Liquid-state NMR spectroscopy for complex carbohydrate structural analysis: A hitchhiker's guide

Speciale, Immacolata; Notaro, Anna; García-Vello, Pilar; Lorenzo, Flaviana Di; Armiento, Samantha; Molinaro, Antonio; Marchetti, Roberta; Silipo, Alba; Castro, Cristina De

doi:10.1016/j.carbpol.2021.118885

Cited by 62 publications

(49 citation statements)

References 42 publications

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“…Firstly, our tentative assignment of proton signals is based on previous work on polysaccharides and sugar analysis [ 46 , 48 , 49 ]. In the low field region (δ5.4-4.3), 1H NMR spectra ( Figure 7 A) of the EPS show different signals corresponding to the protons from anomeric carbons of sugars, suggesting different types of monosaccharides linkages (α and β) in the EPS structure, as previously described by the FTIR study.…”

Section: Resultsmentioning

confidence: 99%

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Optimization and Characterization of a Novel Exopolysaccharide from Bacillus haynesii CamB6 for Food Applications

et al. 2022

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Extremophilic microorganisms often produce novel bioactive compounds to survive under harsh environmental conditions. Exopolysaccharides (EPSs), a constitutive part of bacterial biofilm, are functional biopolymers that act as a protecting sheath to the extremophilic bacteria and are of high industrial value. In this study, we elucidate a new EPS produced by thermophilic Bacillus haynesii CamB6 from a slightly acidic (pH 5.82) Campanario hot spring (56.4 °C) located in the Central Andean Mountains of Chile. Physicochemical properties of the EPS were characterized by different techniques: Scanning electron microscopy- energy dispersive X-ray spectroscopy (SEM-EDS), Atomic Force Microscopy (AFM), High-Performance Liquid Chromatography (HPLC), Gel permeation chromatography (GPC), Fourier Transform Infrared Spectroscopy (FTIR), 1D and 2D Nuclear Magnetic Resonance (NMR), and Thermogravimetric analysis (TGA). The EPS demonstrated amorphous surface roughness composed of evenly distributed macromolecular lumps. GPC and HPLC analysis showed that the EPS is a low molecular weight heteropolymer composed of mannose (66%), glucose (20%), and galactose (14%). FTIR analysis demonstrated the polysaccharide nature (–OH groups, Acetyl groups, and pyranosic ring structure) and the presence of different glycosidic linkages among sugar residues, which was further confirmed by NMR spectroscopic analyses. Moreover, D-mannose α-(1→2) and α-(1→4) linkages prevail in the CamB6 EPS structure. TGA revealed the high thermal stability (240 °C) of the polysaccharide. The functional properties of the EPS were evaluated for food industry applications, specifically as an antioxidant and for its emulsification, water-holding (WHC), oil-holding (OHC), and flocculation capacities. The results suggest that the study EPS can be a useful additive for the food-processing industry.

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Section: Resultsmentioning

confidence: 99%

“…In the COSY spectrum ( Figure 7 D) its α-configuration by low-field H-1 signal at δ5.34 was found and correlated with H-2 (δ4.0), H-6 (δ3.98 and 3.85), and H-5 (δ4.12) [ 49 ]. The β-glucopyranose units appear at δ4.83 ppm [ 51 ].…”

Section: Resultsmentioning

confidence: 99%

Optimization and Characterization of a Novel Exopolysaccharide from Bacillus haynesii CamB6 for Food Applications

et al. 2022

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“…Further structural assignment and sequencing of the residues A–F was accomplished based on the key HMBC correlations of H-1 (δH 5.38, A) to C-2 (δC 76.30, B), H-1 (δH 4.97, B) to C-4 (δC 76.01, F), H-1 (δH 4.99, F) to C-4 (δC 76.01, F), H-6 (δH 3.71, F) to C-6 (δC 71.40, E), H-1 (δH 4.97, E) to C-2 (δC 77.20, C), and H-4 (δH 3.68, F) to C-1 (δC 101.69, D) ( Figure 2 e). In addition, the sulfuric group attached to C-4 (δC 76.01, F) was discerned according to the strong deshielding properties of the sulfate substituent influencing the chemical shifts of both 1 H and 13 C nuclei next to the site of attachment [ 21 ], as well as the NMR data and molecular formula analysis of AUM-1. Based on the monosaccharide composition analysis, FT-IR analysis, methylation analysis, and the details of NMR data, the gross structure of AUM-1 was further concluded ( Figure 2 f).…”

Section: Resultsmentioning

confidence: 99%

Ferroptosis Related Immunomodulatory Effect of a Novel Extracellular Polysaccharides from Marine Fungus Aureobasidium melanogenum

et al. 2022

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Marine fungi represent an important and sustainable resource, from which the search for novel biological substances for application in the pharmacy or food industry offers great potential. In our research, novel polysaccharide (AUM-1) was obtained from marine Aureobasidium melanogenum SCAU-266 were obtained and the molecular weight of AUM-1 was determined to be 8000 Da with 97.30% of glucose, 1.9% of mannose, and 0.08% galactose, owing to a potential backbone of α-D-Glcp-(1→2)-α-D-Manp-(1→4)-α-D-Glcp-(1→6)-(SO3−)-4-α-D-Glcp-(1→6)-1-β-D-Glcp-1→2)-α-D-Glcp-(1→6)-β-D-Glcp-1→6)-α-D-Glcp-1→4)-α-D-Glcp-6→1)-[α-D-Glcp-4]26→1)-α-D-Glcp and two side chains that consisted of α-D-Glcp-1 and α-D-Glcp-(1→6)-α-D-Glcp residues. The immunomodulatory effect of AUM-1 was identified. Then, the potential molecular mechanism by which AUM-1 may be connected to ferroptosis was indicated by metabonomics, and the expression of COX2, SLC7A11, GPX4, ACSL4, FTH1, and ROS were further verified. Thus, we first speculated that AUM-1 has a potential effect on the ferroptosis-related immunomodulatory property in RAW 264.7 cells by adjusting the expression of GPX4, regulated glutathione (oxidative), directly causing lipid peroxidation owing to the higher ROS level through the glutamate metabolism and TCA cycle. Thus, the ferroptosis related immunomodulatory effect of AUM-1 was obtained.

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“…Because it plays a very valuable role in analysis of 1D 1 H NMR spectral data, including those shown here, we remind readers about the benefit of using resolution enhancement [e.g., apodization (in MNova) or line broadening (in TopSpin)] of NMR raw FID data. , Enhanced spectra were used in the doping studies of the BA pyrolysis product mixture to enable distinction between minute differences in chemical shifts for the resonances of similar substructural units present in more than one of the compounds shown in Figure .…”

Section: Results and Discussionmentioning

confidence: 99%

Examples Showing the Utility of Doping Experiments in ¹H NMR Analysis of Mixtures

2022

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Here we provide examples that demonstrate the value of using properly designed and easily performed doping experiments to give insights about the nature of the analyte(s) present in a 1H NMR sample. Two mixtures, the first quite complex and the second far less so, have been chosen: (i) the crude pyrolysate from reaction of butyric acid in (supercritical) water at 600 °C and (ii) a mixture of two basic amines. In the former, 13 distinct carbonyl-containing compounds, ranging in relative concentration of nearly 2 orders of magnitude, were positively identified. The latter highlights the advantage of using a doping experiment as opposed to merely comparing the spectra from two separate samples containing the same analyte.

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Liquid-state NMR spectroscopy for complex carbohydrate structural analysis: A hitchhiker's guide

Cited by 62 publications

References 42 publications

Optimization and Characterization of a Novel Exopolysaccharide from Bacillus haynesii CamB6 for Food Applications

Optimization and Characterization of a Novel Exopolysaccharide from Bacillus haynesii CamB6 for Food Applications

Ferroptosis Related Immunomodulatory Effect of a Novel Extracellular Polysaccharides from Marine Fungus Aureobasidium melanogenum

Examples Showing the Utility of Doping Experiments in ¹H NMR Analysis of Mixtures

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Liquid-state NMR spectroscopy for complex carbohydrate structural analysis: A hitchhiker's guide

Cited by 62 publications

References 42 publications

Optimization and Characterization of a Novel Exopolysaccharide from Bacillus haynesii CamB6 for Food Applications

Optimization and Characterization of a Novel Exopolysaccharide from Bacillus haynesii CamB6 for Food Applications

Ferroptosis Related Immunomodulatory Effect of a Novel Extracellular Polysaccharides from Marine Fungus Aureobasidium melanogenum

Examples Showing the Utility of Doping Experiments in 1H NMR Analysis of Mixtures

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Product

Resources

About

Examples Showing the Utility of Doping Experiments in ¹H NMR Analysis of Mixtures