Significant Biogenesis of Chlorinated Aromatics by Fungi in Natural Environments

Jong, Ed de; Field, Jim A.; Spinnler, Henri-Eric; Wijnberg, J. B. P. A.; Bont, J.A.M. de

doi:10.1128/aem.60.1.264-270.1994

Cited by 120 publications

(47 citation statements)

References 39 publications

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“…The enzyme has a ten times higher affinity for the latter compound [201]. P. ostreatus does not produce significant amounts of veratryl alcohol; however, when grown on either synthetic glucose medium or in fungal associated wood samples [32], anisaldehyde could be detected (unpublished results), indicating an active AAO coupled H202-generating system.…”

Section: The Production Of H20 2 With Aryl Alcohol Oxidase (Aao)mentioning

confidence: 95%

“…Table 1 shows that several basidiomycetes also produce chlorinated anisyl alcohols and aldehydes. The chlorinated anisyl metabolites (CAM) are produced both under laboratory conditions [31, 40,80] and in the environment [32]. It is anticipated that phenylalanine or tyrosine is also a precursor in the biosynthesis of CAM compounds.…”

Section: Chlorination Of Aromatic Compoundsmentioning

confidence: 99%

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Aryl alcohols in the physiology of ligninolytic fungi

DEJONG¹,

FIELD²,

DEBONT³

1994

FEMS Microbiology Reviews

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White-rot fungi have a versatile machinery of enzymes which work in harmony with secondary aryl alcohol metabolites to degrade the recalcitrant, aromatic biopolymer lignin. This review will focus on the important physiological roles of aryl (veratryl, anisyl and chlorinated anisyl) alcohols in the ligninolytic enzyme system. Their functions include stabilization of lignin peroxidase, charge-transfer reactions and as substrate for oxidases generating extracellular H20 2. The aryl alcohol/aldehyde couple is well protected against degradation by the fungi's extracellular ligninolytic enzymes and their concentrations in the extracellular fluid are highly regulated by intracellular enzymes.

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Section: The Production Of H20 2 With Aryl Alcohol Oxidase (Aao)mentioning

confidence: 95%

Section: Chlorination Of Aromatic Compoundsmentioning

confidence: 99%

Aryl alcohols in the physiology of ligninolytic fungi

DEJONG¹,

FIELD²,

DEBONT³

1994

FEMS Microbiology Reviews

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“…The final moisture content of all the inoculated soil samples was 36% (w/w). After addition of the sludge, the microbial biomass to soil ratio was approximately 0.4 g/kg dry weight in the UN 1 and AC 1 samples and 1.6 g/kg (dry wt) in the UN 4 and AC 4 samples. The 2-MCP-contaminated soil samples, both sterile and unsterilized (i.e., native) soil, that were not inoculated with sludge served as controls.…”

Section: Inoculation Of Soil With Acclimated and Unacclimated Sludgementioning

confidence: 96%

Biodegradation of 2‐chlorophenol in forest soil: Effect of inoculation with aerobic sewage sludge

Lallai¹,

Mura²

2004

Enviro Toxic and Chemistry

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Decontamination of 2-monochlorophenol-containing forest soil was studied in laboratory experiments. We found that in sterile soil, sorption of chlorophenol can occur. Chlorophenol disappearance of approximately 55% was observed in native soil; both soil sorption and degradation by indigenous soil populations caused this disappearance. In native soil, however, the rate of chlorophenol disappearance was enhanced up to slightly more than 90% by inoculation with a sludge taken from the aeration tank of a municipal wastewater treatment plant. In this sludge, the presence of Alcaligenes and Pseudomonas spp. was observed. In other experiments, addition to the soil of a laboratory culture preacclimated to 2-monochlorophenol did not lead to a greater increase in chlorophenol disappearance. In contrast to native soil, inoculation of sterile soil had no effect on disappearance of the chlorophenol. A possible explanation for the lack of cometabolic degradation is that autoclaving of the soil destroys the organic substances within it.

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“…H. fasciculare is a known producer of organohalogens. De Jong et al [5] reported the formation of 3,5-dichloro-p-anisyl alcohol and 3,5-dichloro-p-anisyl aldehyde by this fungus up to a concentration of 17 mg per liter when grown in liquid cultures. Grif-¢th et al [7] reported the production of 3,5-dichloro-4-hydroxy-(2P,6P-dichloro-4P-methoxymethylphenyl) benzoate in a concentration of 8.0 mg per liter when grown on an agar medium.…”

Section: Introductionmentioning

confidence: 95%

“…Chemicals and syntheses of authentic compounds All chemicals were purchased from Merck, Darmstadt, Germany, unless stated otherwise. The syntheses of 3,5-dichloro-p-anisyl alcohol and 3,5-dichlorop-anisaldehyde were described by de Jong et al [5]. The synthesis of 3,5-dichloro-p-anisic acid was described by Swarts et al [12].…”

Section: Glucosementioning

confidence: 99%

Dynamics of organohalogen production by the ecologically important fungus Hypholoma fasciculare

Verhagen

1998

FEMS Microbiology Letters

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The ecologically important white rot basidiomycete Hypholoma fasciculare was previously shown to produce large amounts of adsorbable organic halogens (AOX). The purposes of this study were to identify the time period of AOX production in relation to the primary and secondary metabolic phases of the growth cycle of the fungus, to determine the maximal specific AOX production rates and final AOX yields on the different substrates and to account for the measured AOX in identifiable compounds. The AOX production was observed to take place during the transition between the primary and secondary metabolic phases of the growth cycle of the fungus. The maximum AOX production rates ranged from 0.63 to 3.23 mg AOX per gram of dry mycelium per day and the final AOX yields ranged from 0.88 and 1.50 percent of dry weight of mycelium on five different substrates including natural woody substrates. The AOX produced by the fungus was stable in all five substrates, even after prolonged incubation periods. However, the composition of the AOX changed drastically. Initially most of the AOX was accounted for by the compound 3,5-dichloro-p-anisyl alcohol; however, after prolonged incubation this compound was largely converted into 3,5-dichloro-p-anisic acid in N-rich medium and into unidentified organohalogens in N-limited medium. z 1998 Federation of European Microbiological Societies. Published by Elsevier Science B.V.

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Significant Biogenesis of Chlorinated Aromatics by Fungi in Natural Environments

Cited by 120 publications

References 39 publications

Aryl alcohols in the physiology of ligninolytic fungi

Aryl alcohols in the physiology of ligninolytic fungi

Biodegradation of 2‐chlorophenol in forest soil: Effect of inoculation with aerobic sewage sludge

Dynamics of organohalogen production by the ecologically important fungus Hypholoma fasciculare

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