Enrichment of dibenzofuran utilizing bacteria with high co-metabolic potential towards dibenzodioxin and other anellated aromatics

Strubel, V

doi:10.1016/0378-1097(89)90044-x

Cited by 5 publications

(2 citation statements)

References 14 publications

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“…strain RW1 converted 2-CDF and 3-CDF to 5-chloro-and 4-chlorosalicylate, respectively, and salicylate. The two previously described monochlorinated trihydroxybiphenyls (20) could be obtained from 3-CDF in the presence of 3-chlorocatechol (3,37). HPLC analysis of the reaction mixture supernatant fluid and GC-MS analysis of the acidic ethyl acetate extract also demonstrated the formation of traces of 2-methyl-4H-chromen-4-one from 2-CDF.…”

Section: Resultsmentioning

confidence: 74%

Degradation of Chlorinated Dibenzofurans and Dibenzo-p-Dioxins by Sphingomonas sp. Strain RW1

Wilkes¹,

Wittich²,

Timmis³

et al. 1996

Appl Environ Microbiol

138

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The ability of the dibenzofuran-and dibenzo-p-dioxin-mineralizing bacterium Sphingomonas sp. strain RW1 (R.-M. Wittich, H. Wilkes, V. Sinnwell, W. Francke, and P. Fortnagel, Appl. Environ. Microbiol. 58:1005-1010, 1992) to oxidize chlorinated derivatives of dibenzofuran and dibenzo-p-dioxin was analyzed. Strain RW1 degraded several mono-and dichlorinated dibenzofurans and dibenzo-p-dioxins, but it did not degrade more highly chlorinated congeners. Most mono-and dichlorinated dibenzofurans and dibenzo-p-dioxins investigated in this study were degraded to the corresponding mono-and dichlorinated salicylates and catechols, respectively, together with salicylate and catechol. This indicates an initial dioxygenolytic attack on the substituted as well as on the nonsubstituted aromatic nucleus of most of the target compounds. Strain RW1 could not grow at the expense of monochlorinated dibenzo-p-dioxins and dibenzofurans as carbon sources, with the exception of 4-chlorodibenzofuran, which was stoichiometrically converted to 3-chlorosalicylate.

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Section: Resultsmentioning

confidence: 74%

Degradation of Chlorinated Dibenzofurans and Dibenzo-p-Dioxins by Sphingomonas sp. Strain RW1

Wilkes¹,

Wittich²,

Timmis³

et al. 1996

Appl Environ Microbiol

138

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“…For example, 2,3,7,8-tetrachlorodibenzo-p-dioxin, the biologically most active and toxic member of this class of compounds has a wide variety of species-and tissue-specific effect, such as tumor promotion, immuno-, hepato and dermal toxicity, lethality, birth defects, endocrine disruption and induction of numerous enzymes [1,2]. Dibenzo-p-dioxin (DD) and dibenzofuran (DF) are used as model compounds of dioxins for microbial degradation, and several bacteria capable of assimilating DD and DF have been described [3][4][5][6][7][8][9][10]. 0378 Some of these bacteria have also been reported able to degrade chlorinated DDs and DFs [7,[10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Genetic characterization of the dibenzofuran-degrading Actinobacteria carrying thedbfA1A2gene homologues isolated from activated sludge

Noumura

Habe

Widada

et al. 2004

FEMS Microbiology Letters

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Thirteen dibenzofuran (DF)-utilizing bacteria carrying the DF terminal dioxygenase genes homologous to those of Terrabacter sp. strain DBF63 (dbfA1A2) were newly isolated from activated sludge samples. The amplified ribosomal DNA restriction analysis and the hybridization analyses showed that these strains were grouped into five genetically different types of bacteria. The sequence analyses of the 16S rRNA genes and the dbfA1A2 homologues from these five selected isolates revealed that the isolates belonged to the genus Rhodococcus, Terrabacter or Janibacter and that they shared 99-100% conserved dbfA1A2 homologues. We investigated the genetic organizations flanking the dbfA1A2 homologues and showed that the minimal conserved DNA region present in all five selected isolates consisted of an approximately 9.0-kb region and that their outer regions became abruptly non-homologous. Among them, Rhodococcus sp. strain DFA3 possessed not only the 9.0-kb region but also the 6.2-kb region containing dbfA1A2 homologues. Sequencing of their border regions suggested that some genetic rearrangement might have occurred with insertion sequence-like elements. Also, within their conserved regions, some insertions or deletions were observed.

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Bacterial degradation of aromatic compounds via angular dioxygenation.

Nojiri

Habe

Omori

2001

J. Gen. Appl. Microbiol.

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Dioxygenation is one of the important initial reactions of the bacterial degradation of various aromatic compounds. Aromatic compounds, such as biphenyl, toluene, and naphthalene, are dioxygenated at lateral positions of the aromatic ring resulting in the formation of cis-dihydrodiol. This "normal" type of dioxygenation is termed lateral dioxygenation. On the other hand, the analysis of the bacterial degradation of fluorene (FN) analogues, such as 9-fluorenone, dibenzofuran (DF), carbazole (CAR), and dibenzothiophene (DBT)-sulfone, and DF-related diaryl ether compounds, dibenzo-p-dioxin (DD) and diphenyl ether (DE), revealed the presence of the novel mode of dioxygenation reaction for aromatic nucleus, generally termed angular dioxygenation. In this atypical dioxygenation, the carbon bonded to the carbonyl group in 9-fluorenone or to heteroatoms in the other compounds, and the adjacent carbon in the aromatic ring are both oxidized. Angular dioxygenation of DF, CAR, DBT-sulfone, DD, and DE produces the chemically unstable hemiacetal-like intermediates, which are spontaneously converted to 2,2,3-trihydroxybiphenyl, 2-aminobiphenyl-2,3-diol, 2,3-dihydroxybiphenyl-2-sulfinate, 2,2,3-trihydroxydiphenyl ether, and phenol and catechol, respectively. Thus, angular dioxygenation for these compounds results in the cleavage of the three-ring structure or DE structure. The angular dioxygenation product of 9-fluorenone, 1-hydro-1,1a-dihydroxy-9-fluorenone is a chemically stable cis-diol, and is enzymatically transformed to 2-carboxy-2,3-dihydroxybiphenyl. 2-Substituted 2,3-dihydroxybiphenyls formed by angular dioxygenation of FN analogues are degraded to monocyclic aromatic compounds by meta cleavage and hydrolysis. Thus, after the novel angular dioxygenation, subsequent degradation pathways are homologous to the corresponding part of that of biphenyl. Compared to the bacterial strains capable of catalyzing lateral dioxygenation, few bacteria having angular dioxygenase have been reported. Only a few degradation pathways, CARdegradation pathway of Pseudomonas resinovorans strain CA10, DF/DD-degradation pathway of Sphingomonas wittichii strain RW1, DF/DD/FN-degradation pathway of Terrabacter sp. strain DBF63, and carboxylated DE-degradation pathway of P. pseudoalcaligenes strain POB310, have been investigated at the gene level. As a result of the phylogenetic analysis and the comparison of substrate specificity of angular dioxygenase, it is suggested that this atypical mode of dioxygenation is one of the oxygenation reactions originating from the relaxed substrate specificity of the Rieske nonheme iron oxygenase superfamily. Genetic characterization of the degradation pathways of these compounds suggests the possibility that the respective genetic elements constituting the entire catabolic pathway have been recruited from various other bacteria and/or other genetic loci, and that these pathways have not evolutionary matured.

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Enrichment of dibenzofuran utilizing bacteria with high co-metabolic potential towards dibenzodioxin and other anellated aromatics

Cited by 5 publications

References 14 publications

Degradation of Chlorinated Dibenzofurans and Dibenzo-p-Dioxins by Sphingomonas sp. Strain RW1

Degradation of Chlorinated Dibenzofurans and Dibenzo-p-Dioxins by Sphingomonas sp. Strain RW1

Genetic characterization of the dibenzofuran-degrading Actinobacteria carrying thedbfA1A2gene homologues isolated from activated sludge

Bacterial degradation of aromatic compounds via angular dioxygenation.

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