Microbial Metabolism of Alicyclic Hydrocarbons: Isolation and Properties of a Cyclohexane-degrading Bacterium

Stirling, Lynne A.; Watkinson, R. J.; Higgins, I. J.

doi:10.1099/00221287-99-1-119

Cited by 73 publications

(52 citation statements)

References 9 publications

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“…Axenic bacterial strains hitherto reported to grow with cycloalkanes were aerobic. Most microbiological studies with cycloalkanes used cyclohexane as a model substrate (Stirling and Watkinson, 1977;Anderson et al, 1980;Trower et al, 1985;Rouvière and Chen, 2003). Cyclohexane is aerobically activated by cyclohexane monooxygenase yielding cyclohexanol, and further oxidized through cyclohexanone, caprolactone and adipate (Perry, 1984;Cheng et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

Microbial nitrate-dependent cyclohexane degradation coupled with anaerobic ammonium oxidation

et al. 2010

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An anaerobic nitrate-reducing enrichment culture was established with a cyclic saturated petroleum hydrocarbon, cyclohexane, the fate of which in anoxic environments has been scarcely investigated. GC-MS showed cyclohexylsuccinate as a metabolite, in accordance with an anaerobic enzymatic activation of cyclohexane by carbon-carbon addition to fumarate. Furthermore, long-chain cyclohexyl-substituted cell fatty acids apparently derived from cyclohexane were detected. Nitrate reduction was not only associated with cyclohexane utilization but also with striking depletion of added ammonium ions. Significantly more ammonium was consumed than could be accounted for by assimilation. This indicated the occurrence of anaerobic ammonium oxidation (anammox) with nitrite from cyclohexane-dependent nitrate reduction. Indeed, nitrite depletion was stimulated upon further addition of ammonium. Analysis of 16S rRNA genes and subsequent cell hybridization with specific probes showed that approximately 75% of the bacterial cells affiliated with the Geobacteraceae and approximately 18% with Candidatus 'Brocadia anammoxidans' (member of the Planctomycetales), an anaerobic ammonium oxidizer. These results and additional quantitative growth experiments indicated that the member of the Geobacteraceae reduced nitrate with cyclohexane to nitrite and some ammonium; the latter two and ammonium added to the medium were scavenged by anammox bacteria to yield dinitrogen. A model was established to quantify the partition of each microorganism in the overall process. Such hydrocarbon oxidation by an alleged 'denitrification' ('pseudo-denitrification'), which in reality is a dissimilatory loop through anammox, can in principle also occur in other microbial systems with nitrate-dependent hydrocarbon attenuation.

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Section: Introductionmentioning

confidence: 99%

Microbial nitrate-dependent cyclohexane degradation coupled with anaerobic ammonium oxidation

et al. 2010

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“…There are numerous reports of isolation of petroleum hydrocarbon degrader bacteria from oil exposed areas (Kasai et al, 2001;Tazaki, 2005). Biodegr adation of in dividual h ydr ocarbon compounds by pure bacterial strains has been studied extensively and metabolic pathways have been described (Heitkamp and Cerniglia, 1988;Gibson and Subramanian, 1984;Rehm and Reif 1981;Stirling and Watkinson, 1977). The ability to isolate high numbers of certain oil-degrading microorganisms from petroleum-contaminated environment is commonly taken as evidence that these microorganisms are the active degraders of that environment (Okerentugba and Ezeronye, 2003).…”

Section: Introductionmentioning

confidence: 99%

Isolation and characterization of a novel native Bacillus strain capable of degrading diesel fuel

Kebria

Ahmad

Ganjidoust

et al. 2009

Int. J. Environ. Sci. Technol.

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ABSTRACT:The ability of native bacteria to utilize diesel fuel as the sole carbon and energy source was investigated in this research. Ten bacterial strains were isolated from the oil refinery field in Tehran, Iran. Two biodegradation experiments were performed in low and high (500 and 10000 ppm, respectively) concentration of diesel fuel for 15 days. Only two isolates were able to efficiently degrade the petroleum hydrocarbons in the first test and degraded 86.67 % and, 80.60 % of diesel fuel, respectively. The secondary experiment was performed to investigate the toxicity effect of diesel fuel at high concentration (10000 ppm). Only one strain was capable to degrade 85.20 % of diesel fuel at the same time (15 days). Phenotype and phylogeny analysis of this strain was characterized and identified as dieseldegrading bacteria, based on gram staining, biochemical tests, 16S rRNA gene sequence analysis. These results indicate that this new strain was Bacillus sp. and could be considered as Bacillus Cereus with 98 % 16 S rRNA gene sequence similarity. The results indicate that native strains have great potential for in situ remediation of diesel-contaminated soils in oil refinery sites.

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“…only two other microorganisms, a pseudomonad [I51 and a Nocardiu sp. [16], have been isolated with the capacity to grow at the expense of this cycloalkane.…”

Section: Fig 1 Reaction Scheme For the Cyclohexanone-monooxygenllsementioning

confidence: 99%

Characterization of an FMN‐containing cyclohexanone monooxygenase from a cyclohexane‐grown Xanthobacter sp.

Trower

Buckland²,

Griffin

1989

European Journal of Biochemistry

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A soluble cyclohexanone monooxygenase was purified 16.1 -fold to homogeneity from a Xunthobacter sp. grown upon cyclohexane as sole source of carbon and energy. The native enzyme is a 50-kDa single polypeptide chain associated with FMN rather than F A D as flavin prosthetic group in a 1 : 1 stoichiometric relationship. The monooxygenase catalyses the transformation of cyclohexanone to the lactone I-oxa-2-oxocycloheptane in an oxygen ring insertion reaction. Only related cycloalkanone substrates are accepted for oxygenation, no activity is shown towards straight-chain alkanones. Enzyme activity is strongly inhibited by sulphydryl-reactive agents, but is relatively insensitive to metal chelators, electron transport inhibitors and the metal ions Fe3+ and C u 2 + . Cyclohexanone monooxygenase has K, values for cyclohexanone and NADPH of <0.5 pM and 12.5 pM respectively. Kinetic investigations under steady-state conditions demonstrate that the flavoprotein prosthetic group, FMN, is involved in the monooxygenase catalytic mechanism. The systematic name for the enzyme is cyclohexanone, NADPH : oxygen oxidoreductase (6-hydroxylating, 1,2-lactonizing) (EC 1.14.13.22). [5] and substituted cycloalkanes [6]. Members of the genusThe degradation of cyclohexane by a Xunthobucter sp. has been shown to proceed with an initial hydroxylation to form cyclohexanol [5]. This product is then oxidised to adipic acid via cyclohexanone, I-oxa-2-oxocycloheptane and 6-hydroxyhexanoate. Critical to the ring cleavage of cyclohexanone is its transformation to the seven-membered lactone l-oxa-2-oxocycloheptane, a reaction previously shown to be catalysed by an inducible, soluble, NADPH-dependent monooxygenase enzyme [5] (Fig.

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Microbial Metabolism of Alicyclic Hydrocarbons: Isolation and Properties of a Cyclohexane-degrading Bacterium

Cited by 73 publications

References 9 publications

Microbial nitrate-dependent cyclohexane degradation coupled with anaerobic ammonium oxidation

Microbial nitrate-dependent cyclohexane degradation coupled with anaerobic ammonium oxidation

Isolation and characterization of a novel native Bacillus strain capable of degrading diesel fuel

Characterization of an FMN‐containing cyclohexanone monooxygenase from a cyclohexane‐grown Xanthobacter sp.

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