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PubMed1994

Biodegradation and toxicity to fish of di-long-chain tertiary amine salt containing ester and amide bonds.

Biodegradability of N-(3-alkanoylaminopropyl)-N-(2-alkanoyloxyethyl)-N- methylammonium chloride (EAA) was investigated. Biodegradabilities by biochemical oxygen demand (BOD) and dissolved organic carbon (DOC) after 28 days were 79 and 91%, respectively, and almost the same amount of ammonium ion as the theoretical value was detected using a modified MITI test (I) (OECD guidelines, 301C). In the test with activated sludge obtained from a municipal sewage treatment plant, biodegradabilities by BOD and DOC after 35 days were 87 and 98%, respectively, and the 1H-NMR analysis of the tested solution which was done separately under similar conditions indicated the rise and fall of two biodegradation intermediates. Therefore, EEA was considered to be a readily and ultimately biodegradable compound. Besides, the 96-hr LC50 value in red killifish (Oryzias latipes) of EAA was 66 mg/liter. More than 1000 mg/liter was of biodegradation intermediates rapidly made by biodegradation of EAA. These results reveal that EAA has sufficient environmental compatibility.

Animals↗

PubMed2004

Increase in biodegradation of dimethyl phthalate by Closterium lunula using inorganic carbon.

The effect and mechanism of inorganic carbon (IC) on the biodegradation of dimethyl phthalate (DMP) by a green microalga Closterium lunula was investigated. The growth of this microalga and the biodegradation of DMP were significantly enhanced when the initial IC was increased. An intermediate product of DMP biodegradation was identified as phthalic acid (PA) that was accumulated and caused a sharp decrease in pH of microalgal culture medium, which inhibited both the growth of microalga and the biodegradation of DMP. A suggested second-order kinetic equation of organic pollutant biodegradation by microalgae (-dC/dt = kNr) fitted well with the experimental data. The increase of IC caused a decline in biodegradation rate constant for organic carbon (k) and an increase in growth (N) by supplying a favorite carbon source and mitigating the decrease of pH. As the net effect, the overall biodegradation rate of DMP was promoted as IC increased, which was dominated by the increase of microalgal growth.

Biodegradation, Environmental↗

PubMed2005

Comparison of biodegradation of poly(ethylene glycol)s and poly(propylene glycol)s.

The biodegradation of poly(ethylene glycol)s (PEGs) and poly(propylene glycol)s (PPGs), both being major by-products of non-ionic surfactants biodegradation, was studied under the conditions of the River Water Die-Away Test. PEGs were isolated from a water matrix using solid-phase extraction with graphitized carbon black sorbent, then derivatized with phenyl isocyanate and determined by HPLC with UV detection. PPGs were isolated from a water matrix by liquid-liquid extraction with chloroform, then derivatized with naphthyl isocyanate and determined by HPLC with fluorescence detection. The primary biodegradation of both PEGs and PPGs reached approximately 99% during the test. The tests show different biodegradation pathways of PEG and PPG. During PEG biodegradation, their chains are shortened leading to the formation of ethylene glycol and diethylene glycol. During PPG biodegradation, no short-chained biodegradation products were found.

Biodegradation, Environmental↗

PubMed2006

Ultimate biodegradation and elimination of antibiotics in inherent tests.

The biodegradation and elimination of antibiotics in municipal wastewater treatment plants is of particular concern because sewage is the main exposure route for antibiotics used in human medicine. The inherent biodegradability of 17 antibiotics was determined in a combined test design based on the Zahn-Wellens test (OECD 302 B, 1992) and the CO2-evolution test (OECD 301 B, 1992). CO2 Evolution test (Modified Sturm test). OECD Guideline for the Testing of Chemicals, Paris). Only benzylpenicillin sodium salt (Penicillin G) proved to be ultimately biodegradable, reaching ThCO2 degradation extents of 78-87%. Among the others, only amoxicillin, imipenem and nystatin showed certain ultimate biodegradation in few of the parallel flasks and can be regarded as partially biodegradable with formation of stable metabolites. The DOC-elimination of tetracycline-HCl showed a typical degradation curve starting with 18% and reaching the plateau phase at 80% after 21 days. Nevertheless, the CO2-evolution measured in parallel did not support the data, indicating that the time needed for reaching the adsorption equilibrium was underestimated. Several other antibiotics showed considerable DOC-elimination in the inherent test while only minor incidences of ultimate biodegradation were observed. The combination of CO2-evolution and DOC-elimination is a suitable instrument for assessing the behaviour of chemicals within one test. It enables one to assess both inherent ultimate biodegradability and DOC-elimination by sorption. The applicability of the test is limited to substances with a moderate toxicity.

Anti-Bacterial Agents↗

PubMed2004

Mechanisms of electron acceptor utilization: implications for simulating anaerobic biodegradation.

Simulation of biodegradation reactions within a reactive transport framework requires information on mechanisms of terminal electron acceptor processes (TEAPs). In initial modeling efforts, TEAPs were approximated as occurring sequentially, with the highest energy-yielding electron acceptors (e.g. oxygen) consumed before those that yield less energy (e.g., sulfate). Within this framework in a steady state plume, sequential electron acceptor utilization would theoretically produce methane at an organic-rich source and Fe(II) further downgradient, resulting in a limited zone of Fe(II) and methane overlap. However, contaminant plumes often display much more extensive zones of overlapping Fe(II) and methane. The extensive overlap could be caused by several abiotic and biotic processes including vertical mixing of byproducts in long-screened monitoring wells, adsorption of Fe(II) onto aquifer solids, or microscale heterogeneity in Fe(III) concentrations. Alternatively, the overlap could be due to simultaneous utilization of terminal electron acceptors. Because biodegradation rates are controlled by TEAPs, evaluating the mechanisms of electron acceptor utilization is critical for improving prediction of contaminant mass losses due to biodegradation. Using BioRedox-MT3DMS, a three-dimensional, multi-species reactive transport code, we simulated the current configurations of a BTEX plume and TEAP zones at a petroleum-contaminated field site in Wisconsin. Simulation results suggest that BTEX mass loss due to biodegradation is greatest under oxygen-reducing conditions, with smaller but similar contributions to mass loss from biodegradation under Fe(III)-reducing, sulfate-reducing, and methanogenic conditions. Results of sensitivity calculations document that BTEX losses due to biodegradation are most sensitive to the age of the plume, while the shape of the BTEX plume is most sensitive to effective porosity and rate constants for biodegradation under Fe(III)-reducing and methanogenic conditions. Using this transport model, we had limited success in simulating overlap of redox products using reasonable ranges of parameters within a strictly sequential electron acceptor utilization framework. Simulation results indicate that overlap of redox products cannot be accurately simulated using the constructed model, suggesting either that Fe(III) reduction and methanogenesis are occurring simultaneously in the source area, or that heterogeneities in Fe(III) concentration and/or mineral type cause the observed overlap. Additional field, experimental, and modeling studies will be needed to address these questions.

Bacteria, Anaerobic↗

PubMed2005

Analysis of anaerobic BTX biodegradation in a subarctic aquifer using isotopes and benzylsuccinates.

In situ biodegradation of benzene, toluene, and xylenes in a petroleum hydrocarbon contaminated aquifer near Fairbanks, Alaska was assessed using carbon and hydrogen compound specific isotope analysis (CSIA) of benzene and toluene and analysis of signature metabolites for toluene (benzylsuccinate) and xylenes (methylbenzylsuccinates). Carbon and hydrogen isotope ratios of benzene were between -25.9 per thousand and -26.8 per thousand for delta13C and -119 per thousand and -136 per thousand for delta2H, suggesting that biodegradation of benzene is unlikely at this site. However, biodegradation of both xylenes and toluene were documented in this subarctic aquifer. Biodegradation of xylenes was indicated by the presence of methylbenzylsuccinates with concentrations of 17-50 microg/L in three wells. Anaerobic toluene biodegradation was also indicated by benzylsuccinate concentrations of 10-49 microg/L in the three wells with the highest toluene concentrations (1500-5000 microg/L toluene). Since benzylsuccinate typically accounts for a very small fraction of the toluene present in groundwater (generally <1 mol%), the signature metabolite approach works best at higher toluene concentrations when it is not constrained by detection limits. In wells with lower toluene concentrations (410-640 microg/L), carbon and hydrogen isotopic values were enriched by up to approximately 2 per thousand for delta13C and approximately 70 per thousand for delta2H. This evidence of isotopic fractionation verifies the effects of biodegradation in these low concentration wells where metabolites may already be below detection limits. The combined use of signature metabolite and CSIA data is particularly valuable given the challenge of verifying biodegradation in subarctic environments where degradation rates are typically much slower than in temperate environments.

Alaska↗

PubMed2003

Effect of non-aqueous phase liquid on biodegradation of PAHs in spilled oil on tidal flat.

Biodegradation rates of polycyclic aromatic hydrocarbons (PAHs) in spilled oil stranded on tidal flats were evaluated using model reactors to clarify the effects of non-aqueous phase liquid (NAPL) on the biodegradation of PAHs in stranded oil on tidal flat with special emphasis on the relationship between dissolution rates of PAHs into water and viscosity of NAPL. Biodegradation of PAHs in NAPL was limited by the dissolution rates of PAHs into water. Biodegradation rate of chrysene was smaller than that of acenaphtene and phenanthrene due to the smaller dissolution rates. Dissolution rates of PAHs in fuel oil C were smaller than those in crude oil due to high viscosity of fuel oil C. Hence, biodegradation rates of PAHs in fuel oil C were smaller than those in crude oil. Biodegradation rates of PAHs in NAPL with slow rate of decrease like fuel oil C was slower than those in NAPL with rapid rate of decrease like crude oil. The smaller rate of decrease of fuel oil C than crude oil was due to the higher viscosity of fuel oil C. Therefore, not only the dissolution rate of PAHs but also the rates of decrease of NAPL were important factors for the biodegradation of PAHs.

Biodegradation, Environmental↗

PubMed2001

Photo-oxidation of biodegraded crude oil and toxicity of the photo-oxidized products.

We investigated the physicochemical changes resulting from irradiation by sunlight of biodegraded crude oil. An Arabian light crude oil sample was first subjected to microbial degradation. n-Alkanes and aromatic compounds such as naphthalenes, fluorenes, dibenzothiophenes and phenanthrenes possessing short, alkyl side chain(s) were almost completely degraded, while the contents of the saturated and aromatic fractions were reduced by 70% and 40%, respectively. This biodegraded oil was then suspended in seawater and exposed to sunlight irradiation for several weeks. The most remarkable change caused by the irradiation was a substantial decline in the aromatic fraction with a concomitant increase in the resin and asphaltene fractions. A 13C-nuclear magnetic resonance (NMR) spectroscopic analysis showed that the aromaticity of the biodegraded oil was significantly lower in the irradiated sample. A field desorption-mass spectrometric (FD-MS) analysis showed that sunlight irradiation reduced the average molecular weight of the oil components and formed oxygenated compounds. Consistent with this observation is that the oxygen content in the oil increased as the irradiation was prolonged. The bioavailability of the biodegraded oil was increased by the photo-oxidation: the growth of seawater microbes was minimal when the non-irradiated biodegraded oil was used as the source of carbon and energy; however, growth was significant when irradiated biodegraded oil was used. The concentration of dissolved organic carbon (DOC) increased linearly during the sunlight irradiation of the biodegraded oil, and this increase was matched by an increase in ultraviolet-absorptive materials in the seawater. The photochemically formed, water-soluble fraction (WSF) showed acute toxicity against the halophilic crustacean, Artemia.

Animals↗

PubMed2001

Primary biodegradability of mineral base oils in relation to their chemical and physical characteristics.

The primary biodegradability of 32 mineral base (i.e., unformulated) oils of paraffinic nature was evaluated using the CEC L-33-A-93 test. These oils were refinery products obtained by varying manufacturing processes. Biodegradation percentages ranged between 15% and 75%, i.e., below the commonly accepted standards for environmentally-compatible lubricants. Biodegradability values were compared to the overall chemical composition and main physical properties of base oils. Biodegradability decreased with increasing levels of aromatic and/or polar compounds in the tested oils. For most oils, the biodegradation percentage increased with the viscosity index, but was a decreasing function of the kinematic viscosity (KV), the pour point, the flash point (FP) and the refractive index (RI). Linear relationships between biodegradability and FP or RI values were observed. These results show that, beside chemical features such as the contents in polar and aromatic compounds, simple physical magnitudes such as KV and RI, commonly used to characterize lubricant properties, may be useful parameters for predicting the biodegradability of mineral base oils.

Biodegradation, Environmental↗

PubMed2002

Biodegradation of polylactide in aerobic and anaerobic thermophilic conditions.

Biodegradable polymers are designed to resist a number of environmental factors during use, but to be biodegradable under disposal conditions. The biodegradation of polylactide (PLLA) was studied at different elevated temperatures in both aerobic and anaerobic, aquatic and solid state conditions. In the aerobic aquatic headspace test the mineralisation of PLLA was very slow at room temperature, but faster under thermophilic conditions. The clear effect of temperature on the biodegradability of PLLA in the aquatic tests indicates that its polymer structure has to be hydrolysed before microorganisms can utilise it as a nutrient source. At similar elevated temperatures, the biodegradation of PLLA was much faster in anaerobic solid state conditions than in aerobic aquatic conditions. The behaviour of PLLA in the natural composting process was similar to that in the aquatic biodegradation tests, biodegradation starting only after the beginning of the thermophilic phase. These results indicate that PLLA can be considered as a compostable material, being stable during use at mesophilic temperatures, but degrading rapidly during waste disposal in compost or anaerobic treatment facilities.

Bacteria, Aerobic↗

PubMed1999

Laboratory simulation of biodegradation of chemicals in surface waters: closed bottle and respirometric test.

Microbial degradation is the most dominant elimination mechanism of organics from the environment. For evaluation of biodegradability of pure chemicals many standardized tests are available, but no standardized procedure for assessment of biodegradability of chemicals in surface water is agreed upon. Rates of in-situ biodegradation are usually estimated in laboratory simulation where environmental factors are reproduced to some extent. The aim of our study was to compare standardised ready biodegradability assessment, test (Closed bottle test) and its modifications employing the basic agreements on test conditions to simulate biodegradation in surface water. Standard test was modified using various natural river waters to simulate the natural environment in a simplified way. The impact of different types and amounts of nutrients and microorganisms on biodegradation was confirmed. The conditions in the recipient should be examined to extrapolate the results from ready biodegradability tests to real surface water.

Biodegradation, Environmental↗

PubMed2001

Biodegradation of metal-[S,S]-EDDS complexes.

The [S,S]-stereoisomer of ethylenediaminedisuccinic acid (EDDS), a biodegradable strong metal chelant, has substituted traditional chelants in a number of consumer products. However biodegradability of metal-EDDS complexes has remained largely undocumented. In the present study, activated sludge fed with EDDS as sole C and N source, was shown to readily biodegrade 1 mM pulses of Ca-, Cr(III)-, Fe(III)-, Pb-, Al-, Cd-, Mg-, Na-, or ZnEDDS (the latter only after extensive lag phase). On the other hand, the Cu-, Ni-, Co-, and Hg-complexes remained essentially undegraded. Only in the case of HgEDDS was lack of biodegradation due to metal toxicity. Speciation analysis revealed free HEDDS3- concentration was higher than 10(-5.4) M for all readily biodegradable metal-EDDS complexes and smaller than 10(-9.0) M for all recalcitrant complexes at pseudo-steady-state (i.e. after initial rise of aquo metal concentration at onset of biodegradation). The rate of metal-EDDS degradation may be modeled with a Monod expression with HEDDS3- as substrate (half-saturation constant ca. 10(-6) M). This model explains the drastic effect of additional metal ligands, e.g. phosphate or iron, on biodegradation rate of several recalcitrant metal-EDDS complexes. Continuously fed aerated biofilters removed 10 mM Pb- or ZnEDDS at a rate of ca. 0.4 mM h-1.

Biodegradation, Environmental↗

PubMed2002

Carbon and hydrogen isotopic fractionation during biodegradation of methyl tert-butyl ether.

Carbon and hydrogen isotopic fractionation during aerobic biodegradation of MTBE by a bacterial pure culture (PM1) and a mixed consortia from Vandenberg Air Force Base (VAFB) were studied in order to assess the relative merits of stable carbon versus hydrogen isotopic analysis as an indicator of biodegradation. Carbon isotopic enrichment in residual MTBE of up to 8.1/1000 was observed at 99.7% biodegradation. Carbon fractionation was reproducible in the PM1 and VAFB experiments, yielding similar enrichment factors (epsilon) of -2.0/1000 +/- 0.1/1000 to -2.4/1000 +/- 0.3/1000 for replicates in the PM1 experiment and -1.5/1000 +/- 0.1/1000 to -1.8/1000 +/- 0.1/1000 for replicates in the VAFB experiment. Hydrogen isotopic fractionation was highly reproducible for the PM1 pure cultures, with epsilon values of -33/1000 +/- 5/1000 to -37/1000 +/- 4/1000 for replicate samples. In the VAFB microcosms, there was considerably more variability in epsilon values, with values of -29/1000 +/- 4/1000 and -66/1000 +/- 3/1000 measured for duplicate sample bottles. Despite this variability, hydrogen isotopic fractionation always resulted in 2H enrichment of the residual MTBE of >80/1000 at 90% biodegradation. The reproducible carbon fractionation suggests that compound-specific carbon isotope analysis may be used to estimate the extent of biodegradation at contaminated sites. Conversely, the large hydrogen isotopic fractionation documented during biodegradation of MTBE suggests that compound-specific hydrogen isotope analysis offers the most conclusive means of identifying in-situ biodegradation at contaminated sites.

Bacteria↗

PubMed2002

Use of compound-specific stable carbon isotope analyses to demonstrate anaerobic biodegradation of MTBE in groundwater at a gasoline release site.

Currently it is unclear if natural attenuation is an appropriate remedial approach for groundwater impacted by methyl tertiary butyl ether (MTBE). Site-characterization data at most gasoline release sites are adequate to evaluate attenuation in MTBE concentrations over time or distance. But, demonstrating natural biodegradation of MTBE requires laboratory microcosm studies, which could be expensive and time-consuming. Recently, compound-specific carbon isotope ratio analyses (13C/12C expressed in delta13C notation) have been used to demonstrate aerobic biodegradation of MTBE in laboratory incubations. This study explored the potential of this approach to distinguish MTBE biodegradation from other abiotic processes in an anaerobic groundwater plume that showed extensive decrease in MTBE concentrations. To our knowledge, this is the first study to use delta13C of MTBE data in groundwater and laboratory microcosms to demonstrate anaerobic biodegradation of MTBE. The delta13C of MTBE in monitoring wells increased by up to 31 per thousand (-25.5 per thousand to +5.5 per thousand) along with a 40-fold decrease in MTBE concentrations. Anaerobic incubations in laboratory microcosms indicated up to 20-fold reduction in MTBE concentrations with a corresponding increase in delta13C of MTBE of up to 33.4 per thousand (-28.7 per thousand to +4.7 per thousand) in live microcosms. Little enrichment was observed in autoclaved controls. These results demonstrate that anaerobic biodegradation was the dominant natural attenuation mechanism for MTBE at this site. The estimated isotopic enrichment factors (epsilon(field) = -8.10 per thousand and epsilon(lab) = -9.16 per thousand) were considerably larger than the range (-1.4 per thousand to -2.4 per thousand) previously reported for aerobic biodegradation of MTBE in laboratory incubations. These observations strongly suggest that delta13C of MTBE could be potentially useful as an "indicator" of in-situ MTBE biodegradation.

Bacteria, Anaerobic↗

PubMed2006

A multitracer test proving the reliability of Rayleigh equation-based approach for assessing biodegradation in a BTEX contaminated aquifer.

Compound-specific stable isotope analysis (CSIA) is one of the most important methods for assessing biodegradation activities in contaminated aquifers. Although the concept is straightforward, the proof that the method cannot be only used for a qualitative analysis but also to quantify biodegradation in the subsurface was missing. We therefore performed a multitracer test in the field with ring-deuterated (d5) and completely (d8) deuterium-labeled toluene isotopologues (400 g) as reactive tracers as well as bromide as a conservative tracer. The compounds were injected into the anoxic zone of a BTEX plume located down-gradient of the contaminant source. Over a period of 4.5 months the tracer concentrations were analyzed at two control planes located 24 and 35 m downgradient of the injection well. Deuterium-labeled benzylsuccinate was found in the aquifer, indicating the anaerobic biodegradation of deuterated toluene via the benzylsuccinate synthase pathway. Three independent methods were applied to quantify biodegradation of deuterated toluene. First, fractionation of toluene-d8 and toluene-d5 using the Rayleigh equation and an appropriate laboratory-derived isotope fractionation factor was used for the calculation of the microbial decomposition of deuterated toluene isotopologues (CSIA-method). Second, the biodegradation was quantified by the changes of the concentrations of deuterated toluene relative to bromide. Both methods gave similar results, implying that the CSIA-method is a reliable tool to quantify biodegradation in contaminated aquifers. The results of both methods yielded a biodegradation of deuterated toluene isotopologues of approximately 23-29% for the first and 44-51% for the second control plane. Third, the mineralization of deuterated toluene isotopologues was verified by determination of the enrichment of deuterium in the groundwater. This method indicated that parts of deuterium were assimilated into the biomass of toluene degrading microorganisms.

Benzene↗

PubMed2003

Effects of heterogeneity and experimental scale on the biodegradation of diesel.

Biodegradation of petroleum hydrocarbon contamination is a common method for remediating soils and groundwater. Due to complexities with field-scale studies, biodegradation rates are typically evaluated at the bench-scale in laboratory studies. However, important field conditions can be difficult to mimic in the laboratory. This study investigates three scaling factors that can impact laboratory biodegradation rates and that are frequently unaccounted for in typical laboratory experimental procedures. These factors are soil heterogeneity, morphology of petroleum hydrocarbon non-aqueous phase liquids (NAPLs) and soil moisture distribution. The effects of these factors on the biodegradation rate of diesel NAPL is tested under a variety of experimental procedures from well-mixed batch studies to four-foot static soil columns. The results indicate that a high degree of variability results from even small-scale heterogeneities. In addition, it appears that as the experimental scale increases, the measured biodegradation rates slow. The results indicate that diesel biodegradation rates derived from small-scale experiments are not necessarily representative of field-scale biodegradation rates.

Aerobiosis↗

PubMed2002

Prediction of biodegradability from structure: imidazoles.

A project for the development of Structure-Activity Relationship for Biodegradation is presented. The aim of the project is to assemble sets of structural rules governing the potential microbial degradability of (classes of) chemicals. These rules will provide tools to take into account the biodegradation aspects of a product--and all precursors in the production process--early in the product development. The modeling concept is to take all experimental biodegradation data available and combine structural trends in the data with mechanistical information from degradation pathways. The rules that are derived should give insight into the possibility of biodegradation for specific classes of chemicals, thereby revealing why a compound is biodegradable or not. For the class of imidazole derivatives such rules are derived, and a model degradation mechanism is proposed in analogy to the urocanate-hydratase mechanism from histidine metabolism. The model is validated using 12 imidazole-compounds, which are all predicted correctly to be poorly biodegradable. It is demonstrated that both data analysis and information on enzymatic reaction mechanisms are necessary to yield valid Structure-Biodegradation Relationship.

Bacteria↗

PubMed2005

Biodegradation of polyethylene by the thermophilic bacterium Brevibacillus borstelensis.

AIM: To select a polyethylene-degrading micro-organism and to study the factors affecting its biodegrading activity. METHODS AND RESULTS: A thermophilic bacterium Brevibaccillus borstelensis strain 707 (isolated from soil) utilized branched low-density polyethylene as the sole carbon source and degraded it. Incubation of polyethylene with B. borstelensis (30 days, 50 degrees C) reduced its gravimetric and molecular weights by 11 and 30% respectively. Brevibaccillus borstelensis also degraded polyethylene in the presence of mannitol. Biodegradation of u.v. photo-oxidized polyethylene increased with increasing irradiation time. Fourier Transform Infra-Red (FTIR) analysis of photo-oxidized polyethylene revealed a reduction in carbonyl groups after incubation with the bacteria. CONCLUSIONS: This study demonstrates that polyethylene--considered to be inert--can be biodegraded if the right microbial strain is isolated. Enrichment culture methods were effective for isolating a thermophilic bacterium capable of utilizing polyethylene as the sole carbon and energy source. Maximal biodegradation was obtained in combination with photo-oxidation, which showed that carbonyl residues formed by photo-oxidation play a role in biodegradation. Brevibaccillus borstelensis also degraded the CH2 backbone of nonirradiated polyethylene. SIGNIFICANCE AND IMPACT OF THE STUDY: Biodegradation of polyethylene by a single bacterial strain contributes to our understanding of the process and the factors affecting polyethylene biodegradation.

Bacteriological Techniques↗