Biodegradation of Carbazole by<i>Pseudomonas</i>spp. CA06 and CA10

Ouchiyama, Naoki; Zhang, Yan; Omori, Toshio; Kodama, Tohru

doi:10.1271/bbb.57.455

Cited by 149 publications

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“…The strain is capable of growth on carbazole as a sole source of carbon, nitrogen and energy and accumulates anthranilic acid and catechol as catabolic intermediates of carbazole. It also grows on anthranilic acid as carbon and nitrogen source and accumulates catechol suggesting carbazole conversion to catechol via anthranilic acid (Ouchiyama et al 1993). Furthermore, production of 2 0 -aminobiphenyl-2,3-diol and its meta-cleavage product 2-hydroxy-6-oxo-6-(2 0 -aminopheny)-hexa-2,4-dienoate (HOADA) from the culture medium of CA10 grown on carbazole was suggested.…”

Section: Angular Dioxygenation Of Carbazolementioning

confidence: 99%

“…The resulting catechol is converted to a tricarboxylic acid (TCA)-cycle intermediate via ortho-cleavage (as in P. resinovorans CA10) or meta-cleavage (as in Pseudomonas stutzeri strain OM1) pathways (Ouchiyama et al 1993;Fig. 4).…”

Section: Angular Dioxygenation Of Carbazolementioning

confidence: 99%

“…Anthranilic acid has been detected in the culture extracts of several carbazole degraders and is regarded as the main metabolite of carbazole angular dioxygenation (Ouchiyama et al 1993;Gieg et al 1996;Ouchiyama et al 1998;Kirimura et al 1999;Schneider et al 2000;Kilbane II et al 2002;Inoue et al 2005). Recently, carbazole degraders with addictive preference for angular dioxygenation were also isolated from hydrocarbon-contaminated tropical African soil in Lagos, Nigeria (Salam et al 2014).…”

Section: Angular Dioxygenation Of Carbazolementioning

confidence: 99%

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Properties, environmental fate and biodegradation of carbazole

2017

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The last two decades had witnessed extensive investigation on bacterial degradation of carbazole, an Nheterocyclic aromatic hydrocarbon. Specifically, previous studies have reported the primary importance of angular dioxygenation, a novel type of oxygenation reaction, which facilitates mineralization of carbazole to intermediates of the TCA cycle. Proteobacteria and Actinobacteria are the predominant bacterial phyla implicated in this novel mode of dioxygenation, while anthranilic acid and catechol are the signature metabolites. Several studies have elucidated the degradative genes involved, the diversity of the car gene clusters and the unique organization of the car gene clusters in marine carbazole degraders. However, there is paucity of information regarding the environmental fate as well as industrial and medical importance of carbazole and its derivatives. In this review, attempt is made to harness this information to present a comprehensive outlook that not only focuses on carbazole biodegradation pathways, but also on its environmental fate as well as medical and industrial importance of carbazole and its derivatives.

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Section: Angular Dioxygenation Of Carbazolementioning

confidence: 99%

Section: Angular Dioxygenation Of Carbazolementioning

confidence: 99%

Section: Angular Dioxygenation Of Carbazolementioning

confidence: 99%

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Properties, environmental fate and biodegradation of carbazole

2017

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“…strain RJGII.123 Grosser et al, 1991;Schneider et al, 2000 Pseudomonas sp. strain CA06 CAR 1,9a-dioxygenase CAR Ouchiyama et al, 1993 Pseudomonas resinovorans strain CAR 1,9a-dioxygenase CAR, DF, DD Habe et al, 2001a, b;Kimura et al, 1996;Nam et al, 2001;CA10 Nojiri et al, 1999 (in press); Ouchiyama et al, 1993;Sato et al, 1997a, b Pseudomonas stutzeri strain , 1988, 1990, 1993 …”

Section: Microbial Degradation Of Df Dd and Fnmentioning

confidence: 99%

“…Ouchiyama et al (1993) screened soil and activated sludge samples for CARutilizing bacteria as a sole source of carbon, nitrogen, and energy. They isolated Pseudomonas sp.…”

Section: Microbial Degradation Of Carmentioning

confidence: 99%

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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Aerobic co-metabolism of sulfur, nitrogen and oxygen heterocycles by three marine bacterial consortia

Meade¹,

Hellou²,

Patel³

2002

J. Basic Microbiol.

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Bacterial samples were collected from three marine beaches in coastal Newfoundland, Canada, and enriched by growth on 1‐methylnaphthalene. The most prominent bacterial cell type for each consortium was isolated in a serial dilutions test, and a substrate utilization profile was obtained for each using the Biolog MicroStation System. Each bacterial community was tested for its ability to co‐metabolize sulfur heterocycles (benzothiophene: BT, 3‐methylbenzothiophene: 3‐MBT, and dibenzothiophene: DBT), a nitrogen heterocycle (carbazole: CARB), and an oxygen heterocycle (dibenzofuran: DBF). Co‐metabolism of the starting material was determined using gas chromatography‐mass spectroscopy (GC‐MS), and formation of products was investigated by GC‐MS and Fourier transform infrared (FTIR) spectroscopy. Bacterial growth was monitored turbidimetrically to determine the dry weight (μg) of cells/ml. The 2‐ringed heterocycles were co‐metabolized faster and to a greater extent than the 3‐ringed compounds. Co‐metabolism of BT was not statistically different from that for 3‐MBT and, likewise, a comparison of the 3‐ringed heterocycles showed no significant differences in degradation rates. Statistical examination showed that no one culture demonstrated a significantly greater ability to co‐metabolize the heterocycles studied. This study represents the first comprehensive investigation of the ability of local bacteria to co‐metabolize a range of aromatic compounds and provides a preliminary understanding of their fate in sediments should contamination by these compounds occur.

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Biodegradation of Carbazole byPseudomonasspp. CA06 and CA10

Cited by 149 publications

References 0 publications

Properties, environmental fate and biodegradation of carbazole

Properties, environmental fate and biodegradation of carbazole

Bacterial degradation of aromatic compounds via angular dioxygenation.

Aerobic co-metabolism of sulfur, nitrogen and oxygen heterocycles by three marine bacterial consortia

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