Abstract
Eighteen different aerobic bacteria were isolated which utilized quinoline as sole source of carbon, nitrogen, and energy. Attempts were unsuccessful at isolating anaerobic quinoline-degrading bacteria. The optimal concentration of quinoline for growth was in the range of 2.5 to 5 mM. Some organisms excreted 2-hydroxyquinoline as the first intermediate. Hydroxylation of quinoline was catalyzed by a dehydrogenase which was induced in the presence of quinoline or 2-hydroxyquinoline. Quinoline dehydrogenase activity was dependent on the availability of molybdate in the growth medium. Growth on quinoline was inhibited by tungstate, an antagonist of molybdate. Partially purified quinoline dehydrogenase from Pseudomonas putida Chin IK indicated the presence of flavin, iron-sulfur centers, and molybdenum-binding pterin. M r of quinoline dehydrogenase was about 300 kDa in all isolates investigated.
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Abbreviations
- APS:
-
ammonium peroxodisulfate
- DCPIP:
-
2,6-dichlorophenol-indophenol
- EEO:
-
electroendosmosis
- MTT:
-
thiazolyl blue
- PES:
-
phenazine ethosulfate
- TEMED:
-
N,N,N′,N′-tetramethyl-ethylenediamine
References
AislabieJ, BejAK, HurstH, RothenburgerS, AtlasRM (1990) Microbial degradation of quinoline and methylquinolines. Appl Environ Microbiol 56:345–351
BeedhamC (1985) Molybdenum-hydroxylases as drug metabolizing enzymes. Drug Metab Rev 16:119–156
BennettJL, UpdegraffDM, PereiraWE, RostadCE (1985) Isolation and identification of four species of quinoline-degrading pseudomonads from a creosote-contaminated site at Pensacola, Florida. Microbios Lett 29:147–154
BerryDF, FrancisAJ, BollagJ-M (1987) Microbial metabolism of homocyclic and heterocyclic aromatic compounds under anaerobic conditions. Microbiol Rev 51:43–59
BradfordMM (1976) A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254
BrockmanFJ, DenovanBA, HicksRJ, FredricksonJK (1989) Isolation and characterization of quinoline-degrading bacteria from subsurface sediments. Appl Environ Microbiol 55:1029–1032
BuntingJW, LaderouteKR, NorrisDJ (1980) Specificity of xanthine oxidase for nitrogen heteroaromatic cation substrates. Can J Biochem 58:49–57
CoughlanMP (1980) Aldehyde oxidase, xanthine oxidase and xanthine dehydrogenase: hydroxylases containing molybdenum, iron-sulphur and flavin. In: CoughlanMP (ed) Molybdenum and molybdenum-containing enzymes. Pergamon Press, Oxford, pp 119–185
CoughlanMP, JohnsonJL, RajagopalanKV (1980) Mechanism of inactivation of molybdoenzymes by cyanide. J Biol Chem 255:2694–2699
CrippsRE (1973) The microbial metabolism of thiophen-2-carboxylate. Biochem J 134:353–366
DembekG, LingensF (1988) Isolation and characterization of a meta-cleavage product in the degradation of quinaldic acid by Azotobacter sp. FEMS Microbiol Lett 56:261–264
DietrichsD, MeyerM, SchmidtB, AndreesenJR (1990) Purification of NADPH-dependent electron-transferring flavoproteins and N-terminal protein sequence data of dihydrolipoamide dehydrogenases from anaerobic, glycine-utilizing bacteria. J Bacteriol 172:2088–2095
DilworthGL (1983) Occurrence of molybdenum in the nicotinic acid hydroxylase from Clostridium barkeri. Arch Biochem Biophys 221:565–569
DürreP, AndreesenJR (1982) Separation and quantitation of purines and their anaerobic and aerobic degradation products by high-pressure liquid chromatography. Anal Biochem 123:32–42
EnsignJC, RittenbergSC (1964) The pathway of nicotinic acid oxidation by a Bacillus species. J Biol Chem 239:2285–2291
EnsignJC, RittenbergSC (1965) The formation of a blue pigment in bacterial oxidation of isonicotinic acid. Arch Mikrobiol 51:384–392
FreudenbergW, KoenigK, AndreesenJR (1988) Nicotine dehydrogenase from Arthrobacter oxidans: a molybdenum-containing hydroxylase. FEMS Microbiol Lett 52:13–18
GrantDJW, Al-NajjarTR (1976) Degradation of quinoline by a soil bacterium. Microbiols 15:177–189
HintonSM, DeanD (1990) Biogenesis of molybdenum cofactors. Crit Rev Microbiol 17:169–188
HochsteinLI, RittenbergSC (1959) The bacterial oxidation of nicotine. II. The isolation of the first oxidative product and its identification as 6-hydroxynicotine. J Biol Chem 234:156–160
JagusR, PollardJW (1988) Use of dried milk for immunoblotting. In: WalkerJM (ed) New protein techniques. Humana Press, Clifton, NJ, pp 403–408
JohnsonJL, RajagopalanKV (1982) Structural and metabolic relationship between the molybdenum cofactor and urothione. Proc Natl Acad Sci USA 79:6856–6860
JohnsonJL, BastianNR, RajagopalanKV (1990) Molybdopterin guanine dinucleotide — a modified form of molybdopterin identified in the molybdenum cofactor of dimethyl sulfoxide reductase from Rhodobacter sphaeroides forma-specialis denitrificans. Proc Natl Acad Sci USA 87:3190–3194
KadoCI, LiuS-T (1981) Rapid procedure for detection and isolation of large and small plasmids. J Bacteriol 145:1365–1373
KoenigK, AndreesenJR (1989) Molybdenum involvement in aerobic degradation of 2-furoic acid by Pseudomonas putida Fu1. Appl Environ Microbiol 55:1829–1834
KoenigK, AndreesenJR (1990) Xanthine dehydrogenase and 2-furoyl-CoenzymeA dehydrogenase from Pseudomonas putida Fu1: two molybdenum-containing dehydrogenases of novel structural composition. J Bacteriol 172:5999–6009
KrenitskyTA, NeilSM, ElionGB, HitchingsGH (1972) A comparison of the specificities of xanthine oxidase and aldehyde oxidase. Arch Biochem Biophys 150:585–599
KrügerB, MeyerO (1986) The pterin (bactopterin) of carbon monoxide dehydrogenase from Pseudomonas carboxydoflava. Eur J Biochem 157:121–128
KrügerB, MeyerO, NagelM, AndreesenJR, MeinckeM, BockE, BlümleS, ZumftWG (1987) Evidence for the presence of bactopterin in the eubacterial molybdoenzymes nicotinic acid dehydrogenase, nitrite oxidoreductase, and respiratory nitrate reductase. FEMS Microbiol Lett 48:225–227
KuhnEP, SuflitaJM (1989) Microbial degradation of nitrogen, oxygen and sulfur heterocyclic compounds under anaerobic conditions: studies with aquifer samples. Environ Toxicol Chem 8:1149–1158
MillsCF, BremnerJ (1980) Nutritional aspects of molybdenum in animals. In: CoughlanMP (ed) Molybdenum and molybdenum-containing enzymes. Pergamon Press, Oxford, pp 517–542
NagelM, AndreesenJR (1989) Molybdenum-dependent degradation of nicotinic acid by Bacillus sp. DSM 2923. FEMS Microbiol Lett 59:147–152
NagelM, AndreesenJR (1990) Purification and characterization of the two molybdenum-containing enzymes nicotinate dehydrogenase and 6-hydroxynicotinate dehydrogenase from Bacillus niacini. Arch Microbiol 154:605–613
Nagel M, Andreesen JR (1991) Bacillus niacini sp. nov., a nicotinate metabolizing mesophile isolated from soil. Int J Syst Bacteriol 41 (in press)
NagelM, KoenigK, AndreesenJR (1989) Bactopterin as component of eubacterial dehydrogenases involved in hydroxylation reactions initiating the degradation of nicotine, nicotinate, and 2-furancarboxylate. FEMS Microbiol Lett 60:323–326
PereiraWE, RostadCE, UpdegraffDM, BennettJL (1987) Fate and movement of azaarenes and their anaerobic biotransformation products in an aquifer contaminated by wood-treatment chemicals. Environ Toxicol Chem 6:163–176
PereiraWE, RostadCE, LeikerTJ, UpdegraffDM, BennettJL (1988) Microbial hydroxylation of quinoline in contaminated groundwater: evidence for incorporation of the oxygen atom of water. Appl Environ Microbiol 54:827–829
RajagopalanKV (1988) Molybdenum: An essential trace element in human nutrition. Annu Rev Nutr 8:401–427
RögerP, LingensF (1989) Degradation of quinoline-4-carboxylic acid by Microbacterium sp. FEMS Microbiol Lett 57:279–282
SchwarzG, SenghasE, ErbenA, SchäferB, LingensF, HökeH (1988) Microbial metabolism of quinoline and related compounds. I. Isolation and characterization of quinoline-degrading bacteria. System Appl Microbiol 10:185–190
SchwarzG, BauderR, SpeerM, RommelTO, LingensF (1989) Microbial metabolism of quinoline and related compounds. II. Degradation of quinoline by Pseudomonas fluorescens 3, Pseudomonas putida 86 and Rhodococcus spec. B1. Biol Chem Hoppe-Seyler 370:1183–1189
ShuklaOP (1984) Microbial transformation of pyridine derivatives. J Sci Ind Res 43:98–116
ShuklaOP (1986) Microbial transformation of quinoline by a Pseudomonas sp. Appl Environ Microbiol 51:1332–1342
ShuklaOP (1989) Microbiological degradation of quinoline by Pseudomonas stutzeri: the coumarin pathway of quinoline catabolism. Microbios 59:47–63
SiegmundI, KoenigK, AndreesenJR (1990) Molybdenum involvement in aerobic degradation of picolinic acid by Arthrobacter picolinophilus. FEMS Microbiol Lett 67:281–284
SouthworthGR, KellerJL (1984) Mobilization of azaarenes from wastewater treatment plant biosludge. Bull Environ Contam Toxicol 32:445–452
StubleyC, StellJGP, MathiesonDW (1979) The oxidation of azaheterocycles with mammalian liver aldehyde oxidase. Xenobiotica 9:475–484
TadaM, TakahashiK, KawazoeY, ItoN (1980) Binding of quinoline to nucleic acids in a subcellular microsomal system. Chem Biol Interact 29:257–266
TibblesPE, MüllerR, LingensF (1989) Microbial degradation of quinoline and related compounds. III. Degradation of 3-chloroquinoline-8-carboxylic acid by Pseudomonas spec. EK III. Biol Chem Hoppe-Seyler 370:1191–1196
TrudgillPW (1969) The microbial metabolism of furans. In: GibsonDT (ed) Microbial degradation of organic compounds. Marcel Dekker, New York, pp 295–308
VogelsGD, van derDriftC (1976) Degradation of purines and pyrimidines by microorganisms. Bacteriol Rev 40:403–468
WagnerR, CammackR, AndreesenJR (1984) Purification and characterization of xanthine dehydrogenase from Clostridium acidiurici grown in the presence of selenium. Biochim Biophys Acta 791:63–74
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Blaschke, M., Kretzer, A., Schäfer, C. et al. Molybdenum-dependent degradation of quinoline by Pseudomonas putida Chin IK and other aerobic bacteria. Arch. Microbiol. 155, 164–169 (1991). https://doi.org/10.1007/BF00248612
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DOI: https://doi.org/10.1007/BF00248612