Degradation of chlorinated nitroaromatic compounds

Applied Microbiology and Biotechnology

Volumn 93, Issue 6, 2012, Pages 2265-2277

  Arora, Pankaj Kumar ^a   Sasikala, C ^b   Ramana, Ch Venkata ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

Biodegradation; Chloronitrobenzene; Chloronitrophenol; Microbial metabolism

Indexed keywords

ANTHROPOGENIC ACTIVITY; CHLORONITROBENZENES; CHLORONITROPHENOL; ENVIRONMENTAL POLLUTANTS; IN-SITU BIOREMEDIATION; METABOLIC PATHWAYS; MICROBIAL METABOLISM; NITROAROMATIC COMPOUND; PHYSICOCHEMICAL METHODS;

BACTERIA; BIODEGRADATION; BIOREMEDIATION; DETOXIFICATION;

METABOLISM;

2 NITROPHENOL; 4 NITROPHENOL; AROMATIC NITRO COMPOUND; CHLORINATED NITROAROMATIC COMPOUND; NITROBENZOIC ACID DERIVATIVE; QUINTOZENE; UNCLASSIFIED DRUG; CHLORINATED HYDROCARBON; NITRO DERIVATIVE;

BIODEGRADATION; BIOREMEDIATION; BIOTRANSFORMATION; DETOXIFICATION; HUMAN ACTIVITY; METABOLISM; MICROBIAL ACTIVITY; ORGANIC NITROGEN COMPOUND; ORGANIC POLLUTANT; ORGANOCHLORINE; PHYSICOCHEMICAL PROPERTY; WASTE TREATMENT; WASTEWATER;

BIOREMEDIATION; BIOTRANSFORMATION; DEHALOGENATION; DELFTIA ACIDOVORANS; DETOXIFICATION; GENETIC ENGINEERING; MICROBIAL DEGRADATION; MICROBIAL METABOLISM; MINERALIZATION; NONHUMAN; OXIDATION; OZONATION; PHOTOOXIDATION; PSEUDOMONAS PUTIDA; PSEUDOMONAS STUTZERI; REVIEW; RHIZOPUS ARRHIZUS; RHODOCOCCUS; SOIL MICROFLORA; BACTERIUM; CHEMISTRY; FUNGUS; GENETICS; METABOLISM; POLLUTANT;

ACTINOBACTERIA (CLASS); FUNGI;

BACTERIA; BIODEGRADATION, ENVIRONMENTAL; ENVIRONMENTAL POLLUTANTS; FUNGI; HYDROCARBONS, CHLORINATED; NITRO COMPOUNDS;

EID: 84862298308     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-012-3927-1     Document Type: Review

References (86)

1. Arora PK, Jain RK (2011a) Biotransformation of 4-chloro-2-nitrophenol into 5-chloro-2-methylbenzoxazole by a marine Bacillus sp. strain MW-1. Biodegradation. doi:10.1007/s10532-011-9512-y
2. Arora PK, Jain RK (2011b) Pathway for degradation of 4-chloro-2- nitrophenol by Arthrobacter sp. SJCon. Curr Microbiol 63:568-573
3. Arora PK, Kumar M, Chauhan A, Raghava GP, Jain RK (2009) OxDBase: A database of oxygenases involved in biodegradation. BMC Res Notes 2:67
4. Arora PK, Srivastava A, Singh VP (2010) Application of monooxygenases in dehalogenation, desulphurization, denitrification and hydroxylation of aromatic compounds. J Bioremed Biodegrad 1:110
5. Betts JJ, James SP, Thorpe WV (1955) The metabolism of pentachloronitrobenzene and 2,3,4,6-tetrachloronitrobenzene and the formation of mercapturic acids in the rabbit. Biochem J 61:611-617
6. Beunink J, Rehm HJ (1990) Coupled reductive and oxidative degradation of 4-chloro-2-nitrophenol by a co-immobilized mixed culture system. Appl Microbiol Biotechnol 34:108-115
7. Bhushan B, Samanta SK, Chauhan A, Chakraborti AK, Jain RK (2000) Chemotaxis and biodegradation of 3-methyl-4-nitrophenol by Ralstonia sp. SJ98. Biochem Biophys Res Commun 275:129-133
8. Bruhn C, Bayly RC, Knackmuss HJ (1988) The in vivo construction of 4-chloro-2-nitrophenol assimilatory bacteria. Arch Microbiol 150:171-177
9. Capek A, Simek A, Leiner J, Weichet J (1970) Antimicrobial agents. VII. Microbial degradation of the antifungal agent 2-chloro-4-nitrophenol (Nitrofungin). Folia Microbiol (Praha) 15:350-353
10. Chacke CI, Lockwood JL, Zabik M (1966) Chlorinated hydrocarbon pesticides: Degradation by microbes. Science 154:893-895
11. Chauhan A, Chakraborti AK, Jain RK (2000) Plasmid-encoded degradation of p-nitrophenol and 4-nitrocatechol by Arthrobacter protophormiae. Biochem Biophys Res Commun 270:733-740
12. de Vos RH, ten Noever de Brauw MC, Olthof PDA (1974) Residues of pentachloronitrobenzene and related compounds in greenhouse soils. Bull Environ Contam Toxicol 11:567-571
13. Field JA, Sierra-Alvarez R (2008) Microbial degradation of chlorinated benzenes. Biodegradation 19:463-480
14. Gharbani P, KhosraviM, TabatabaiiSM, Zare K, Dastmalchi S,Mehrizad A (2010) Degradation of trace aqueous 4-chloro-2-nitrophenol occurring in pharmaceutical industrial wastewater by ozone. Int J Environ Sci Technol 7:377-384
15. Ghosh A, Khurana M, Chauhan A, Takeo M, Chakraborti AK, Jain RK (2010) Degradation of 4-nitrophenol, 2-chloro-4-nitrophenol, and 2,4-dinitrophenol by Rhodococcus imtechensis strain RKJ300. Environ Sci Technol 44:1069-1077
16. Gonzalez LF, Sarria V, Sanchez OF (2010) Degradation of chlorophenols by sequential biological-advanced oxidative process using Trametes pubescens and TiO2/U. Bioresour Technol 101:3493-3499
17. Holliger C, Wohlfarth G, Diekert G (1998) Reductive dechlorination in the energy metabolism of anaerobic bacteria. FEMS Microbiol Rev 22:383-398
18. Jechorek M, Wendlandt KD, Beck M (2003) Cometabolic degradation of chlorinated aromatic compounds. J Biotechnol 102:93-98
19. Ju KS, Parales RE (2009) Application of nitroarene dioxygenases in the design of novel strains that degrade chloronitrobenzenes. Microb Biotechnol 2:241-252
20. Ju KS, Parales RE (2010) Nitroaromatic compounds, from synthesis to biodegradation. Microbiol Mol Biol Rev 74:250-272
21. Kanaly RA, Kim IS, Hur HG (2005) Biotransformation of 3-methyl-4-nitrophenol, a main product of the insecticide fenitrothion, by Aspergillus niger. J Agric Food Chem 53:6426-6431
22. Karn SK, Chakrabarti SK, Reddy MS (2011) Degradation of pentachlorophenol by Kocuria sp. CL2 isolated from secondary sludge of pulp and paper mill. Biodegradation 22:63-69
23. Katsivela E,Wray V, Pieper DH, Wittich RM (1999) Initial reactions in the biodegradation of 1-chloro-4-nitrobenzene by a newly isolated bacterium, strain LW1. Appl Environ Microbiol 65:1405-1412
24. Klecka GM, Maier WJ (1988) Kinetics of microbial growth on mixtures of pentachlorophenol and chlorinated aromatic compounds. Biotechnol Bioeng 31:328-335
25. Kogel W, Müller WF, Coulston F, Korte F (1979) Biotransformation of pentachloronitrobenzene-14C in rhesus monkeys after single and chronic oral administration. Chemosphere 8:97-105
26. Korde VM, Phelps TJ, Bienkowski PR, White DC (1993) Biodegradation of chlorinated aliphatics and aromatic compounds in totalrecycle expanded-bed biofilm reactors. Appl Biochem Biotechnol 39:631-641
27. Kuhlmann A, Hegemann W (1997) Degradation of monochloronitrobenzenes by Pseudomonas acidovorans CA50. Acta Hydrochim Hydrobiol 25:298-305
28. Larsen GL, Huwe JK, Bakke JE (1998) Intermediary metabolism of pentachloronitrobenzene in the control and germ-free rat and rat with cannulated bile ducts. Xenobiotica 28:973-984
29. Lenke H, Knackmuss HJ (1996) Initial hydrogenation and extensive reduction of substituted 2,4-dinitrophenols. Appl Environ Microbiol 62:784-790
30. Li Q, Minami M, Hanaoka, Yamamura Y (1999) Acute immunotoxicity of p-chloronitrobenzene in mice: II. Effect of p-chloronitrobenzene on the immunophenotype ofmurine splenocytes determined by flow cytometry. Toxicology 137:35-45
31. Li B, Xu X, Zhu L (2009) Ozonation of chloronitrobenzenes in aqueous solution: Kinetics and mechanism. J Chem Tech Biotechnol 84:167-175
32. Li BZ, Xu XY, Zhu L (2010) Catalytic ozonation-biological coupled processes for the treatment of industrial wastewater containing refractory chlorinated nitroaromatic compounds. J Zhejiang Univ-Sc B 11:177-189
33. Li R, Zheng JW, Ni B, Chen K, Yang XJ, Li SP, Jiang JD (2011) Biodegradation of pentachloronitrobenzene by Labrys portucalensis pcnb-21 isolated from polluted soil. Pedosphere 21:31-36
34. Lievremont D, SeigleMurandi F, BenoitGuyod JL, Steiman R (1996) Biotransformation and biosorption of pentachloronitrobenzene by fungal mycelia. Mycol Res 100:948-954
35. Lievremont D, SeigleMurandi F, BenoitGuyod JL (1998) Removal of PCNB from aqueous solution by a fungal adsorption process. Water Res 32:3601-3606
36. Liu H, Wang SJ, Zhou NY (2005) A new isolate of Pseudomonas stutzeri that degrades 2-chloronitrobenzene. Biotechnol Lett 27:275-278
37. Liu L, Jiang CY, Liu XY, Wu JF, Han JG, Liu SJ (2007a) Plant-microbe association for rhizoremediation of chloronitroaromatic pollutants with Comamonas sp. strain CNB-1. Environ Microbiol 9:465-473
38. Liu L, Wu JF, Ma YF, Wang SY, Zhao GP, Liu SJ (2007b) A novel deaminase involved in chloronitrobenzene and nitrobenzene degradation with Comamonas sp. strain CNB-1. J Bacteriol 189:2677-2682
39. Liu H,Wang SJ, Zhang JJ, Dai H, Tang H, Zhou NY (2011) Patchwork assembly of nag-like nitroarene dioxygenase genes and the 3-chlorocatechol degradation cluster for evolution of the 2-chloronitrobenzene catabolism pathway in Pseudomonas stutzeri ZWLR2-1. Appl Environ Microbiol 77:4547-4552
40. Livingston AG (1993) A novel membrane bioreactor for detoxifying industrial wastewater: II. Biodegradation of 3-chloronitrobenzene in an industrially produced wastewater. Biotechnol Bioeng 41:927-936
41. Ma YF, Wu JF, Wang SY, Jiang CY, Zhang Y, Qi SW, Liu L, Zhao GP, Liu SJ (2007) Nucleotide sequence of plasmid pCNB1 from Comamonas strain CNB-1 reveals novel genetic organization and evolution for 4-chloronitrobenzene degradation. Appl Environ Microbiol 73:4477-4483
42. Mohn WW, Tiedje JM (1992) Microbial reductive dehalogenation. Microbiol Rev 56:482-507
43. Murphy SE, Drotar AM, Fall AR (1982) Biotransformation of the fungicide pentachloronitrobenzene by Tetrahymena thermophila. Chemosphere 11:33-39
44. Murthy BKN, Kaufman DD (1978) Degradation of pentachloronitrobenzene (PCNB) in anaerobic soils. J Agric Food Chem 26:1151-1156
45. Nair RS, Johannsen FR, Levinskas GJ, Terrill JB (1986) Assessment of toxicity of o-nitrochlorobenzene in rats following a 4-week inhalation exposure. Fundam Appl Toxicol 7:609-614
46. Nakanishi T, Oku H (1969) Metabolism and accumulation of pentachloronitrobenzene by phytopathogenic fungi in relation to selective toxicity. Phytopathology 59:1761-1762
47. Niu GL, Zhang JJ, Zhao S, Liu H, Boon N, Zhou NY (2009) Bioaugmentation of a 4-chloronitrobenzene contaminated soil with Pseudomonas putida ZWL73. Environ Pollut 157:763-771
48. Pandey J, Heipieper HJ, Chauhan A, Arora PK, Prakash D, Takeo M, Jain RK (2011) Reductive dehalogenation mediated initiation of aerobic degradation of 2-chloro-4-nitrophenol (2C4NP) by Burkholderia sp. strain SJ98. Appl Microbiol Biotechnol 92:597-607
49. Park HS, Lim SJ, Chang YK, Livingston AG, Kim HS (1999) Degradation of chloronitrobenzenes by a coculture of Pseudomonas putida and a Rhodococcus sp. Appl Environ Microbiol 65:1083-1091
50. Prakash D, Kumar R, Jain RK, Tiwary BN (2011) Novel pathway for the degradation of 2-chloro-4-nitrobenzoic acid by Acinetobacter sp. strain RKJ12. Appl Environ Microbiol 77:6606-6613
51. Priya MH, Madras G (2006) Kinetics of photocatalytic degradation of phenols with multiple substituent groups. J Photochem Photobiol 179:256-262
52. Renner G (1980) Metabolic studies on pentachloronitrobenzene (PCNB) in rats. Xenobiotica 10:537-550
53. Renner G (1981) Biotransformation of the fungicides hexachlorobenzene and pentachloronitrobenzene. Xenobiotica 11:435-446
54. Renner G, Nguyen PT (1984) Mechanisms of the reductive denitration of pentachloronitrobenzene (PCNB) and the reductive dechlorination of hexachlorobenzene (HCB). Xenobiotica 14:705-710
55. Renner G, Ruckdeschel G (1983) Effects of pentachloronitrobenzene and some of its known and possible metabolites on fungi. Appl Environ Microbiol 46:765-768
56. Rieger PG, Preuss A, Sinnwell V, Francke W, Lenke H, Knackmuss HJ (1994) H2 additions as initial steps of aerobic degradation of 2,4,6-trinitrophenol (picric acid), abstr. Q-120, p. 409. In: Abstracts of the 94th General Meeting of the American Society for Microbiology 1994. American Society for Microbiology, Washington, DC
57. Sabbioni G, Jones CR, Sepai O, Liu YY, Yan H (2007) Urinary metabolites and health effects in workers exposed chronically to chloronitrobenzene. Biomarkers 12:1-20
58. Sahasrabudhe SR, Modi VV (1987) Microbial degradation of chlorinated aromatic compounds. Microbiol Sci 4:300-303
59. Saritha P, Aparna C, Himabindu V, Anjaneyulu Y (2007) Comparison of various advanced oxidation processes for the degradation of 4-chloro-2 nitrophenol. J Hazard Mater 149:609-614
60. Schenzle A, Lenke H, Spain JC, Knackmuss HJ (1999) Chemoselective nitro group reduction and reductive dechlorination initiate degradation of 2-chloro-5-nitrophenol by Ralstonia eutropha JMP134. Appl Environ Microbiol 65:2317-2323
61. Shen JM, Chen ZL, Xu ZZ, Li XY, Xu BB, Qi F (2008) Kinetics and mechanism of degradation of p-chloronitrobenzene in water by ozonation. J Hazard Mater 152:1325-1331
62. Smith AG, Francis JE (1983) Evidence for the active renal secretion of S-pentachlorophenyl-N-acetyl-L-cysteine by female rats. Biochem Pharmacol 2:3797-3801
63. Spain JC (1995a) Bacterial degradation of nitroaromatic compounds under aerobic conditions. Environ Sci Res 49:19-35232
64. Spain JC (1995b) Biodegradation of nitroaromatic compounds. Annu Rev Microbiol 49:523-555
65. Susarla S, Masunaga S, Yonezawa Y (1996) Transformations of chloronitrobenzenes in anaerobic sediment. Chemosphere 32:967-977
66. Symons ZC, Bruce NC (2006) Bacterial pathways for degradation of nitroaromatics. Nat Prod Rep 23:845-850
67. Tabak HH, Chambers CW, Kabler PW (1964) Microbial metabolism of aromatic compounds. I. Decomposition of phenolic compounds and aromatic hydrocarbons by phenol-adapted bacteria. J Bacteriol 87:910-919
68. Takagi K, Iwasaki A, Kamei I, Satsuma K, Yoshioka Y, Harada N (2009) Aerobic mineralization of hexachlorobenzene by newly isolated pentachloronitrobenzene-degrading Nocardioides sp. strain PD653. Appl Environ Microbiol 75:4452-4458
69. Tas DO, Pavlostathis SG (2005) Microbial reductive transformation of pentachloronitrobenzene under methanogenic conditions. Environ Sci Technol 39:8264-8272
70. Tas DO, Pavlostathis SG (2007) Temperature and pH effect on the microbial reductive transformation of pentachloronitrobenzene. J Agric Food Chem 55:5390-5398
71. Tas DO, Pavlostathis SG (2008) Effect of nitrate reduction on the microbial reductive transformation of pentachloronitrobenzene. Environ Sci Technol 42:3234-3240
72. Tas DO, Pavlostathis SG (2010) Microbial transformation of pentachloronitrobenzene under nitrate reducing conditions. Biodegradation 21:691-702
73. Thiele J, Muller R, Lingens F (1988) Enzymatic dehalogenation of chlorinated nitroaromatic compounds. Appl Environ Microbiol 54:1199-1202
74. Torres RM, Grosset C, Steiman R, Alary J (1996) Liquid chromatography study of degradation and metabolism of pentachloronitrobenzene by four soil micromycetes. Chemosphere 33:683-692
75. Travlos GS, Mahler J, Ragan HA, Chou BJ, Bucher JR (1996) Thirteenweek inhalation toxicity of 2-and 4-chloronitrobenzene in F344/N rats and B6C3F1 mice. Fundam Appl Toxicol 30:75-92
76. van der Meer JR (1997) Evolution of novel metabolic pathways for the degradation of chloroaromatic compounds. Antonie Van Leeuwenhoek 7:159-178
77. Vilhunen S, Sillanpaa M (2010) Recent developments in photochemical and chemical AOPs in water treatment: A mini review. Rev Environ Sci Biotechnol 9:323-330
78. Volskay VT, Grady CPL (1990) Respiration inhibition kinetic-analysis. Water Res 24:863-874
79. Wu JF, Sun CW, Jiang CY, Liu ZP, Liu SJ (2005) A novel 2-aminophenol 1,6-dioxygenase involved in the degradation of pchloronitrobenzene by Comamonas strain CNB-1: Purification, properties, genetic cloning and expression in Escherichia coli. Arch Microbiol 183:1-8
80. Wu JF, Jiang CY, Wang BJ, Ma YF, Liu ZP, Liu SJ (2006) Novel partial reductive pathway for 4-chloronitrobenzene and nitrobenzene degradation in Comamonas sp. strain CNB-1. Appl Environ Microbiol 72:1759-1765
81. Wu HZ, Wei CH, Wang YQ, He QC, Liang SZ (2009) Degradation of o-chloronitrobenzene as the sole carbon and nitrogen sources by Pseudomonas putida OCNB-1. J Environ Sci-China 21:89-95
82. Xiao Y,Wu JF, Liu H,Wang SJ, Liu SJ, Zhou NY (2006) Characterization of genes involved in the initial reactions of 4-chloronitrobenzene degradation in Pseudomonas putida ZWL73. Appl Microbiol Biotechnol 73:166-171
83. Yamamoto K, Nishimura M, Kato D, Takeo M, Negoro S (2011) Identification and characterization of another 4-nitrophenol degradation gene cluster, nps, in Rhodococcus sp. strain PN1. J Biosci Bioeng 111:687-694
84. Yin Y, Zhou NY (2010) Characterization of MnpC, a hydroquinone dioxygenase likely involved in the meta-nitrophenol degradation by Cupriavidus necator JMP134. Curr Microbiol 61:471-476
85. Zhao JS, Ward OP (1999) Microbial degradation of nitrobenzene and mono-nitrophenol by bacteria enriched from municipal activated sludge. Can J Microbiol 45:427-432
86. Zhen D, Liu H, Wang SJ, Zhang JJ, Zhao F, Zhou NY (2006) Plasmidmediated degradation of 4-chloronitrobenzene by newly isolated Pseudomonas putida strain ZWL73. Appl Microbiol Biotechnol 72:797-803