Microbial transformation of testosterone by Rhizopus stolonifer and Fusarium lini

Natural Product Research

Volumn 22, Issue 17, 2008, Pages 1498-1509

  Al Aboudi, Amal ^a   Mohammad, Mohammad Yasin ^a   Musharraf, S Ghulam ^b   Choudhary, M Iqbal ^b   Atta ur Rahman, ^b  

^a UNIVERSITY OF JORDAN   (Jordan)

^b UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

1 dehydrogenation; 11 hydroxylation; Fusarium lini; lactonisation; Microbial transformation; Rhizopus stolonifer; Testosterone

Indexed keywords

11ALPHA HYDROXYANDROST 1,4 EN 3,17 DIONE; 11ALPHA HYDROXYANDROST 4 EN 3,17 DIONE; 11ALPHA HYDROXYTESTOLACTONE; 11ALPHA HYDROXYTESTOSTERONE; 11ALPHA,17BETA DIHYDROXYANDROST 1,4 DIEN 3 ONE; 17BETA HYDROXY 5ALPHA ANDROSTAN 1,6 DIONE; ANDROST 1,4 DIEN 3,17 DIONE; ANDROST 4 EN 3,7 DIONE; BOLDENONE; HYDROXYL GROUP; TESTOLACTONE; TESTOSTERONE; TESTOSTERONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; DEHYDROGENATION; ENZYME MECHANISM; FERMENTATION; FUNGAL METABOLISM; FUNGUS CULTURE; FUSARIUM; HETERONUCLEAR NUCLEAR MAGNETIC RESONANCE; HYDROXYLATION; LACTONIZATION; METABOLITE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; RHIZOPUS; RHIZOPUS STOLONIFER;

BIOTRANSFORMATION; FUSARIUM; HYDROXYLATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RHIZOPUS; TESTOSTERONE;

FUNGI; FUSARIUM; FUSARIUM OXYSPORUM F. SP. LINI; RHIZOPUS; RHIZOPUS STOLONIFER;

EID: 57049142705     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786410802234528     Document Type: Article

References (32)

1. Adham, NZ, El-Hady, AA and Naim, N. (2003) Biochemical studies on 1-dehydrogenation of cortisol by Pseudomonas fluorescens. Process Biochemistry, 38, pp. 897-902.
2. Ahmed, F., Williams, RA and Smith, KE (1996) Microbial transformations of Steroids-X. Cytochromes P-450 11-hydroxylase and C17-C20 lyase and a 1-ene dehydrogenase transform steroids in Nectria haematococca. Journal of Steroid Biochemistry and Molecular Biology, 58, pp. 337-349.
3. Al-Awadi, S., Afzal, M. and Oommen, S. (2005) Studies on Bacillus stearothermophilus. Part IV. Influence of enhancers on biotransformation of testosterone. Steroids, 70, pp. 327-333.
4. Al-Awadi, S., Afzal, M. and Oommen, S. (2003) Studies on Bacillus stearothermophilus. Part III. Transformation of'testosterone. Applied Microbiology and Biotechnology, 62, pp. 48-52.
5. Atta-ur-Rahman, Choudhary, MI, Asif, F., Farooq, A. and Yaqoob, M. (1998) Microbial transformation of testosterone. Natural Product Letters, 12, pp. 255-261.
6. Bartmánska, A. and Dmochowska-Gładysz, J. (2007) Transformation of steroids by Trichoderma hamatum. Enzyme and Microbial Technology, 40, pp. 1615-1621.
7. Bartmánska, A., Dmochowska-Gładysz, J. and Huszcza, E. (2005) Steroids' transformations in Penicillium notatum culture. Steroids, 70, pp. 193-198.
8. Brzezowska, E., Dmochowska-Gladysz, J. and Kolek, T. (1996) Biotransformation XXXIX. Metabolism of testosterone, androstenedione, progesterone and testosterone derivatives in Absidia coerulea culture. Journal of Steroid Biochemistry and Molecular Biology, 57, pp. 357-362.
9. Cabeza, M., Gutierrez, E., Garcia, G., Avalos, A. and Hernandez, M. (1999) Microbial transformation of testosterone to 5alpha-dihydrotestosterone by two species of Penicillium: Penicillium chrysogenum and Penicillium crustosum. Steroids, 64, pp. 379-384.
10. Cepa, MM, Tavares da Silva, EJ, Correia-da-Silva, G., Roleira, FM and Teixeira, NA (2005) Structure-activity relationships of new A,D-ring modified steroids as aromatase inhibitors: Design, synthesis, and biological activity evaluation. Journal of Medicinal Chemistry, 48, pp. 6379-6385.
11. Choudhary, MI, Musharraf, SG, Shaheen, F. and Atta-ur-Rahman. (2002) Microbial transformation of (+)-androsta-l,4-diene-3,17-dione by Cephalosporium aphidicola. Natural Product Letters, 16, pp. 377-382.
12. Choudhary, MI, Sultan, S., Hassan Khan, MT and Atta-ur-Rahman. (2005) Microbial transformation of 17α-ethynyl- and 17αc-ethylsteroids, and tyrosinase inhibitory activity of transformed products. Steroids, 70, pp. 798-802.
13. DellaGreca, M., Previtera, L., Fiorentino, A., Pinto, G. and Pollio, A. (1996) Bioconversion of 1713-hydroxy-17cx-methyl-androsta-l,4-dien-3-one and androsta-l,4-diene-3,17-dione in cultures of the green alga T76 Scenedesmus quadricauda. Tetrahedron, 52, pp. 13981-13990.
14. Farooq, A. and Tahara, S. (2000) Biotransformation of testosterone and pregnenolone catalyzed by the fungus Botrytis cinerea. Journal of Natural Products, 63, pp. 489-491.
15. Fernandes, P., Cruz, A., Angelova, B., Pinheiro, H. and Cabral, J. (2003) Microbial conversion of steroid compounds: Recent developments. Enzyme and Microbial Technology, 32, pp. 688-705.
16. 1-testosterone acetates by Rhizopusarrhizus. Canadian Journal of Chemistry, 63, pp. 1127-1131.
17. Holland, HL, Lakshmaiah, G. and Ruddock, PL (1998) Microbial hydroxylation of acetylaminosteroids. Steroids, 63, pp. 484-495.
18. Hu, S., Genain, G. and Azerad, R. (1995) Microbial transformations of steroids: Contribution to 14α-hydroxylations. Steroids, 60, pp. 337-352.
19. Hunter, AC and Carragher, NE (2003) Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus tamarii KITA: transformation of a series of cortical steroid analogues. Journal of Steroid Biochemistry and Molecular Biology, 87, pp. 301-308.
20. Huszcza, E., Dmochowska-Gladysz, J. and Bartmanska, A. (2005) Transformations of steroids by Beauveria bassiana. Journal of Biosciences, 60, pp. 103-108.
21. Kołek, T. and Swizdor, A. (1998) Biotransformation XLV. Transformations of 4-ene-3-oxo steroids in Fusarium culmorum culture. Journal of Steroid Biochemistry and Molecular Biology, 67, pp. 63-69.
22. Lamma, AS, Chena, AR, Reynoldsb, WF and Reesea, PB (2007) Steroid hydroxylation by Whetzelinia sclerotiorum, Phanerochaete chrysosporium and Mucor plumbeus. Steroids, 72, pp. 713-722.
23. Liu, M-H, Li, H., Shan, L. and Wu., W (2006) Synthesis of steroidal lactone by penicillium citreo-viride. Steroids, 71, pp. 931-934.
24. Mahato, SB and Mukherjee, A. (1984) Microbial transformation of testosterone by Aspergillus fumigatus. Journal of Steroid Biochemistry, 21, pp. 341-342.
25. Musharraf, SG, Atta-ur-Rahman, Choudhary, MI and Sultan, S. (2002) Microbial Transformation of (+)adrenosterone. Natural Product Letters, 16, pp. 345-349.
26. Samantha, TB and Ghosh, DK (1987) Characterisation of progesterone 11-α-hydroxylase of Aspergillus ochraceus TS: A cytochrome P-450 linked mono-oxygenase. Journal of Steroid Biochemistry, 28, pp. 327-332.
27. Sedlaczek, L. (1988) Biotransformation of steroid. CRC Critical Reviews in Biotechnology, 7, pp. 186-236.
28. Shuvalova, SD, Gabinskaya, KN, Popova, EV, Savinova, TS and Andryushina, VA (2001) Hydroxylation of androst-4-ene-3,7-dione with the aid of Curvularia lunata fungus. Journal of Pharmaceutical Chemistry, 35, pp. 279-281.
29. Smith, KF and Kirk, DN (1989) Microbial transformation of steroids - II. Transformations of progesterone, testosterone and androstenedione by Phycomyces blakesleeanus. Journal of Steroid Biochemistry, 32, pp. 445-451.
30. Smith, KF, Latif, S. and Kirk, DN (1990) Microbial transformations of steroids - VI. Transformation of testosterone and androstenedione by Botryosphaerica obtusa. Journal of Steroid Biochemistry, 35, pp. 115-120.
31. Wilson, MR, Gallimore, WA and Reese, PB (1999) Steroid transformations with Fusarium oxysporum var. cubense and Colletotrichum musae. Steroids, 64, pp. 834-843.
32. Zeelen, FJ (1990) The cytochrome P-450 isozymes. Medicinal chemistry of steroid, p. 73. Elsevier, Amsterdam