Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa

Steroids

Volumn 73, Issue 1, 2008, Pages 13-18

  Faramarzi, Mohammad Ali ^a   Aghelnejad, Maryam ^a   Tabatabaei Yazdi, Mojtaba ^a   Amini, Mohsen ^a   Hajarolasvadi, Naghmeh ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Androst 4 en 3,17 dione; Biotransformation; Neurospora crassa

Indexed keywords

14ALPHA HYDROXYANDROST 4 EN 3,17 DIONE; 6BETA,9ALPHA DIHYDROXYANDROST 4 EN 3,17 DIONE; 7ALPHA HYDROXYANDROST 4 EN 3,17 DIONE; 7BETA,14ALPHA DIHYDROXYANDROST 4 EN 3,17 DIONE; 9ALPHA HYDROXYANDROST 4 EN 3,17 DIONE; ANDROST 4,6 DIEN 3,17 DIONE; ANDROSTENEDIONE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION RESPONSE; CULTURE MEDIUM; DEHYDROGENATION; FERMENTATION; FUNGAL METABOLISM; FUNGUS CULTURE; HORMONE METABOLISM; HYDROXYLATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NEUROSPORA CRASSA; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; THIN LAYER CHROMATOGRAPHY; TIME;

ANDROSTENEDIONE; BIOTRANSFORMATION; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; NEUROSPORA CRASSA; TEMPERATURE;

FUNGI; NEUROSPORA CRASSA;

EID: 36849091348     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2007.06.008     Document Type: Article

References (34)

1. Smith L.L. Steroids. In: Rehm H.J., and Reed G. (Eds). Biotechnology. 1st ed. vol. 6a (1984), Verlag Chemie GmbH, Wienheim 31-78
2. Fullerton D.S. In: Delgado J.N., and Remers W.A. (Eds). Willson and Gisvold's text book of organic medicinal and pharmaceutical chemistry. 9th ed. (1991), J.B. Lippincott Co., Philadelphia 672-765 [Chapter 18]
3. Michels P.C., and Rosazza P.N. Methods for biocatalysis and biotransformations. In: Demain A.L., and Davies J.E. (Eds). Manual of industrial microbiology and biotechnology (1999), American Society for Microbiology, Washington, DC 165-180
4. Han S.W., Michelin M.A., Barbosa J.E., and Rossi A. Purification and constitutive excretion of acid phosfatase in Neurospora crassa. Phytochemistry 35 (1994) 1131-1135
5. Phadtare S.U., Rawat U.B., and Rao M.B. Purification and characterization of xylitol dehydrogenase from Neurospora crassa. FEMS Microbiol Lett 146 (1997) 79-83
6. Paula R.M., Wilson W.A., Roach P.J., Terenzi H.F., and Bertolini M.C. Biochemical characterization of Neurospora crassa glycogenin (GNN), the self-glucosylating initiator of glycogen synthesis. FEBS Lett 579 (2005) 2208-2214
7. Diaz A., Rangel P., Oca Y.M., Lledias F., and Hansberg W. Molecular and kinetic study of catalase-1, a durable large catalase of Neurospora crassa. Free Radical Biol Med 31 (2001) 1323-1333
8. Luke A.K., and Burton S.G. A novel application for Neurospora crassa: progress from batch culture to a membrane bioreactor for the bioremediation of phenols. Enzyme Microb Technol 29 (2001) 348-356
9. Mishra N.C. Genetics and molecular biology of Neurospora crassa-a review. Adv Genet 29 (1991) 2-62
10. Fincham J.R.S. Transformation in fungi. Microbiol Rev 53 (1989) 148-170
11. Swiegers J.H., Vaz F.M., Pretorius I.S., Wanders R.J.A., and Bauer F.F. Carnitine biosynthesis in Neurospora crassa: identification of a cDNA coding for ε-N-trimethyl lysine hydroxylase and its functional expression in Sacharomyces cerevisiae. FEMS Microbiol Lett 210 (2002) 19-23
12. Wang G.Y., and Keasling J.D. Amplification of HMG-CoA reductase production enhances carotenoid accumulation in Neurospora crassa. Metab Eng 4 (2002) 193-201
13. Maugras M.M., Savigny P., and Lematre J. Microbiological transformation of estrogens. 11β-Hydroxylation of estradiol by Neurospora crassa. CR Acad Sci Hebd Seances Acad Sci D 176 (1973) 3221-3223
14. Maugras M.M., Hartemann D., Granger P., and Lematre J. Microbiological transformation of estrogens. Transformation of equilenine into 12β-dihydroequilenin by Neurospora crassa. C R Acad Sci D 277 (1973) 681-683
15. Stone D., Hayano M., Dorfman R.I., Hechter O., Robinson C.R., and Djerassi C. Hydroxylation of desoxycorticosterone with Neurospora crassa. J Am Chem Soc 77 (1955) 3926-3927
16. Tabatabaei Yazdi M., Amani A., Faramarzi M.A., Amini M., Shafiee A., and Gharaee Fathabad E. Nandrolone decanoate transformation by Neurospora crassa. Pharm. Biol. 43 (2005) 630-635
17. Gharaei-Fathabad E., Tabatabaei Yazdi M., Faramarzi M.A., and Amini M. Biotransformation of hydrocortisone by Neurospora crassa. J Sci IR Iran 17 (2006) 309-312
18. Faramarzi M.A., Hajarolasvadi N., Tabatabaei Yazdi M., Amini M., and Aghelnejad M. Microbiological hydroxylation of androst-1,4-dien-3,17-dione by Neurospora crassa. Biocatal Biotransform 25 (2007) 72-78
19. Yoshihama M., Nakakoshi M., Tamura K., Miyata N., Kawanishi G., and Iida M. Microbial production of two new dihydroxylated androstenedione derivatives by Acremonium strictum. J Ferment Bioeng 67 (1989) 238-243
20. Hill R.A., Kirk D.N., Makin H.L., and Murphy G.M. Dictionary of steroids: chemical data, Structures and bibliographics. 1st ed. (1991), Chapman & Hall Ltd., London
21. Holland H.L., and Thomas E.M. Microbial hydroxylation of steroids. 8. Incubation of CN haloxylated and other substituted steroids with CN hydroxylating fungi. Can J Chem 60 (1982) 160-164
22. Horinouchi M., Toshiaki H., Yamamoto T., and Kudo T. A new bacterial steroid degredation gene cluster in Comamonas testosteroni TA441 which consists of aromatic-compound degradation genes for seco-steroids and 3-ketosteroid dehydrogenase genes. Appl Environ Microbiol 69 (2003) 4421-4430
23. 13C NMR spectra of steroids-A survey and commentary. Org Mag Res 9 (1977) 439-464
24. 1H NMR spectra of the steroid hormones, their hydroxylated derivatives and related compound. J Chem Soc, Perkin Trans II (1990) 1567-1594
25. Banerjee S., Mukerjee E., and Mahato S.B. Metabolism of androst-4-en-3,17-dione by Aspergillus fumigatus. J Chem Res (Suppl) (1993) 236-237
26. Madayastha K.M. Preparatively useful transformation of steroids and morphine alkaloids by Mucor piriformis. Proc Indian Acad Sci Chem Sci 106 (1994) 1203-1212
27. Yoshioka H, Asada H, Fujita S. Process for production of 6β,14α-dihydroxy-4-androstene-3,17-dion. European Patent 599,658; 1994.
28. Angelova B., Mutafor S., Avramova T., Dimova I., and Boyadjieva L. 9α-Hydroxylation of 4-androsten-3,17-dione by resting Rhodococcus sp. cells. Process Biochem 31 (1996) 179-184
29. Petzoldt K. Process for the preparation of 15α-hydroxyandrost-4-ene-3,17-dione. German Patent 3,403,862; 1985.
30. Asada S. Microbial manufacture of 14α-hydroxy-4-androsten-3,17-dione. Japanese Patent 06,225,791; 1994.
31. Weber A, Kewnnecke M. Preparation of 14α-hydroxy-4-androsten-3,17-dione by fermentation. German Patent 4,129,005; 1993.
32. Huszcza E., and Gladysz J.D. Transformations of testosterone and related steroids by Botrytis cinerea. Phytochemistry 62 (2003) 166-168
33. Adham N.A., El-Hady A.A., and Naim N. Biochemical studies on the microbial Δ1-dehydrogenation of cortisol by Pseudomonas fluorescens. Process Biochem 36 (2003) 897-902
34. Arinbasarova A.Y., Karpov A.V., Fokina V.V., Medentsev A.G., and Koshcheyenko K.A. Kinetic characteristics of 1-en-dehydrogenation of 6α-methylhydrocortison by cells of Arthrobacter globiformis 193. Enzyme Microb Technol 19 (1996) 501-506