New metabolites from fungal biotransformation of an oral contraceptive agent: Methyloestrenolone

Steroids

Volumn 78, Issue 4, 2013, Pages 418-425

  Zafar, Salman ^a,b   Bibi, Marium ^a   Yousuf, Sammer ^a   Choudhary, M Iqbal ^a,c  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b ABDUL WALI KHAN UNIVERSITY   (Pakistan)

^c KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

Aspergillus niger; Biotransformation; Gibberella fujikuroi; Macrophomina phaseolina; Methyloestrenolone; Oral contraceptive

Indexed keywords

17ALPHA (HYDROXYMETHYL) 11BETA,17BETA DIHYDROXYESTR 4 EN 3 ONE; 17ALPHA (HYDROXYMETHYL) 17BETA HYDROXYESTR 4 EN 3 ONE; 17ALPHA METHYL 10BETA,17BETA DIHYDROXYESTR 4 EN 3 ONE; 17ALPHA METHYL 11ALPHA,17BETA DIHYDROXYESTR 4 EN 3 ONE; 17ALPHA METHYL 11BETA,17BETA DIHYDROXYESTR 4 EN 3 ONE; 17ALPHA METHYL 1BETA,17BETA DIHYDROXYESTR 4 EN 3 ONE; 17ALPHA METHYL 2ALPHA,11BETA,17BETA TRIHYDROXYESTR 4 EN 3 ONE; 17ALPHA METHYL 3,17BETA DIHYDROXYESTR 1,3,5(10) TRIEN 6 ONE; 17ALPHA METHYL 6BETA,10BETA,17BETA TRIHYDROXYESTR 4 EN 3 ONE; 17ALPHA METHYL 6BETA,17BETA DIHYDROXYESTR 4 EN 3 ONE; 17ALPHA METHYLESTR 1,3,5(10) TRIEN 3,17BETA DIOL; METHYLESTRENOLONE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; ASPERGILLUS NIGER; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CUNNINGHAMELLA ECHINULATA; FERMENTATION; FUNGAL CELL CULTURE; GIBBERELLA FUJIKUROI; HORMONE DETERMINATION; HYDROXYLATION; MACROPHOMINA PHASEOLINA; METABOLITE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEROID METABOLISM;

BIOTRANSFORMATION; CONTRACEPTIVES, ORAL, COMBINED; ESTRENES; FUNGI; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

ASPERGILLUS NIGER; CUNNINGHAMELLA ECHINULATA; GIBBERELLA FUJIKUROI; MACROPHOMINA PHASEOLINA;

EID: 84874001953     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2013.01.002     Document Type: Article

References (34)

1. A.J.J. Straathof, S. Panke, and A. Schmid The production of fine chemicals by biotransformations Curr Opin Biotech 13 2002 548 556 (Pubitemid 35448055)
2. P. Fernandes, A. Cruz, B. Angelova, H.M. Pinheiro, and J.M.S. Cabral Microbial conversion of steroid compounds: recent developments Enzyme Microb Technol 32 2003 688 705 (Pubitemid 36513765)
3. A. Saure, T. Teravainen, and O. Karjalainen The effect of synthetic gestagens on progesterone formation in vitro in human placenta of early pregnancy Reprod Fert 51 1977 369 373 (Pubitemid 8212473)
4. M.I. Choudhary, S. Zafar, N.T. Khan, S. Ahmad, S. Noreen, B.P. Marisini, A.A. Al-Khedairy, and Atta-ur-Rahman Biotransformation of dehydroepiandrosterone with Macrophomina phaseolina and β-glucuronidase inhibitory activity of transformed products. J Enz Inhib Med Chem 27 2012 348 355
5. M.I. Choudhary, S. Erum, M. Atif, R. Malik, N.T. Khan, and Atta-ur-Rahman Biotransformation of (20S)-20-hydroxymethylpregna-1,4-dien-3-one by four filamentous fungi Steroids 76 2011 1288 1296
6. M.I. Choudhary, S.A.A. Shah, Atta-ur-Rahman, S.N. Khan, and M.N.T. Khan α-Glucosidase and tyrosinase inhibitors from fungal hydroxylation of tibolone and hydroxytibolones Steroids 75 2010 956 966
7. M.I. Choudhary, M. Atif, and Atta-ur-Rahman Oxidation of lynestrenol by the fungus Cunninghamella elegans Nat Prod Res 24 2010 1 6
8. M.I. Choudhary, Y.M. Mohammad, S.G. Musharraf, M. Parvez, A. Al-Aboudi, and Atta-ur-Rahman New oxandrolone derivatives by biotransformation using Rhizopus stolonifer Steroids 74 2009 1040 1044
9. A. Al-Aboudi, M.Y. Mohammad, S. Haddad, R. Al-Far, M.I. Choudhary, and Atta-ur-Rahman Biotransformation of methyl cholate by Aspergillus niger Steroids 74 2009 483 486
10. M.I. Choudhary, Z.A. Siddiqui, S.A. Nawaz, and Atta-ur-Rahman Microbial transformation of 18β-glycyrrhetinic acid by Cunninghamella elegans and Fusarium lini, and lipoxygenase inhibitory activity of transformed products Nat Prod Res 23 2009 507 513
11. Azizuddin, Saifullah, S. Khan, M.I. Choudhary, and Atta-ur-Rahman Biotransformation of dydrogesterone by cell suspension cultures of Azadirachta indica Turk J Chem 32 2008 141 146
12. A. Al-Aboudi, M.Y. Mohammad, S.G. Musharraf, M.I. Choudhary, and Atta-ur-Rahman Microbial transformation of testosterone by Rhizopus stolonifer and Fusarium lini Nat Prod Res 22 2008 1498 1509
13. M.I. Choudhary, S.A.A. Shah, and Atta-ur-Rahman Microbial oxidation of anabolic steroids Nat Prod Res 22 2008 1289 1296
14. M.I. Choudhary, Azizuddin, S. Jalil, S.G. Musharraf, and Atta-ur-Rahman Fungal transformation of dydrogesterone and inhibitory effect of its metabolites on the respiratory burst in human neutrophils Chem Biodiv 5 2008 324 331
15. M.I. Choudhary, N.T. Khan, S.G. Musharraf, S. Anjum, and Atta-ur-Rahman Biotransformation of adrenosterone by filamentous fungus Cunninghamella elegans Steroids 72 2007 923 929 (Pubitemid 47600275)
16. M.I. Choudhary, M. Nasir, S.N. Khan, M. Atif, R.A. Ali, S.M. Khalil, and Atta-ur-Rahman Microbial hydroxylation of hydroxyprogesterone and α-glucosidase inhibition activity of its metabolites Z Naturforsch 62b 2006 593 599
17. M.I. Choudhary, S. Yousuf, Samreen, S.A.A. Shah, S. Ahmed, and Atta-ur-Rahman Biotransformation of physalin H and antileishmanial activity of its transformed products Chem Pharm Bull 54 2006 927 930
18. M.I. Choudhary, I. Batool, S.A.A. Shah, S.A. Nawaz, and Atta-ur-Rahman Microbial hydroxylation of pregnenolone derivatives Chem Pharm Bull 53 2005 1455 1459 (Pubitemid 41634216)
19. M.I. Choudhary, S. Sultan, M.N.T. Khan, and Atta-ur-Rahman Microbial transformation of 17α-ethynyl-and 17α-ethylsteroids, and tyrosinase inhibitory activity of transformed products Steroids 70 2005 798 802 (Pubitemid 41330981)
20. M.I. Choudhary, S. Sultan, S. Jalil, S. Anjum, A.A. Rahman, H.-K. Fun, and Atta-ur-Rahman Microbial transformation of mesterolone Chem Biodiv 2 2005 392 400 (Pubitemid 40485739)
21. M.I. Choudhary, S. Sultan, M.T.H. Khan, A. Yasin, F. Shaheen, and Atta-ur-Rahman Biotransformation of (+)-androst-4-ene-3,17-dione Nat Prod Res 18 2004 529 535 (Pubitemid 39585533)
22. S.G. Musharraf, Atta-ur-Rahman, M.I. Choudhary, and S. Sultan Microbial transformation of (+)-adrenosterone Nat Prod Lett 16 2002 345 349 (Pubitemid 35264626)
23. Atta-ur-Rahman, M.I. Choudhary, F. Asif, A. Farooq, and M. Yaqoob Fungal transformations of steroids by Cephalosporium aphidicola and Trichothecium roseum Nat Prod Lett 14 2000 217 224 (Pubitemid 30311348)
24. Siemens SMART and SAINT 1996 Siemens Analytical X-ray Instruments Inc Madison, WI, USA
25. A. Altomare, G. Cascarano, C. Giacovazzo, and A. Guagliardi Completion and refinement of crystal structures with SIR92 J Appl Cryst 26 1993 343 350 (Pubitemid 23679266)
26. G.M. Sheldrick SHELXTL-PC (Version 5.1) 1997 Siemens Analytical Instruments Inc Madison, WI, USA
27. C.K. Jhonson 'ORTEPII' Report ORNL-5138 1976 Oak Ridge National Laboratory TN, USA
28. B.J. Magerlein, and J.A. Hogg 11-β-Hydroxy-17α-alkyl estrogens vol. 2 1961 Upjohn Co. US 2991295 19610704
29. K. Sasaki 10Hydroxy-4-estren-3-one derivatives vol. 7 1967 Shionogi and Co., Ltd. Jpn. Tokyo Koho CODEN: JAXXAD JP 42016299 19670904 Showa
30. Muller G, Poittevin A. Steroid Derivatives. Roussel-UCLAF 1964;18:FR 1359646.
31. S. Yousuf, S. Zafar, M.I. Choudhary, and S.W. Ng 17β-Hydroxy- 17α-(hydroxymethyl)estr-4-en-3-one Acta Cryst E66 2010 o2894
32. E. Haack, G. Stoeck, and H. Voigt 17-Methylestradiol, an orally very active estrogen Naturwissenschaften 41 1954 429
33. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, and R. Taylor Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds J Chem Soc Perkin Trans 2 12 1987 S1 S19
34. Oxygenation of Steroids by Mucorales Fungi 1955 Upjohn Co. GB 724149 19550216