title: Unspecific degradation of halogenated phenols by the soil fungus Penicillium frequentans Bi 7/2.
abstract: Resting phenol-grown mycelia of the fungus Penicillium frequentans strain Bi 7/2 were shown to be capable of metabolizing various monohalogenated phenols as well as 3,4-dichlorophenol. 2,4.dichlorophenol could be metabolized in the presence of phenol as cosubstrate. In the first degradation step the halogenated phenols were oxidized to the corresponding halocatechols. Halocatechols substituted in para-position (4-halocatechols) were further degraded under formation of 4-carboxymethylenbut-2-en-4-olide. A partial dehalogenation took place splitting the ring system. 3-Halocatechols were cleaved to 2-halomuconic acids as dead end metabolites without a dehalogenation step. Dichlorophenols were only transformed to the corresponding catechols. In addition 3,5-dichloro-catechol was O-methylated to give two isomers of dichloroguiacol. The halogenated catechols with the exception of 4-fluorocatechol partly polymerized oxidatively in the culture fluid to form insoluble dark-brown products. The degradation of halophenols are due to the action of unspecific intracellular enzymes responsible for phenol catabolism (phenol hydroxylase, catechol-1,2-dioxygenase, muconate cycloisomerase I).
authors.affiliation: Friedrich-Schiller-Universität Jena, Institut für Mikrobiologie, Germany.
authors.forename: M
authors.initials: M
authors.lastname: Hofrichter
authors.forename: F
authors.initials: F
authors.lastname: Bublitz
authors.forename: W
authors.initials: W
authors.lastname: Fritsche
mesh_terms: D001673:Biodegradation, Environmental; D050548:Catechol 1,2-Dioxygenase; D002733:Chlorophenols / Q000378:metabolism; D049308:Dioxygenases; D006899:Mixed Function Oxygenases / Q000378:metabolism; D010084:Oxidation-Reduction; D010105:Oxygenases / Q000378:metabolism; D010407:Penicillium / Q000378:metabolism*; D010636:Phenols / Q000378:metabolism*; D012988:Soil Microbiology
chemical_list: D002733:Chlorophenols; D010636:Phenols; D006899:Mixed Function Oxygenases; D010105:Oxygenases; D049308:Dioxygenases; D050548:Catechol 1,2-Dioxygenase; C022336:phenol 2-monooxygenase