A novel degradation pathway in the assimilation of phenanthrene by Staphylococcus sp. strain PN/Y via meta-cleavage of 2-hydroxy-1-napthoic acid: Formation of trans-2,3-dioxo-5-(2′-hydroxyphenyl)-pent-4-enoic acid

Microbiology

Volumn 153, Issue 7, 2007, Pages 2104-2115

  Mallick, Somnath ^a   Chatterjee, Subhankar ^a   Dutta, Tapan K ^a  

^a BOSE INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY 1 NAPHTHOIC ACID; 2,3 DIOXO 5 (2' HYDROXYPHENYL) 4 PENTENOIC ACID; CATECHOL; NAPHTHALENE; PHENANTHRENE; POLYCYCLIC AROMATIC HYDROCARBON; SALICYLIC ACID; UNCLASSIFIED DRUG; VALERIC ACID;

ARTICLE; BACTERIAL STRAIN; BACTERIUM ISOLATE; BACTERIUM ISOLATION; CARBON SOURCE; CHROMATOGRAPHY; CONTROLLED STUDY; ENZYME ACTIVITY; MICROBIAL DEGRADATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN METABOLISM; PROTEIN SYNTHESIS; SPECTROMETRY; STAPHYLOCOCCUS;

BIODEGRADATION, ENVIRONMENTAL; MOLECULAR SEQUENCE DATA; NAPHTHOLS; PHENANTHRENES; POLYCYCLIC HYDROCARBONS, AROMATIC; STAPHYLOCOCCUS;

POSIBACTERIA; STAPHYLOCOCCUS SP.;

EID: 34447529272     PISSN: 13500872     EISSN: None     Source Type: Journal    
DOI: 10.1099/mic.0.2006/004218-0     Document Type: Article

References (58)

1. Adachi, K, Iwabuchi, T., Sano, H. & Harayama, S. (1999). Structure of the ring cleavage product of 1-hydroxy-2-naphthoate, an intermediate of the phenanthrene-degradative pathway of Nocardioides sp. strain KP7. J Bacteriol 181, 757-763.
2. Altschul, S. F., Gish, W., Miller, W., Myers, E. W. & Lipman, D. J. (1990). Basic local alignment search tool. J Mol Biol 215, 403-410.
3. Balashova, N. V., Kosheleva, I. A., Golovchenko, N. P. & Boronin, A. M. (1999). Phenanthrene metabolism by Pseudomonas and Burkholderia strains. Process Biochem 35, 291-296.
4. Barnsley, E. A. (1983). Phthalate pathway of phenanthrene metabolism: Formation of 2′-carboxybenzalpyruvate. J Bacteriol 154, 113-117.
5. Birnboim, H. C. & Doly, J. A. (1979). A rapid alkaline procedure for screening recombinant plasmid DNA. Nucleic Acids Res 7, 1513-1523.
6. Dean-Ross, D., Moody, J. D., Freeman, J. P., Doerge, D. R. & Cerniglia, C. E (2001). Metabolism of anthracene by a Rhodococcus species. FEMS Microbiol Lett 204, 205-211.
7. Eaton, R. W. & Chapman, P. J. (1992). Bacterial metabolism of naphthalene: Construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions. J Bacteriol 174, 7542-7554.
8. Evans, W. C., Fernley, H. N. & Griffiths, E. (1965). Oxidative metabolism of phenanthrene and anthracene by soil pseudomonads: The ring fission mechanism. Biochem 195, 819-831.
9. Fitzgerald, L J., Gallucci, J. C. & Gerkin, R. E. (1992). 1,2-Naphthalenedicarboxylic acid: Structures of channel clathrates and an unsolvated crystalline phase. Acta Crystallogr B 48, 290-297.
10. Gibson, D. T. & Subramanian, V. (1984). Microbial degradation of aromatic hydrocarbons. In Microbial Degradation of Organic Compounds, pp. 181-252. Edited by D. T. Gibson. New York: Dekker.
11. Goodwin, K. D., Tokaczyk, R., Stephens, F. C. & Saltzman, E. S. (2005). Degradation of toluene inhibition of methyl bromide biodegradation in seawater and isolation of a marine toluene oxidizer that degrades methyl bromide. Appl Environ Microbiol 71, 3495-3503.
12. Guerin, W. F. & Jones, G. E. (1988). Mineralization of phenanthrene by a Mycobacterium sp. Appl Environ Microbiol 54, 937-944.
13. Habe, H. & Omori, T. (2003). Genetics of polycyclic aromatic hydrocarbon metabolism in diverse aerobic bacteria. Biosci Biotechnol Biochem 67, 225-243.
14. Harayama, S. (1997). Polycyclic aromatic hydrocarbon bioremediation design. Curr Opin Biotechnol 8, 268-273.
15. Harpel, M. R. & Lipscomb, J. D. (1990). Gentisate 1,2-dioxygenase from Pseudomonas. Purification, characterization, and comparison of the enzymes from Pseudomonas testosteroni and Pseudomonas acidovorans. J Biol Chem 265, 6301-6311.
16. Herrick, J. B., Stuart-Keil, K. G., Ghirose, N. C. & Madsen, E. L. (1997). Natural horizontal transfer of a naphthalene dioxygenase gene between bacteria native to a coal tar-contaminated field site. Appl Environ Microbiol 63, 2330-2337.
17. Houghton, J. E. & Shanley, M. S. (1994). Catabolic potential of pseudomonads: A regulatory perspective. In Biological Degradation and Bioremediation of Toxic Chemicals, pp. 11-32. Edited by R. G. Chaudhry. London: Chapman & Hall.
18. Jerina, D. M., Selander, H., Yagi, H., Wells, M. C., Davey, J. F., Mahadevan, V. & Gibson, D. T. (1976). Dihydrodiols from anthracene and phenanthrene. J Am Chem Soc 98, 5988-5996.
19. Kanaly, R. A. & Harayama, S. (2000). Biodegradation of high molecular weight polycyclic aromatic hydrocarbons by bacteria. J Bacteriol 182, 2059-2067.
20. Keum, Y. S., Sao, J. S., Hu, Y. & Li, Q. X. (2006). Degradation pathways of phenanthrene by Sinorhizobium sp. C4. Appl Microbiol Biotechnol 71, 935-941.
21. Kim, Y. H., Moody, J. D., Freeman, J. P., Brezna, B., Engesser, K. H. & Cerniglia, C. E. (2004). Evidence for the existence of PAH-quinone reductase and catechol-O-methyltransferase in Mycobacterium vanbaalenii PYR-I. J Ind Microbiol Biotechnol 31, 507-516.
22. Kim, Y. H., Freeman, J. P., Moody, J. D., Engesser, K. H. & Cerniglia, C. E. (2005). Effects of PH on the degradation of phenanthrene and pyrene by Mycobacterium vanbaalenii PYR-1. Appl Microbiol Biotechnol 67, 275-285.
23. Kiyohara, H. & Nagao, K (1978). The catabolism of phenanthrene and naphthalene by bacteria. J Gen Microbiol 105, 69-75.
24. Kiyohara, H., Nagao, K & Nomi, R. (1976). Degradation of phenanthrene through o-phthalate by an Aeromonas sp. Agric Biol Chem 40, 1075-1082.
25. Kiyohara, H., Nagao, K, Kouno, K. & Yano, K (1982). Phenanthrene-degrading phenotype of Alcaligenes faecalis AFK2. Appl Environ Microbiol 43, 458-461.
26. Kiyohara, H., Takizawa, N., Data, H., Torigoe, S. & Yano, K. (1990). Characterization of a phenanthrene degradation plasmid from Alcaligenes faecalis AFK2. J Ferment Bioeng 69, 54-56.
27. AL, Nom. Cons. Opin. 17 Jud. Comm. 1958,153. In Bergey's Manual of Systematic Bacteriology, vol. 2, pp. 1013-1035. Edited by P. H. A. Sneath, N. S. Mair, M. E. Sharpe & J. G. Holt. Baltimore: Williams & Wilkins.
28. Kojima, Y., Itada, N. & Hayaishi, O. (1961). Metapyrocatachase: A new catechol-cleaving enzyme. J Biol Chem 236, 2223-2228.
29. Kreiswirth, B. N., Lofdahl, S., Belley, M. J., O'Reilly, M., Shlievert P. M., Bergdoll, M. S. & Novick, R. P. (1983). The toxic shock syndrome exotoxin structural gene is not detectably transmitted by a prophage. Nature 305, 709-712.
30. Lopez, Z., Vila, J., Minguillon, C. & Grifoll, M. (2006). Metabolism of fluoranthene by Mycobacterium sp. strain AP1. Appl Microbiol Biotechnol 70, 747-756.
31. Ma, Y., Wang, L. & Shao, Z. (2006). Pseudomonas, the dominant polycyclic aromatic hydrocarbon-degrading bacteria isolated from Antarctic soils and the role of large plasmids in horizontal gene transfer. Environ Microbiol 8, 455-465.
32. Marston, C. P., Pereira, Z. C., Ferguson, J., Fischer, L., Hedstrom, O., Dashwood, W. M. & Baird, W. M. (2001). Effect of a complex environmental mixture from coal tar containing polycyclic aromatic hydrocarbons (PAH) on tumor initiation, PAH-DNA binding and metabolic activation of carcinogenic PAH in mouse epidermis. Carcinogenesis 22, 1077-1086.
33. Mastrangelo, G., Fadda, E. & Marzia, V. (1996). Polycyclic aromatic hydrocarbons and cancer in man. Environ Health Perspect 104, 1166-1170.
34. Moody, J. D., Freeman, J. P., Doerge, D. R. & Cerniglia, C. E (2001). Degradation of phenanthrene and anthracene by cell suspensions of Mycrobacterium sp. strain PYR-1. Appl Environ Microbiol 67, 1476-1483.
35. Moreira, L. M. & Sa-Correia, I. (1997). Megaplasmids in Thermus oshimai isolates from two widely separated geographical areas: restriction fragment profiling and DNA homology. Arch Microbiol 168, 473-479.
36. Mrozik, A. & Labuzek, S. (2002). A comparison of biodegradation of phenol and homologous compounds by Pseudomonas vesicularis and Staphylococcus sciuri strains. Acta Microbiol Pol 51, 367-378.
37. Narro, M. L., Cerniglia, C. E., Baalen, C. V. & Gibson, D. T. (1992). Metabolism of phenanthrene by the marine cyanobacterium. Agmenellum quadruplicatum PR-6. Appl Environ Microbiol 58, 1351-1359.
38. Parrish, Z. D., Banks, M. K. & Schwab, A. P. (2004). Effectiveness of phytoremediation as a secondary treatment for polycyclic aromatic hydrocarbons (PAHs) in composted soil. Int J Phytoremediation 6, 119-137.
39. Pelkonen, O. & Nebert, D. W. (1982). Metabolism of polycyclic hydrocarbons: Etiologic role in carcenogenesis. Pharmacol Rev 34, 189-222.
40. Pinyakong, O., Habe, H., Supaka, N., Pinpanichkarn, P., Juntongjin, K, Yoshida, T., Furihata, K., Nojiri, H., Yamane, H. & Omori, T. (2000). Identification of novel metabolites in the degradation of phenanthrene by Sphingomonas sp. strain P2. FEMS Microbiol Lett 191, 115-121.
41. Pothuluri, J. V. & Cerniglia, C. E. (1994). Microbial metabolism of polycyclic aromatic hydrocarbons. In Biological Degradation and Bioremediation of Toxic Chemicals, pp. 92-124. Edited by R. G. Chaudhry. London: Chapman & Hall.
42. Prabhu, Y. & Phale, P. S. (2003). Biodegradation of phenanthrene by Pseudomonas sp. strain PP2: Novel metabolic pathway, role of biosurfactant and cell surface hydrophobicity in hydrocarbon assimilation. Appl Microbiol Biotechnol 61, 342-35 1.
43. Rehmann, K, Noll, H. P., Steinberg, C. E. W. & Kettrup, A. A. (1998). Pyrene degradation by Mycobacterium sp. strain KR2. Chemosphere 36, 2977-2992.
44. Rehmann, K., Hertkorn, N. & Kettrup, A. A. (2001). Fluoranthene metabolism in Mycobacterium sp. strain KR20: Identity of pathway intermediates during degradation and growth. Microbiology 147, 2783-2794.
45. Samanta, S. K., Chakraborti, A. K & Jain, R. K. (1999). Degradation of phenanthrene by different bacteria: Evidence for novel transformation sequences involving the formation of 1-naphthol. Appl Microbiol Biotechnol 53, 98-107.
46. Samante, S. K., Singh, O. V. & Jain, R. K (2002). Polycyclic aromatic hydrocarbons: Environmental pollution and bioremediation. Trends Biotechnol 20, 243-248.
47. Schenk S. & Laddaga, R. A. (1992). Improved method for electroporation of Staphylococcus aureus. FEMS Microbiol Lett 94, 133-138.
48. Seo, J. S., Keum, Y. S., Hu, Y., Lee, S. E & Li, Q. X. (2006a). Degradation of phenanthrene by Burkholderia sp. C3: initial 1,2- and 3,4-dioxygenation and meta- and ortho-cleavage of naphthalene-1,2-diol. Biodegradation 18, 123-131.
49. Sao, J. S., Keum, Y. S., Hu, Y., Lee, S. E & Li, Q. X. (2006b). Phenanthrene degradation in Arthrobacter sp. PI-1: initial 1,2-, 3,4-and 9,10-dioxygenation, and meta- and ortho-cleavages of naphtha- lene-1,2-diol after its formation from naphthalene- 1,2-dicarboxylic acid and hydroxyl naphthoic acids. Chemosphere 65, 2388-2394.
50. Shuttleworth, K L. & Cerniglia, C. E (1995). Environmental aspects of PAH biodegradation. Appl Biochem Biotechnol 54, 291-302.
51. Smibert, R. M. & Krieg, N. R. (1994). Phenotypic characterization. In Methods for General and Molecular Bacteriology, pp. 611-654. Edited by P. Gerhardt, R. G. E. Murray, W. A. Wood & N. R. Krieg. Washington, DC: American Society for Microbiology.
52. Survery, S., Ahmad, S., Subhan, S. A., Ajaz, M. & Rasool, S. A. (2004). Hydrocarbon degrading bacteria from Pakistani soil: isolation, identification, screening and genetical studies. Pak J Biol Sci 7, 1518-1522.
53. Sutherland, J. B., Freeman, J. P., Selby, A. L., Miller, D. W. & Cerniglia, C. E. (1990). Stereoselective formation of a K-region dihydrodiol from phenanthrene by Streptomyces flavovirens. Arch Microbiol 154, 260-266.
54. Tortella, G. R., Diez, M. C. & Duran, N. (2005). Fungal diversity and use in decomposition of environmental pollutants. Crit Rev Microbiol 31, 197-212.
55. Tsuda, M., Tan, H. M., Nishi, A. & Furukawa, K (1999). Mobile catabolic genes in bacteria. J Biosci Bioeng 87, 401-4 10.
56. Vila, J., López, Z., Sabaté, J., Minguillón, C., Solanas, A.M. & Grifoll, M. (2001). Identification of a novel metabolite in the degradation of pyrene by Mycobacterium sp. strain AP1: Actions of the isolate on two- and three-ring polycyclic aromatic hydrocarbons. Appl Environ Microbiol 67, 5497-5505.
57. Vinas, M., Sabate, J., Espuny, M. J. & Solanas, A. M. (2005). Bacterial community dynamics and polycyclic aromatic hydrocarbon degradation during bioremediation of heavily creosote-contaminated soil. Appi Environ Microbiol 71, 7008-7018.
58. Xue, W. & Warshawsky, D. (2005). Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: A review. Toxicol Appl Pharmacol 206, 73-93.