Mycobacterium aromativorans JS19b1 T degrades phenanthrene through C-1,2, C-3,4 and C-9,10 dioxygenation pathways

International Biodeterioration and Biodegradation

Volumn 70, Issue , 2012, Pages 96-103

  Seo, Jong Su ^a,c   Keum, Young Soo ^b,c   Li, Qing X ^c  

^a Korea Institute of Toxicology   (South Korea)

^b Konkuk University   (South Korea)

^c UNIVERSITY OF HAWAII   (United States)

Author keywords

Biodegradation; Bioremediation; Dioxygenation; Monooxygenation; Mycobacterium aromativorans; Phenanthrene

Indexed keywords

1 ,2-DIHYDROXYNAPHTHALENE; BACTERIAL DEGRADATION; DIOXYGENATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; META-CLEAVAGE; METABOLIC PATHWAYS; MONOOXYGENATION; MYCOBACTERIUM AROMATIVORANS; NAPHTHOIC ACIDS; PHENANTHRENE; PHTHALIC ACID; RING OPENING; SOLE SOURCE OF CARBON;

BIODEGRADATION; BIOREMEDIATION; CARBOXYLATION; CARBOXYLIC ACIDS; GAS CHROMATOGRAPHY; METABOLISM; METABOLITES; NAPHTHALENE; OXYGENATION;

ANTHRACENE;

BACTERIUM; BIODEGRADATION; BIOREMEDIATION; EXPERIMENTAL STUDY; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; PAH; PHENANTHRENE;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM;

EID: 84862794779     PISSN: 09648305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ibiod.2012.02.005     Document Type: Article

References (56)

1. Adachi K., Iwabuchi T., Sano H., Harayama S. Structure of the ring cleavage product of 1-hydroxy-2-naphthoate, an intermediate of the phenanthrene-degradative pathway of Nocardioides sp. strain KP7. Journal of Bacteriology 1999, 181:757-763.
2. Anderson D.R., Koch T.H. 2,3-Bis(trimethylsilyloxy)-1,3-butadiene as a useful reactive diene in the Diels-Alder reaction. The Journal of Organic Chemistry 1978, 43:2726-2728.
3. Annweiler E., Richnow H.H., Antranikian G., Hebenbrock S., Grams C., Franke S., Franke W., Michaelis W. Naphthalene degradation and incorporation of naphthalene-derived carbon into biomass by the thermophile Bacillus thermoleovorans. Applied and Environmental Microbiology 2000, 66:518-523.
4. Atsushi H., Yoshie T., Jiro S., Junko K., Toshio I., Michiyo S., Yoshiki S., Takashi M. Comparison between in vivo mutagenicity and carcinogenicity in multiple organs by benzo[a]pyrene in the lacZ transgenic mouse (MutaMouse). Mutation Research 1998, 398:123-130.
5. Balashova N.V., Stolz A., Knackmuss H.J., Kosheleva I.A., Naumov A.V., Boronin A.M. Purification and characterization of a salicylate hydroxylase involved in 1-hydroxy-2-naphthoic acid hydroxylation from the naphthalene and phenanthrene-degrading bacterial strain Pseudomonas putida BS202-P1. Biodegradation 2001, 12:179-188.
6. Bastiaens L., Springael D., Wattiau P., Harms H., deWachter R., Verachtert H., Diels L. Isolation of adherent polycyclic aromatic hydrocarbon (PAH)-degrading bacteria using PAH-sorbing carriers. Applied and Environmental Microbiology 2000, 66:1834-1843.
7. Boldrin B., Tiehm A., Fritzsche C. Degradation of phenanthrene, fluorene, fluoranthene, and pyrene by a Mycobacterium sp. Applied and Environmental Microbiology 1993, 59:1927-1930.
8. Briganti F., Pessione E., Giunta C., Scozzafava A. Purification, biochemical properties and substrate specificity of a catechol 1,2-dioxygenase from a phenol degrading Acinetobacter radioresistens. FEBS Letters 1997, 416:61-64.
9. Cerniglia C.E. Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 1992, 3:351-368.
10. Cerniglia C.E. Fungal metabolism of polycyclic aromatic hydrocarbons: past, present and future applications in bioremediation. Journal of Industrial Microbiology & Biotechnology 1997, 19:324-333.
11. Daane L.L., Harjono I., Zylstra G.J., Häggblom M.M. Isolation and characterization of polycyclic aromatic hydrocarbon-degrading bacteria associated with the rhizosphere of salt marsh plants. Applied and Environmental Microbiology 2001, 67:2683-2691.
12. Dean-Ross D., Moody J.D., Freeman J.P., Doerge D.R., Cerniglia C.E. Metabolism of anthracene by a Rhodococcus species. FEMS Microbiology Letters 2001, 204:205-211.
13. De Voss J.J., Rutter K., Schroeder B.G., Barry C.E. Iron acquisition and metabolism by Mycobacteria. Journal of Bacteriology 1999, 181:4443-4451.
14. Eaton R.W., Chapman P.J. Bacterial metabolism of naphthalene: construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reaction. Journal of Bacteriology 1992, 174:7542-7554.
15. Friedrich M., Grosser R.J., Kern E.A., Inskeep W.P., Ward D.M. Effect of model sorptive phases on phenanthrene biodegradation: molecular analysis of enrichments and isolates suggests selection based on bioavailability. Applied and Environmental Microbiology 2000, 66:2703-2710.
16. Garnier T., Eiglmeier K., Camus J.-C., Medina N., Mansoor H., Pryor M., Duthoy S., Grondin S., Lacroix C., Monsempe C., Simon S., Harris B., Atkin R., Doggett J., Mayes R., Keating L., Wheeler P.R., Parkhill J., Barrell B.G., Cole S.T., Gordon S.V., Hewinson R.G. The complete genome sequence of Mycobacterium bovis. Proceedings of the National Academy of Science 2003, 100:7877-7882.
17. Geiselbrecht A.D., Hedlund B.P., Tichi M.A., Staley J.T. Isolation of marine polycyclic aromatic hydrocarbon (PAH)-degrading Cycloclasticus strains from the Gulf of Mexico and comparison of their PAH degradation ability with that of Puget Sound Cycloclasticus strains. Applied and Environmental Microbiology 1998, 64:4703-4710.
18. Gibson D.T., Resnick S.M., Lee K., Brand J.M., Torok D.S., Wackett L.P., Schocken M.J., Heigler B.E. Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4. Journal of Bacteriology 1995, 177:2615-2621.
19. Grifoll M., Selifonov F.A., Chapman P.J. Evidence for a novel pathway in the degradation of fluorene by Pseudomonas sp. Strain F274. Applied and Environmental Microbiology 1994, 60:2438-2449.
20. Haritash A.K., Kaushik C.P. Biodegradation aspects of polycyclic aromatic hydrocarbons (PAHs): a review. Journal of Hazardous Materials 2009, 169:1-15.
21. Haroune N., Combourieu B., Besse P., Sancelme M., Reemtsma T., Kloepfer A., Diab A., Knapp J.S., Baumberg S., Delort A.-M. Benzothiazole degradation by Rhodococcus pyridinovorans strain PA: evidence of a catechol 1,2-dioxygenase activity. Applied and Environmental Microbiology 2002, 68:6114-6120.
22. Hennessee C.T., Seo J.-S., Alvarez A.M., Li Q.X. Isolation and characterization of five new polycyclic aromatic hydrocarbon-degrading species isolated from Hawaiian soils: Mycobacterium crocinum sp. nov., Mycobacterium pallens sp. nov., Mycobacterium rutilum sp. nov., Mycobacterium rufum sp. nov., and Mycobacterium aromaticivorans sp. nov. International Journal of Systematic and Evolutionary Microbiology 2009, 59:378-387.
23. Iwabuchi T., Harayama S. Biochemical and genetic characterization of trans-2'-carboxybenzalpyruvate hydratase-aldolase from a phenanthrene-degrading Nocardioides strain. Journal of Bacteriology 1998, 180:945-949.
24. Iwabuchi T., Harayama S. Biochemical and molecular characterization of 1-hydroxy-2-naphthoate dioxygenase from Nocardioides sp. KP7. The Journal of Biological Chemistry 1998, 273:8332-8336.
25. Johnsen K., Andersen S., Jacobsen C.S. Phenotypic and genotypic characterization of phenanthrene-degrading fluorescent Pseudomonas biovars. Applied and Environmental Microbiology 1996, 62:3818-3825.
26. Kenner G.W., Murray M.A., Tylor C.M.B. Oxidative cyclisation of diphenyl-2-carboxylic acid. Tetrahedron 1957, 1:259-268.
27. Keum Y.-S., Seo J.-S., Li Q.X. Synthesis of bacterial metabolites of polycyclic aromatic hydrocarbons: benzochromenones, o-carboxyvinylnaphthoates, and o-substituted aryl-α-oxobutenoates. Synthetic Communications 2005, 35:2685-2693.
28. Kim S.J., Kweon O., Jones R.C., Freeman J.P., Edmondson R.D., Cerniglia C.E. Complete and integrated pyrene degradation pathway in Mycobacterium vanbaalenii PYR-1 based on systems biology. Journal of Bacteriology 2007, 189:464-472.
29. Kim Y.-H., Freeman J.P., Moody J.D., Engesser K.-H., Cerniglia C.E. Effects of pH on the degradation of phenanthrene and pyrene by Mycobacterium vanbaalenii PYR-1. Applied Microbiology and Biotechnology 2005, 67:275-285.
30. Krivobok S., Kuony S., Meyer C., Louwagie M., Willison J.C., Jouanneau Y. Identification of pyrene-induced proteins in Mycobacterium sp. strain 6PY1: evidence for two ring-hydroxylating dioxygenases. Journal of Bacteriology 2003, 185:3828-3841.
31. Mallick S., Chatterjee S., Dutta T.K. A novel degradation pathway in the assimilation of phenanthrene by Staphylococcus sp. strain PN/Y via meta-cleavage of 2-hydroxy-1-naphthoic acid: formation of trans-2,3-dioxo-5-(2'-hydroxyphenyl)-pent-4-enoic acid. Microbiology 2007, 153:2104-2115.
32. Maltseva O.V., Solyanikova I.P., Golovleva L.A. Chlorocatechol 1,2-dioxygenase from Rhodococcus erythrpolis 1CP. kinetic and immunochemical comparison with analogous enzymes from gram-negative strains. European Journal of Biochemistry 1994, 226:1053-1061.
33. Moody J.D., Freeman J.P., Doerge D.R., Cerniglia C.E. Degradation of phenanthrene and anthracene by cell suspensions of Mycobacterium sp. strain PYR-1. Applied and Environmental Microbiology 2001, 67:1476-1483.
34. Moody J.D., Fu P.P., Freeman J.P., Cerniglia C.E. Regio- and stereoselective metabolism of 7,12-dimethylbenz[a]anthracene by Mycobacterium vanbaalenii PYR-1. Applied and Environmental Microbiology 2003, 69:3924-3931.
35. Moody J.D., Freeman J.P., Fu P.P., Cerniglia C.E. Degradation of benzo[a]pyrene by Mycobacterium vanbaalenii PYR-1. Applied and Environmental Microbiology 2004, 70:340-345.
36. + aniline-assimilating Rhodococcus erythropolis AN-13. Gene 1997, 185:49-54.
37. Parrish Z.D., Banks M.K., Schwab A.P. Effectiveness of phytoremediation as a secondary treatment for polycyclic aromatic hydrocarbons (PAHs) in composted soil. International Journal of Phytoremediation 2004, 6:119-137.
38. Pinyakong O., Habe H., Supaka N., Pinpanichkarn P., Juntongjin K., Yoshida T., Furihata K., Nojiri H., Yamane H., Omori T. Identification of novel metabolites in the degradation of phenanthrene by Sphingomonas sp. strain P2. FEMS Microbiology Letters 2000, 191:115-121.
39. Piskonen R., Merja I. Evaluation of chemical pretreatment of contaminated soil for improved PAH bioremediation. Applied Microbiology and Biotechnology 2004, 65:627-634.
40. Pradhan S.P., Conrad J.R., Paterek J.R., Srivastava V.J. Potential of phytoremediation for treatment of PAHs in soil at MGP sites. Journal of Soil Contamination 1998, 7:467-480.
41. Seo J.-S., Keum Y.-S., Harada R.M., Li Q.X. Isolation and characterization of bacteria capable of degrading polycyclic aromatic hydrocarbons (PAHs) and organophosphorus pesticides from PAH-contaminated soil in Hilo, Hawaii. Journal of Agricultural and Food Chemistry 2007, 55:5383-5389.
42. Seo J.-S., Keum Y.-S., Hu Y., Lee S.-E., Li Q.X. Phenanthrene degradation in Arthrobacter sp. P1-1: initial 1,2-, 3,4- and 9,10-dioxygenation, and meta- and ortho-cleavages of naphthalene-1,2-diol after its formation from naphthalene-1,2-dicarboxylic acid and hydroxyl naphthoic acids. Chemosphere 2006, 65:2388-2394.
43. Seo J.-S., Keum Y.-S., Hu Y., Lee S.-E., Li Q.X. 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 2007, 18:123-131.
44. Seo J.-S., Keum Y.-S., Li Q.X. Comparative protein and metabolite profiling revealed a metabolic network in response to multiple environmental contaminants in Mycobacterium aromativorans JS19b1. Journal of Agricultural and Food Chemistry 2011, 59:2876-2882.
45. Shing T.K.M., Tai W.F.V., Tam E.K.V. Practical and rapid vicinal hydroxylation of alkenes by catalytic ruthenium tetraoxide. Angewandte Chemie International Edition in English 1994, 33:2312-2313.
46. Stringfellow W.T., Aitken M.D. Competitive metabolism of naphthalene, methylnaphthalenes, and fluorene by phenanthrene-degrading pseudomonads. Applied and Environmental Microbiology 1995, 61:357-362.
47. Stingley R.L., Khan A.A., Cerniglia C.E. Molecular characterization of a phenanthrene degradation pathway in Mycobacterium vanbaalenii PYR-1. Biochemical and Biophysical Research Communications 2004, 322:133-146.
48. Ting W.T.E., Yuan S.Y., Wu S.D., Chang B.V. Biodegradation of phenanthrene and pyrene by Ganoderma lucidum. International Biodeterioration & Biodegradation 2011, 65:238-242.
49. Tittabutr P., Cho I.K., Li Q.X. Phn and Nag-like dioxygenases metabolize polycyclic aromatic hydrocarbons in Burkholderia sp. C3. Biodegradation 2011, 22:1119-1133.
50. van Herwijnen R., Wattiau P., Bastiaens L., Daal L., Jonker L., Springael D., Govers H.A.J., Parsons J.R. Elucidation of the metabolic pathway of fluorene and cometabolic pathways of phenanthrene, fluoranthene, anthracene and dibenzothiophene by Sphingomonas sp. LB126. Research in Microbiology 2003, 154:199-206.
51. Venturello C., Chiusoli G.P. Isocoumarin tricyclic derivatives from benzenediazonium salts. Journal of Heterocyclic Chemistry 1972, 9:1155-1157.
52. Vila J., López Z., Sabaté J., Minguillón C., Solanas A.M., Grifoll M. 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. Applied and Environmental Microbiology 2001, 67:5497-5505.
53. Walter U., Beyer M., Klein J., Rehm H.-J. Degradation of pyrene by Rhodococcus sp. UW1. Applied Microbiology and Biotechnology 1991, 34:671-676.
54. White E.H., Bursey M.M. Analogs of luminal synthesis and chemiluminescence of two methoxy-substituted aminophthalic hydrazides. The Journal of Organic Chemistry 1966, 31:1912-1917.
55. Yousef S.E.-A., Huang X.-D., Dixon D.G., Greenberg B.M. Quantitative structure-activity relationship for the photoinduced toxicity of polycyclic aromatic hydrocarbons to the luminescent bacteria Vibrio fischeri. Environmental Toxicology and Chemistry 2002, 21:2225-2232.
56. Zeinali M., Vossoughi M., Ardestani S.K. Degradation of phenanthrene and anthracene by Nocardia otitidiscaviarum strain TSH1, a moderately thermophilic bacterium. Journal of Applied Microbiology 2008, 105:398-406.