Mycobacterium aromativorans JS19b1T degrades phenanthrene through C-1,2, C-3,4 and C-9,10 dioxygenation pathways

Seo, Jong‐Su; Keum, Young‐Soo; Li, Qing X.

doi:10.1016/j.ibiod.2012.02.005

Cited by 36 publications

(27 citation statements)

References 59 publications

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“…Naphthalene-1,2-dicarboxylic acid anhydride, 1-hydroxy-2-naphthaldehyde, 2-hydroxy-1-naphthaldehyde, and naphthalene-1,2-diol were purchased from TCI America (Portland, OR). Chemicals that were not commercially available were synthesized previously in our laboratory, including 5,6-benzocoumarin, 7,8-benzocoumarin, 1-(2-carboxyvinyl)-2-naphthoic acid, 2-(2-carboxyvinyl)-1-naphthoic acid, 4-(2-hydroxynaphth-1-yl)-2-oxobut-3-enoic acid, 4-(1-hydroxynaphth-2-yl)-2-oxo-but-3-enoic acid (44), cis-9,10-dihydrophenanthrene-9,10-diol, naphthalene-1,2-dicarboxylic acid (32), 4-oxapyren-5-one, and phenanthrene-4,5-dicarboxylic acid (40). Solvents, including ethyl acetate, acetonitrile, acetone, ethanol, and methyl-tert-butyl ether (MTBE), were purchased from Fisher Scientific (Morris Plains, NJ).…”

Section: Methodsmentioning

confidence: 99%

“…and meta-cleavage (27,32,40). The presence of diphenic acid (F-III) demonstrated a degradation route through the 9,10-dioxygenation pathway.…”

Section: Metabolite Series a C And F; See This Figure Also For The mentioning

confidence: 99%

“…The degradation of phenanthrene is initiated by dioxygenation at the C-1 and C-2, C-3 and C-4, or C-9 and C-10 positions. Some bacteria produce metabolites of two (27,30,38) or all three (32,39,40) pathways. The best-characterized pathway for phenanthrene degradation proceeds initially through dioxygenation at the C-3 and C-4 positions, and enzymes involved in breakdown through phthalic acid have been elucidated in Mycobacterium vanbaalenii PYR-1 (41).…”

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confidence: 99%

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Effects of Polycyclic Aromatic Hydrocarbon Mixtures on Degradation, Gene Expression, and Metabolite Production in Four Mycobacterium Species

Hennessee

2016

Appl Environ Microbiol

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Polycyclic aromatic hydrocarbons (PAHs) are widespread environmental contaminants that are hazardous to human health. It has been demonstrated that members of the Mycobacterium genus are among the most effective degraders of PAHs, but few studies have focused on the degradation of PAH mixtures. In this study, single and mixed PAH metabolism was investigated in four phylogenetically distinct Mycobacterium species with respect to (i) parent compound degradation, (ii) bacterial growth, (iii) catabolic gene expression, and (iv) metabolite production. Synergistic and antagonistic effects on four model PAH compounds (benzo[a]pyrene, pyrene, fluoranthene, and phenanthrene) characterized degradation of mixtures in a strain-and mixture-dependent manner. The mixture of pyrene and phenanthrene, in particular, resulted in antagonized degradation by three out of four bacterial species, and further studies were narrowed to investigate the degradation of this mixture. Antagonistic effects persisted over time and were correlated with reduced bacterial growth. Antagonized degradation of PAH was not caused by preferential degradation of secondary PAHs, nor were mixture compounds or concentrations toxic to cells growing on sugars. Reverse transcription-PCR (RT-PCR) studies of the characterized catabolic pathway of phenanthrene showed that in one organism, antagonism of mixture degradation was associated with downregulated gene expression. Metabolite profiling revealed that antagonism in mixture degradation was associated with the shunting of substrate through alternative pathways not used during the degradation of single PAHs. The results of this study demonstrate metabolic differences between single and mixed PAH degradation with consequences for risk assessment and bioremediation of PAH-contaminated sites. IMPORTANCEMycobacterium species are promising organisms for environmental bioremediation because of their ubiquitous presence in soils and their ability to catabolize aromatic compounds. PAHs can be degraded effectively as single compounds, but mixed substrates often are subject to degradative inhibition, which may explain the persistence of these pollutants in soils. Single and mixed PAH degradation by diverse Mycobacterium species was compared, with associated bacterial growth, gene expression, and metabolite production. The results demonstrate that antagonism characterized degradation in a strain-and mixture-dependent manner. One strain that was versatile in its pathway use of single chemicals also efficiently degraded the mixture, whereas antagonism in other the strains was associated with altered metabolic profiles, indicating unusual pathway use. The impacts of this work on risk assessment and bioremediation modeling studies indicate the need to account for mixture-generated intermediates and to recognize mixture degradation as a property distinct from that of PAH substrate range. P olycyclic aromatic hydrocarbons (PAHs) are a class of chemical pollutants that are widespread and persistent in the environment (1-3...

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Section: Methodsmentioning

confidence: 99%

“…and meta-cleavage (27,32,40). The presence of diphenic acid (F-III) demonstrated a degradation route through the 9,10-dioxygenation pathway.…”

Section: Metabolite Series a C And F; See This Figure Also For The mentioning

confidence: 99%

mentioning

confidence: 99%

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Effects of Polycyclic Aromatic Hydrocarbon Mixtures on Degradation, Gene Expression, and Metabolite Production in Four Mycobacterium Species

Hennessee

2016

Appl Environ Microbiol

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“…PHE degradation by the strain Stenotrophomonas maltophilia C6 has been proposed as protocatechuate and salicylate pathway (Gao et al, 2013). Seo et al (2012) reported a highly branched metabolic pathways of PHE biodegradation, including dioxygenation on C-1, 2 and C-3,4 and C-9,10 positions and ring opening by both ortho-and meta-cleavage by Mycobacterium aromativorans strain JS19b1…”

Section: Degradation Of Phenanthrenementioning

confidence: 99%

Biodegradation of phenanthrene by Pseudomonas sp. BZ-3, isolated from crude oil contaminated soil

Meng

Chen

et al. 2014

International Biodeterioration & Biodegradation

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a b s t r a c tA phenanthrene (PHE) degrading bacterium strain BZ-3 was isolated from the crude oil contaminated soil in Binzhou, China. The isolate was identified as Pseudomonas sp. BZ-3 on the basis of 16S rRNA gene sequence. Various experiments were conducted to investigate the effect of pH, salinity and PHE concentration on the degradation efficiency of PHE. The degradation efficiency and degradation metabolites of PHE were detected by using GCeMS and HPLC-MS analyses. The strain BZ-3 could degrade 75% of PHE at an initial concentration of 50 mg/L under 20 g/L salinity in 7 days. PHE degradation kinetics was estimated in a first-order degradation rate model and the rate coefficient was calculated as 0.108 d À1. On the basis of the identified degradation metabolites, the strain BZ-3 could degrade PHE in the salicylate metabolic pathway. In a mixture system consisting of PHE and other PAHs including naphthalene (NA), anthracene (ANTH), and pyrene (PYR), the strain BZ-3 showed an efficiently degradation capability. Further study showed that the strain BZ-3 could also use NA, ANTH, PYR, xylene, 1-hydroxy-2-naphthoic acid, and hexane as the sole carbon and energy source, but did not grow on nitrobenzene-containing medium.

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“…The studies based on the profiling of produced metabolites revealed that strain JS19b1 T had the unique-and branched metabolic pathways for PAHs degradation, e.g. 4,5-dioxygenation and mono-oxidation as the start point for pyrene (4-fused benzene rings) metabolism (Seo et al, 2010), intra-/extradiol cleavages required for the phenanthrene (3-fused benzene rings) metabolism (Seo et al, 2012). Through the study by the proteomic approaches, various proteins such as PAH ring-hydroxylating dioxygenase (PAH-RDH), PAH extradiol dioxygenase, and phthalate dioxygenase were investigated as key enzymes for the PAHs metabolism, with a feature as induced degrading enzymes that depends on the chemical specificity of substrate (Seo et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Genome sequence of Mycobacterium aromaticivorans JS19b1T, a novel isolate from Hawaiian soil

Kwak

Park

Lee

et al. 2014

Journal of Biotechnology

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Mycobacterium aromativorans JS19b1T degrades phenanthrene through C-1,2, C-3,4 and C-9,10 dioxygenation pathways

Cited by 36 publications

References 59 publications

Effects of Polycyclic Aromatic Hydrocarbon Mixtures on Degradation, Gene Expression, and Metabolite Production in Four Mycobacterium Species

Effects of Polycyclic Aromatic Hydrocarbon Mixtures on Degradation, Gene Expression, and Metabolite Production in Four Mycobacterium Species

Biodegradation of phenanthrene by Pseudomonas sp. BZ-3, isolated from crude oil contaminated soil

Genome sequence of Mycobacterium aromaticivorans JS19b1T, a novel isolate from Hawaiian soil

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