scholarly journals 1H NMR-based metabolomic observation of a two-phased toxic mode of action in Eisenia fetida after sub-lethal phenanthrene exposure

2011 ◽  
Vol 8 (2) ◽  
pp. 105 ◽  
Author(s):  
Brian P. Lankadurai ◽  
David M. Wolfe ◽  
André J. Simpson ◽  
Myrna J. Simpson
Keyword(s):  
1H Nmr ◽  
Mode Of Action ◽  
Eisenia Fetida ◽  
Nmr Spectra ◽  
Metabolic Response ◽  
Exposure Concentration ◽  
Multivariate Statistical ◽  
Contaminant Exposure ◽  
Tissue Extracts ◽  
1H Nuclear Magnetic Resonance

Environmental contextPhenanthrene is a persistent soil contaminant, whose toxic mode of action in earthworms has not been fully examined. We adopt a metabolomics approach, using 1H nuclear magnetic resonance (NMR) spectroscopy, to measure the response of earthworms to sub-lethal phenanthrene exposure. The results indicate that NMR-based metabolomics may be used to monitor responses to sub-lethal levels of contaminants and to delineate their toxic mode of action. Abstract1H NMR-based metabolomics was used to examine the response of the earthworm Eisenia fetida to sub-lethal phenanthrene exposure. E. fetida were exposed via contact tests to six sub-lethal (below the measured LC50 of 1.6 mg cm–2) concentrations of phenanthrene (0.8–0.025 mg cm–2) for 48 h. Multivariate statistical analysis of the 1H NMR spectra of earthworm tissue extracts revealed a two-phased mode of action (MOA). At exposures below 1/16th of the LC50, the MOA was characterised by a linear correlation between the metabolic response and exposure concentration. At exposures ≥1/16th of the LC50, the metabolic response to phenanthrene appeared to plateau, indicating a distinct change in the MOA. Further data analysis suggested that alanine, lysine, arginine, isoleucine, maltose, ATP and betaine may be potential indicators for sub-lethal phenanthrene exposure. Metabolite variation was also found to be proportional to the exposure concentration suggesting that NMR-based earthworm metabolomics is capable of elucidating concentration-dependent relationships in addition to elucidating the MOA of sub-lethal contaminant-exposure.

scholarly journals 1H-NMR Metabolite Fingerprinting Analysis Reveals a Disease Biomarker and a Field Treatment Response in Xylella fastidiosa subsp. pauca-Infected Olive Trees

Plants ◽  
2019 ◽  
Vol 8 (5) ◽  
pp. 115 ◽  
Author(s):  
Girelli ◽  
Angilè ◽  
Del Coco ◽  
Migoni ◽  
Zampella ◽  
...  
Keyword(s):  
Citric Acid ◽  
1H Nmr ◽  
Metabolic Response ◽  
Xylella Fastidiosa ◽  
Quinic Acid ◽  
Multivariate Statistical ◽  
Metabolic Pattern ◽  
Disease Biomarker ◽  
Olive Cultivars ◽  
Olive Trees

Xylella fastidiosa subsp. pauca is a xylem-limited bacterial phytopathogen currently found associated on many hectares with the “olive quick decline syndrome” in the Apulia region (Southern Italy), and the cultivars Ogliarola salentina and Cellina di Nardò result in being particularly sensitive to the disease. In order to find compounds showing the capability of reducing the population cell density of the pathogen within the leaves, we tested, in some olive orchards naturally-infected by the bacterium, a zinc-copper-citric acid biocomplex, namely Dentamet®, by spraying it to the crown, once per month, during spring and summer. The occurrence of the pathogen in the four olive orchards chosen for the trial was molecularly assessed. A 1H NMR metabolomic approach, in conjunction with a multivariate statistical analysis, was applied to investigate the metabolic pattern of both infected and treated adult olive cultivars, Ogliarola salentina and Cellina di Nardò trees, in two sampling periods, performed during the first year of the trial. For both cultivars and sampling periods, the orthogonal partial least squares discriminant analysis (OPLS-DA) gave good models of separation according to the treatment application. In both cultivars, some metabolites such as quinic acid, the aldehydic form of oleoeuropein, ligstroside and phenolic compounds, were consistently found as discriminative for the untreated olive trees in comparison with the Dentamet®-treated trees. Quinic acid, a precursor of lignin, was confirmed as a disease biomarker for the olive trees infected by X. fastidiosa subsp. pauca. When treated with Dentamet®, the two cultivars showed a distinct response. A consistent increase in malic acid was observed for the Ogliarola salentina trees, whereas in the Cellina di Nardò trees the treatments attenuate the metabolic response to the infection. To note that in Cellina di Nardò trees at the first sampling, an increase in γ-aminobutyric acid (GABA) was observed. This study highlights how the infection incited by X. fastidiosa subsp. pauca strongly modifies the overall metabolism of olive trees, and how a zinc-copper-citric acid biocomplex can induce an early re-programming of the metabolic pathways in the infected trees.

1H NMR metabolomics of Eisenia fetida responses after sub-lethal exposure to perfluorooctanoic acid and perfluorooctane sulfonate

2012 ◽  
Vol 9 (6) ◽  
pp. 502 ◽  
Author(s):  
Brian P. Lankadurai ◽  
André J. Simpson ◽  
Myrna J. Simpson
Keyword(s):  
1H Nmr ◽  
Eisenia Fetida ◽  
Principal Component ◽  
Atp Synthesis ◽  
Perfluorooctane Sulfonate ◽  
Perfluorooctanoic Acid ◽  
Acid Oxidation ◽  
Inner Mitochondrial Membrane ◽  
Contaminant Exposure ◽  
Pfos Exposure

Environmental contextPerfluoroalkyl acids are persistent environmental contaminants that are also found in soils. We use a metabolomics approach based on nuclear magnetic resonance analyses to investigate the responses of earthworms to exposure to sub-lethal levels of two perfluoroalkyl acids. The results indicate that this metabolomics approach is able to delineate the toxic mode of action of contaminants present at sub-lethal levels. AbstractMetabolomics entails the analysis of endogenous metabolites within organisms exposed to an external stressor such as an environmental contaminant. We utilised 1H NMR-based metabolomics to elucidate sub-lethal toxic mechanisms of Eisenia fetida earthworms after exposure to perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS). Earthworms were exposed to a range of concentrations of PFOA (6.25 to 50 μg cm–2) and PFOS (3.125 to 25 μg cm–2) by contact tests for 2 days. Earthworm tissues were extracted using a mixture of chloroform, methanol and water, and the polar fraction was analysed by 1H NMR spectroscopy. NMR-based metabolomic analysis revealed heightened E. fetida toxic responses with higher PFOA and PFOS exposure concentrations. Principal component analysis (PCA) exhibited significant separation between control and exposed earthworms along PC1 for all PFOA and PFOS exposure concentrations. Leucine, arginine, glutamate, maltose and adenosine triphosphate (ATP) are potential indicators of PFOA and PFOS exposure as these metabolite concentrations fluctuated with exposure. Our data also indicate that PFOA and PFOS exposure may increase fatty acid oxidation and interrupt ATP synthesis due to a disruption in the inner mitochondrial membrane structure. NMR-based metabolomics has promise as an insightful tool for elucidating the environmental toxicology of sub-lethal contaminant exposure.

scholarly journals Effects of the Chiral Fungicides Metalaxyl and Metalaxyl-M on the Earthworm Eisenia fetida as Determined by 1H-NMR-Based Untargeted Metabolomics

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1293 ◽  
Author(s):  
Renke Zhang ◽  
Zhiqiang Zhou
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Citric Acid ◽  
Magnetic Resonance ◽  
1H Nmr ◽  
Eisenia Fetida ◽  
Tricarboxylic Acid ◽  
Untargeted Metabolomics ◽  
1H Nuclear Magnetic Resonance ◽  
Endogenous Metabolites ◽  
Arginine Aspartate

Although metalaxyl and metalaxyl-M are widely used fungicides, very little is known about their subacute and enantiospecific effects on the earthworm metabolome. In this study, Eisenia fetida were exposed to metalaxyl and metalaxyl-M at three concentrations (0.5, 5 and 50 mg/kg) for seven days. 1H nuclear magnetic resonance (1H-NMR)-based untargeted metabolomics showed that metalaxyl and metalaxyl-M exposure disturbed earthworms’ metabolism at all three concentrations. Endogenous metabolites, such as succinate, arginine, aspartate, urea, asparagine, alanine, trimethylamine, taurine, cysteine, serine, threonine, histidine, lysine, glucose, choline, carnitine, citric acid, alpha-ketoisovaleric acid, fumaric acid and so on, were significantly changed. These results indicate that metalaxyl and metalaxyl-M produce different, enantiospecific disturbances in the earthworm metabolism, particularly in the tricarboxylic acid (TCA) and urea cycles. The application of untargeted metabolomics thus provides more information for evaluating the toxic risks of metalaxyl and metalaxyl-M.

scholarly journals Computational and Experimental 1H-NMR Study of Hydrated Mg-Based Minerals

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 933 ◽  
Author(s):  
Eric G. Sorte ◽  
Jessica M. Rimsza ◽  
Todd M. Alam
Keyword(s):  
1H Nmr ◽  
Density Functional ◽  
Nmr Spectra ◽  
Magic Angle Spinning ◽  
Magic Angle ◽  
Functional Theory ◽  
Nmr Study ◽  
1H Nuclear Magnetic Resonance ◽  
Angle Spinning ◽  
Periodic Calculations

Magnesium oxide (MgO) can convert to different magnesium-containing compounds depending on exposure and environmental conditions. Many MgO-based phases contain hydrated species allowing 1H-nuclear magnetic resonance (NMR) spectroscopy to be used in the characterization and quantification of proton-containing phases; however, surprisingly limited examples have been reported. Here, 1H-magic angle spinning (MAS) NMR spectra of select Mg-based minerals are presented and assigned. These experimental results are combined with computational NMR density functional theory (DFT) periodic calculations to calibrate the predicted chemical shielding results. This correlation is then used to predict the NMR shielding for a series of different MgO hydroxide, magnesium chloride hydrate, magnesium perchlorate, and magnesium cement compounds to aid in the future assignment of 1H-NMR spectra for complex Mg phases.

scholarly journals 1H-NMR Metabolomics Analysis of the Effects of Sulfated Polysaccharides from Masson Pine Pollen in RAW264.7 Macrophage Cells

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1841 ◽  
Author(s):  
Fangchen Su ◽  
Mengmeng Sun ◽  
Yue Geng
Keyword(s):  
1H Nmr ◽  
Sulfated Polysaccharides ◽  
Metabolomic Analysis ◽  
Multivariate Statistical ◽  
Masson Pine ◽  
Macrophage Cells ◽  
1H Nuclear Magnetic Resonance ◽  
Beneficial Uses ◽  
Pine Pollen ◽  
Raw264.7 Macrophage

Many polysaccharides have been shown to be bioactive, with the addition of sulfate often enhancing or altering this bioactivity. In previous studies, masson pine pollen polysaccharides, to include a sulfate derivative, have been shown to promote macrophage proliferation similarly to LPS. However, the exact metabolic mechanisms promoting this proliferation remain unclear. In this study, RAW264.7 macrophage cells were treated with a purified masson pine pollen polysaccharide (PPM60-D), a sulfate derivative (SPPM60-D), or LPS. Proliferation levels at a variety of concentrations were examined using MTT assay, with optimal concentration used when performing metabolomic analysis via 1H nuclear magnetic resonance (1H-NMR). This process resulted in the identification of thirty-five intracellular metabolites. Subsequent multivariate statistical analysis showed that both LPS and SPPM60-D promote RAW264.7 proliferation by promoting aerobic respiration processes and reducing processes associated with glycolysis. While some insight was gained regarding the mechanistic differences between SPPM60-D and LPS, the specific mechanisms governing the effect of SPPM60 on RAW264.7 cells will require further elucidation. These findings show that both LPS and SPPM60-D effectively promote RAW264.7 proliferation and may have beneficial uses in maintaining cellular vitality or inhibiting cancer.

The Electron Effect of Aromatic Group: Control Conformation of 2-Aromatic Cyclododecanone Derivatives

2020 ◽  
Vol 24 (10) ◽  
pp. 1139-1147
Author(s):  
Yang Mingyan ◽  
Wang Daoquan ◽  
Wang Mingan
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Coupling Constants ◽  
The Other ◽  
Repulsive Interaction ◽  
X Ray Diffraction ◽  
X Ray ◽  
Electron Effect ◽  
Group Control

2-Phenylcyclododecanone and 2-cyclohexylcyclododecanone derivatives were synthesized and characterized by 1H NMR, 13C NMR, HR-ESI-MS and X-ray diffraction. Their preferred conformations were analyzed by the coupling constants in the 1H NMR spectra and X-ray diffraction, which showed the skeleton ring of these derivatives containing [3333]-2-one conformation, and the phenyl groups were located at the side-exo position of [3333]-2-one conformation due to the strong π-π repulsive interaction between the π- electron of benzene ring and π-electron of carbonyl group. The cyclohexyl groups were located at the corner-syn or the side-exo position of [3333]-2-one conformation depending on the hindrance of the other substituted groups. The π-π electron effect played a crucial role in efficiently controlling the preferred conformation of 2-aromatic cyclododecanone and the other 2-aromatic macrocyclic derivatives with the similar preferred square and rectangular conformations.

1H-NMR spectra of high-boiling adamantylaromatic compounds

1978 ◽  
Vol 43 (1) ◽  
pp. 250-256
Author(s):  
Jaroslava Podehradská ◽  
Milan Hájek ◽  
Slavoj Hála
Keyword(s):  
1H Nmr ◽  
Nmr Spectra ◽  
1H Nmr Spectra

119Sn, 13C and 1H NMR Spectra of Tris(1-butyl)stannyl D-Glucuronate

1997 ◽  
Vol 62 (8) ◽  
pp. 1169-1176 ◽  
Author(s):  
Antonín Lyčka ◽  
Jaroslav Holeček ◽  
David Micák
Keyword(s):  
Chemical Shift ◽  
Carbonyl Group ◽  
1H Nmr ◽  
Equatorial Plane ◽  
Title Compound ◽  
Nmr Spectra ◽  
Hydroxyl Groups ◽  
Carboxylic Group ◽  
H Nmr ◽  
Oxygen Atoms

The 119Sn, 13C and 1H NMR spectra of tris(1-butyl)stannyl D-glucuronate have been measured in hexadeuteriodimethyl sulfoxide, tetradeuteriomethanol and deuteriochloroform. The chemical shift values have been assigned unambiguously with the help of H,H-COSY, TOCSY, H,C-COSY and 1H-13C HMQC-RELAY. From the analysis of parameters of 119Sn, 13C and 1H NMR spectra of the title compound and their comparison with the corresponding spectra of tris(1-butyl)stannyl acetate and other carboxylates it follows that in solutions of non-coordinating solvents (deuteriochloroform) the title compound is present in the form of more or less isolated individual molecules with pseudotetrahedral environment around the central tin atom and with monodentately bound carboxylic group. The interaction of tin atom with oxygen atoms of carbonyl group and hydroxyl groups of the saccharide residue - if they are present at all - are very weak. In solutions in coordinating solvents (hexadeuteriodimethyl sulfoxide or tetradeuteriomethanol), the title compound forms complexes with one molecule of the solvent. Particles of these complexes have a shape of trigonal bipyramid with the 1-butyl substituents in equatorial plane and the oxygen atoms of monodentate carboxylic group and coordinating solvent in axial positions.

A 15N, 13C, and 1H NMR study of reaction products from arylguanidines and chloroformate esters

1991 ◽  
Vol 56 (7) ◽  
pp. 1505-1511 ◽  
Author(s):  
Antonín Lyčka ◽  
Karel Palát
Keyword(s):  
1H Nmr ◽  
Nmr Spectra ◽  
Reaction Products ◽  
H Nmr ◽  
Nmr Study

The 15N, 13C, and 1H NMR spectra of the reaction products from arylguanidines with two mols of chloroformate esters have been measured. With application of the corresponding 15N isotopomer it has been proved that the reaction products have the structures IIIa-IIIc.

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