Startseite Concentrations of dioxins, furans and dioxin-like PCBs in natural animal feed additives
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Concentrations of dioxins, furans and dioxin-like PCBs in natural animal feed additives

  • Mateusz Ossowski , Łukasz Wlazło , Bożena Nowakowicz-Dębek EMAIL logo , Anna Chmielowiec-Korzeniowska und Hanna Bis-Wencel EMAIL logo
Veröffentlicht/Copyright: 26. September 2020
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Open Chemistry
Aus der Zeitschrift Open Chemistry Band 18 Heft 1

Abstract

The study aimed to assess the concentration of dioxins, furans, and dioxin-like polychlorinated biphenyls (PCBs) in natural feed additives used in animal nutrition. The research material consisted of four natural sorbents used as feed additives registered in the EU. The samples were analysed for the content of six octachlorodibenzo-p-dioxins (OCDDs) congeners, nine octachlorodibenzofurans (OCDFs) and fourteen dL-PCBs, and seven PCB congeners. Detailed analysis was performed using gas chromatography with high-resolution mass spectrometry. Analysing the results of congeners of individual sorbents, it was found that they were below the limit of detection or quantification and can be used as feed additives.

Keywords: montmorillonite; activated carbon; contamination; gas chromatography; mass spectrometry

1 Introduction

Polychlorinated biphenyls (PCBs), dioxins, furans and derivatives of these compounds arise as by-products of many industrial processes and during uncontrolled combustion in households. These compounds have been detected in nearly all components of the environment. They are classified as persistent organic pollutants (POPs). Due to their structure and properties, they are toxic and resistant to degradation in the environment (enabling their accumulation and preservation of their toxic properties). The degree of accumulation in living organisms depends on the duration of exposure and the position of the link in the food chain. To address these hazards, the European Commission has developed legal guidelines to reduce the presence of dioxins and PCBs in the environment and the food chain. The guidelines indicate acceptable levels of these compounds in feed and food and describe procedures for a rapid response system if their presence is detected [1,2,3,4,5,6]. According to the Commission Regulation (EC) setting the maximum dioxin content in animal feed additives, the limit for bentonite–montmorillonite is 20 g/kg of complete feed for all animal species or categories of animals. In the case of a naturally occurring mineral mixture, containing at least 65% hydrated aluminium silicate complex, the main component of kaolinite, the maximum dioxin content is 500 pg WHO-PCCD/F-TEQ/kg. For zeolites containing a minimum of 85% clinoptilolite and a maximum of 15% feldspar, mica and clay, free of fibres and quartz, the maximum dioxin content in complete feed for pigs should not exceed 20 g/kg [7]. Congeners of polychlorinated dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs) have varied toxicity depending on the amount and position of chlorine substituents. The most toxic are congeners having substituents in positions 2, 3, 7 and 8. The toxicity of dioxins is assessed using the toxic equivalency factor (TEF), which enables determination of congener toxicity relative to the most toxic dioxin 2,3,7,8-TCDD (TEF = 1). In the case of a mixture of dioxins, toxicity is determined using toxic equivalents (TEQ) expressed in pg. It is the sum of the product of the concentrations of individual congeners and their TEFs. Congeners 77, 126 and 169 are particularly toxic. Their presence in soil is associated with environmental contamination [8,9,10].

Natural sorbents, including bentonite and many others, have been entered into the Register of Feed Additives as existing products in accordance with art. 10 of Regulation (EC) No. 1831/2003 and are a frequent component of animal feed rations, especially on large-scale farms. They are used as sorbents of mycotoxins from feed or gaseous pollutants from the air, or for binding heavy metals in the environment [11,12,13]. In choosing sorbents, besides high adsorption capacity between ion packets, safety is an important consideration. Due to their origin (they are sedimentary rocks) and the high possibility of binding with metal ions in the environment, there is a risk that they may contain excessive amounts of harmful admixtures in the form of dioxins or furans and their derivatives [11,14]. Therefore, their use as feed additives requires careful control in accordance with applicable EU regulations 644/2017 and 771/2017. Owing to technological achievements in the use of gas chromatography to analyse gaseous pollutants, these methods can be used to control PCDDs, PCDFs, and dioxin-like polychlorinated biphenyls in samples used for the production of feed components [6,15]. Most PCDDs, PCDFs and PCBs occur in low concentrations in the environment, but chronic exposure in animals ingesting them with feed can result in their bioconcentration in the food chain. This poses a threat to every organism above this trophic link. When these contaminants are absorbed with food they are metabolized and excreted only to a small degree, while a significant amount is accumulated in adipose tissue. Prolonged exposure to PCBs leads to disorders of many systems, e.g. the nervous, immune, and reproductive systems [9,10,16]. Thus for health safety reasons, there is a need to control their occurrence and concentrations in feed and food additives [6]. Therefore, we analysed the content of PCDDs, PCDFs and polychlorinated biphenyls with dioxin-like properties (PCBs) in selected natural sorbents used in animal feed.

2 Materials and methods

2.1 Research material

The research material comprised natural sorbents used as feed additives registered in the EU. Bentonite, zeolite, perlite and activated carbon were selected for analysis. Samples of four sorbents were obtained from various producers, who sold them as natural feed additives/sorbents. The samples were analysed for the content of six congeners of OCDDs, nine of OCDFs, fourteen of dioxin-like PCBs and seven of PCBs. Detailed analysis was performed using gas chromatography with high-resolution mass spectrometry (HRGC/HRMS).

2.2 Procedure for determination of PCDD/Fs and PCBs in natural feed additives

Extraction standard containing 13C12-labelled PCDD/F and PCB congeners was added to 10 g of soil. The spiked sample was mixed with Hydromatrix and transferred to an extraction thimble, which was placed in a Soxhlet extractor. Extraction with toluene lasted for 20 h. The toluene extract was concentrated in a rotary vacuum evaporator and re-dissolved in hexane. Then the cleanup standard was added, and the raw extract was pre-cleaned by shaking with concentrated sulphuric acid at room temperature. The pre-cleaned hexane extract was transferred to the top of a multilayer silica gel column, eluted with hexane, and then concentrated to 0.5–1 mL with a modified Kuderna-Danish concentrator. Then PCDD/Fs were separated from similar structures by fractionation with a Florisil column. A combination of hexane and dichloromethane was used for elution of PCDD/F + non-orthoPCB and PCB fractions. The first hexane fraction, containing mono-ortho and non-dioxin-like PCBs, was concentrated to about 0.5 mL using a Kuderna-Danish concentrator. The dichloromethane fraction, containing PCDD/Fs and non-ortho PCBs, was concentrated on a Kuderna-Danish concentrator. The final extract, containing mono-ortho PCBs and non-dioxin-like PCBs, was spiked with 13C12-labelled injection standard. The concentrated final extract containing PCDD/Fs and non-ortho PCBs was further concentrated to dryness under a nitrogen stream and then spiked with the 13C12-labelled injection standard. Finally, 2–4 microlitres were injected into the HRGC-HRMS system in splitless mode.

The HRGC-HRMS system, consisting of a Trace GC Ultra gas chromatograph equipped with a Thermo Electron Corp. Tri Plus autosampler, was used for specific determinations. The determinations were made using an MXT-500 (Restek) capillary column (60 m × 0.25 mm × 0.15 µm; 2 µL injection volume, injected in splitless mode; carrier gas He 99.999% at a flow rate of 1 mL/min). The DFS was operated in multi-ion detection (MID) mode, with resolution of R10 ≈ 10,000. The ionization mode was EI positive, and electron energy was 48 eV. The reference gas was PFTBA (perfluorotributylamine – FC-43). The oven temperature programme for PCDD/Fs was 140°C (2 min); 60°C/min to 245°C (8 min); 6°C/min to 255°C (15 min); 6°C/min to 265°C (8 min); 8°C/min to 300°C; 15°C/min to 360°C (5 min). The oven temperature programme for PCBs was 110°C (2 min); 30°C/min to 200°C; 4°C/min to 245°C (7 min); 5.5°C/min to 290°C; 10°C/min to 335°C (1 min). The MID parameters for the PCB analyses are shown in Table 1, and the settings for PCDD/F are presented in Table 2.

Table 1

MID for the PCB procedure

MID instrument setup
MID window 1MID window 2MID window 3MID window 4MID window 5
Start 7:17 minStart 11:48 minStart 18:48 minStart 25:48 minStart 32:47 min
Measure 4:30 minMeasure 7:00 minMeasure 7:00 minMeasure 6:59 minMeasure 3:42 min
End 11:48 minEnd 18:48 minEnd 25:48 minEnd 32:47 minEnd 36:30 min
Cycle time 0.70 sCycle time-0.80 sCycle time 0.80 sCycle time 0.80 sCycle time 0.80 s
Targeted masses m/zDwell time [ms]Targeted masses m/zDwell time [ms]Targeted masses m/zDwell time [ms]Targeted masses m/zDwell time [ms]Targeted masses m/zDwell time [ms]
186.00001253.00001312.00002357.00002411.00002
188.038832255.960946313.9834 L6359.841545413.9770 L2
190.036032257.958046323.883466361.838545427.763054
200.079032263.9866 L2325.880466371.881745429.760054
202.076032268.001046335.923766373.878845439.803054
213.9897 L6269.998046337.920766393.802545441.800054
222.000032289.922146359.841566395.799545461.724054
223.99732291.91946361.83966405.84345463.72154
234.0432301.96346371.88266407.8445463.9738c5
236.03732303.9646373.87966413.9770 L2473.76454
255.96132323.88346393.80366427.76345475.76154
257.95832325.8846395.866429.7645495.68554
268.00132335.92446413.9770 c3439.80345497.68254
269.99832337.92146441.845507.72554
283.8132359.84246461.72445509.72254
285.80732361.83946463.72145
289.8332413.9769 c4463.974 c4
291.82732
313.9834 c6
Table 2

MID for PCDD/F method procedure.

MID instrument setup
MID window 1MID window 2MID window 3MID window 4MID window 5
Start 9:48 minStart 13:11 minStart 17:18 minStart 23:11 minStart 34:12 min
Measure 3:23 minMeasure 4:06 minMeasure 5:55 minMeasure 11:00 minMeasure 15:47 min
End 13:11 minEnd 11:18 minEnd 23:11 minEnd 34:12 minEnd 50:00 min
Cycle time 1.20 sCycle time 1.20 sCycle time 1.20 sCycle time 1.40 sCycle time 1.00 s
Targeted masses m/zDwell time [ms]Targeted masses m/zDwell time [ms]Targeted masses m/zDwell time [ms]Targeted masses m/zDwell time [ms]Targeted masses m/zDwell time [ms]
263.9866 L4263.9866 13336136214051
289.92299303.90166339.85982363.9802 L9407.78150
291.91999305.89866341.85682373.82143409.77850
301.96399315.94166351.89982375.817143413.9770 L2
303.90199317.93866353.89682385.86143419.82250
303.9699319.89666355.85482387.858143421.81950
305.89899321.89366357.85182389.815143423.77650
323.88499323.88366359.84282391.812143425.77350
325.88199325.88166361.83982401.855143435.81650
335.92499327.88566363.9802 L8403.852143437.81350
337.92199331.93666367.89482413.9770 c5441.74250
375.83699333.93366369.89182445.756143443.73950
413.9770 c4335.92466371.88282453.78350
337.92166373.87982455.7850
339.8666409.79782457.73750
341.85766413.9770 c4459.73450
375.83666463.9738 c5
413.9770 c3469.77750
471.77550
479.71750

The limit of quantification was defined as twice the detection limit. The detection limit was defined as the amount of analyte producing a signal of S/N ≥ 3. The detection limit was determined as the actual value on the day of registration. Measurement uncertainty was expressed as double (k = 2) the relative standard deviation (RSD%) and corresponded to a 95% confidence interval. The estimated uncertainty of each congener of 2,3,7,8-PCDD/Fs was 30%, and that of total TEQs was 20%. These values were verified by analysing certified reference material under conditions of internal reproducibility. Results marked “<” are below the limit of detection or quantification. “Lower bound” and “upper bound” are levels defined in Commission Regulation 2017/644 and EN 1948-4. The “medium bound” level is defined in Commission Regulation 2017/644 [4]. The procedure for determination of PCDD/Fs and PCBs meets the conditions and requirements of US EPA 1613 and US EPA 1668. The analyses were conducted in an accredited ALS laboratory in the Czech Republic. The results are presented as the mean of the measurements.

3 Results

The results of the analyses for the concentrations of PCDDs and PCDFs (PCDD/Fs) and dioxin-like PCB compounds contained in the sorbents are presented in Tables 3 and 4. Sample chromatograms of evaluated sorbents (PCDD/Fs and PCBs concentrations) are presented in Figures S1 and S2. Concentrations of PCDD/Fs were tested for 17 substituted congeners. The PCDD concentrations in the samples ranged from <0.4 to 2,300 pg/g DW (dry weight), (Table 3). The lowest concentration was obtained in bentonite for 2378-TCDD and 12378-PeCDD, and the highest for OCDD, also in bentonite samples.

Table 3

Concentrations of PCDDs and PCDFs (dioxins and furans) in sorbent samples (pg/g DW)

CongenerBentoniteZeolitePerliteActivated carbon
PCDDs
2378-TCDD<0.4<0.765<0.91<0.92
12378-PeCDD<0. 4<1.75<2.0<1.7
123478-HxCDD<2.0<2.95<1.8<2.2
123678-HxCDD<2.2<2.95<1.8<2.2
123789-HxCDD<4.3<2.95<1.8<2.2
1234678-HpCDD41.01.3<2.8<3.4
OCDD230045.0<1.9<3.6
PCDFs
2378-TCDF<0.1<0.495<0.86<0.9
12378-PeCDF<0.2<0.77<1.0<1.1
23478-PeCDF<0.2<0.77<1.0<1.1
123478-HxCDF<0.8<1.6<1.8<1.6
123678-HxCDF<0.8<1.6<1.8<1.6
123789-HxCDF<0.8<1.6<1.8<1.6
234678-HxCDF<0.8<1.6<1.8<1.6
1234678-HpCDF<2.9<1.25<2.5<2.3
1234789-HpCDF<1.8<1.25<2.5<2.3
OCDF<2.5<11.15<1.6<2.9
Lower-bound TEQ2.7000
Upper-bound TEQ4.73.753.93.8
Table 4

Concentration of PCBs in sorbents (pg/g DW)

CongenerBentoniteZeolitePerliteActivated carbon
PCB77<8.7<4.65<10.0<6.4
PCB81<2.6<1.345<12.0<9.7
PCB105<10.3<3.65<82.0<29.0
PCB114<2.9<2.7<55.0<23.0
PCB118<43.0<26.5<56.0<56.0
PCB123<2.0<3.2<68.0<26.0
PCB126<2.0<0.935<7.5<4.8
PCB156<14.1<2.7<68.0<28.0
PCB157<2.4<2.95<70.0<34.0
PCB167<8.3<5.6<48.0<23.0
PCB169<2.4<1.35<11.0<6.3
PCB170<11.7<28.5<82.0<39.0
PCB180<53.0<65.0<67.0<32.0
PCB189<2.3<2.6<58.0<30.0
Lower-bound TEQ from quantified PCBs 0.000.000.000.00
Medium-bound TEQ from PCBs0.5
Upper-bound TEQ 0.20.120.990.6
Indicator PCBs (HRMS)
PCB28<85.0<56.5<190.0<130.0
PCB52<69.5<45.5<81.0<79.0
PCB101<114.5<62.5<65.0<130.0
PCB118<43.0<26.5<56.0<56.0
PCB138<65.0<41.5<65.0<110.0
PCB153<109.0<87.0<200.0<28.0
PCB180<53.0<65.0<67.0<32.0
Lower-bound Σ indicator PCB-7 0.000.000.000.00
Upper-bound Σ indicator PCB-7540.0385.0730.0570.0

“Lower-bound” and “Upper-bound” are levels defined in Commission Regulation 2017/644 and EN 1948-4. “Medium-bound” is defined in Commission Regulation 2017/644.

Analysis of PCDD isomer profiles showed the highest concentrations of octachlorodibenzo-p-dioxin (OCDD) in bentonite and zeolite samples. In perlite and activated carbon samples, the congener showed concentrations below 3.6 pg/g DW.

Very low concentrations were obtained for dibenzofuran (PCDF) congeners. They ranged from <0.1 pg/g DW for 2378-TCDF in bentonite samples to <11.15 pg/g DW for OCDF in zeolite samples (Table 3).

To calculate concentrations of the PCDD, PCDF and PCB congeners, the upper-bound concept was adopted. This means that when calculating the TEQ for all congeners at a level below the limit of quantification, a numerical value equal to their limit of quantification is adopted [4,17]. The values of the lower-bound and upper-bound TEQs in the samples of individual sorbents are given in Table 3. The concentrations of PCDD/Fs in the test material did not exceed World Health Organization (WHO) recommendations.

Table 4 presents the results of analyses of PCB congeners. The results of congener tests for individual sorbents showed that they were below the detection or quantification limit. Estimation of the uncertainty of each PCB congener is 30% and that of total TEQ and PCB6/PCB7 is 20%. These values were verified by analyses of certified reference material under conditions of internal reproducibility.

Identification and quantification of PCB-7 congeners was performed by comparing mass spectra of compounds obtained from standard solutions. Upper-bound ΣPCB-7 for individual congeners ranged from 380 to 540 pg/g DW. The concentrations of PCBs, dioxins, furans and their derivatives were below detection and quantification limits. These values were not exceeded in the sorbents tested, so they can be used as feed components [18].

4 Discussion

The need to control the quality of feedstuffs and foodstuffs arises from EU regulations. This also applies to the content of dioxins and dioxin-like compounds, to determine their concentration in the food chain. Most human exposure to these compounds results from consumption of food of animal origin, as farmed animals are exposed to dioxins and their derivatives, mainly through their ingestion with feed [6,19,20]. WHO has established the maximum (tolerable) daily intake of dioxins as 1 pg-TEQ/kg/day. It is believed that a level of 3–5 pg-TEQ/kg/day may cause accumulation of dioxins that stimulate genotoxic and carcinogenic activity. On the initiative of the EU, for some time it was required to state the proportions of individual components included in compound feed. More recently an obligation has been introduced to monitor levels of these contaminants to maintain safe levels in feed and food [21]. European Commission recommendations set action thresholds for dioxins, furans and dioxin-like compounds (WHO-TEQ). In clays used as dietary supplements, these thresholds have been set at 0.50 pg/g raw weight [22]. The upper concentration limits are calculated under the assumption that all values of the various congeners below the limit of quantification are equal to the limit of quantification. According to the EU commission regulation, in products intended for feed the content of dioxins (ΣPCDDs and PCDFs expressed in WHO-TEFs for the feed additives kaolinitic clay, vermiculite, synthetic calcium aluminates, and clinoptilolite of sedimentary origin belonging to the functional group of binders and anti-caking agents should not exceed the level of 0.75 ng WHO-PCDD/F-TEQ/kg. The sum of dioxins and dioxin-like PCBs, i.e. ΣPCDDs, PCDFs and PCBs, expressed in WHO TEQs, when WHO-TEF is used, should not exceed the maximum level of 1.5 ng WHO-PCDD/F-PCB-TEQ/kg for these additives. Based on a number of studies and observations, WHO established that a dioxin level of 1 ng/kg BW (body weight) per day constitutes a health hazard. This was associated with the “Dioxin affair,” when feed containing about 50 kg of polychlorinated biphenyls (including 2 g TEQdl-PCB) and about 1 g TEQ of dioxins was placed on the market. Similar incidents of feed contamination have been reported in Germany, where pork, poultry and eggs contaminated with PCDD/Fs and PCBs were produced [1,11,23,24,25]. Weber et al. [26] suggests that PCDD/F or dioxin-like PCB levels in soils raise their levels in feed, especially when animals (cows or poultry) are exposed to them in densely populated, industrialized areas. Toxic concentrations of PCDD/Fs and PCBs have also been found in fish feed, which translated into high concentrations in meat [25,27,28]. Wang et al. [28] indicated feed-grade cupric sulphate obtained from the chloralkali industry as a source of PCDD/Fs. Similar PCDD/F congeners have been identified during printed circuit board production, indicating that they could be transported to the food chain in this manner. Over half exceeded the maximum levels set by the European Commission for feed additives. The dominant congeners were isomers of OCDD and OCDF, while PCDD/Fs predominated among PCDFs. Piskorska-Pliszczyńska et al. [17] conducted quality control of poultry feed and found that the samples did not contain elevated concentrations of PCDD/PCDFs. Their concentrations in feed ranged from 0.05 ± 0.01 to 0.07 ± 0.01 ng WHO-TEQ/kg, with a moisture content of 12% (acceptable limit 0.75 ng/kg feed). This means that this feed could not be a source of egg contamination, and no characteristic dioxin congeners were identified in the eggs tested. However, analysis of soil samples from the area where the hens were kept showed high concentrations of the same dioxin congeners. This confirms that soil and sediments may be one of the main reservoirs of POPs, including dioxins and PCBs. In their analysis of Polish feed materials, Piskorska-Pliszczyńska et al. [6] report that PCDD/F and DL-PCB concentrations were low enough to ensure low concentrations in animal products, but for safety reasons they should be continually monitored.

5 Conclusion

Among the many chemical impurities found in feed or food, dioxins, furans and dioxin-like PCBs are considered the most hazardous to health. Their uptake with animal feed is an important element of the food chain. Feed additives, including natural sorbents, should be monitored for the content of these contaminants in feed and the possibility of their introduction into food, which would increase human exposure to them.

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Acknowledgments

Research was funded under the project “Development of innovative technologies of comprehensive utilization of waste generated during pig fattening-Computil” cofinanced by the National Center for Research and Development as part of the Strategic Research and Development Program “Natural Environment, Agriculture and Forestry” Biostrateg 2/298357/8/NCBR/2016 and as part of the statutory research of the University of Life Sciences in Lublin, Poland.

  1. Ethical approval: The conducted research is not related to either human or animal use.

  2. Conflict of interest: The authors declare no conflict of interest.

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Received: 2020-06-14
Revised: 2020-07-28
Accepted: 2020-08-09
Published Online: 2020-09-26

© 2020 Mateusz Ossowski et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Regular Articles
  2. Electrochemical antioxidant screening and evaluation based on guanine and chitosan immobilized MoS2 nanosheet modified glassy carbon electrode (guanine/CS/MoS2/GCE)
  3. Kinetic models of the extraction of vanillic acid from pumpkin seeds
  4. On the maximum ABC index of bipartite graphs without pendent vertices
  5. Estimation of the total antioxidant potential in the meat samples using thin-layer chromatography
  6. Molecular dynamics simulation of sI methane hydrate under compression and tension
  7. Spatial distribution and potential ecological risk assessment of some trace elements in sediments and grey mangrove (Avicennia marina) along the Arabian Gulf coast, Saudi Arabia
  8. Amino-functionalized graphene oxide for Cr(VI), Cu(II), Pb(II) and Cd(II) removal from industrial wastewater
  9. Chemical composition and in vitro activity of Origanum vulgare L., Satureja hortensis L., Thymus serpyllum L. and Thymus vulgaris L. essential oils towards oral isolates of Candida albicans and Candida glabrata
  10. Effect of excess Fluoride consumption on Urine-Serum Fluorides, Dental state and Thyroid Hormones among children in “Talab Sarai” Punjab Pakistan
  11. Design, Synthesis and Characterization of Novel Isoxazole Tagged Indole Hybrid Compounds
  12. Comparison of kinetic and enzymatic properties of intracellular phosphoserine aminotransferases from alkaliphilic and neutralophilic bacteria
  13. Green Organic Solvent-Free Oxidation of Alkylarenes with tert-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex
  14. Ducrosia ismaelis Asch. essential oil: chemical composition profile and anticancer, antimicrobial and antioxidant potential assessment
  15. DFT calculations as an efficient tool for prediction of Raman and infra-red spectra and activities of newly synthesized cathinones
  16. Influence of Chemical Osmosis on Solute Transport and Fluid Velocity in Clay Soils
  17. A New fatty acid and some triterpenoids from propolis of Nkambe (North-West Region, Cameroon) and evaluation of the antiradical scavenging activity of their extracts
  18. Antiplasmodial Activity of Stigmastane Steroids from Dryobalanops oblongifolia Stem Bark
  19. Rapid identification of direct-acting pancreatic protectants from Cyclocarya paliurus leaves tea by the method of serum pharmacochemistry combined with target cell extraction
  20. Immobilization of Pseudomonas aeruginosa static biomass on eggshell powder for on-line preconcentration and determination of Cr (VI)
  21. Assessment of methyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl] sulfamoyl}methyl)benzoate through biotic and abiotic degradation modes
  22. Stability of natural polyphenol fisetin in eye drops Stability of fisetin in eye drops
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  26. Study on the interaction between catechin and cholesterol by the density functional theory
  27. Analysis of some pharmaceuticals in the presence of their synthetic impurities by applying hybrid micelle liquid chromatography
  28. Two mixed-ligand coordination polymers based on 2,5-thiophenedicarboxylic acid and flexible N-donor ligands: the protective effect on periodontitis via reducing the release of IL-1β and TNF-α
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  30. Development of ultrasound-assisted dispersive solid-phase microextraction based on mesoporous carbon coated with silica@iron oxide nanocomposite for preconcentration of Te and Tl in natural water systems
  31. N,N′-Bis[2-hydroxynaphthylidene]/[2-methoxybenzylidene]amino]oxamides and their divalent manganese complexes: Isolation, spectral characterization, morphology, antibacterial and cytotoxicity against leukemia cells
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https://doi.org/10.1515/chem-2020-0158
Schlagwörter für diesen Artikel
montmorillonite; activated carbon; contamination; gas chromatography; mass spectrometry
Creative Commons
BY 4.0

Artikel in diesem Heft

  1. Regular Articles
  2. Electrochemical antioxidant screening and evaluation based on guanine and chitosan immobilized MoS2 nanosheet modified glassy carbon electrode (guanine/CS/MoS2/GCE)
  3. Kinetic models of the extraction of vanillic acid from pumpkin seeds
  4. On the maximum ABC index of bipartite graphs without pendent vertices
  5. Estimation of the total antioxidant potential in the meat samples using thin-layer chromatography
  6. Molecular dynamics simulation of sI methane hydrate under compression and tension
  7. Spatial distribution and potential ecological risk assessment of some trace elements in sediments and grey mangrove (Avicennia marina) along the Arabian Gulf coast, Saudi Arabia
  8. Amino-functionalized graphene oxide for Cr(VI), Cu(II), Pb(II) and Cd(II) removal from industrial wastewater
  9. Chemical composition and in vitro activity of Origanum vulgare L., Satureja hortensis L., Thymus serpyllum L. and Thymus vulgaris L. essential oils towards oral isolates of Candida albicans and Candida glabrata
  10. Effect of excess Fluoride consumption on Urine-Serum Fluorides, Dental state and Thyroid Hormones among children in “Talab Sarai” Punjab Pakistan
  11. Design, Synthesis and Characterization of Novel Isoxazole Tagged Indole Hybrid Compounds
  12. Comparison of kinetic and enzymatic properties of intracellular phosphoserine aminotransferases from alkaliphilic and neutralophilic bacteria
  13. Green Organic Solvent-Free Oxidation of Alkylarenes with tert-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex
  14. Ducrosia ismaelis Asch. essential oil: chemical composition profile and anticancer, antimicrobial and antioxidant potential assessment
  15. DFT calculations as an efficient tool for prediction of Raman and infra-red spectra and activities of newly synthesized cathinones
  16. Influence of Chemical Osmosis on Solute Transport and Fluid Velocity in Clay Soils
  17. A New fatty acid and some triterpenoids from propolis of Nkambe (North-West Region, Cameroon) and evaluation of the antiradical scavenging activity of their extracts
  18. Antiplasmodial Activity of Stigmastane Steroids from Dryobalanops oblongifolia Stem Bark
  19. Rapid identification of direct-acting pancreatic protectants from Cyclocarya paliurus leaves tea by the method of serum pharmacochemistry combined with target cell extraction
  20. Immobilization of Pseudomonas aeruginosa static biomass on eggshell powder for on-line preconcentration and determination of Cr (VI)
  21. Assessment of methyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl] sulfamoyl}methyl)benzoate through biotic and abiotic degradation modes
  22. Stability of natural polyphenol fisetin in eye drops Stability of fisetin in eye drops
  23. Production of a bioflocculant by using activated sludge and its application in Pb(II) removal from aqueous solution
  24. Molecular Properties of Carbon Crystal Cubic Structures
  25. Synthesis and characterization of calcium carbonate whisker from yellow phosphorus slag
  26. Study on the interaction between catechin and cholesterol by the density functional theory
  27. Analysis of some pharmaceuticals in the presence of their synthetic impurities by applying hybrid micelle liquid chromatography
  28. Two mixed-ligand coordination polymers based on 2,5-thiophenedicarboxylic acid and flexible N-donor ligands: the protective effect on periodontitis via reducing the release of IL-1β and TNF-α
  29. Incorporation of silver stearate nanoparticles in methacrylate polymeric monoliths for hemeprotein isolation
  30. Development of ultrasound-assisted dispersive solid-phase microextraction based on mesoporous carbon coated with silica@iron oxide nanocomposite for preconcentration of Te and Tl in natural water systems
  31. N,N′-Bis[2-hydroxynaphthylidene]/[2-methoxybenzylidene]amino]oxamides and their divalent manganese complexes: Isolation, spectral characterization, morphology, antibacterial and cytotoxicity against leukemia cells
  32. Determination of the content of selected trace elements in Polish commercial fruit juices and health risk assessment
  33. Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study
  34. Keratin 17 is induced in prurigo nodularis lesions
  35. Anticancer, antioxidant, and acute toxicity studies of a Saudi polyherbal formulation, PHF5
  36. LaCoO3 perovskite-type catalysts in syngas conversion
  37. Comparative studies of two vegetal extracts from Stokesia laevis and Geranium pratense: polyphenol profile, cytotoxic effect and antiproliferative activity
  38. Fragmentation pattern of certain isatin–indole antiproliferative conjugates with application to identify their in vitro metabolic profiles in rat liver microsomes by liquid chromatography tandem mass spectrometry
  39. Investigation of polyphenol profile, antioxidant activity and hepatoprotective potential of Aconogonon alpinum (All.) Schur roots
  40. Lead discovery of a guanidinyl tryptophan derivative on amyloid cascade inhibition
  41. Physicochemical evaluation of the fruit pulp of Opuntia spp growing in the Mediterranean area under hard climate conditions
  42. Electronic structural properties of amino/hydroxyl functionalized imidazolium-based bromide ionic liquids
  43. New Schiff bases of 2-(quinolin-8-yloxy)acetohydrazide and their Cu(ii), and Zn(ii) metal complexes: their in vitro antimicrobial potentials and in silico physicochemical and pharmacokinetics properties
  44. Treatment of adhesions after Achilles tendon injury using focused ultrasound with targeted bFGF plasmid-loaded cationic microbubbles
  45. Synthesis of orotic acid derivatives and their effects on stem cell proliferation
  46. Chirality of β2-agonists. An overview of pharmacological activity, stereoselective analysis, and synthesis
  47. Fe3O4@urea/HITh-SO3H as an efficient and reusable catalyst for the solvent-free synthesis of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one and indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine derivatives
  48. Adsorption kinetic characteristics of molybdenum in yellow-brown soil in response to pH and phosphate
  49. Enhancement of thermal properties of bio-based microcapsules intended for textile applications
  50. Exploring the effect of khat (Catha edulis) chewing on the pharmacokinetics of the antiplatelet drug clopidogrel in rats using the newly developed LC-MS/MS technique
  51. A green strategy for obtaining anthraquinones from Rheum tanguticum by subcritical water
  52. Cadmium (Cd) chloride affects the nutrient uptake and Cd-resistant bacterium reduces the adsorption of Cd in muskmelon plants
  53. Removal of H2S by vermicompost biofilter and analysis on bacterial community
  54. Structural cytotoxicity relationship of 2-phenoxy(thiomethyl)pyridotriazolopyrimidines: Quantum chemical calculations and statistical analysis
  55. A self-breaking supramolecular plugging system as lost circulation material in oilfield
  56. Synthesis, characterization, and pharmacological evaluation of thiourea derivatives
  57. Application of drug–metal ion interaction principle in conductometric determination of imatinib, sorafenib, gefitinib and bosutinib
  58. Synthesis and characterization of a novel chitosan-grafted-polyorthoethylaniline biocomposite and utilization for dye removal from water
  59. Optimisation of urine sample preparation for shotgun proteomics
  60. DFT investigations on arylsulphonyl pyrazole derivatives as potential ligands of selected kinases
  61. Treatment of Parkinson’s disease using focused ultrasound with GDNF retrovirus-loaded microbubbles to open the blood–brain barrier
  62. New derivatives of a natural nordentatin
  63. Fluorescence biomarkers of malignant melanoma detectable in urine
  64. Study of the remediation effects of passivation materials on Pb-contaminated soil
  65. Saliva proteomic analysis reveals possible biomarkers of renal cell carcinoma
  66. Withania frutescens: Chemical characterization, analgesic, anti-inflammatory, and healing activities
  67. Design, synthesis and pharmacological profile of (−)-verbenone hydrazones
  68. Synthesis of magnesium carbonate hydrate from natural talc
  69. Stability-indicating HPLC-DAD assay for simultaneous quantification of hydrocortisone 21 acetate, dexamethasone, and fluocinolone acetonide in cosmetics
  70. A novel lactose biosensor based on electrochemically synthesized 3,4-ethylenedioxythiophene/thiophene (EDOT/Th) copolymer
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  73. PCSK9 concentrations in different stages of subclinical atherosclerosis and their relationship with inflammation
  74. Development of trace analysis for alkyl methanesulfonates in the delgocitinib drug substance using GC-FID and liquid–liquid extraction with ionic liquid
  75. Electrochemical evaluation of the antioxidant capacity of natural compounds on glassy carbon electrode modified with guanine-, polythionine-, and nitrogen-doped graphene
  76. A Dy(iii)–organic framework as a fluorescent probe for highly selective detection of picric acid and treatment activity on human lung cancer cells
  77. A Zn(ii)–organic cage with semirigid ligand for solvent-free cyanosilylation and inhibitory effect on ovarian cancer cell migration and invasion ability via regulating mi-RNA16 expression
  78. Polyphenol content and antioxidant activities of Prunus padus L. and Prunus serotina L. leaves: Electrochemical and spectrophotometric approach and their antimicrobial properties
  79. The combined use of GC, PDSC and FT-IR techniques to characterize fat extracted from commercial complete dry pet food for adult cats
  80. MALDI-TOF MS profiling in the discovery and identification of salivary proteomic patterns of temporomandibular joint disorders
  81. Concentrations of dioxins, furans and dioxin-like PCBs in natural animal feed additives
  82. Structure and some physicochemical and functional properties of water treated under ammonia with low-temperature low-pressure glow plasma of low frequency
  83. Mesoscale nanoparticles encapsulated with emodin for targeting antifibrosis in animal models
  84. Amine-functionalized magnetic activated carbon as an adsorbent for preconcentration and determination of acidic drugs in environmental water samples using HPLC-DAD
  85. Antioxidant activity as a response to cadmium pollution in three durum wheat genotypes differing in salt-tolerance
  86. A promising naphthoquinone [8-hydroxy-2-(2-thienylcarbonyl)naphtho[2,3-b]thiophene-4,9-dione] exerts anti-colorectal cancer activity through ferroptosis and inhibition of MAPK signaling pathway based on RNA sequencing
  87. Synthesis and efficacy of herbicidal ionic liquids with chlorsulfuron as the anion
  88. Effect of isovalent substitution on the crystal structure and properties of two-slab indates BaLa2−xSmxIn2O7
  89. Synthesis, spectral and thermo-kinetics explorations of Schiff-base derived metal complexes
  90. An improved reduction method for phase stability testing in the single-phase region
  91. Comparative analysis of chemical composition of some commercially important fishes with an emphasis on various Malaysian diets
  92. Development of a solventless stir bar sorptive extraction/thermal desorption large volume injection capillary gas chromatographic-mass spectrometric method for ultra-trace determination of pyrethroids pesticides in river and tap water samples
  93. A turbidity sensor development based on NL-PI observers: Experimental application to the control of a Sinaloa’s River Spirulina maxima cultivation
  94. Deep desulfurization of sintering flue gas in iron and steel works based on low-temperature oxidation
  95. Investigations of metallic elements and phenolics in Chinese medicinal plants
  96. Influence of site-classification approach on geochemical background values
  97. Effects of ageing on the surface characteristics and Cu(ii) adsorption behaviour of rice husk biochar in soil
  98. Adsorption and sugarcane-bagasse-derived activated carbon-based mitigation of 1-[2-(2-chloroethoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea-contaminated soils
  99. Antimicrobial and antifungal activities of bifunctional cooper(ii) complexes with non-steroidal anti-inflammatory drugs, flufenamic, mefenamic and tolfenamic acids and 1,10-phenanthroline
  100. Application of selenium and silicon to alleviate short-term drought stress in French marigold (Tagetes patula L.) as a model plant species
  101. Screening and analysis of xanthine oxidase inhibitors in jute leaves and their protective effects against hydrogen peroxide-induced oxidative stress in cells
  102. Synthesis and physicochemical studies of a series of mixed-ligand transition metal complexes and their molecular docking investigations against Coronavirus main protease
  103. A study of in vitro metabolism and cytotoxicity of mephedrone and methoxetamine in human and pig liver models using GC/MS and LC/MS analyses
  104. A new phenyl alkyl ester and a new combretin triterpene derivative from Combretum fragrans F. Hoffm (Combretaceae) and antiproliferative activity
  105. Erratum
  106. Erratum to: A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  107. Review Articles
  108. Sinoporphyrin sodium, a novel sensitizer for photodynamic and sonodynamic therapy
  109. Natural products isolated from Casimiroa
  110. Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review
  111. Evaluation of elastomeric heat shielding materials as insulators for solid propellant rocket motors: A short review
  112. Special Issue on Applied Biochemistry and Biotechnology 2019
  113. An overview of Monascus fermentation processes for monacolin K production
  114. Study on online soft sensor method of total sugar content in chlorotetracycline fermentation tank
  115. Studies on the Anti-Gouty Arthritis and Anti-hyperuricemia Properties of Astilbin in Animal Models
  116. Effects of organic fertilizer on water use, photosynthetic characteristics, and fruit quality of pear jujube in northern Shaanxi
  117. Characteristics of the root exudate release system of typical plants in plateau lakeside wetland under phosphorus stress conditions
  118. Characterization of soil water by the means of hydrogen and oxygen isotope ratio at dry-wet season under different soil layers in the dry-hot valley of Jinsha River
  119. Composition and diurnal variation of floral scent emission in Rosa rugosa Thunb. and Tulipa gesneriana L.
  120. Preparation of a novel ginkgolide B niosomal composite drug
  121. The degradation, biodegradability and toxicity evaluation of sulfamethazine antibiotics by gamma radiation
  122. Special issue on Monitoring, Risk Assessment and Sustainable Management for the Exposure to Environmental Toxins
  123. Insight into the cadmium and zinc binding potential of humic acids derived from composts by EEM spectra combined with PARAFAC analysis
  124. Source apportionment of soil contamination based on multivariate receptor and robust geostatistics in a typical rural–urban area, Wuhan city, middle China
  125. Special Issue on 13th JCC 2018
  126. The Role of H2C2O4 and Na2CO3 as Precipitating Agents on The Physichochemical Properties and Photocatalytic Activity of Bismuth Oxide
  127. Preparation of magnetite-silica–cetyltrimethylammonium for phenol removal based on adsolubilization
  128. Topical Issue on Agriculture
  129. Size-dependent growth kinetics of struvite crystals in wastewater with calcium ions
  130. The effect of silica-calcite sedimentary rock contained in the chicken broiler diet on the overall quality of chicken muscles
  131. Physicochemical properties of selected herbicidal products containing nicosulfuron as an active ingredient
  132. Lycopene in tomatoes and tomato products
  133. Fluorescence in the assessment of the share of a key component in the mixing of feed
  134. Sulfur application alleviates chromium stress in maize and wheat
  135. Effectiveness of removal of sulphur compounds from the air after 3 years of biofiltration with a mixture of compost soil, peat, coconut fibre and oak bark
  136. Special Issue on the 4th Green Chemistry 2018
  137. Study and fire test of banana fibre reinforced composites with flame retardance properties
  138. Special Issue on the International conference CosCI 2018
  139. Disintegration, In vitro Dissolution, and Drug Release Kinetics Profiles of k-Carrageenan-based Nutraceutical Hard-shell Capsules Containing Salicylamide
  140. Synthesis of amorphous aluminosilicate from impure Indonesian kaolin
  141. Special Issue on the International Conf on Science, Applied Science, Teaching and Education 2019
  142. Functionalization of Congo red dye as a light harvester on solar cell
  143. The effect of nitrite food preservatives added to se’i meat on the expression of wild-type p53 protein
  144. Biocompatibility and osteoconductivity of scaffold porous composite collagen–hydroxyapatite based coral for bone regeneration
  145. Special Issue on the Joint Science Congress of Materials and Polymers (ISCMP 2019)
  146. Effect of natural boron mineral use on the essential oil ratio and components of Musk Sage (Salvia sclarea L.)
  147. A theoretical and experimental study of the adsorptive removal of hexavalent chromium ions using graphene oxide as an adsorbent
  148. A study on the bacterial adhesion of Streptococcus mutans in various dental ceramics: In vitro study
  149. Corrosion study of copper in aqueous sulfuric acid solution in the presence of (2E,5E)-2,5-dibenzylidenecyclopentanone and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone: Experimental and theoretical study
  150. Special Issue on Chemistry Today for Tomorrow 2019
  151. Diabetes mellitus type 2: Exploratory data analysis based on clinical reading
  152. Multivariate analysis for the classification of copper–lead and copper–zinc glasses
  153. Special Issue on Advances in Chemistry and Polymers
  154. The spatial and temporal distribution of cationic and anionic radicals in early embryo implantation
  155. Special Issue on 3rd IC3PE 2020
  156. Magnetic iron oxide/clay nanocomposites for adsorption and catalytic oxidation in water treatment applications
  157. Special Issue on IC3PE 2018/2019 Conference
  158. Exergy analysis of conventional and hydrothermal liquefaction–esterification processes of microalgae for biodiesel production
  159. Advancing biodiesel production from microalgae Spirulina sp. by a simultaneous extraction–transesterification process using palm oil as a co-solvent of methanol
  160. Topical Issue on Applications of Mathematics in Chemistry
  161. Omega and the related counting polynomials of some chemical structures
  162. M-polynomial and topological indices of zigzag edge coronoid fused by starphene
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Heruntergeladen am 19.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2020-0158/html
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