Unspecific degradation of halogenated phenols by the soil fungus <i>Penicillium frequentans</i> 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).