and cytochrome P450-containing dehydroepiandrosterone 7α-hydroxylating enzyme system of Fusarium moniliforme J Steroid Biochem Mol Biol 62 1997 467 475
7. A.C. Cotillon, and R. Morfin Transformation of 3-hydroxy-steroids by Fusarium moniliforme J Steroid Biochem Mol Biol 68 1999 229 237
8. M.R. Wilson, W.A. Gallimore, and P.B. Reese Steroid transformation with Fusarium oxysporum var. cubense and Colletotrichum musae Steroids 64 1999 834 843
9. A. Jakkel, É. Ilkoy, G. Horváth, I. Pallagi, J. Süto, and G. Ambrus Microbial hydroxylation of 13β-ethyl-4-gonene-3,17-dione J Mol Catal B: Enzymatic 5 1998 385 387
10. T. Kołek, and A. Świzdor Biotransformation XLV. Transformations of 4-ene-3-oxo steroids in Fusarium culmorum culture J Steroid Biochem Mol Biol 67 1998 63 69
11. T. Kołek Biotransformation XLVII: transformations of 5-ene steroids in Fusarium culmorum culture J Steroid Biochem Mol Biol 71 1999 83 90
12. D.R. Brannon, F.W. Parrish, BJ Wiley, and L. Long Jr. Microbial transformation of a series of androgens with Aspergillus tamarii J Org Chem 32 1967 1521 1527
13. E.H. Mosbach, S. Shefer, and L.L. Abell Identification of the fecal metabolites of 17α-methyltestosterone in the dog J Lipid Res 9 1968 93 97
14. L. Stàrka, L. Siekmann, H.O. Hoppen, and H. Breuer Stoffwechsel von 4-Chlortestosteron in der Leber des Menschen Arzneim-Forsch 19 1969 2022 2025
15. E. Castegnaro, and G. Sala Absorpion and metabolism of 4-chlorotestosterone acetate by oral route Steroids Lipids Res 4 1973 184 192
16. J.F. Templeton, and C.C. Jackson Metabolism of 17α- methyltestosterone in the rabbit: C-6 and C-16 hydroxylated metabolites Steroids 42 1983 115 121
17. W. Schänzer, and M. Donike Metabolism of anabolic steroids in man: synthesis and use of reference substances for identification of anabolic steroid metabolites Anal Chim Acta 275 1993 23 48
18. D. Thieme, P. Anielski, J. Grosse, H. Sachs, and R.K. Mueller Identyfication of anabolic steroids in serum, urine, sweat and hair comparison if metabolic patterns Anal Chim Acta 483 2003 299 306
19. C. Ayotte, D. Goudreault, and A. Charlebois Testing for natural and synthetic anabolic agents in human urine J Chromatogr B 687 1996 3 25
20. M. Walshe, M. O'Keeffe, and B. Le Bizec Studies on the determination of chlorotestosterone and its metabolites in bovine urine Analyst 123 1998 2687 2691
21. S. Rendic, E. Nolteernsting, and W. Schänzer Metabolism of anabolic steroids by recombinant human cytochrome P450 enzymes. Gas chromatographic-mass spectrometric determination of metabolites J Chromatogr B 735 1999 73 83
22. C. Schoene, Nedderman ANR, and E. Haughton Preliminary study of the metobolism of 17α-methyltestosterone in horses utilizing gas chromatography-mass spectrometric techniques Analyst 119 1994 2537 2542
23. F. André, B. Le Bizec, M.P. Montrade, D. Maume, F. Monteau, and P. Marchand Developments in residue assays and metabolism study of growth-promoters by mass spectrometric analysis Analyst 119 1994 2529 2535
24. L. Leyssens, E. Royackers, B. Gielen, M. Missotten, J. Schoofs, and J. Czech Metabolites of 4-chlorotestosterone acetate in cattle urine as diagnostic markers for its illegal use J Chromatogr B 654 1994 43 54
25. W. Schänzer, S. Horning, and M. Donike Metabolism of anabolic steroids in humans: synthesis of 6β-hydroxy metabolites of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and metandienone Steroids 60 1995 353 366
26. B. Le Bizec, M.P. Momtrade, F. Monteau, I. Gaudin, and F. Andre 4-Chlorotestosterone acetate metabolites in cattle after intramuscular and oral administrations Clin Chem 44 1998 973 984
27. T.M. Williams, A.J. Kind, and D.W. Hill In vitro biotransformation of anabolic steroids in canines J Vet Pharmacol Ther 23 2000 57 66
28. T.M. Williams, A.J. Kind, W.G. Hyde, and D.W. Hill Characterization of urinary metabolites of testosterone, methyltestosterone, mibolerone and boldenone in greyhound dogs J Vet Pharmacol Ther 23 2000 121 129
29. E. Huszcza, and J. Dmochowska-Gładysz Transformations of testosterone and related steroids in Absidia glauca culture J Basic Microbiol 43 2003 113 120
30. K. Von Schubert, J. Schlegel, H. Groh, G. Rose, and Cläre Hörhold VIII Struktur-Stoffwechel-Beziehungen bei der mikrobiellen Hydrierung unterschiedlich substituierter Testosteronderivate Endokrinologie 59 1972 99 114
31. 1H NMR spectra of the steroid hormones, their hydroxylated derivatives, and related compounds J Chem Soc Perkin Trans 2 1990 1567 1594
32. A. Hammoumi, J.P. Girault, R. Azerad, G. Revial, and J. d'Angelo Microbial hydroxylation and functionaliztion of synthetic policyclic enones Tetrahedron Asymmetry 4 1993 1295 1306
33. N.S. Bhacca, and D.H. Williams Applications of NMR Spectroscopy in organic chemistry 1964 Holden-Day, Inc. San Francisco/London/Amsterdam p. 189-190
34. R.F. Zürcher Protonenresonanzspektroskopie und Steroidstruktur II. Die Lage der C-18- und C-19-Methylsignale in Abhängigkeit von den Substituenten am Steroidgerüst Helv Chim Acta 46 1963 2054 2088
35. G. Kaufman, G. Schumann, and C. Horhold Influence of 1-double bond and 11β-hydroxy on stereospecific microbial reductions of 4-en-3-oxo steroids J Steroid Biochem 25 1986 561 566
36. H.L. Holland, F.M. Brown, P.C. Chenchaiah, M.J. Chernishenko, S.H. Khan, and J. Appa Rao Microbial hydroxylation of steroids. Part 12. Hydroxylation of testosterone and related steroids by Gnomonia fructicola ATCC 11430 Can J Chem 67 1989 268 274
37. M. Newcomb, R. Shen, S.-Y. Choi, P.H. Toy, P.F. Hollenberg, and A.D.N. Vaz Cytochrome P450-catalyzed hydroxylation of mechanistic probes that distinguish between radicals and cations. evidence for cationic but not for radical intermediates J Am Chem Soc 122 2000 2677 2686
38. K. Kieslich New examples of microbial transformations in pharmaceutical chemistry Bull Soc Chim France 1-2 1980 9 17
39. J. Dmochowska-Gładysz, T. Kołek, and A. Siewiński Reduction of testosterone, androstenedione and derivatives by Aphanocladium album J Basic Microbiol 29 1989 3 12
40. R.B.R. Porter, W.A. Gallimore, and P.B. Reese Steroid transformations with Exophiala jeanselmei var. lecanii-corni and Ceratocystis paradoxa Steroids 64 1999 770 779
41. H.J. Ringold, S. Ramachandran, and E. Forchielli The effect of electron-withdrawing and electron-releasing substituents on the enzymic reduction of steroids Biochim Biophys Acta 82 1964 143 157