Branched Metabolic Pathway for Phenanthrene Degradation in a Pyrene-Degrading Bacterium

Rehmann, Klaus; Steinberg, Christian; Kettrup, A.

doi:10.1080/10406639608544657

Cited by 10 publications

(6 citation statements)

References 9 publications

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“…Rehmann et al (41) showed that Mycobacterium sp. strain KR2 metabolizes phenanthrene in the 3,4 and 9,10 positions to form cis-3,4-and 9,10-dihydrodiols.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Degradation of Phenanthrene and Anthracene by Cell Suspensions ofMycobacteriumsp. Strain PYR-1

Moody

Freeman

Doerge

et al. 2001

Appl Environ Microbiol

277

185

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Cultures of Mycobacterium sp. strain PYR-1 were dosed with anthracene or phenanthrene and after 14 days of incubation had degraded 92 and 90% of the added anthracene and phenanthrene, respectively. The metabolites were extracted and identified by UV-visible light absorption, high-pressure liquid chromatography retention times, mass spectrometry, 1 H and 13 C nuclear magnetic resonance spectrometry, and comparison to authentic compounds and literature data. Neutral-pH ethyl acetate extracts from anthracene-incubated cells showed four metabolites, identified as cis-1,2-dihydroxy-1,2-dihydroanthracene, 6,7-benzocoumarin, 1-methoxy-2-hydroxyanthracene, and 9,10-anthraquinone. A novel anthracene ring fission product was isolated from acidified culture media and was identified as 3-(2-carboxyvinyl)naphthalene-2-carboxylic acid. 6,7-Benzocoumarin was also found in that extract. When Mycobacterium sp. strain PYR-1 was grown in the presence of phenanthrene, three neutral metabolites were identified as cis-and trans-9,10-dihydroxy-9,10-dihydrophenanthrene and cis-3,4-dihydroxy-3,4-dihydrophenanthrene. Phenanthrene ring fission products, isolated from acid extracts, were identified as 2,2-diphenic acid, 1-hydroxynaphthoic acid, and phthalic acid. The data point to the existence, next to already known routes for both gram-negative and gram-positive bacteria, of alternative pathways that might be due to the presence of different dioxygenases or to a relaxed specificity of the same dioxygenase for initial attack on polycyclic aromatic hydrocarbons.Anthracene and phenanthrene are tricyclic aromatic hydrocarbons that are found in high concentrations in polycyclic aromatic hydrocarbon (PAH)-contaminated sediments, surface soils, and waste sites. These hydrophobic contaminants are widely distributed in the environment, occurring as natural constituents of fossil fuels and their anthropogenic pyrolysis products (6,24,55). Unlike the higher-molecular-weight PAHs, phenanthrene and anthracene do not pose a risk to human health, since they exhibit no genotoxic or carcinogenic effects. However, they have been shown to be toxic to fish and algae (45,46). Anthracene and phenanthrene are considered prototypic PAHs and serve as signature compounds to detect PAH contamination, since their chemical structures are found in carcinogenic PAHs, such as benzo[a]pyrene and benz[a]anthracene. They have also been used as model PAHs to determine factors that affect the bioavailability, biodegradation potential, and rate of microbial degradation of PAHs in the environment (5,6,24,48).A variety of bacterial species have been isolated that have the ability to utilize anthracene or phenanthrene as the sole source of carbon and energy (6,33,48). The initial reactions in the degradation of anthracene and phenanthrene are catalyzed by multicomponent dioxygenases that incorporate both atoms of molecular oxygen into the PAH nucleus to produce cisdihydrodiols (1,22). Genes involved in PAH metabolism and its regulation have been described for Pseudomonas, Sphin...

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“…Rehmann et al (41) showed that Mycobacterium sp. strain KR2 metabolizes phenanthrene in the 3,4 and 9,10 positions to form cis-3,4-and 9,10-dihydrodiols.…”

Section: Discussionmentioning

confidence: 99%

“…However, detailed metabolite structure elucidation and degradation pathways for anthracene and phenanthrene catabolism by this group of microorganisms are not well known (4,16,41,50). Mycobacterium species metabolize phenanthrene at different sites of the molecule, presumably via both dioxygenase and monooxygenase attacks on the aromatic nucleus.…”

mentioning

confidence: 99%

Degradation of Phenanthrene and Anthracene by Cell Suspensions ofMycobacteriumsp. Strain PYR-1

Moody

Freeman

Doerge

et al. 2001

Appl Environ Microbiol

277

185

View full text Add to dashboard Cite

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“…KR2 was supplied by Dr. Rehmann from GSF/IÖC, Germany. It was isolated from PAH contaminated soils, capable of degrading phenanthrene and pyrene [15,16]. Mycobacterium spp.…”

Section: Microorganism and Growth Conditionmentioning

confidence: 99%

“…KR2, the PAHsdegradation microorganism [15,16], was used to elucidate the surfactant effects on the degradation of PAHs and their toxicity. Phenanthrene and 14 C-phenanthrene, a three-ring PAH, were selected as the model compounds.…”

Section: Introductionmentioning

confidence: 99%

Effects of concentration, head group, and structure of surfactants on the degradation of phenanthrene

Jin¹,

Xia

Jing³

et al. 2007

Journal of Hazardous Materials

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“…hazardous chemicals, including high-molecular-mass polycyclic aromatic hydrocarbons (PAH) (Boldrin et al, 1993 ;Cerniglia, 1981 ;Churchill et al, 1999 ;Dean-Ross & Cerniglia, 1996 ;Fritzsche, 1994 ;Grosser et al, 1991Grosser et al, , 1995Guerin & Jones, 1988 ;Jimenez & Bartha, 1996 ;Ka$ stner et al, 1994 ;Kelley et al, 1990 ;Kleespies et al, 1996 ;Lloyd-Jones & Hunter, 1997 ;Molina et al, 1999 ;Rehmann et al, 1996Rehmann et al, , 1998Schneider et al, 1996 ;Tiehm & Fritzsche, 1995 ;Tongpim & Pickard, 1999). A rapidly growing, acid-alcohol-fast, scotochromogenic, PAH-degrading Mycobacterium strain, PYR-1 T , was isolated from oil-contaminated sediment (Heitkamp et al, 1988).…”

Section: Members Of the Genusmentioning

confidence: 99%

Classification of a polycyclic aromatic hydrocarbon-metabolizing bacterium, Mycobacterium sp. strain PYR-1, as Mycobacterium vanbaalenii sp. nov.

Khan¹,

Kim²,

Paine³

et al. 2002

International Journal of Systematic and Evolutionary Microbiology

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A polycyclic aromatic hydrocarbon (PAH)-utilizing Mycobacterium strain, PYR-1(T), was isolated from petroleum-contaminated estuarine sediments and has been shown by 16S rRNA gene sequencing to be closely related to Mycobacterium aurum ATCC 23366(T) and Mycobacterium vaccae ATCC 15438(T). In this investigation, the 16S rDNA, fatty acid methyl esters, DNA-DNA hybridization, PFGE analysis of restriction-digested total genomic DNA and biochemical tests were used to determine the taxonomic relationship of strain PYR-1(T) to other closely related Mycobacterium species. The sequence of the 16S rRNA gene of strain PYR-1(T) was similar to that of Mycobacterium austroafricanum ATCC 33464(T), except for one gap at position 43. Fatty acid methyl ester analysis also showed similarity to M. austroafricanum ATCC 33464(T); however, the Euclidean distance was greater than 4.0, indicating that these strains were not identical. Dot-blot DNA-DNA hybridization of strain PYR-1(T) with M. austroafricanum indicated less than 40% relatedness. When the total chromosomal DNA of M. aurum ATCC 23366(T), M. austroafricanum ATCC 33464(T) and strain PYR-1(T) was digested with restriction enzyme Xbal and analysed by PFGE, all three organisms gave different restriction patterns. Previous studies from our laboratory have shown that the reverse-phase HPLC elution profiles of mycolic acids of strain PYR-1(T) and M. austroafricanum ATCC 33464(T) have different patterns. Based on phylogenetic analysis using 165 rRNA gene sequences, fatty acid analysis, DNA-DNA hybridization and PFGE analysis and physiological and chemotaxonomic characteristics, it is concluded that strain PYR-1(T) (= DSM 7251(T) = NRRL B-24157(T)) represents a novel species of the genus Mycobacterium, for which the name Mycobacterium vanbaalenii sp. nov. is proposed.

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Branched Metabolic Pathway for Phenanthrene Degradation in a Pyrene-Degrading Bacterium

Cited by 10 publications

References 9 publications

Degradation of Phenanthrene and Anthracene by Cell Suspensions ofMycobacteriumsp. Strain PYR-1

Degradation of Phenanthrene and Anthracene by Cell Suspensions ofMycobacteriumsp. Strain PYR-1

Effects of concentration, head group, and structure of surfactants on the degradation of phenanthrene

Classification of a polycyclic aromatic hydrocarbon-metabolizing bacterium, Mycobacterium sp. strain PYR-1, as Mycobacterium vanbaalenii sp. nov.

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