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PubMed2001

Biotransformation of nitrophenols in upflow anaerobic sludge blanket reactors.

Four identical bench-scale upflow anaerobic sludge blanket (UASB) reactors, R1, R2, R3 and R4, were used to assess nitrophenols degradation at four different hydraulic retention times (HRT). Reactor R1 was used as control, whereas R2, R3, and R4 were fed with 2-nitrophenol (2-NP), 4-nitrophenol (4-NP), and 2,4-dinitrophenol (2,4-DNP), respectively. The concentration of each nitrophenol was gradually varied from 2 to 30 mg/l during acclimation. After acclimation reactors were operated under steady-state conditions at four different HRTs--30, 24, 18, and 12 h, to study its effect on the removal of nitrophenols. Overall removal of 2-NP and 4-NP was always more than 99% but 2,4-DNP removal decreased from 96% to 89.7% as HRT was lowered from 30 to 12 h. 2-Aminophenol (2-AP), 4-aminophenol (4-AP) and 2-amino,4-nitrophenol (2-A,4-NP) were found to be the major intermediates during the degradation of 2-NP, 4-NP and 2,4-DNP, respectively. Out of the total input of nitrophenolic concentration (30 mg/l), on molar basis, about 41.248.4% of 2-NP, 59.4-68% of 4-NP, 30-26.6% of 2,4-DNP was recovered in the form of their respective amino derivatives at 30-12 h HRT. COD removal was 98-89%, 97-56%, 97-52%, and 94-46% at 30-12 h HRT for R1, R2, R3 and R4, respectively. Average cell growth was observed to be 0.15 g volatile suspended solid (VSS) per g COD consumed. Methanogenic inhibition was observed at lower HRTs (18 and 12 h), however denitrification was always more than 99% with non-detectable level of nitrite. The granules developed inside the reactors were black in color and their average size varied between 1.9 and 2.1 mm.

Biomass↗

PubMed2004

Estrogenic and anti-androgenic activity of nitrophenols in diesel exhaust particles (DEP).

We recently isolated 4-nitrophenol, 2-methyl-4-nitrophenol, 3-methyl-4-nitrophenol, and 4-nitro-3-phenylphenol from diesel exhaust particles (DEP) and identified them as vasodilators. Because these compounds are alkylphenolic derivatives that might mimic hormones, we evaluated their estrogenic activity by human estrogen receptor (hER)-yeast screen assay. All of these nitrophenol derivatives except 2-methyl-4-nitrophenol exhibited estrogenic activity. Some estrogenic compounds are also anti-androgenic, so we measured the anti-androgenic activity of the same compounds by human androgen receptor (hAR)-yeast screen assay. We found anti-androgenicity in all four nitrophenols. Nitrophenols in DEP possess not only vasodilatory activity but also estrogenic and anti-androgenic activity.

Androgen Receptor Antagonists↗

PubMed2005

Slurry-phase biological treatment of nitrophenol using bioaugmentation technique.

OBJECTIVE: To investigate the performance of soil-slurry bioreactor used for remediating contaminated soil with 4-nitrophenol (4-NP). METHODS: The slurry bioreactor was used to degrade different concentrations of 4-nitrophenol with or without inoculating the acclimated activated sludge. HPLC system (Hewlett-Packard model 5050 with a UV detector) was used for the quantification of 4-nitrophenol. RESULTS: The indigenous microorganisms exhibited a little activity for simulated soil with 50 mg 4-NP/kg soil. However, at the concentration of 10 mg 4-NPkg soil, a considerable degradation occurred within two weeks. It appeared that high concentrations of 4-nitrophenol apparently produced an inhibitory effect on microbial activity. For system receiving 50 mg 4-NP/kg soil, the maximum rate of 4-NP degradation measured in the reactor inoculated with 25 g sludge/kg soil was approximately 10 times higher than the uninoculated reactor, suggesting that the degradation rate of 4-nitrophenol could be enhanced greatly by means of inoculating acclimated sludge. CONCLUSION: The addition of sludge capable of degrading 4-nitrophenol can result in enhance the degradation rate of 4-nitrophenol.

Biodegradation, Environmental↗

PubMedDate not supplied

p-Nitrophenol hydroxylation. A microsomal oxidation which is highly inducible by ethanol.

p-Nitrophenol is widely employed as a substrate for the study of the glucuronide and sulfate conjugation pathways. However, in perfused livers from ethanol-treated rats, p-nitrophenol was rapidly metabolized to 4-nitrocatechol. The 4-nitrocatechol formed competed with p-nitrophenol for conjugation with glucuronic acid and sulfate, and interfered with the direct spectral measurement of p-nitrophenol. In isolated microsomes, rates of p-nitrophenol hydroxylation were increased 6-fold after chronic ethanol treatment. Much smaller induction was observed after pretreatment of rats with phenobarbital (70% increase) or beta-naphthoflavone (30% increase). In addition, the 6-fold increase in rates of p-nitrophenol hydroxylation after chronic ethanol treatment was greater than increases in activity observed for the microsomal metabolism of aniline, 7-ethoxycoumarin, benzo(a)pyrene, ethanol, or aminopyrine. These data demonstrate that p-nitrophenol may be an extremely useful substrate for the study of changes in drug-metabolizing activity induced by ethanol treatment.

Animals↗

PubMed1999

Chlorophenol and nitrophenol metabolism by Sphingomonas sp UG30.

Sphingomonas sp UG30 is a pentachlorophenol (PCP)-degrading bacterial strain capable of degrading several nitrophenolic compounds, including p-nitrophenol (PNP), 2,4-dinitrophenol (2,4-DNP), p-nitrocatechol and 4,6-dinitro-o-cresol (DNOC). The ability to degrade both chlorophenolic and nitrophenolic compounds is probably not restricted to UG30, but may also be possessed by other pentachlorophenol-degrading Sphingomonas spp. The interesting question arises as to whether there is any point of convergence between the initial pathways of PCP and nitrophenol degradation in these microorganisms. There is some experimental evidence that PCP-4-monooxygenase is involved in metabolism of both p-nitrophenol and 2,4-dinitrophenol. Further studies are needed to confirm this and to examine the role(s) of other PCP-degrading enzymes in nitrophenol metabolism by this microorganism. In this paper, we review some of the taxonomic, biochemical, physiological and ecological properties of Sphingomonas sp UG30 with respect to biodegradation of PCP and nitrophenolic compounds.

Journal Article↗

PubMed1976

Metabolism of nitrophenols by bacteria isolated from parathion-amended flooded soil.

Two bacterial isolates from parathion-amended flooded soil, Pseudomonas sp. and Bacillus sp., were examined for their ability to decompose nitrophenols. Uniformly labelled 14C-p-nitrophenol was metabolized by both bacteria, 14CO2 and nitrite being end products. A substantial portion (23% for Pseudomonas sp. and 80% for Bacillus sp.) of radioactivity applied as p-nitrophenol was accounted for as 14CO2 at the end of a 72-h period; 8 to 16% remained in the water phase after solvent extraction. Pseudomonas sp. produced nitrite also from 2,4-dinitrophenol, but only after a lag, and not from o- and m-nitrophenols. Interestingly, m-nitrophenol, known for its resistance to biodegradation because of meta substitution, was decomposed by Bacillus sp., resulting in the formation of nitrite and phenol; o-nitrophenol and 2,4-dinitrophenol resisted degradation by this bacterium.

Bacillus↗

PubMed2000

Placental transfer and pharmacokinetics of a single oral dose of [14C]p-nitrophenol in rats.

The pharmacokinetics and placental transfer of a single oral dose of 100 mg/kg (10 microCi/kg, 16% of acute oral LD50) of uniformly phenyl-labeled [14C]p-nitrophenol were investigated in pregnant Sprague-Dawley rats at 14-18 days of gestation. Three animals were killed on gestation day 18, at 0.5, 1, 2, 4, 12, 24, and 48 h after dosing. Radioactivity was rapidly absorbed and distributed throughout the maternal and fetal tissues. The gastrointestinal tract contents retained 20% and 2% of the dose at 0.5 h and 4 h after dosing. The peak maternal plasma concentration of radioactivity (microg p-nitrophenol equivalent/ml) was 7.17 compared with 0.37 for fetal plasma at 0.5 h. Maximum concentration of radioactivity (microg p-nitrophenol equivalent/g fresh tissue) was detected in most tissues 0.5 h after dosing and was in descending order: kidney 23.27, liver 12.37, placenta 3.56, fetus 2.17, and brain 1.99. Radioactivity was eliminated from plasma and all tissues beiexponentially. The half-lives of elimination of 14C were 34.65 h and 69.30 h for maternal and fetal plasma, respectively. p-Nitrophenol, detected by HPLC, was the major compound identified in plasma and tissues. While p-nitrophenol disappeared biphasically from maternal plasma and kidney, it was eliminated monophasically from brain, placenta, and liver. p-Nitrocatechol and p-aminophenol were detected in the liver with peak concentrations at 0.5 h of 1.13 and 1.00 microg/g fresh tissue, respectively. While the change in the concentration of p-nitrocatechol with time was monophasic, that of p-aminophenol showed a biphasic pattern with elimination half-lives of 1.93 h and 4.95 h, respectively. Radioactivity was rapidly excreted in the urine mostly as polar metabolites, while only 3% of the dose was recovered in the feces. Radioactive materials excreted in the urine comprised: glucuronides 4%, sulfates 8%, hot-acid hydrolysates 11%, nonconjugated compounds 16%, and water-soluble metabolites 61%. This study demonstrated that although orally administered p-nitrophenol is a rapidly absorbed and excreted compound, it is transported to the maternal brain and the fetus and may pose a health risk following exposure to toxic doses during pregnancy.

Animals↗

PubMed2004

Amperometric microbial biosensor for p-nitrophenol using Moraxella sp.-modified carbon paste electrode.

An amperometric microbial biosensor for highly specific, sensitive and rapid quantitative determination of p-nitrophenol was developed. The biosensor takes advantage of the ability of Moraxella sp. to specifically degrade p-nitrophenol to hydroquinone, a more electroactive compound than p-nitrophenol. The electrochemical oxidation current of hydroquinone formed in biodegradation of p-nitrophenol was measured at Moraxella sp.-modified carbon paste electrode and correlated to p-phenol concentrations. The optimum response was realized by electrode constructed using 15 mg of dry cell weight per 1 g of carbon paste and operating at 0.3 V (versus Ag/AgCl reference) in pH 7.5, 20 mM sodium phosphate buffer. Operating at these optimum conditions the biosensor had excellent selectivity against phenol derivatives and was able to measure as low as 20 nM (2.78 ppb) p-nitrophenol with very good accuracy and reproducibility. The biosensor was stable for approximately 3 weeks when stored at 4 degrees C. The applicability of the biosensor to measure p-nitrophenol in lake water was demonstrated.

Biological Assay↗

PubMed2005

Effect of copper on the adsorption of p-nitrophenol onto soils.

The effect of copper on adsorption of p-nitrophenol on two typical Chinese soils was investigated using a batch-equilibration method. Adsorption experiments were carried out when both copper and p-nitrophenol were adsorbed simultaneously, and when copper was previously adsorbed on soils. It was observed that adsorption of p-nitrophenol decreased with increasing copper concentrations thereby indicating a competition between copper and p-nitrophenol for occupying the adsorption sites on soils. Moisture increased the hydrated sphere and the acidity of water surrounding the cation, which further reduced the adsorption of p-nitrophenol. Fourier transform infrared spectroscopy study provided the direct evidence for the coordination of p-nitrophenol sorbed by soils with metal cation in n-hexane system. It was observed that the perturbations included a red shift of the nu(asym) (NO) band, a concomitant blue-shift of the nu(sym) (NO) band and a blue-shift of C-N band when compared with the infrared spectra obtained from water solution.

Adsorption↗

PubMed2006

Treatment of nitrophenols by cathode reduction and electro-Fenton methods.

This study deals with the degradation of various nitrophenols by cathode reduction and electro-Fenton methods. Phenols (Poh), 2-nitrophenol (2-NP), 3-nitrophenol (3-NP), 4-nitrophenol (4-NP), and 2,4-dinitrophenol (2,4-DNP) are treated and different degradation sequences are obtained. The relationship between the structure and activities of nitrophenols is discussed. Using 4-NP as a model nitrophenol, the electrochemical behaviors on graphite cathode and Pt anode are analyzed by cyclic voltammetry. The contribution of different reactions to the degradation of 4-NP is investigated in divided cells. The degradation of 4-NP is much faster in the cathode cell than in the anodic cell. In the cathode cell, the degradation of 4-NP is significantly enhanced by the introduction of aeration and Fe(2+). Ultraviolet-visible (UV-vis) spectra reveal different reaction pathways for the degradation in the anodic cell and cathode cell. Treatment of high concentration of 4-NP in the undivided cell shows that more than 98% removal of 4-NP and about 13% removal of total organic carbon (TOC) are obtained for both processes, while the subsequent biodegradability test shows that electro-Fenton can eliminate the toxicity and improve the biodegradability of 4-NP. Negligible quantity of nitrate and nitrite ions detected in both processes indicates that there is no direct release of -NO(2) and -NO groups from 4-NP and its degradation intermediates. Intermediates such as hydroquinone and bezoquinone are detected by gas chromatography/mass spectrum (GC/MS). The degradation pathway of 4-NP in electro-Fenton process is proposed as the cathode reduction followed by hydroxyl oxidation.

Benzoquinones↗

PubMed2003

Continuous biotransformation and removal of nitrophenols under denitrifying conditions.

The effect of COD/NO(3)(-)-N ratio on the biotransformation and removal of 2-nitrophenol (2-NP), 4-nitrophenol (4-NP), and 2,4-dinitrophenol (2,4-DNP) was studied in bench scale upflow anaerobic sludge blanket (UASB) reactors. Sodium acetate and sodium nitrate were used as electron donor (substrate) and electron acceptor, respectively. Nitrate nitrogen loading was increased from 0.098 to 0.6 kg/m(3)d in order to keep COD/NO(3)(-)-N ratio as 20.8, 14.3, 9.8, 5.0, 4.0 and 3.33. Throughout the study, input nitrophenolic concentration and hydraulic retention time (HRT) were kept constant as 30 mg/l and 24h, respectively. 2-Aminophenol (2-AP), 4-aminophenol (4-AP) and 2-amino,4-nitrophenol (2-A,4-NP) were found as the major intermediate metabolite of 2-NP, 4-NP and 2,4-DNP, respectively. Removal of all the three nitrophenols increased with lowering of COD/NO(3)(-)-N ratio. However, nitrophenols removal got adversely affected when COD/NO(3)(-)-N ratio was reduced below 5. Maximum removal achieved were 91.63%, 90.17% and 86.10% for 2-NP, 4-NP and 2,4-DNP, respectively at a COD/NO(3)(-)-N ratio of 5. Simultaneous denitrification and methanogenesis was observed in all the reactors throughout the study.

Bioreactors↗

PubMed1989

Surface-enhanced resonance Raman spectroscopy as an ancillary high-performance liquid chromatography detector for nitrophenol compounds.

In this study, the potential application of surface-enhanced resonance Raman scattering (SERRS) spectroscopy as an off-line secondary detector for HPLC has been evaluated. Four nitrophenol compounds, 2-nitrophenol, 4-nitrophenol, 2,4-dinitrophenol, and 4,6-dinitrocresol were separated by isocratic reverse-phase high-performance liquid chromatography (RP-HPLC) and monitored with a conventional UV detector. Resonance Raman (RR) and SERRS spectroscopy were next used to provide the required specificity for distinguishing the nitrophenol compounds. The SERRS detection limit for both 2-nitrophenol and 4-nitrophenol was calculated to be 14 ppb and that for 2,4-dinitrophenol and 4,6-dinitrocresol was estimated to lie near the parts-per-billion level as well. This detection limit is 2-3 orders of magnitude lower than that obtained by RR spectroscopy.

Chromatography, High Pressure Liquid↗

PubMed1993

Intraluminal calcium of the liver endoplasmic reticulum stimulates the glucuronidation of p-nitrophenol.

The relationship between the intraluminal Ca2+ content of endoplasmic reticulum and the rate of the glucuronidation of p-nitrophenol was investigated in isolated rat hepatocytes. Different agents which decrease the Ca2+ level in the endoplasmic reticulum [calcium ionophores (A23187, ionomycin) or Ca(2+)-ATPase inhibitors(thapsigargin,2,5-di-(t-butyl)-1,4-benzohydroquinone+ ++)] inhibited the conjugation of p-nitrophenol. Depletion of intracellular Ca2+ stores by preincubation of hepatocytes in the absence of free Ca2+ (in the presence of excess EGTA) also decreased the rate of glucuronidation; Ca2+ re-admission to EGTA-treated hepatocytes restored glucuronidation. In intact liver microsomes the p-nitrophenol UDP-glucuronosyl-transferase activity was not modified by varying the external free Ca2+ concentrations within a cytosol-like range. Emptying of the Ca2+ from the lumen of microsomal vesicles by A23187, after MgATP-stimulated Ca2+ sequestration, decreased the glucuronidation of p-nitrophenol. A similar effect was observed in filipin-permeabilized hepatocytes. In native and in detergent-treated microsomes, Ca2+ (1-10 mM) increased the p-nitrophenol UDP-glucuronosyltransferase activity. It is suggested that the physiological concentration of Ca2+ in the lumen of the endoplasmic reticulum is necessary for the optimal activity of p-nitrophenol UDP-glucuronosyltransferase; the depletion of Ca2+ decreases the activity of the enzyme.

Animals↗

PubMed1958

The action of nitrophenols on the metabolic rate of rats.

The effect of the mono- and di-nitrophenols and certain related compounds has been determined on the rate of oxygen consumption, the rate of carbon dioxide output and the rectal temperature of the Wistar albino rat.Of the compounds examined, only 2:4-dinitrophenol and its derivative, 3:5-dinitro-o-cresol, stimulated metabolic rate. 2-Nitrophenol and 2:3-, 2:6-, and 3:5-dinitrophenol produced no change in metabolic rate; 3-nitrophenol and 2:5-dinitrophenol had no action on carbon dioxide production although they caused a decrease in oxygen consumption. 4-Nitrophenol and 3:4-dinitrophenol increased only the rate of carbon dioxide output; 2-amino-4-nitrophenol increased the rate of carbon dioxide output and decreased the rate of oxygen consumption; 4-amino-2-nitrophenol caused depression of metabolic rate.It was confirmed that neither rectal temperature nor carbon dioxide output could replace rate of oxygen consumption as a reliable index of metabolic stimulant action. An apparatus is described which facilitates measurement of the oxygen consumption of small mammals.

Animals↗

PubMed1999

The role of the Sphingomonas species UG30 pentachlorophenol-4-monooxygenase in p-nitrophenol degradation.

Pentachlorophenol-4-monooxygenase is an aromatic flavoprotein monooxygenase which hydroxylates pentachlorophenol and a wide range of polyhalogenated phenols at their para position. The PCP-degrading Sphingomonas species UG30 was recently shown to mineralize p-nitrophenol. In this study, the UG30 pcpB gene encoding the pentachlorophenol-4-monooxygenase gene was cloned for use to study its potential role in p-nitrophenol degradation. The UG30 pcpB gene consists of 1614 bp with a predicted translational product of 538 amino acids and a molecular mass of 59,933 Da. The primary sequence of pentachlorophenol-4-monooxygenase contained a highly conserved FAD binding site at its N-terminus associated with a beta alpha beta fold. UG30 has been shown previously to convert p-nitrophenol to 4-nitrocatechol. We observed that pentachlorophenol-4-monooxygenase catalyzed the hydroxylation of 4-nitrocatechol to 1,2,4-benzenetriol. About 31.2% of the nitro substituent of 4-nitrocatechol (initial concentration of 200 microM) was cleaved to yield nitrite over 2 h, indicating that the enzyme may be involved in the second step of p-nitrophenol degradation. The enzyme also hydroxylated p-nitrophenol at the para position, but only to a very slight extent. Our results confirm that pentachlorophenol-4-monooxygenase is not the primary enzyme in the initial step of p-nitrophenol metabolism by UG30.

Biodegradation, Environmental↗

PubMed2006

Decomposition of 2-nitrophenol in aqueous solution by ozone and UV/ozone processes.

The decomposition of 2-nitrophenol in aqueous solutions by ozone and UV/ozone processes was found to be technically feasible under adequate experimental conditions. Formation of nitrate ions was observed following the decomposition of 2-nitrophenol by ozone and UV/ ozone processes. Increasing ozone dosage and UV light intensity accelerated the decomposition rate of 2-nitrophenol in an aqueous solution. The species distribution of 2-nitrophenol under various solution conditions plays a significant role in determining decomposition behavior. In most experiments conducted in this study, the decomposition of 2-nitrophenol by ozone and UV/ozone processes was favored to occur in alkaline conditions. The addition of 2-butanol accelerated the rate of gaseous ozone transfer to an aqueous phase by reducing the surface tension of aqueous solution and therefore enhancing the decomposition rate of 2-nitrophenol by ozone and UV/ozone processes.

Hazardous Substances↗

PubMed1991

Pathway for Biodegradation of p-Nitrophenol in a Moraxella sp.

A Moraxella strain grew on p-nitrophenol with stoichiometric release of nitrite. During induction of the enzymes for growth on p-nitrophenol, traces of hydroquinone accumulated in the medium. In the presence of 2,2'-dipyridyl, p-nitrophenol was converted stoichiometrically to hydroquinone. Particulate enzymes catalyzed the conversion of p-nitrophenol to hydroquinone in the presence of NADPH and oxygen. Soluble enzymes catalyzed the conversion of hydroquinone to gamma-hydroxymuconic semialdehyde, which was identified by high-performance liquid chromatography (HPLC)-mass spectroscopy. Upon addition of catalytic amounts of NAD, gamma-hydroxymuconic semialdehyde was converted to beta-ketoadipic acid. In the presence of pyruvate and lactic dehydrogenase, substrate amounts of NAD were required and gamma-hydroxymuconic semialdehyde was converted to maleylacetic acid, which was identified by HPLC-mass spectroscopy. Similar results were obtained when the reaction was carried out in the presence of potassium ferricyanide. Extracts prepared from p-nitrophenol-growth cells also contained an enzyme that catalyzed the oxidation of 1,2,4-benzenetriol to maleylacetic acid. The enzyme responsible for the oxidation of 1,2,4-benzenetriol was separated from the enzyme responsible for hydroquinone oxidation by DEAE-cellulose chromatography. The results indicate that the pathway for biodegradation of p-nitrophenol involves the initial removal of the nitro group as nitrite and formation of hydroquinone. 1,4-Benzoquinone, a likely intermediate in the initial reaction, was not detected. Hydroquinone is converted to beta-ketoadipic acid via gamma-hydroxymuconic semialdehyde and maleylacetic acid.

Journal Article↗

PubMed1997

Catabolism of 3-Nitrophenol by Ralstonia eutropha JMP 134.

Ralstonia eutropha JMP 134 utilizes 3-nitrophenol as the sole source of nitrogen, carbon, and energy. The entire catabolic pathway of 3-nitrophenol is chromosomally encoded. An initial NADPH-dependent reduction of 3-nitrophenol was found in cell extracts of strain JMP 134. By use of a partially purified 3-nitrophenol nitroreductase from 3-nitrophenol-grown cells, 3-hydroxylaminophenol was identified as the initial reduction product. Resting cells of R. eutropha JMP 134 metabolized 3-nitrophenol to N-acetylaminohydroquinone under anaerobic conditions. With cell extracts, 3-hydroxylaminophenol was converted into aminohydroquinone. This enzyme-mediated transformation corresponds to the acid-catalyzed Bamberger rearrangement. Enzymatic conversion of the analogous hydroxylaminobenzene yields a mixture of 2- and 4-aminophenol.

Journal Article↗