Effect of nonionic surfactant addition on bacterial metabolism of naphthalene: Assessment of toxicity and overflow metabolism potential

Auger, Robert L.; Jacobson, Annette M.; Domach, Michael M.

doi:10.1016/0304-3894(95)00038-v

Cited by 21 publications

(19 citation statements)

References 11 publications

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“…Similar to the isotope-trapping experiment with strain P15, it is likely that the rate of formation of 4,5-dihydroxypyrene at high concentrations of PYRdHD exceeds the subsequent rate of metabolism, resulting in the accumulation of 4,5-dihydroxypyrene and its consequent autoxidation to PYRQ. A similar phenomenon has been noted before in the bacterial degradation of naphthalene, for which the accumulation of naphthoquinone has been suggested to increase as the rate of naphthalene availability increased (2,19). Strain PYR-1 is able to consume PYRQ as a growth substrate, which suggests that it would only accumulate transiently if formed by this organism or by other bacteria that might also be transforming pyrene in a complex system.…”

Section: Discussionsupporting

confidence: 77%

Products from the Incomplete Metabolism of Pyrene by Polycyclic Aromatic Hydrocarbon-Degrading Bacteria

Kazunga

Aitken

2000

Appl Environ Microbiol

161

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Pyrene is a regulated pollutant at sites contaminated with polycyclic aromatic hydrocarbons (PAH). It is mineralized by some bacteria but is also transformed to nonmineral products by a variety of other PAHdegrading bacteria. We examined the formation of such products by four bacterial strains and identified and further characterized the most apparently significant of these metabolites. Pseudomonas stutzeri strain P16 and Bacillus cereus strain P21 transformed pyrene primarily to cis-4,5-dihydro-4,5-dihydroxypyrene (PYRdHD), the first intermediate in the known pathway for aerobic bacterial mineralization of pyrene. Sphingomonas yanoikuyae strain R1 transformed pyrene to PYRdHD and pyrene-4,5-dione (PYRQ). Both strain R1 and Pseudomonas saccharophila strain P15 transform PYRdHD to PYRQ nearly stoichiometrically, suggesting that PYRQ is formed by oxidation of PYRdHD to 4,5-dihydroxypyrene and subsequent autoxidation of this metabolite. A pyrene-mineralizing organism, Mycobacterium strain PYR-1, also transforms PYRdHD to PYRQ at high initial concentrations of PYRdHD. However, strain PYR-1 is able to use both PYRdHD and PYRQ as growth substrates. PYRdHD strongly inhibited phenanthrene degradation by strains P15 and R1 but had only a minor effect on strains P16 and P21. At their aqueous saturation concentrations, both PYRdHD and PYRQ severely inhibited benzo[a]pyrene mineralization by strains P15 and R1. Collectively, these findings suggest that products derived from pyrene transformation have the potential to accumulate in PAH-contaminated systems and that such products can significantly influence the removal of other PAH. However, these products may be susceptible to subsequent degradation by organisms able to metabolize pyrene more extensively if such organisms are present in the system. Polycyclic aromatic hydrocarbons (PAH) are known to be degradable by a variety of soil bacteria (40). Consequently, the bioremediation of PAH contamination with naturally occurring microorganisms has been attempted at a number of sites (43,45). Most of the interest in the biodegradation of PAH in the field has been in the removal of the parent compounds, while most research on pure cultures of PAH-degrading bacteria has focused on their ability to grow on or mineralize specific PAH substrates. Relatively little attention has been paid to the potential formation of products from the partial transformation of PAH.Most of the information that does exist on PAH metabolites has been obtained in the context of identifying transient metabolites formed by isolates during growth on the parent compound (13,33,35,40) or metabolites formed by mutants of wild-type degraders (4, 40). Some bacteria, however, are capable of transforming one or more PAH despite an inability to grow on or mineralize the PAH in question (1,20,31,47). It is important to evaluate the products of such incomplete PAH metabolism because of their potential effects on PAH-degrading microorganisms or on potentially exposed human populations (44). Identification of common pr...

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Section: Discussionsupporting

confidence: 77%

Products from the Incomplete Metabolism of Pyrene by Polycyclic Aromatic Hydrocarbon-Degrading Bacteria

Kazunga

Aitken

2000

Appl Environ Microbiol

161

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“…Davies & Evans (1964) showed that a 25 mM solution of 1,2-dihydroxynaphthalene is converted by non-enzymic oxidation to 1,2-naphthoquinone at a rate of approximately 20 % min 21 at pH 6.5. 1,2-Naphthoquinone has been reported to accumulate and inhibit both growth and naphthalene metabolism when ferrous and magnesium salts are omitted from growth media (Murphy & Stone, 1955) or when naphthalene bioavailability is increased by the addition of surfactant (Auger et al, 1995). Our analysis by HPLC suggests that 1,2-naphthoquinone (presumably produced abiotically from 1,2-dihydroxynaphthalene) and two abiotic transformation products of 1,2-naphthoquinone accumulate when strain CJ2 is exposed to inhibitory concentrations of naphthalene.…”

Section: Discussionmentioning

confidence: 73%

“…Previous reports have suggested that the accumulation of an orange metabolite in naphthalene-metabolizing cultures results from the abiotic oxidative transformation of 1,2-dihydroxynaphthalene to 1,2-naphthoquinone (Auger et al, 1995;Davies & Evans, 1964;Murphy & Stone, 1955). Spectrophotometric scans (240-400 nm) of 1,2-naphthoquinone standards and coloured media from naphthaleneinhibited cultures of strain CJ2 suggested that 1,2-naphthoquinone was present at concentrations between 50 and 100 mM (data not shown).…”

Section: Analysis Of Toxic Accumulated Metabolitesmentioning

confidence: 74%

“…Although the genetics and biochemistry of naphthalene metabolism have been studied in depth, the inhibition of naphthalene metabolism due to the toxicity of naphthalene and naphthalene metabolites has received less attention (Auger et al, 1995;Murphy & Stone, 1955;Park et al, 2004). Naphthalene has been reported to be directly toxic to P. putida G7 under oxygen-and nitrogen-limited conditions, although it is unclear if the toxicity was due to naphthalene or a naphthalene metabolite (Ahn et al, 1998).…”

Section: Introductionmentioning

confidence: 99%

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Naphthalene metabolism and growth inhibition by naphthalene in Polaromonas naphthalenivorans strain CJ2

Pumphrey

Madsen

2007

Microbiology

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This study was designed to characterize naphthalene metabolism in Polaromonas naphthalenivorans CJ2. Comparisons were completed using two archetypal naphthalenedegrading bacteria: Pseudomonas putida NCIB 9816-4 and Ralstonia sp. strain U2, representative of the catechol and gentisate pathways, respectively. Strain CJ2 carries naphthalene catabolic genes that are homologous to those in Ralstonia sp. strain U2. Here we show that strain CJ2 metabolizes naphthalene via gentisate using respirometry, metabolite detection by GC-MS and cell-free enzyme assays. Unlike P. putida NCIB 9816-4 or Ralstonia sp. strain U2, strain CJ2 did not grow in minimal medium saturated with naphthalene. Growth assays revealed that strain CJ2 is inhibited by naphthalene concentrations of 78 mM (10 p.p.m.) and higher, and the inhibition of growth is accompanied by the accumulation of orange-coloured, putative naphthalene metabolites in the culture medium. Loss of cell viability coincided with the appearance of the coloured metabolites, and analysis by HPLC suggested that the accumulated metabolites were 1,2-naphthoquinone and its unstable auto-oxidation products. The naphthoquinone breakdown products accumulated in inhibited, but not uninhibited, cultures of strain CJ2. Furthermore, naphthalene itself was shown to directly inhibit growth of a regulatory mutant of strain CJ2 that is unable to metabolize naphthalene. These results suggest that, despite being able to use naphthalene as a carbon and energy source, strain CJ2 must balance naphthalene utilization against two types of toxicity.

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“…A dihydroxygenease enzyme is responsible for conversion of the 1,2-dihydroxynaphthalene to further metabolites. In aqueous solutions at neutral or alkaline pH, 1,2-dihydroxynaphthalene may be abiotically oxidized to 1,2-naphthoquinone if the residence time is greater than approximately 2 min (Auger et al, 1995;Kuhm et al, 1991;Murphy and Stone, 1955).…”

Section: Naphthalene Biodegradation Productsmentioning

confidence: 99%

Biodegradation kinetics of naphthalene in nonaqueous phase liquid-water mixed batch systems: Comparison of model predictions and experimental results

Ghoshal

Luthy

1998

Biotechnol. Bioeng.

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Effect of nonionic surfactant addition on bacterial metabolism of naphthalene: Assessment of toxicity and overflow metabolism potential

Cited by 21 publications

References 11 publications

Products from the Incomplete Metabolism of Pyrene by Polycyclic Aromatic Hydrocarbon-Degrading Bacteria

Products from the Incomplete Metabolism of Pyrene by Polycyclic Aromatic Hydrocarbon-Degrading Bacteria

Naphthalene metabolism and growth inhibition by naphthalene in Polaromonas naphthalenivorans strain CJ2

Biodegradation kinetics of naphthalene in nonaqueous phase liquid-water mixed batch systems: Comparison of model predictions and experimental results

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