1887

Abstract

Steroid compounds have many important physiological activities in higher organisms. Testosterone and related steroids are important environmental contaminants that disrupt the endocrine systems of animals. The degradation of steroids, especially under anoxic conditions, is challenging because of their complex chemical structure. A denitrifying -proteobacterium, , able to grow anaerobically on a variety of steroids as the sole carbon and energy source was adopted as a model organism to study the anoxic degradation of testosterone. We identified the initial intermediates involved in the anoxic testosterone degradation pathway of . We demonstrated that under anoxic conditions, initially oxidizes testosterone to 1-dehydrotestosterone, which is then transformed to androsta-1,4-diene-3,17-dione. In addition, it seems that androst-4-en-3,17-dione can also be directly produced from testosterone by cells. In general, the initial steps of anoxic testosterone degradation by are similar to those of the oxic pathway demonstrated in .

Loading

Article metrics loading...

/content/journal/micro/10.1099/mic.0.037788-0
2010-07-01
2024-03-28
Loading full text...

Full text loading...

/deliver/fulltext/micro/156/7/2253.html?itemId=/content/journal/micro/10.1099/mic.0.037788-0&mimeType=html&fmt=ahah

References

  1. Anderson J., Iyaduri R. 2003; Integrated urban water planning: big picture planning is good for the wallet and the environment. Water Sci Technol 47:19–23
    [Google Scholar]
  2. Chiang Y. R., Ismail W., Müller M., Fuchs G. 2007; Initial steps in the anoxic metabolism of cholesterol by the denitrifying Sterolibacterium denitrificans. J Biol Chem 282:13240–13249
    [Google Scholar]
  3. Chiang Y. R., Ismail W., Gallien S., Heintz D., Van Dorsselaer A., Fuchs G. 2008; Cholest-4-en-3-one-Δ1-dehydrogenase: a flavoprotein catalyzing the second step in anoxic cholesterol metabolism. Appl Environ Microbiol 74:107–113
    [Google Scholar]
  4. Coulter A. W., Talalay P. 1968; Studies on the microbiological degradation of steroid ring A. J Biol Chem 243:3238–3247
    [Google Scholar]
  5. Egorova O. V., Nikolayeva V. M., Suzina N. E., Donova M. V. 2005; Localization of 17 β-hydroxysteroid dehydrogenase in Mycobacterium sp. VKM Ac-1815D mutant strain. J Steroid Biochem Mol Biol 94:519–525
    [Google Scholar]
  6. Fahrbach M., Kuever J., Meinke R., Kämpfer P., Hollender J. 2006; Denitratisoma oestradiolicum gen. nov., sp. nov: a 17 β-oestradiol-degrading, denitrifying betaproteobacterium. Int J Syst Evol Microbiol 56:1547–1552
    [Google Scholar]
  7. Fahrbach M., Kuever J., Remesch M., Huber B. E., Kämpfer P., Dott W., Hollender J. 2008; Steroidobacter denitrificans gen. nov., sp. nov., a steroidal hormone-degrading gammaproteobacterium. Int J Syst Evol Microbiol 58:2215–2223
    [Google Scholar]
  8. Fernandes P., Cruz A., Angelova B., Pinheiro H. M., Cabral J. M. S. 2003; Microbial conversion of steroid compounds: recent developments. Enzyme Microb Technol 32:688–705
    [Google Scholar]
  9. Gibson D. T., Wood J. M., Chapman P. J., Dagley S. 1967; The bacterial degradation of aromatic compounds. Biotechnol Bioeng 9:33–44
    [Google Scholar]
  10. Groman E. V., Engel L. L. 1977; Hydroxysteroid dehydrogenases of Pseudomonas testosteroni. Separation of a 17 beta-hydroxysteroid dehydrogenase from the 3(17) beta-hydroxysteroid dehydrogenase and comparison of the two enzymes. Biochim Biophys Acta 485:249–254
    [Google Scholar]
  11. Hanselman T. A., Graetz D. A., Wilkie A. C. 2003; Manure-borne estrogens as potential environmental contaminants: a review. Environ Sci Technol 37:5471–5478
    [Google Scholar]
  12. Harder J., Probian C. 1997; Anaerobic mineralization of cholesterol by a novel type of denitrifying bacterium. Arch Microbiol 167:269–274
    [Google Scholar]
  13. Horinouchi M., Hayashi T., Yamamoto T., Kudo T. 2003; A new bacterial steroid degradation gene cluster in Comamonas testosteroni TA441 which consists of aromatic-compound degradation genes for seco-steroids and 3-ketosteroid dehydrogenase genes. Appl Environ Microbiol 69:4421–4430
    [Google Scholar]
  14. Kieslich K. 1985; Microbial side-chain degradation of sterols. J Basic Microbiol 25:461–474
    [Google Scholar]
  15. Lack N. A., Yam K. C., Lowe E. D., Horsman G. P., Owen R. L., Sim E., Eltis L. D. 2010; Characterization of a carbon-carbon hydrolase from Mycobacterium tuberculosis involved in cholesterol metabolism. J Biol Chem 285:434–443
    [Google Scholar]
  16. Larsson D. G. J., Hällman H., Förlin L. 2000; More male fish embryos near a pulp mill. Environ Toxicol Chem 19:2911–2917
    [Google Scholar]
  17. Mindnich R., Möller G., Adamski J. 2004; The role of 17beta-hydroxysteroid dehydrogenases. Mol Cell Endocrinol 218:7–20
    [Google Scholar]
  18. Payne D. W., Talalay P. 1985; Isolation of novel microbial 3 α-, 3 β-, and 17 β-hydroxysteroid dehydrogenases. J Biol Chem 260:13648–13655
    [Google Scholar]
  19. Rabus R., Widdel F. 1995; Anaerobic degradation of ethylbenzene and other aromatic hydrocarbons by new denitrifying bacteria. Arch Microbiol 163:96–103
    [Google Scholar]
  20. Sih C. J., Wang K. C., Tai H. H. 1967; C22 acid intermediates in the microbiological cleavage of the cholesterol side chain. J Am Chem Soc 89: 1956
    [Google Scholar]
  21. Tarlera S., Denner E. B. M. 2003; Sterolibacterium denitrificans gen. nov., sp. nov., a novel cholesterol-oxidizing, denitrifying member of the β-Proteobacteria. Int J Syst Evol Microbiol 53:1085–1091
    [Google Scholar]
  22. Teles M., Gravato C., Pacheco M., Santos M. A. 2004; Juvenile sea bass biotransformation, genotoxic and endocrine responses to β-naphthoflavone, 4-nonylphenol and 17 β-estradiol individual and combined exposures. Chemosphere 57:147–158
    [Google Scholar]
  23. Tschech A., Pfennig N. 1984; Growth yield increase linked to caffeate reduction in Acetobacterium woodii. Arch Microbiol 137:163–167
    [Google Scholar]
  24. van der Geize R., Yam K., Heuser T., Wilbrink M. H., Hara H., Anderton M. C., Sim E., Dijkhuizen L., Davies J. E. other authors 2007; A gene cluster encoding cholesterol catabolism in a soil actinomycete provides insight into Mycobacterium tuberculosis survival in macrophages. Proc Natl Acad Sci U S A 104:1947–1952
    [Google Scholar]
  25. Williams R. J., Johnson A. C., Smith J. J. L., Kanda R. 2003; Steroid estrogens profiles along river stretches arising from sewage treatment works discharges. Environ Sci Technol 37:1744–1750
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/mic.0.037788-0
Loading
/content/journal/micro/10.1099/mic.0.037788-0
Loading

Data & Media loading...

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error