Fluoranthene metabolism in Mycobacterium sp. strain KR20: identity of pathway intermediates during degradation and growth

Rehmann, Klaus; Hertkorn, Norbert; Kettrup, A.

doi:10.1099/00221287-147-10-2783

Cited by 77 publications

(69 citation statements)

References 46 publications

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“…5D). HPLC and UV spectral analysis indicated that this metabolite had a UV absorption spectrum similar to that reported for fluoranthene cis-2,3-dihydrodiol (52). As shown in Table 2, we also detected compounds whose mass spectra were similar to those of monohydroxyfluoranthene ([M ϩ ·] at m/z 290) and fluoranthenediols ([M ϩ ·] at m/z 378) which we considered to be derived from dehydration of fluoranthene cis-dihydrodiol.…”

Section: Resultsmentioning

confidence: 51%

Molecular Cloning and Expression of Genes Encoding a Novel Dioxygenase Involved in Low- and High-Molecular-Weight Polycyclic Aromatic Hydrocarbon Degradation in Mycobacterium vanbaalenii PYR-1

Kim

Kweon

Freeman

et al. 2006

Appl Environ Microbiol

138

121

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Mycobacterium vanbaalenii PYR-1 is able to metabolize a wide range of low-and high-molecular-weight (HMW) polycyclic aromatic hydrocarbons (PAHs). A 20-kDa protein was upregulated in PAH-metabolizing M. vanbaalenii PYR-1 cells compared to control cultures. The differentially expressed protein was identified as a ␤ subunit of the terminal dioxygenase using mass spectrometry. PCR with degenerate primers designed based on de novo sequenced peptides and a series of plaque hybridizations were done to screen the M. vanbaalenii PYR-1 genomic library. The genes, designated nidA3B3, encoding the ␣ and ␤ subunits of terminal dioxygenase, were subsequently cloned and sequenced. The deduced enzyme revealed close similarities to the corresponding PAH ring-hydroxylating dioxygenases from Mycobacterium and Rhodococcus spp. but had the highest similarity, 61.9%, to the ␣ subunit from Nocardioides sp. strain KP7. The ␣ subunit also showed 52% sequence homology with the previously reported NidA from M. vanbaalenii PYR-1. The genes nidA3B3 were subcloned into the expression vector pET-17b, and the enzyme activity in Escherichia coli cells was reconstituted through coexpression with the ferredoxin (PhdC) and ferredoxin reductase (PhdD) genes of the phenanthrene dioxygenase from Nocardioides sp. strain KP7. The recombinant PAH dioxygenase appeared to favor the HMW PAH substrates fluoranthene, pyrene, and phenanthrene. Several other PAHs, including naphthalene, anthracene, and benz[a]anthracene, were also converted to their corresponding cis-dihydrodiols. The recombinant E. coli, however, did not show any dioxygenation activity for phthalate and biphenyl. The upregulation of nidA3B3 in M. vanbaalenii PYR-1 induced by PAHs was confirmed by reverse transcription-PCR analysis.

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Section: Resultsmentioning

confidence: 51%

Molecular Cloning and Expression of Genes Encoding a Novel Dioxygenase Involved in Low- and High-Molecular-Weight Polycyclic Aromatic Hydrocarbon Degradation in Mycobacterium vanbaalenii PYR-1

Kim

Kweon

Freeman

et al. 2006

Appl Environ Microbiol

138

121

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“…5,6-Benzocoumarin was reported earlier as one of the compounds produced from phenanthrene-1,2-dihydrodiol (Pinyakong et al, 2000). Although the intradiol cleavage of highmolecular-mass PAH diols is usually limited to K-region diols (Rehmann et al, 1998;Vila et al, 2001), there are reports on intradiol cleavage of the non-K region diol of PAHs (Dean-Ross et al, 2001;Rehmann et al, 2001;Keum et al, 2006;Kim et al, 2005;Lopez et al, 2006). Naphthalene-1,2-dicarboxylic acid identified in this study was found to be a dead-end metabolite and was not degraded further by strain PN/Y.…”

Section: Discussionmentioning

confidence: 99%

A novel degradation pathway in the assimilation of phenanthrene by Staphylococcus sp. strain PN/Y via meta-cleavage of 2-hydroxy-1-naphthoic acid: formation of trans-2,3-dioxo-5-(2′-hydroxyphenyl)-pent-4-enoic acid

2007

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Staphylococcus sp. strain PN/Y, capable of utilizing phenanthrene as a sole source of carbon and energy, was isolated from petroleum-contaminated soil. In the degradation of phenanthrene by strain PN/Y, various metabolites, isolated and identified by a combination of chromatographic and spectrometric analyses, revealed a novel phenanthrene assimilation pathway involving 2-hydroxy-1-naphthoic acid. Metabolism of phenanthrene was initiated by the dioxygenation on the 1,2-position of phenanthrene followed by meta-cleavage of phenanthrene-1,2-diol, leading to 2-hydroxy-1-naphthoic acid, which was then processed via a novel meta-cleavage pathway, leading to the formation of trans-2,3-dioxo-5-(29-hydroxyphenyl)-pent-4-enoic acid and subsequently to salicylic acid. In the lower pathway, salicylic acid was transformed to catechol, which was then metabolized by catechol-2,3-dioxygenase to 2-hydroxymuconaldehyde acid, ultimately forming TCA cycle intermediates. The catabolic genes involved in phenanthrene degradation were found to be plasmid-encoded. This detailed study of polycyclic aromatic hydrocarbon (PAH) metabolism by a Gram-positive species involving a unique ring-cleavage dioxygenase in a novel phenanthrene degradation pathway provides a new insight into the microbial degradation of PAHs. INTRODUCTIONPolycyclic aromatic hydrocarbons (PAHs) constitute a group of priority environmental pollutants, which are ubiquitous contaminants in soils and sediments and are of environmental concern because of their toxic, mutagenic and/or carcinogenic effects (Mastrangelo et al., 1996;Marston et al., 2001;Xue & Warshawsky, 2005). In recent years, the biodegradation of PAHs has received considerable attention and a variety of micro-organisms have been reported to play important roles in the process (Pothuluri & Cerniglia, 1994;Shuttleworth & Cerniglia, 1995;Kanaly & Harayama, 2000;Habe & Omori, 2003;Tortella et al., 2005). Bioremediation technologies have increasingly been proposed to decontaminate PAH-contaminated sites (Harayama, 1997;Samanta et al., 2002;Parrish et al., 2004;Vinas et al., 2005).Phenanthrene, a PAH with three condensed rings fused in angular fashion, has a 'bay-region' and a 'K-region' and is often used as a model substrate for studies on the metabolism of carcinogenic PAHs. Over the last 60 years, a number of studies on phenanthrene degradation by several Gram-negative and Gram-positive bacterial species have been reported (Evans et al., 1965;Kiyohara et al., 1976Kiyohara et al., , 1982Kiyohara & Nagao, 1978;Barnsley, 1983;Gibson & Subramanian, 1984;Houghton & Shanley, 1994;Adachi et al., 1999;Samanta et al., 1999), where various pathways and metabolic diversity involved in phenanthrene degradation were documented. In general, the metabolic pathway is initiated by the double hydroxylation of the bay-region of phenanthrene by a dioxygenase enzyme to form cis-3,4-phenanthrenedihydrodiol. The resultant dihydrodiol is then converted by the action of dihydrodiol dehydrogenase to 3,4-dihydroxyphenanthrene, which und...

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“…In the short time since these reviews appeared, more examples of novel metabolic pathways and cooxidation products have been described. For example, Rehmann et al (507) outlined a new pathway for fluoranthene metabolism in Mycobacterium sp. strain KR20, whereby initial dioxygenation commences at the 2,3 position (Fig.…”

Section: Aerobic Pah Metabolismmentioning

confidence: 99%

Recent Advances in Petroleum Microbiology

Hamme¹,

Singh

Ward

2003

Microbiol Mol Biol Rev

1,203

640

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Recent advances in molecular biology have extended our understanding of the metabolic processes related to microbial transformation of petroleum hydrocarbons. The physiological responses of microorganisms to the presence of hydrocarbons, including cell surface alterations and adaptive mechanisms for uptake and efflux of these substrates, have been characterized. New molecular techniques have enhanced our ability to investigate the dynamics of microbial communities in petroleum-impacted ecosystems. By establishing conditions which maximize rates and extents of microbial growth, hydrocarbon access, and transformation, highly accelerated and bioreactor-based petroleum waste degradation processes have been implemented. Biofilters capable of removing and biodegrading volatile petroleum contaminants in air streams with short substrate-microbe contact times (<60 s) are being used effectively. Microbes are being injected into partially spent petroleum reservoirs to enhance oil recovery. However, these microbial processes have not exhibited consistent and effective performance, primarily because of our inability to control conditions in the subsurface environment. Microbes may be exploited to break stable oilfield emulsions to produce pipeline quality oil. There is interest in replacing physical oil desulfurization processes with biodesulfurization methods through promotion of selective sulfur removal without degradation of associated carbon moieties. However, since microbes require an environment containing some water, a two-phase oil-water system must be established to optimize contact between the microbes and the hydrocarbon, and such an emulsion is not easily created with viscous crude oil. This challenge may be circumvented by application of the technology to more refined gasoline and diesel substrates, where aqueous-hydrocarbon emulsions are more easily generated. Molecular approaches are being used to broaden the substrate specificity and increase the rates and extents of desulfurization. Bacterial processes are being commercialized for removal of H2S and sulfoxides from petrochemical waste streams. Microbes also have potential for use in removal of nitrogen from crude oil leading to reduced nitric oxide emissions provided that technical problems similar to those experienced in biodesulfurization can be solved. Enzymes are being exploited to produce added-value products from petroleum substrates, and bacterial biosensors are being used to analyze petroleum-contaminated environments

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Fluoranthene metabolism in Mycobacterium sp. strain KR20: identity of pathway intermediates during degradation and growth

Cited by 77 publications

References 46 publications

Molecular Cloning and Expression of Genes Encoding a Novel Dioxygenase Involved in Low- and High-Molecular-Weight Polycyclic Aromatic Hydrocarbon Degradation in Mycobacterium vanbaalenii PYR-1

Molecular Cloning and Expression of Genes Encoding a Novel Dioxygenase Involved in Low- and High-Molecular-Weight Polycyclic Aromatic Hydrocarbon Degradation in Mycobacterium vanbaalenii PYR-1

A novel degradation pathway in the assimilation of phenanthrene by Staphylococcus sp. strain PN/Y via meta-cleavage of 2-hydroxy-1-naphthoic acid: formation of trans-2,3-dioxo-5-(2′-hydroxyphenyl)-pent-4-enoic acid

Recent Advances in Petroleum Microbiology

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