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

被引:33
作者
Schlosser, D
Fahr, K
Karl, W
Wetzstein, HG
机构
[1] UFZ Helmholtz Ctr Environm Res, D-06120 Halle, Germany
[2] Hans Knoll Inst Nat Stoff Forsch EV, Dept Cell & Mol Biol, D-07745 Jena, Germany
[3] Bayer AG, Cent Res, D-51368 Leverkusen, Germany
[4] Bayer AG, Anim Hlth Res & Dev, D-51368 Leverkusen, Germany
关键词
D O I
10.1128/AEM.66.6.2479-2483.2000
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
While degrading 2,4-dichlorophenol, two strains of Gloeophyllum striatum, a basidiomycetous fungus causing brown rot decay of wood, simultaneously produced 4-chlorocatechol and 3,5-dichlorocatechol. These metabolites were identified by comparing high-performance liquid chromatography retention times and mass spectral data with those of chemically synthesized standards. Under similar conditions, 3-hydroxyphthalic hydrazide was generated from phthalic hydrazide, a reaction assumed to indicate hydroxyl radical formation. Accordingly, during chemical degradation of 2,4-dichlorophenol by Fenton's reagent, identical metabolites were formed. Both activities, the conversion of 2,4-[U-C-14]dichlorophenol into (CO2)-C-14 and the generation of 3-hydroxyphthalic hydrazide, were strongly inhibited by the hydroxyl radical scavenger mannitol and in the absence of iron. These results provide new evidence in favor of a Fenton-type degradation mechanism operative in Gloeophyllum.
引用
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页码:2479 / 2483
页数:5
相关论文
共 24 条
[1]   HYDROXYL RADICAL ACTIVITY IN BROWN-ROT FUNGI STUDIED BY A NEW CHEMILUMINESCENCE METHOD [J].
BACKA, S ;
GIERER, J ;
REITBERGER, T ;
NILSSON, T .
HOLZFORSCHUNG, 1992, 46 (01) :61-67
[2]   Detection of hydroxyl radicals by a chemiluminescence method - A critical review [J].
Backa, S ;
Jansbo, K ;
Reitberger, T .
HOLZFORSCHUNG, 1997, 51 (06) :557-564
[3]   VANILLIC ACID METABOLISM BY SELECTED SOFT-ROT, BROWN-ROT, AND WHITE-ROT FUNGI [J].
BUSWELL, JA ;
ERIKSSON, KE ;
GUPTA, JK ;
HAMP, SG ;
NORDH, I .
ARCHIVES OF MICROBIOLOGY, 1982, 131 (04) :366-374
[4]   Sulfur tuft and turkey tail: Biosynthesis and biodegradation of organohalogens by basidiomycetes [J].
deJong, E ;
Field, JA .
ANNUAL REVIEW OF MICROBIOLOGY, 1997, 51 :375-414
[5]   Involvement of 3,4-dichlorophenol hydroxylase in degradation of 3,4-dichlorophenol by the white rot fungus Phanerochaete chrysosporium [J].
Deschler, C ;
Duran, R ;
Junqua, M ;
Landou, G ;
Salvado, JC ;
Goulas, P .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1998, 5 (1-4) :423-428
[6]   Chemiluminescent organic compounds. Part II. The effect of substituents on the closure of phthalhydrazides to 5-and 6-membered rings. [J].
Drew, HDK ;
Pearman, FH .
JOURNAL OF THE CHEMICAL SOCIETY, 1937, :26-33
[7]  
ELSTNER EF, 1990, SAUERSTOFF BIOCH BIO, P22
[8]   1,4-DIMETHOXYPHTHALAZINE AND THE OTHER O-METHYL AND N-METHYL DERIVATIVES OF PHTHALHYDRAZIDE [J].
ELVIDGE, JA ;
REDMAN, AP .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (APR) :1710-1714
[9]  
Fahr K, 1999, FEMS MICROBIOL LETT, V175, P127, DOI 10.1111/j.1574-6968.1999.tb13611.x
[10]   THE REACTIONS OF HYDROXYL RADICALS WITH AROMATIC RINGS IN LIGNINS, STUDIED WITH CREOSOL AND 4-METHYLVERATROL [J].
GIERER, J ;
YANG, E ;
REITBERGER, T .
HOLZFORSCHUNG, 1992, 46 (06) :495-504