Hydroxylated metabolites of 2,4-dichlorophenol imply a Fenton-type reaction in Gloeophyllum striatum

Applied and Environmental Microbiology

Volumn 66, Issue 6, 2000, Pages 2479-2483

  Schlosser, Dietmar ^a   Fahr, Kristina ^b   Karl, Wolfgang ^c   Wetzstein, Heinz Georg ^c  

^a HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

^b HANS KNÖLL INSTITUTE   (Germany)

^c BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DICHLOROPHENOL; HYDRAZIDE; MANNITOL;

ARTICLE; BASIDIOMYCETES; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; GLOEOPHYLLUM STRIATUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; REACTION ANALYSIS;

BASIDIOMYCOTA; CARBON DIOXIDE; CARBON RADIOISOTOPES; CHLOROPHENOLS; FERROUS COMPOUNDS; HYDROGEN PEROXIDE; HYDROXYLATION; IRON;

BASIDIOMYCOTA; FUNGI; GLOEOPHYLLUM; GLOEOPHYLLUM STRIATUM;

EID: 0034129589     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.66.6.2479-2483.2000     Document Type: Article

References (24)

1. 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.
2. Backa, S., K. Jansho, and T. Reitberger. 1997. Detection of hydroxyl radicals by a chemiluminescence method - a critical review. Holzforschung 51:557-564.
3. Buswell, J. A., K.-E. Eriksson, J. K. Gupta, S. G. Hamp, and I. Nordh. 1982. Vanillic acid metabolism by selected soft-rot, brown-rot, and white-rot fungi. Arch. Microbiol. 131:366-374.
4. De Jong, E., and J. A. Field. 1997. Sulfur tuft and turkey tail: biosynthesis and biodegradation of organohalogens by basidiomycetes. Annu. Rev. Microbiol. 51:375-414.
5. Deschler, C., R. Duran, M. Junqua, C. Landou, J.-C. Salvado, and P. Gaulas. 1998. Involvement of 3,4-dichlorophenol hydroxylase in degradation of 3,4-dichlorophenol by the white rot fungus Phanerochaete chrysosporium. J. Mol. Catal. B Enzym. 5:423-428.
6. Drew, H. D. K., and F. H. Pearmann. 1937. Chemiluminescent organic compounds. Part II. The effect of substituents on the closure of phthalhydrazides to 5-and 6-membered rings. J. Chem. Soc. 1937:26-33.
7. Elstner, E. F. 1990. Der Sauerstoff. Biochemie, Biologie, Medizin, p. 22-40. Wissenschaftsverlag, Mannheim, Germany.
8. Elvidge, J. A., and A. P. Redman. 1960. 1,4-Dimethoxyphthalazine and the other O-and N-methyl derivatives of phthalhydrazide. J. Chem. Soc. 1960: 1710-1714.
9. Fahr, K., H.-G. Wetzstein, R. Grey, and D. Schlosser. 1999. Degradation of 2,4-dichlorophenol and pentachlorophenol by two brown rot fungi. FEMS Microbiol. Lett. 175:127-132.
10. Gierer, J., E. Yang, and T. Reitberger. 1992. The reactions of hydroxyl radicals with aromatic rings in lignins, studied with creosot and 4-methylveratrol. Holzforschung 46:495-504.
11. Grey, R., C. Höfer, and D. Schlosser. 1998. Degradation of 2-chlorophenol and formation of 2-chloro-1,4-benzoquinone by mycelia and cell-free crude culture liquids of Trametes versicolor in relation to extracellular laccase activity. J. Basic Microbiol. 38:371-382.
12. Hofrichter, M., F. Bublitz, and W. Fritsche. 1994. Unspeciflc degradation of halogenated phenols by the soil fungus Penicillium frequentans Bi 7/2. J. Basic Microbiol. 34:163-172.
13. Hyde, S. M., and P. M. Wood. 1997. A mechanism for the production of hydroxyl radicals by the brown-rot fungus Coniophora putanea: Fe(II) reduction by cellobiose dehydrogenase and Fe(II) oxidation at a distance from the hyphae. Microbiology 143:259-266.
14. Kerem, Z., K. A. Jensen, and K. E. Hammel. 1999. Biodegradative mechanism of the brown rot hasidiomycete Gloeophyllum trabeum: evidence for an extracellular hydroquinone-driven Fenton reaction. FEBS Lett. 446:49-54.
15. Koenigs, J. W. 1974. Hydrogen peroxide and iron: a proposed system for decomposition of wood by brown-rot basidiomycetes. Wood Fiber 6:66-80.
16. Ojima, H. 1987. Chemiluminescence and metal chelate formation properties of 5-hydroxyphthalohydrazide. Bull. Aichi Univ. Educ. 36:39-48.
17. Paszczynski, A., R. Crawford, D. Funk, and B. Goodell. 1999. De novo synthesis of 4,5-dimethoxycatechol and 2,5-dimethoxyhydroquinone by the brown rot fungus Gloeophyllum trabeum. Appl. Environ. Microbiol. 65:674-679.
18. Perkins, E. J., M. P. Gordon, O. Caceres, and P. F. Lurquin. 1990. Organization and sequence analysis of the 2,4-dichlorophenol hydroxylase and dichlorocatechol oxidative operons of plasmid pJP4. J. Bacteriol. 172:2351-2359.
19. Schiller, J., J. Arnold, J. Schwinn, H. Sprinz, O. Brede, and K. Arnold. 1998 Reactivity of cartilage and selected carbohydrates with hydroxyl radicals. An NMR study to detect degradation products. Free Radic. Res. 28:215-228.
20. Schwien, U., E. Schmidt, H.-J. Knackmuss, and W. Reineke. 1988. Degradation of chlorosubstituted aromatic compounds by Pseudomonas sp. strain b13: fate of 3,5-dichlorocatechol. Arch. Microbiol. 150:78-84.
21. Tang, W. Z., and C. P. Huang. 1996. 2,4-Dichlorophenol oxidation kinetics by Fenton's reagent. Environ. Technol. 17:1371-1376.
22. 2 system, γ-radiolysis, and microsomes. Biochem. Biophys. Res. Commun. 192:568-574.
23. Wetzstein, H.-G., N. Schmeer, and W. Karl. 1997. Degradation of the fluoroquinolone enrofloxacin by the brown rot fungus Gloeophyllum striatum: identification of metabolites. Appl. Environ. Microbiol. 63:4272-4281.
24. Wetzstein, H.-G., M. Stadler, H.-V. Tichy, A. Dalhoff, and W. Karl. 1999. Degradation of ciprofloxacin by basidiomycetes and identification of metabolites generated by the brown rot fungus Gloeophyllum striatum. Appl. Environ. Microbiol. 65:1556-1563.