Degradation of the fluoroquinolone enrofloxacin by the brown rot fungus Gloeophyllum striatum: Identification of metabolites

Applied and Environmental Microbiology

Volumn 63, Issue 11, 1997, Pages 4272-4281

  Wetzstein, Heinz Georg ^a   Schmeer, Norbert ^a   Karl, Wolfgang ^a  

^a BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ENROFLOXACIN; HYDROXYL RADICAL; QUINOLINE DERIVED ANTIINFECTIVE AGENT; XENOBIOTIC AGENT;

ARTICLE; DRUG DEGRADATION; FUNGUS; FUNGUS GROWTH; NONHUMAN; WOOD;

EID: 0030721747     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.63.11.4272-4281.1997     Document Type: Article

References (51)

1. Alef, K. 1991. Methodenhandbuch Bodenmikrobiologie, p. 89. Ecomed Verlagsgesellschaft mbH, Landsberg, Germany.
2. Andreoni, V., G. Baggi, and S. Bernasconi. 1995. Microbial degradation of nitrogenous xenobiotics of environmental concern. Prog. Ind. Microbiol. 32:1-36.
3. Backa, S., J. Gierer, T. Reitberger, and T. Nilsson. 1992. Hydroxyl radical activity in brown-rot fungi studied by a new chemiluminescence method. Holzforschung 46:61-67.
4. Barr, D. P., and S. D. Aust. 1994. Pollutant degradation by white rot fungi, p. 49-72. In G. W. Ware (ed.), Reviews of environmental contamination and toxicology. Springer Verlag, New York, N.Y.
5. Bauer, I., A. de Beyer, B. Tshisuaka, S. Fetzner, and F. Lingens. 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.
6. Boominathan, K., and C. A. Reddy. 1991. Fungal degradation of lignin: biotechnological applications, p. 763-822. In D. K. Arora, B. Rai, K. G. Mukerji, and G. R. Knudsen (ed.), Handbook of applied mycology, vol. 4. Marcel Dekker, Inc., New York, N.Y.
7. Booth, D. M. 1994. Enrofloxacin revisited. Vet. Med. 89:744-753.
8. Bumpus, J. A. 1993. White rot fungi and their potential use in soil bioremediation processes. Soil Biochem. 8:65-100.
9. Bumpus, J. A., M. Tien, D. Wright, and S. D. Aust. 1985. Oxidation of persistent environmental pollutants by a white rot fungus. Science 228:1434-1436.
10. Buswell, J. A. 1991. Fungal degradation of lignin, p. 425-480. In D. K. Arora, B. Rai, K. G. Mukerji, and G. R. Knudsen (ed.), Handbook of applied mycology, vol. 1. Marcel Dekker, Inc., New York, N.Y.
11. Collett, O. 1992. Aromatic compounds as growth substrates for isolates of the brown-rot fungus Lentinus lepideus (Fr. ex. Fr.) Fr. Mater. Org. 27:67-77.
12. Domagala, J. M. 1994. Structure-activity and structure-side-effect relationship for the quinolonc antibacterials. J. Antimicrob. Chemother. 33:685-706.
13. Edlund, C., L. Lindqvist, and C. E. Nord. 1988. Norfloxacin binds to human fecal material. Antimicrob. Agents Chemother. 32:1869-1874.
14. Eggert, C., U. Temp, J. F. D. Dean, and K.-E. L. Eriksson. 1996. A fungal metabolite mediates degradation of non-phenolic lignin structures and synthetic lignin by laccase. FEBS Lett. 391:144-148.
15. Evans, C. S., M. V. Dutton, F. Guillen, and R. G. Veness. 1994. Enzymes and small molecular mass agents involved with lignocellulose degradation. FEMS Microbiol. Rev. 13:235-240.
16. 14C-labeled lignocelluloses by basidiomycetes: degradation and soluhilization of the lignin and cellulose components. Mycologia 74:943-951.
17. Frost, A. J. 1991. Antibiotics and animal production, p. 181-194. In J. B. Woolcock (ed.), Microbiology of animals and animal products. Elsevier, Amsterdam, The Netherlands.
18. Greene, C. E., and S. C. Budsberg. 1993. Veterinary use of quinolones, p. 473-488. In D. C. Hooper and J. S. Wolfson (ed.), Quinolone antimicrobial agents, 2nd ed. American Society for Microbiology, Washington, D.C.
19. Halliwell, B., and J. M. Gutterridge. 1989. Free radicals in biology and medicine, 2nd ed. Oxford University Press, Oxford, United Kingdom.
20. Harper, D. B., and D. O'Hagan. 1994. The fluorinated natural products. Nat. Products Rep. 11:123-133.
21. Hektoen, H., J. A. Berge, V. Hormazabal, and M. Yndestad. 1995. Persistence of antibacterial agents in marine sediments. Aquaculture 133:175-184.
22. Hirano, T., H. Tanaka, and A. Enoki. 1995. Extracellular substance from the brown-rot basidiomycete Tyromyces palustris that reduces molecular oxygen to hydroxyl radicals and ferric iron to ferrous iron. Mokuzai Gakkaishi 41:334-341.
23. Holzman, D. 1995. Refractory chemical residues in soils may be safe. ASM News 61:445-446.
24. Hyde, S. M., and P. M. Wood. 1996. Kinetic and antigenic similarities for cellobiose dehydrogenase from the brown rot fungus Coniophora puteana and the white rot fungus Phanerochaete chrysosporium. FEMS Microbiol. Lett. 145:439-444.
25. Joseleau, J.-P., S. Gharibian, J. Comtat, A. Lefebvre, and K. Ruel. 1994. Indirect involvement of ligninolytic enzyme systems in cell wall degradation. FEMS Microbiol. Rev. 13:255-264.
26. Kaiser, J.-P., Y. Feng, and J.-M. Bollag. 1996. Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions. Microbiol. Rev. 60:483-498.
27. Karabalut, N., and G. L. Drusano. 1993. Pharmacokinetics of the quinolone antimicrobial agents, p. 195-223. In D. C. Hooper and J. S. Wolfson (ed.), Quinolone antimicrobial agents, 2nd ed. American Society for Microbiology, Washington, D.C.
28. Kirk, T. K., R. Ibach, M. D. Mozuch, A. H. Conner, and T. L. Highley. 1991. Characteristics of cotton cellulose depolymerized by a brown-rot fungus, by acid, or by chemical oxidants. Holzforschung 45:239-244.
29. Kleman-Leyer, K., E. Agosin, A. H. Conner, and T. K. Kirk. 1992. Changes in molecular size distribution of cellulose during attack by white rot and brown rot fungi. Appl. Environ. Microbiol. 58:1266-1270.
30. Koenigs, J. W. 1974. Hydrogen peroxide and iron: a proposed system for decomposition of wood by brown-rot basidiomycetes. Wood Fiber 6:66-80.
31. 14C)-sarafloxacin hydrochloride in soil. Environ. Toxicol. Chem. 16:462-471.
32. Markham, P., and M. J. Bazin. 1991. Decomposition of cellulose by fungi, p. 379-424. In D. K. Arora, B. Rai, K. G. Mukerji, and G. R. Knudsen (ed.), Handbook of applied mycology, vol. 1. Marcel Dekker, Inc., New York, N.Y.
33. Martens, R., H.-G. Wetzstein, F. Zadrazil, M. Capelari, P. Hoffmann, and N. Schmeer. 1996. Degradation of the fluoroquinolone enrofloxacin by wood-rotting fungi. Appl. Environ. Microbiol. 62:4206-4209.
34. Nowara, A., J. Burhenne, and M. Spiteller. 1997. Binding of fluoroquinolone carboxylic acid derivatives to clay. J. Agric. Food Chem. 45:1459-1463.
35. Orth, A. B., and M. Tien. 1995. Biotechnology of lignin degradation, p. 287-302. In K. Esser and P. A. Lemke (ed.), The mycota, vol. II. Genetics and biotechnology. Springer Verlag, Berlin, Germany.
36. Ribbons, D. W., A. E. Cass, J. T. Rossiter, S. J. C. Taylor, M. P. Woodland, D. A. Widdowson, S. R. Williams, P. B. Baker, and R. E. Martin. 1987. Biotransformation of fluoroaromatic compounds. J. Fluorine Chem. 37:299-326.
37. Ritschkoff, A.-C., M. Rättö, J. Buchert, and L. Viikari. 1995. Effect of carbon source on the production of oxalic acid and hydrogen peroxide by brown-rot fungus Poria placenta. J. Biotechnol. 40:179-186.
38. Schlosser, D., R. Grey, and W. Fritsche. 1997. Patterns of ligninolytic enzymes in Trametes versicolor. Distribution of extra-and intracellular enzyme activities during cultivation on glucose, wheat straw and beech wood. Appl. Microbiol. Biotechnol. 47:412-418.
39. Schwarz, G., and F. Lingens. 1994. Bacterial degradation of N-heterocyclic compounds, p. 459-486. In C. Ratledge (ed.), Biochemistry of microbial degradation. Kluwer Academic Publishers, Dordrecht, The Netherlands.
40. Stalpers, J. A. 1978. Identification of wood-inhabiting fungi in pure culture. Studies in mycology, no. 16. Centraalbureau voor Schimmelcultures, Baarn, The Netherlands.
41. Thorn, G. R., C. A. Reddy, D. Harris, and E. A. Paul. 1996. Isolation of saprophytic basidiomycetes from soil. Appl. Environ. Microbiol. 62:4288-4292.
42. Vancutsem, P. M., J. G. Babish, and W. S. Schwark. 1940. The fluoroquinolone antimicrobials: structure, antimicrobial activity, pharmacokinetics, clinical use in domestic animals and toxicity. Cornell Vet. 80:173-186.
43. Wetzstein, H.-G. Unpublished data.
44. Wetzstein, H.-G., and A. de Jong. 1996. In vitro bactericidal activity and postantibiotic effect of fluoroquinulones used in veterinary medicine. Compend. Contin. Educ. Pract. Vet. 18(Suppl.):S22-S29.
45. Wetzstein, H.-G., H.-G. Rast, J. P. E. Anderson, J. Köster, and N. Schmeer. 1996. In vitro degradation of the fluoroquinolone enrofloxacin by two species of wood-rot fungi, p. 414, abstr. Q-168. In Abstracts of the 96th General Meeting of the American Society for Microbiology 1996. American Society for Microbiology, Washington, D.C.
46. Wetzstein, H.-G., N. Schmeer, A. Dalhoff, and W. Karl. 1997. Degradation of the fluoroquinolone ciprofloxacin by the brown rot fungus Gloeophyllum striatum DSM 9592, p. 519, abstr. Q-388. In Abstracts of the 97th General Meeting of the American Society for Microbiology 1997. American Society for Microbiology, Washington, D.C.
47. Wicklow, D. T. 1992. The coprophilous fungal community: an experimental system. p. 715-728. In G. C. Carrol and D. T. Wicklow (ed.), The fungal community. Its organisation and role in the ecosystem, 2nd ed. Marcel Dekker, Inc., New York, N.Y.
48. Wicklow, D. T., R. W. Detroy, and B. A. Jessee. 1980. Decomposition of lignocellulose by Cyathus stercoreus (Schw.) de Toni NRRL 6473, a "white rot" fungus from entile dung. Appl. Environ. Microbiol. 40:169-170.
49. Wolfson, J. S., and D. C. Hooper. 1989. Fluoroquinolone antimicrobial agents. Clin. Microbiol. Rev. 2:378-424.
50. Wood, P. M. 1994. Pathways for production of Fenton's reagent by wood-rotting fungi. FEMS Microbiol. Rev. 13:313-320.
51. World Health Organization. 1995. Evaluation of certain veterinary drug residues in food. Forty-third report of the Joint FAO/WHO Expert Committee on Food Additives. WHO Tech. Rep. Sci. 855:17-24.