Pyrene degradation by a Mycobacterium sp.: identification of ring oxidation and ring fission products

Heitkamp, Michael A.; Freeman, Jeremiah P.; Miller, Dwight W.; Cerniglia, Carl E.

doi:10.1128/aem.54.10.2556-2565.1988

Cited by 291 publications

(126 citation statements)

References 27 publications

(27 reference statements)

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“…However, Mycobacterium sp. strain PYR-1 has been shown to form both cisand trans-pyrene dihydrodiols and metabolize phenanthrene to trans-9,10-dihydrodiol in addition to cis-3,4-dihydrodiol and cis-9,10-dihydrodiol intermediates, suggesting an alternate pathway for PAH degradation or a relaxed specificity of a dioxygenase system [15,16].…”

Section: Introductionmentioning

confidence: 99%

THE EFFECT OF POLYCYCLIC AROMATIC HYDROCARBONS ON THE DEGRADATION OF BENZO[a]PYRENE BY MYCOBACTERIUM SP. STRAIN RJGII-135

McLellan¹,

Warshawsky²,

Shann³

2002

Environ Toxicol Chem

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Mycobacterium sp. strain RJGII-135 is capable of degrading a wide range of polycyclic aromatic hydrocarbons (PAHs), including benzo[a]pyrene (BaP). In this study, critical aspects of degradation were investigated, including compound uptake, relative rates of PAH degradation, and the effects of co-occurring PAH substrates on BaP degradation and mineralization to CO2. Mycobacterium sp. strain RJGII-135 was capable of degrading phenanthrene, anthracene, and pyrene at a 10- to 20-fold greater rate than benz[a]anthracene (BaA) and BaP. A significant amount of phenanthrene and pyrene, 30% and 10%, respectively, was completely mineralized, whereas less than 4% of anthracene, BaA, and BaP was mineralized. The PAH uptake assays demonstrated that high amounts of BaP and BaA, 81% and 75% of added compound, respectively, could be recovered from bacterial cell fractions after a 4-h incubation compared with pyrene (61%), anthracene (53%), and phenanthrene (47%). The half-saturation constant (Km) for pyrene was threefold lower for pyrene over BaP, suggesting that the degradation system in Mycobacterium sp. strain RJGII-135 has a higher affinity for pyrene, reaching maximal degradative activity at lower concentrations. No hybridization to dioxygenase gene probes nahAc, bphA1, or tolC1C2 was detected. Studies to investigate competition between different PAH substrates demonstrated that the rate of BaP metabolism was influenced by the presence of a second PAH substrate. The BaP metabolism was inhibited when coincubated with BaA, pyrene, and anthracene. Phenanthrene did not inhibit but enhanced BaP metabolism sixfold. These data suggest that induction effects of components of complex mixtures may be as important as competitive metabolism when assessing the ability of bacteria to effectively degrade high-molecular-weight PAHs in the environment.

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Section: Introductionmentioning

confidence: 99%

THE EFFECT OF POLYCYCLIC AROMATIC HYDROCARBONS ON THE DEGRADATION OF BENZO[a]PYRENE BY MYCOBACTERIUM SP. STRAIN RJGII-135

McLellan¹,

Warshawsky²,

Shann³

2002

Environ Toxicol Chem

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“…Peak 5, at a retention time of 15.66 min, was confirmed as 4-phenanthrol by authentic standard. Peak 6, at a retention time of 18.55 min, was tentatively identified as 4-phenanthrene-carboxylic acid based on mass spectra reported in the literature[5,12,14] (Fig. 4B).Peak 7, at a retention time of 20.24 min, was confirmed as dihydroxyphenanthrene according to the characteristic of the molecular ion, with M ϩ at m/z 354 and major fragment ions at m/z 339 [M-CH 3 ] ϩ , 266 [M-C 3 H 8 SiO] ϩ , and 236 [M-C 5 H 14 SiO] ϩ…”

mentioning

confidence: 98%

Metabolite production in degradation of pyrene alone or in a mixture with another polycyclic aromatic hydrocarbon by Mycobacterium sp.

Zhong¹,

Luan²,

Zhou³

et al. 2006

Enviro Toxic and Chemistry

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Degradation of pyrene (PYR) alone and in the presence of phenanthrene or fluoranthene by Mycobacterium sp. strain A1-PYR isolated from mangrove sediments was investigated. When PYR was the only polycyclic aromatic hydrocarbon compound and the sole carbon source, only 33% of the added PYR was slowly degraded during 7 d of incubation. Seven metabolites were obtained, including four-ring metabolites (monohydroxypyrene and three different dihydroxypyrenes) and three-ring metabolites (dihydroxyphenanthrene, 4-phenanthrene-carboxylic acid, and 4-phenanthrol), of which more four-ring metabolites accumulated compared with three-ring metabolites. To our knowledge, this is the first report in which PYR was initially attacked by Mycobacterium sp. to form three different dihydroxypyrenes. Pyrene degradation was significantly stimulated when mixed with phenanthrene or fluoranthene. In the presence of fluoranthene, PYR was rapidly degraded (up to 57%), and significant amounts of dihydroxypyrene were formed within 3 d of incubation, followed by a period of minimal PYR degradation from 3 to 7 d with disappearance of four-ring metabolites and accumulation of three-ring metabolites. In contrast, PYR was removed completely, and little evidence of metabolites was detected in the presence of phenanthrene. These results showed that PYR was degraded to a larger extent when mixed with another polycyclic aromatic hydrocarbon concomitant with a higher turnover of PYR metabolites. The induction of complex enzyme systems and increase in biomass possibly affected the transformation of PYR metabolites in the mixture with phenanthrene or fluoranthene.

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“…The consensus from various investigations with PAH compounds and soils is that two-through five-ring PAH compounds can be biodegraded in liquid cultures given suitable physicochemical conditions and environments that sustain appropriate microbial populations [2,3]. However, as explained below, current understanding is very incomplete regarding achievable treatment rates and end points for microbial treatment of PAH mixtures in contaminated soil.…”

Section: Bioavailability Of Pah Compoundsmentioning

confidence: 99%

Bioavailability of Hydrophobic Organic Compounds From Nonaqueous-Phase Liquids: The Biodegradation of Naphthalene From Coal Tar

Ghoshal¹,

Luthy²

1996

Environ Toxicol Chem

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The literature on microbial degradation of polycyclic aromatic hydrocarbon (PAH) compounds in soils and sediments shows that microbial biotreatment rates are highly variable. Although it is believed that these disparate results are somehow attributable to the bioavailability of PAH compounds, current understanding does not allow prediction of this phenomenon. This work evaluated relationships between coal tar composition and aqueous naphthalene concentration and between the rate of naphthalene mass transfer and microbial mineralization of naphthalene. The use of a dissolution-degradation framework for identifying rate-controlling phenomena in slurry biotreatment of coal tar is discussed. Experiments were performed in slurry systems with two coal tars for which naphthalene was the principal component. In slurry systems coal tar was present either as a single 0.7-ml globule or as coated onto 250-mdiameter microporous silica beads. Independent tests were conducted with these systems to assess the rates of naphthalene mass transfer and rates of naphthalene biomineralization. The area-dependent mass transfer coefficient of naphthalene in the coal tar-silica beads system was three orders of magnitude greater than for the single coal tar globule. A coupled, solute-mass transfer biodegradation model was used to compare initial biomineralization rates with rates of naphthalene dissolution. Analysis of the results showed that the rate of biomineralization of naphthalene in the systems containing single coal tar globules was influenced by the rate of mass transfer of naphthalene.

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Pyrene degradation by a Mycobacterium sp.: identification of ring oxidation and ring fission products

Cited by 291 publications

References 27 publications

THE EFFECT OF POLYCYCLIC AROMATIC HYDROCARBONS ON THE DEGRADATION OF BENZO[a]PYRENE BY MYCOBACTERIUM SP. STRAIN RJGII-135

THE EFFECT OF POLYCYCLIC AROMATIC HYDROCARBONS ON THE DEGRADATION OF BENZO[a]PYRENE BY MYCOBACTERIUM SP. STRAIN RJGII-135

Metabolite production in degradation of pyrene alone or in a mixture with another polycyclic aromatic hydrocarbon by Mycobacterium sp.

Bioavailability of Hydrophobic Organic Compounds From Nonaqueous-Phase Liquids: The Biodegradation of Naphthalene From Coal Tar

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