Bacterial degradation of pyridine, indole, quinoline, and their derivatives under different redox conditions

Applied Microbiology and Biotechnology

Volumn 49, Issue 3, 1998, Pages 237-250

  Fetzner, S ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; CREOSOTE; INDOLE; INDOLE DERIVATIVE; PYRIDINE; PYRIDINE DERIVATIVE; QUINOLINE; QUINOLINE DERIVATIVE;

AEROBIC METABOLISM; BACTERIAL METABOLISM; BACTERIUM TRANSFORMATION; BIODEGRADATION; METHANOBACTERIUM; NONHUMAN; SHORT SURVEY; SOIL TREATMENT; SULFATE REDUCING BACTERIUM;

EID: 0031944612     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002530051164     Document Type: Short Survey

References (150)

1. Adams JD, LaVoie EJ, Shigematsu A, Owens P, Hoffmann D (1983) Quinoline and methylquinolines in cigarette smoke: comparative data and the effect of filtration. J Anal Toxicol 7: 293-296
2. Adrian NR, Suflita JM (1994) Anaerobic biodegradation of halogenated and nonhalogenated N-, S-, and O-heterocyclic compounds in aquifer slurries. Environ Toxicol Chem 13: 1551-1557
3. Aislabie J, Rothenhurger S, Atlas RM (1989) Isolation of microorganisms capable of degrading isoquinoline under aerobic conditions. Appl Environ Microbiol 55: 3247-3249
4. Aislabie J, Richards NK, Lyttle TC (1994) Description of bacteria able to degrade isoquinoline in pure culture. Can J Microbiol 40: 555-560
5. Alvarez M, Salas M, Joule JA (1991) Marine, nitrogen-containing heterocyclic natural products. Structures and syntheses of compounds containing quinoline and or isoquinoline units. Heterocycles 32: 759-794
6. Baechler FE, MacFarlane DS (1992) Sydney Tar Ponds clean up: hydrogeologic assessment. In: Weyer KU (ed) Proceedings of the 1992 International Conference on Coke Oven Complexes and Subsurface Contaminating Immiscible Fluids. Balkema: Rotterdam, Neth. pp 543-550
7. Bak F, Widdel F (1986) Anaerobic degradation of indolic compounds by sulfate-reducing enrichment cultures, and description of Desulfobacterium indolicum gen. nov., sp.nov. Arch Microbiol 146: 170-176
8. Barrick RC, Furlong ET, Carpenter R (1984) Hydrocarbon and azaarene markers of coal transport to aquatic sediments. Environ Sci Technol 18: 846-854
9. Battersby NS, Wilson V (1989) Survey of the anaerobic biodegradation potential of organic chemicals in digesting sludge. Appl Environ Microbiol 55: 433-439
10. Bauer I, Beyer A de, Tshisuaka B, Fetzner S, Lingens F (1994) A novel type of oxygenolytic ring cleavage: 2,4-oxygenation and decarbonylation of 1H-3-hydroxy-4-oxoquinaldine and 1H-3-hydroxy-4-oxoquinoline. FEMS Microbiol Lett 117: 299-304
11. Bauer I, Max N, Fetzner S, Lingens F (1996) 2,4-Dioxygenases catalyzing N-heterocyclic-ring cleavage and formation of carbon monoxide. Purification and some properties of 1H-3-hydroxy-4-oxo-quinaldine 2,4-dioxygenase from Arthrobacter sp. Rü61a and comparison with 1H-3-hydroxy-4-oxoquinoline 2,4-dioxygenase from Pseudomonas putida 33 1. Eur J Biochem 240: 576-583
12. Becker D, Schräder Th, Andreesen JR (1997) Two-component flavin-dependent pyrrole-2-carboxylate monooxygenase from Rhodococcus sp. Eur J Biochem 249: 739-747
13. Behrman EJ, Stanier RY (1957) The bacterial oxidation of nicotinic acid. J Biol Chem 228: 923-945
14. Berry DF, Francis AJ, Bollag JM (1987a) Microbial metabolism of homocyclic and heterocyclic aromatic compounds under anaerobic conditions. Microbiol Rev 51: 43-59
15. Berry DF, Madsen EL, Bollag JM (1987b) Conversion of indole to oxindole under methanogenic conditions. Appl Einviron Microbiol 53: 180-182
16. Bett G, Harvey TG, Matheson TW, Pratt KC (1983) Determination of polar compounds in Rundle shale oil. Fuel 62: 1445-1454
17. Böhlendorf B, Forche E, Bedorf N, Gerth K, Irschik H, Jansen R, Kunze B, Trowitzsch-Kienast W, Reichenbach H, Höfle G (1996) Antibiotics from gliding bacteria. LXXIII. Indole and quinoline derivatives as metabolites of tryptophan in myxobacteria. Liebigs Ann 1996: 49-53
18. Bollag JM, Kaiser JP (1991) The transformation of heterocyclic aromatic compounds and their derivatives under anaerobic conditions. Crit Rev Environ Control 21: 297-329
19. Bott G, Schmidt M, Rommel TO, Lingens F (1990) Degradation of 1H-4-oxoquinoline by Pseudomonas putida 33 1. Biol Chem Hoppe-Seyler 371: 999-1003
20. Cain RB, Houghton C, Wright KA (1974) Microbial metabolism of the pyridine ring. Metabolism of 2- and 3-hydroxypyridines by the maleamate pathway in Achromobacter sp. Biochem J 140: 293-300
21. Callely AG (1978) The microbial degradation of heterocyclic compounds. Prog Ind Microbiol 14: 205-281
22. Canter LW, Sabatini DA (1994) Contamination of public ground water supplies by Superfund sites. Int J Environ Stud 46: 35-57
23. Catallo WJ (1996) Transformation of N-, O-, and S-heterocycles (NOSHs) in estuarine sediments: effects of redox potential and sediment particle size. Chemosphere 33: 2543-2563
24. Claus G, Kutzner HJ (1983) Degradation of indole by Alcaligenes spec. System Appl Microbiol 4: 169-180
25. Collin G, Höke H (1989) Indole. In: Elvers B, Hawkins S, Ravenscroft M, Schulz G (eds) Ullmann's encyclopedia of industrial chemistry, vol. A14. VCH, Weinheim, pp 167-170
26. Collin G, Höke H (1993) Quinoline and isoquinoline. In: Elvers B, Hawkins S, Russey W, Schulz G (eds) Ullmann's encyclopedia of industrial chemistry, vol. A22. VCH, Weinheim, pp 465-469
27. Collin G, Höke H (1995) Tar and pitch. In: Elvers B, Hawkins S, Russey W (eds) Ullmann's encyclopedia of industrial chemistry, vol A26. VCH, Weinheim, pp 91-127
28. Cook AM (1987) Biodegradation of s-triazine xenobiotics. FEMS Microbiol Rev 46: 93-116
29. Dobson KR, Stephenson M, Greenfield PF, Bell PRF (1985) Identification and treatability of organics in oil shale retort water. Water Res 19: 849-856
30. Dunlap WJ, Shew DC, Roberton JM, Toussaint CR (1976) Organic pollutants contributed to groundwater by a landfill. In: Genetelli EJ, Cirello J (eds) Gas and leachate from landfills -formation, collection and treatment. EPA-600 9-76-004. US Environmental Protection Agency, Cincinnati, Ohio, pp 96-110
31. Dyreborg S, Arvin E, Broholm K (1996) The influence of creosote compounds on the aerobic degradation of toluene. Biodegradation 7: 97-107
32. Dyreborg S, Arvin E, Broholm K (1997) Biodegradation of NSO-compounds under different redox-conditions. J Contam Hydrol 25: 177-197
33. Edler B, Zwiener C, Frimmel FH (1997) Particle beam LC/MS screening of polar compounds of contaminated ground water samples from a former gas plant. Fresenius J Anal Chem 359: 288-292
34. Ensign JC, Rittenherg SC (1964) The pathway of nicotinic acid oxidation by a Bacillus species. J Biol Chem 239: 2285-2291
35. Ensign JC, Rittenberg SC (1965) The formation of a blue pigment in the bacterial oxidation of isonicotinic acid. Arch Mikrobiol 51: 384-392
36. Feng V, Kaiser JP, Minard RD, Bollag JM (1994) Microbial transformation of ethylpyridines. Biodegradation 5: 121-128
37. Fetzner S, Tshisuaka B, Lingens F, Kappl R, Hüttermann J (1998) Bacterial degradation of quinoline and -derivatives - pathways and their biocatalysts. Angew. Chem. Int. Ed. 37: 4000-4021
38. Fowler MG, Brooks PW, Northcott M, King MWG, Barker JF, Snowdon LR (1994) Preliminary results from a field experiment investigating the fate of some creosote components in a natural aquifer. Org Geochem 22: 641-649
39. Fredrickson JK, Bolton H Jr, Brockman FJ (1993) In situ and onsite bioreclamation. Environ Sci Technol 27: 1711-1716
40. Godsy EM, Goerlilz DF, Grbic-Galic D (1992) Methanogenic biodegradation of creosote contaminants in natural and simulated ground-water ecosystems. Ground Water 30: 232-242
41. Godsy EM, Goerlilz DF, Grbic-Galic D (1994) Methanogenic biodegradation of creosote derived components in an aquifer at Pensacola, Florida. In: Outton AR (ed) Toxic Substances Hydrological Science Selected Paper Conference 1994. American Institute of Hydrology: Minneapolis, Minn. pp 1-18
42. Grbic-Galic D (1989) Microbial degradation of homocyclic and heterocyclic aromatic hydrocarbons under anaerobic conditions. Dev Ind Microbiol 30: 237-253
43. Gupta RC, Shukla OP (1979) Isonicotinic and 2-hydroxy-isonicotinic acid hydroxylases of Sarcina sp. Indian J Biochem Biophys 16: 72-75
44. Hale RC, Aneiro KM (1997) Determination of coal tar and creosote constituents in the aquatic environment. J Chromatogr A 774: 79-95
45. Hansch C, Leo A (1979) Substituent constants for correlation analysis in chemistry and biology. Wiley, New York
46. Harmsen J (1983) Identification of organic compounds in leachate from a waste tip. Water Res 17: 699-705
47. Helmy AK, Bussetti SG de, Ferreiro EA (1983) Adsorption of quinoline from aqueous solutions by some clays oxides. Clays Clay Minerals 31: 29-36
48. Hille R (1996) The mononuclear molybdenum enzymes. Chem Rev 96: 2757-2816
49. Hirao K, Shinohara Y, Tsuda H, Fukushima S, Takahashi M, Ito N (1976) Carcinogenic activity of quinoline on rat liver. Cancer Res 36: 329-335
50. Hirschberg R, Ensign JC (1971) Oxidation of nicolinic acid by a Bacillus species: purification and properties of nicolinic acid and 6-hydroxynicotinic acid hydroxylases. J Bacteriol 108: 751-756
51. Hormann K, Andreesen JR (1991) A flavin-dependent oxygenase reaction initiates the degradation of pyrrole-2-carboxylate in Arthrobactre strain Py1 (DSM 6386). Arch Microbiol 157: 43-48
52. Hormann K, Andreesen JR (1994) Purification and characterization of a pyrrole-2-carboxylate oxygenase from Arthrobacter strain Py1. Biol Chem Hoppe-Seyler 375: 211-218
53. Houghton C, Cain RB (1972) Microbial metabolism of the pyridine ring. Formation of pyridinediols (dihydroxypyridines) as intermediates in the degradation of pyridine compounds by micro-organisms. Biochem J 130: 879-893
54. Hund HK, Beyer A de, Lingens F (1990) Degradation of quinaldine by Arthrobacter sp. Biol Chem Hoppe-Seyler 371: 1005-1008
55. Imhoff-Stuckle D, Pfennig N (1983) Isolation and characterization of a nicotinic acid-degrading sulfate-reducing bacterium. Desulfococcus niacini sp. nov. Arch Microbiol 136: 194-198
56. Johansen SS, Hansen AB, Moshaek H, Arvin E (1997a) Identification of heteroaromatic and other organic compounds in ground waler at creosote-contaminated sites in Denmark. Ground Water Monit Rem 17: 106-115
57. Johansen SS, Licht D, Arvin E, Mosbaek H, Hansen AB (1997b) Metabolic pathways of quinoline. indole and their methylated analogs by Desulfobacterium indolicum (DSM 3383). Appl Microbiol Biotechnol 47: 292-300
58. Johansen SS, Arvin E, Mosbaek H, Hansen AB (1997c) Degradation pathway of quinolines in a biofilm system under denitrifying conditions. Environ Toxicol Chem 16: 1821-1828
59. Kaiser JP, Bollag JM (1991) Metabolism of pyridine and 3-hydroxypyridine under aerobic, denitrifying and sulfate-reducing conditions. Experientia 47: 292-296
60. Kaiser JP, Bollag JM (1992) Influence of soil inoculum and redox potential on the degradation of several pyridine derivatives. Soil Biol Biochem 24: 351-357
61. Kaiser JP, Minard RD, Bollag JM (1993) Transformation of 3- and 4-picoline under sulfate-reducing conditions. Appl Environ Microbiol 59: 701-705
62. Kaiser JP, Feng Y, Bollag JM (1996) Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions. Microbiol Rev 60: 483-498
63. Kitts CL, Lapointe JP, Lam VT, Ludwig RA (1992) Elucidation of the complete Azorhizobium nieotinate catabolism pathway. J Bacteriol 174: 7791-7797
64. Kobayashi Y, Arima K (1962) Bacterial oxidation of dipicolinic acid II. Identification of α-ketoglutaric acid and 3-hydroxydipicolinic acid and some properties of cell-free extracts. J Bacteriol 84: 765-771
65. Koenig K, Andreesen JR (1992) Aerober und anaerober Abbau von heterocyclischen, aromatischen Verbindungen durch Bakterien. BioEngineering 8: 78-84
66. Kretzer A, Frunzke K, Andreesen JR (1993) Catabolism of isonicotinate by Mycobacterium sp. INA1: extended description of the pathway and purification of the molybdoenzyme isonicotinate dehydrogenase. J Gen Microbiol 139: 2763-2772
67. Kuhn EP, Suflita JM (1989) Microbial degradation of nitrogen, oxygen and sulfur heterocyclic compounds under anaerobic conditions: studies wilh aquifer samples. Environ Toxicol Chem 8: 1149-1158
68. LaVoic EJ, Dolan S, Little P, Wang CX, Sugie S, Rivenson A (1988) Carcinogenicity of quinoline, 4- and 8-methylquinoline and benzoquinolines in newborn mice and rats. Food Chem Toxicol 26: 625-629
69. Lee MD, Thomas JM, Borden RC, Bedient PB, Ward CH, Wilson JT (1988) Biorestoration of aquifers contaminated with organic compounds. CRC Crit Rev Environ Control 18: 29-89
70. Leenheer JA, Noyes TI, Stuber HA (1982) Determination of polar organic solutes in oil-shale retort water. Environ Sci Technol 16: 714-723
71. Licht D, Ahring BK, Arvin E (1996) Effects of electron acceptors, reducing agents, and toxic metabolites on anaerobic degradation of heterocyclic compounds. Biodegradation 7: 83-90
72. Licht D, Johansen SS, Arvin E, Ahring BK (1997) Transformation of indole and quinoline by Desulfabacterium indolicum (DSM 3383). Appl Microbiol Biotechnol 47: 167-172
73. Liu SM, Kuo CL (1996) Microbial potential for the anaerobic transformation of simple homocyclic and heterocyclic compounds in sediments of the Tsengwen River, Taiwan. Chem Ecol 12: 41-56
74. Liu SM, Jones WJ, Rogers JE (1994a) Influence of redox potential on the anaerobic biotransformation of nitrogen-heterocyclic compounds in anoxic freshwater sediments. Appl Microbiol Biotechnol 41: 717-724
75. Liu SM, Jones WJ, Rogers JE (1994b) Biotransformation of quinoline and methylquinolines in anoxic freshwater sediment. Biodegradation 5: 113-120
76. Madsen EL, Bollag JM (1989) Pathway of indole metabolism by a denitrifying microbial community. Arch Microbiol 151: 71-76
77. Madsen EL, Francis AJ, Bollag JM (1988) Environmental factors affecting indole metabolism under anaerobic conditions. Appl Environ Microbiol 54: 74-78
78. Mandelbaum RT, Shati MR, Ronen D (1997) In situ microcosms in aquifer bioremediation studies. FEMS Microbiol Rev 20: 489-502
79. Mattraw HC Jr, Franks BJ (1986) Description of hazardous-waste research at a creosote works. Pensacola, Florida. In: Mattraw HC, Franks BJ (eds) US Geological Survey: Water-Supply paper 2285. US Government Printina Office, Washington, DC, pp 1-8
80. Mayer AS, Carriere PPE, Gallo C, Pennell KD, Taylor TP, Williams GA, Zhong L (1997) Fate and effects of pollutants. Groundwater quality. Water Environ Res 69: 777-844
81. McBride JF, Brockman FJ, Szecsody JE, Streile GP (1992) Kinetics of quinoline biodegradation, sorption and desorption in a clay-coated model soil containing a quinoline-degradine bacterium. J Contam Hydrol 9: 133-154
82. Middaugh DP, Lantz SE, Heard CS, Mueller JG (1994) Field-scale testing of a two-stage bioreactor for removal of creosote and pentachlorophenol from ground water: chemical and biological assessment. Arch Environ Contam Toxicol 26: 320-328
83. Mueller JG, Chapman PJ, Pritchard PH (1989) Creosote-contaminated sites. Their potential for bioremediation. Environ Sci Technol 23: 1197-1201
84. Mueller JG, Lantz SE, Thomas RL, Kline EL, Chapman PJ, Middaugh DP, Pritchard PH, Colvin RJ, Rozich AP, Ross D (1991) Bioremediation of the American Creosote Works Superfund site, Pensacola, Florida. In: Proceedings of the 84th Annual Meeting of the Air Waste Management Association, vol 11, paper 91-18.4
85. Mueller JG, Lantz SE, Ross D, Colvin RJ, Middaugh DP, Pritchard PH (1993) Strategy using bioreactors and specially selected microorganisms for bioremediation of groundwater contaminated with creosote and pentachlorophenol. Environ Sci Technol 27: 691-698
86. Mueller JG, Borchert SM, Desrosier RJ, Klingel EJ, Langley W, Smyth DJA, Sudicky EA, Shikaze SG, Tischuk M, Brourman MD (1997) Integrated funnel-and-gate/GZB product recovery and containment technologies for in situ management of a creosote NAPL-impacted aquifer. In: Proceedings of the 11th National Outdoor Action Conference Ground Water Publishing: Westerville, Ohio, pp 193-203
87. Nagao M, Yahagi T, Seino Y, Sugimura T, Ito N (1977) Mutagenicities of quinoline and its derivatives. Mutat Res 42: 335-342
88. Nagel M, Andreesen JR (1989) Molybdenum-dependent degradation of nicotinic acid by Bacillus sp. DSM 2923. FEMS Microbiol Lett 59: 147-152
89. Nagel M, Andreesen JR (1990) Purification and characterization of the molybdoenzymes nicotinate dehydrogenase and 6-hydroxynicotinate dehydrogenase from Bacillus niacini. Arch Microbiol 154: 605-613
90. Nagel M, Andreesen JR (1991) Bacillus niacini sp. nov., a nicotinate-metabolizing mesophile isolated from soil. Int J Syst Bacteriol 41: 134-139
91. Naik MN, Jackson RB, Stokes J, Swaby RJ (1972) Microbial degradation and phytotoxicity of picloram and other substituted pyridines. Soil Biol Biochem 4: 313-323
92. Ondrus MG, Steinheimer TR (1990) High-performance liquid chromatographic determination of azaarenes and their metabolites in groundwater affected by creosote wood preservatives. J Chromatogr Sci 28: 324-330
93. Orjala J, Gerwick WH (1997) Two quinoline alkoloids from the Caribbean cyanobacterium Lyngbya majuscula. Phytochemistry 45: 1087-1090
94. Parker WJ, Monteith HD, Melcer H (1994) Estimation of anaerobic biodegradation rates for toxic organic compounds in municipal sludge digestion. Water Res 28: 1779-1789
95. Pereira WE, Rostad CE, Garbarino JR, Huit MF (1983) Groundwater contamination by organic bases derived from coal-tar wastes. Environ Toxicol Chem 2: 283-294
96. Pereira WE, Rostad CE, Updegraff DM, Bennett JL (1987a) Fate and movement of azaarenes and their anaerobic biotransformation products in an aquifer contaminated by wood-treatment chemicals. Environ Toxicol Chem 6: 163-176
97. Pereira WE, Rostad CE, Updegraff DM, Bennett JL (1987b) Anaerobic microbial transformations of azaarenes in ground water at hazardous-waste sites. In: Averett RC, McKnight DM (eds) Chemical quality of water and the hydrologic cycle. Lewis, Chelsea, Mich, pp 111-123
98. Pereira WE, Rostad CE, Leiker TJ, Updegraff DM, Bennett JL (1988) Microbial hydroxylation of quinoline in contaminated groundwater: evidence for incorporation of the oxygen atom of water. Appl Environ Microbiol 54: 827-829
99. Rhee SK, Lee GM, Yoon JH, Park YH, Bae, HS, Lee ST (1997) Anaerobic and aerobic degradation of pyridine by a newly isolated denitrifying bacterium. Appl Environ Microbiol 63: 2578-2585
100. Richard JJ, Junk GA (1984) Steam distillation, solvent extraction, and ion exchange for determining polar organics in shale process waters. Anal Chem 56: 1625-1628
101. Riley RG, Garland TR, Shiosaki K, Mann DC, Wildung RE (1981) Alkylpyridines in surface waters, groundwaters, and subsoils of a drainage located adjacent to an oil shale facility. Environ Sci Technol 15: 697-701
102. Röger P, Erben A, Lingens F (1990) Degradation of isoquinoline by Alcaligenes faecalis Pa and Pseudomonas diminuta 7. Biol Chem Hoppe-Seyler 371: 511-513
103. Röger P, Bär G, Lingens F (1995) Two novel metabolites in the degradation pathway of isoquinoline by Pseudomonas diminuta 7. FEMS Microbiol Lett 129: 281-286
104. Romào MJ, Huber R (1998) Structure and function of the xanthine-oxidase family of molybdenum enzymes. Structure and Bonding 90: 69-95
105. Ronen Z, Bollag JM (1991) Pyridine metabolism by a denitrifying bacterium. Can J Microbiol 37: 725-729
106. Ronen Z, Bollag JM (1992) Rapid anaerobic mineralization of pyridine in a subsurface sediment inoculated with a pyridine-degrading Alcaligenes sp. Appl Microbiol Biotechnol 37: 264-269
107. Ronen Z, Bollag TM, Hsu CH, Young JC (1996) Feasibility of bioremediation of a ground water polluted with alkylpyridines. Ground Water 34: 194-199
108. Rüger A, Schwarz G, Lingens F (1993) Degradation of 4-methylquinoline and quinoline by Pseudomonas putida K1. Biol Chem Hoppe-Seyler 374: 479-488
109. Sainsbury M (1978) The quinoline alkaloids. In: Coffey S (ed) Rodd's chemistry of carbon compounds, 2nd edn, vol IV, part G. Elsevier, Amsterdam, pp 171-255
110. Sainsbury M (1987) The quinoline alkaloids. In: Ansell MF (ed) Rodd's chemistry of carbon compounds. Supplement to vol IV part G. Elsevier, Amsterdam, pp 209-244
111. Santodonato J, Howard PH (1981) Azaarenes: sources, distribution, environmental impact, and health effects. In: Saxena J. Fisher F (eds) Hazard assessment of chemicals, vol 1. Academic Press, New York, pp 421-441
112. Scazzocchio C (1994) The purine degradation pathway, genetics, biochemistry and regulation. Prog Ind Microbiol 29: 221-257
113. Schach S, Schwarz G, Fetzner S, Lingens F (1993) Degradation of 3-methylquinoline by Comamonas testosteroni 63. Biol Chem Hoppe-Seyler 374: 175-181
114. Schach S, Tshisuaka B, Fetzner S, Lingens F (1995) Quinoline 2-oxidoreductase and 2-oxo-1,2-dihydroquinoline 5,6-dioxygenase from Comamonas testosteroni 63. The first two enzymes in quinoline and 3-methylquinoline degradation. Eur J Biochem 232: 536-544
115. Schwarz G, Lingens F (1994) Bacterial degradation of N-heterocyclic compounds. In: Ratledge C (ed) Biochemistry of microbial degradation. Kluwer, London New York, pp 459-486
116. Schwarz G, Bauder R, Speer M, Rommel TO, Lingens F (1989) Degradation of quinoline by Pseudomonas fluorescens 3. Pseudomonas putida 86 and Rhodococcus spec. B1. Biol Chem Hoppe-Seyler 370: 1183-1189
117. Seyfried B, Schink B (1990) Fermentative degradation of dipicolinic acid (pyridine-2,6-dicarboxylic acid) by a defined co-culture of strictly anaerobic bacteria. Biodegradation 1: 1-7
118. Shanker R, Bollag JM (1990) Transformation of indole by methanogenic and sulfate-reducing microorganisms isolated from digested sludge. Microb Ecol 20: 171-183
119. Shanker R, Kaiser JP, Bollag JM (1991) Microbial transformation of heterocyclic molecules in deep subsurface sediments. Microb Ecol 22: 305-316
120. Shimizu S, Watanabe N, Kataoka T, Shoji T, Abe N, Morishita S, Ichimura H (1993) Pyridine and pyridine derivatives, In: Elvers B, Hawkins S, Russey W, Schulz G (eds) Ullmann's Encyclopedia of Industrial Chemistry, vol A22. VCH Weinheim, pp 399-430
121. Shukla OP (1974) Microbial decomposition of α-picoline. Indian J Biochem Biophys 11: 192-200
122. Shukla OP (1984) Microbial transformation of pyridine derivatives. J Sci Ind Res 43: 98-116
123. Shukla OP (1986) Microbial transformation of quinoline by a Pseudomonas sp. Appl Environ Microbiol 51: 1332-1342
124. Shukla OP (1989) Microbiological degradation of quinoline by Pseudomonas stutzeri: the coumarin pathway of quinoline catabolism. Microbios 59: 47-63
125. Shukla OP, Kaul SM (1973) Microbial transformation of α-picolinate by Bacillus sp. Indian J Biochem Biophys 10: 176-178
126. Shukla OP, Kaul SM (1974) A constitutive pyridine degrading system in Corynebacterium sp. Indian J Biochem Biophys 11: 201-207
127. Shukla OP, Kaul SM (1986) Microbiological transformation of pyridine N-oxide and pyridine by Nocardia sp. Can J Microbiol 32: 330-341
128. Shukla OP, Kaul SM, Khanna M (1977) Microbial transformation of pyridine derivatives: α-picolinate metabolism by a gram-negative coccus. Indian J Biochem Biophys 14: 292-295
129. Sims GK, O'Loughlin EJ (1989) Degradation of pyridines in the environment. CRC Crit Rev Environ Control 19: 309-340
130. Sims GK, Sommers EE (1985) Degradation of pyridine derivatives in soil. J Environ Qual 14: 580-584
131. Sims GK, Sommers LE (1986) Biodegradation of pyridine derivatives in soil suspensions. Environ Toxicol Chem 5: 503-509
132. Sims GK, Sommers LE, Konopka A (1986) Degradation of pyridine by Micrococcus luteus isolated from soil. Appl Environ Microbiol 51: 963-968
133. Singh RP, Shukla OP (1986) Isolation, characterization, and metabolic activities of Bacillus brevis degrading isonicotinic acid. J Ferment Technol 64: 109-117
134. Smith SC, Ainsworth CC, Traina SJ, Hicks RJ (1992) Effect of sorption on the biodegradation of quinoline. Soil Sci Soc Am J 56: 737-746
135. Southworth GR, Keller JL (1984) Mobilization of azaarenes from wastewater treatment plant biosludge. Bull Environ Contam Toxicol 32: 445-452
136. Stadtman ER, Stadtman TC, Pastan I, Smith LD (1972) Clostridium barkeri sp. n. J Bacteriol 110: 758-760
137. Stuermer DH, Ng DJ, Morris CJ (1982) Organic contaminants in groundwater near an underground coal gasification site in northeastern Wyoming. Environ Sci Technol 16: 582-587
138. Szecsody JE, Streile GP (1992) Process controlling the slow sorption of quinoline onto clay during transport in columns. Chemosphere 24: 1127-1145
139. Thomas JM, Wilson JT, Ward CH (1997) Microbial processes in the subsurface. Subsurf Restor 1997: 99-111
140. Turney GL, Goerlitz OF (1990) Organic contamination of ground water at gas works park, Seattle, Washington. Ground Water Monit Rev 10: 187-198
141. Vogels GD, Drift C van der (1976) Degradation of purines and pyrimidines by microorganisms. Bacteriol Rev 40: 403-468
142. Wang YT, Suidan MT, Pfeffer JT (1984) Anaerobic biodegradation of indole to methane. Appl Environ Microbiol 48: 1058-1060
143. Warshawsky D (1992) Environmental sources, carcinogenicity, mutagenicity, metabolism and DNA binding of nitrogen and sulfur heterocyclic aromatics. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev 10: 1-71
144. Watson GK, Cain RB (1975) Microbial metabolism of the pyridine ring. Metabolic pathways of pyridine biodegradation by soil bacteria. Biochem J 146: 157-172
145. Watson GK, Houghton C, Cain RB (1974) Microbial metabolism of the pyridine ring. The metabolism of pyridine-3,4-diol (3,4-dihydroxypyridine) by Agrobacterium sp. Biochem J 140: 277-292
146. Willems MI, Dubois G, Boyd DR, Davies RJH, Hamilton L, McCullough JJ, Bladeren PJ van (1992) Comparison of the mutagenicity of quinoline and all monohydroxyquinolines with a series of arene oxide, trans-dihydrodiol, diol epoxide, N-oxide and arene hydrate derivatives of quinoline in the Ames Salmonella microsome test. Mutat Res 278: 227-236
147. Zachara JM, Ainsworth CC, Felice LJ, Resch CT (1986) Quinoline sorption to subsurface materials: role of pH and retention of the organic cation. Environ Sci Technol 20: 620-627
148. Zachara JM, Ainsworth CC, Cowan CE, Schmidt RL (1990) Sorption of aminonaphthalene and quinoline on amorphous silica. Environ Sci Technol 24: 118-126
149. Zefirov NS, Agapova SR, Terentiev PB, Bulakhova IM, Vasyukova NI, Modyanova LV (1994) Degradation of pyridine by Arthrobacter crystallopoietes and Rhodococcus opacus strains. FEMS Microbiol Lett 118: 71-74
150. Zhu S, Bell PRF, Greenfield PF (1988) Adsorption of pyridine onto spent Rundle oil shale in dilute aqueous solution. Water Res 22: 1331-1337