Biotransformation of adrenosterone by filamentous fungus, Cunninghamella elegans

Steroids

Volumn 72, Issue 14, 2007, Pages 923-929

  Choudhary, Muhammad Iqbal ^a   Khan, Naik T ^a   Musharraf, Syed G ^a   Anjum, Shazia ^a   Atta ur Rahman, ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

Adrenosterone; Cunninghamella elegans; Hydroxylation; Microbial transformation

Indexed keywords

11 OXOTESTOSTERONE; 6BETA HYDROXY 11 KETOTESTOSTERONE; 6BETA HYDROXYADRENOSTERONE; 9ALPHA HYDROXY 11 KETOTESTOSTERONE; 9ALPHA HYDROXYADRENOSTERONE; ADRENOSTERONE; DRUG METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CULTURE; CONTROLLED STUDY; CUNNINGHAMELLA ELEGANS; DRUG ISOLATION; DRUG STRUCTURE; DRUG TRANSFORMATION; FUNGUS CULTURE; HYDROXYLATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; X RAY DIFFRACTION;

ANDROSTENES; BIOTRANSFORMATION; CRYSTALLOGRAPHY, X-RAY; CUNNINGHAMELLA; MASS SPECTROMETRY; MOLECULAR CONFORMATION;

CUNNINGHAMELLA ELEGANS; FUNGI;

EID: 35348949978     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2007.08.002     Document Type: Article

References (25)

1. Fernandes P., Cruz A., Angelova B., Pinheiro H.M., and Cabral J.M.S. Microbial conversion of steroid compounds: recent developments. Enzyme Microb Technol 32 (2003) 688-705
2. Charney W., and Herzog H.L. Microbial transformations of steroids (1967), Academic Press, New York p. 16-73
3. Cha C.J., Doerge D.R., and Cerniglia C.E. Biotransformation of malachite green by the fungus Cunninghamella elegans. Appl Environ Microbiol 67 (2001) 4358-4360
4. Reichstein T. Über cortin, das hormon der nebennieren-rinde. Helv Chim Acta 29 (1936) 29-63
5. Cavaco J.E.B., Van Blijswijk B., Leatherland J.F., Goos H.J.T., and Schulz R.W. Androgen-induced changes in Leydig cell ultrastructure and steroidogenesis in juvenile African catfish Clarias gariepinus. Cell Tissue Res 297 (1999) 291-299
6. Lone K.P., and Matty A.J. The effects of feeding androgenic hormones on the proteolytic activity of the alimentary canal of carp Cyprinus carpio L. J Fish Biol 18 (1981) 353-358
7. Yoshihama M., Tamura K., Nakakoshi M., Nakamura J., Fujise N., and Kawanishi G. 14α-Hydroxyandrost-4-ene-3,6-17-trione as a mechanical-based irreversible inhibitor of estrogen biosynhthesis. Chem Pharm Bull 38 (1990) 2834-2837
8. Musharraf S.G., Atta-ur-Rahman, Choudhary M.I., and Sultan S. Microbial transformation of (+)-adrenosterone. Nat Prod Lett 16 (2002) 345-349
9. Greca M.D., Fiorentino A., Guerriero I., Pinto G., Pollio A., and Previtera L. Biotransformation of adrenosterone into 11-ketotestosterone by Scenedesmus quadricauda grown in myxotrophic conditions. Biotechnol Lett 19 (1997) 1123-1124
10. Greca M.D., Fiorentino A., Pinto G., Pollio A., and Previtera L. Regiospecific reduction of adrenosterone to 11-ketotestosterone by microalga Scenedesmus quadricauda T76. Biotechnol Lett 18 (1996) 639-642
11. Hamada H., Naka S., and Kurban H. Stereoselective reduction in the biotransformation of androstane derivatives by cell suspension cultures of Marchantia polymorpha. Chem Lett 12 (1993) 2111-2112
12. Brannon D.R., Parrish F.W., Wiely B.J., and Long Jr. L. Microbial transformation of a series of androgens with Aspergillus tamarii. J Org Chem 32 (1967) 1521-1527
13. Kondo E. Shionogi and Co. Ltd., Japan. Reduction of steroids by microorganisms. Japanese Patent 39012320; 2 July 1964.
14. Kondo E. Transformation of steroids by microorganisms. IX. Inhibition of ring D cleavage by the 11-hydroxyl group. Kogyo Kagaku Zasshi 67 (1964) 724-727
15. Takahashi T. The microbiological transformation of steroids. IX. Transformation of C19 steroids by Pellicularia filamentosa microsclerotia IFO 6298. Agric Biol Chem 28 (1964) 38-47
16. Choudhary M.I., Ranjit R., Atta-ur-Rahman, Devkota K.P., Musharraf S.G., and Shrestha T.M. Hydroxylation of the sesterterpene leucosceptrine by the fungus Rhizopus stolonifer. Phytochemistry 67 (2006) 439-443
17. Choudhary M.I., Siddiqui Z.A., Hussain S., and Atta-ur-Rahman. Structure elucidation and antibacterial activity of new fungal metabolites of sclareol. Chem Biodiv 3 (2006) 54-61
18. Choudhary M.I., Sultan S., Jalil S., Anjum S., Rahman A.A., Fun H.K., et al. Microbial transformation of mesterolone. Chem Biodiv 2 (2005) 392-400
19. Choudhary M.I., Shah S.A.A., Sami A., Ajaz A., Shaheen F., and Atta-ur-Rahman. Fungal metabolites of (E)-guggulsterone and their antibacterial and radical-scavenging activities. Chem Biodiv 2 (2005) 516-524
20. Choudhary M.I., Sultan S., Khan M.T.H., and Atta-ur-Rahman. Microbial transformation of 17α-ethynyl- and 17α-ethylsteroids, and tyrosinase inhibitory activity of transformed products. Steroids 70 (2005) 798-802
21. Siemens. SMART and SAINT. Siemens Analytical X-ray Instruments Inc. (1996), Madison, WI, USA
22. Altomare A., Cascarano G., Giacovazzo C., and Guagliardi A. Completion and refinement of crystal structures with SIR92. J Appl Cryst 26 (1993) 343-350
23. Sheldrick G.M. SHELXTL-PC (Version 5.1). Siemens Analytical Instruments Inc. (1997), Madison, WI, USA
24. Jhnson CK. 'ORTEPII' Report ORNL-5138. Oak Ridge National Laboratory, TN, USA; 1976.
25. Urech J., Vischer E., and Wettstein A. Substratspezifische hydroxylierungen von steroiden mittels pilz-stämmen der gattung Gibberella. Helv Chim Acta 43 (1960) 1077-1086