NMR-Based Μetabolomics of the Lipid Fraction of Organic and Conventional Bovine Milk

Tsiafoulis, Constantinos G.; Papaemmanouil, Christina; Alivertis, Dimitrios; Tzamaloukas, Ouranios; Miltiadou, Despoina; Balayssac, Stéphane; Malet‐Martino, Myriam; Gerothanassis, Ioannis P.

doi:10.3390/molecules24061067

Cited by 38 publications

(46 citation statements)

References 66 publications

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“…The assignment of the minor components of fat milk reported in Table 1, along with the experimental measured chemical shifts and some of the other principal resonances, was performed according to the available literature data, [20,24,27], 13 C-NMR data (full spectrum in Figure S2), and 2D spectroscopy (TOCSY full spectrum in Figure S3 and HSQC experiments in Figures S4 and S5). The minor components identified were CLA, caproleic acid (C10:1 cis-9), diacylglycerols (DAGs), linoleic acid, and linolenic acid.…”

Section: Resultsmentioning

confidence: 99%

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NMR Lipid Profile of Milk from Alpine Goats with Supplemented Hempseed and Linseed Diets

et al. 2020

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The supplementation of goat diets with natural products to obtain milk with nutraceutical components is a common practice. In these last years, the influence of supplementation of specifically designed diets has been studied with different analytical tools in order to explore possible beneficial effects in human consumption of animal milk and milk-derived products. In this study, the lipid fraction of milk from Alpine goats undergoing different dietary regimens was studied by 1H-NMR spectroscopy. Alpine goats were fed with linseed or hempseed supplements, and after 14 weeks of treatment, milk was collected and analyzed. Results showed that feeding diets supplemented with seeds positively affected the fatty acid composition with a pronounced increase in unsaturated fatty acids for both diets compared to a control diet. Specifically, linolenic acid content was more than doubled for linseed diet compared with the hempseed and control groups, while linoleic acid greatly increased only upon hempseed supplementation. However, a number of conjugated linoleic acid (CLA) isomers and higher levels of fatty acids with trans configuration were found in supplemented diets, particularly in the linseed diet.

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Section: Resultsmentioning

confidence: 99%

“…In previous studies, the lipid profile of milk and dairy products has been studied by high-resolution NMR spectroscopy for differentiating the animal provenience [20][21][22][23], while other studies reported the presence of different CLA isomers [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

NMR Lipid Profile of Milk from Alpine Goats with Supplemented Hempseed and Linseed Diets

et al. 2020

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“…(b) It allows the unequivocal identification and quantification of minor analytes even in strongly overlapped spectral regions, and thus, it is of importance in the emerging field of lipidomics [ 56 , 57 , 58 , 59 , 60 , 61 ], provided that a spectrometer with 1 H resonance frequency ≥600 MHz is used.…”

Section: Discussionmentioning

confidence: 99%

NMR and Computational Studies as Analytical and High-Resolution Structural Tool for Complex Hydroperoxides and Diastereomeric Endo-Hydroperoxides of Fatty Acids in Solution-Exemplified by Methyl Linolenate

et al. 2020

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A combination of selective 1D Total Correlation Spectroscopy (TOCSY) and 1H-13C Heteronuclear Multiple Bond Correlation (HMBC) NMR techniques has been employed for the identification of methyl linolenate primary oxidation products without the need for laborious isolation of the individual compounds. Complex hydroperoxides and diastereomeric endo-hydroperoxides were identified and quantified. Strongly deshielded C–O–O–H 1H-NMR resonances of diastereomeric endo-hydroperoxides in the region of 8.8 to 9.6 ppm were shown to be due to intramolecular hydrogen bonding interactions of the hydroperoxide proton with an oxygen atom of the five-member endo-peroxide ring. These strongly deshielded resonances were utilized as a new method to derive, for the first time, three-dimensional structures with an assignment of pairs of diastereomers in solution with the combined use of 1H-NMR chemical shifts, Density Functional Theory (DFT), and Our N-layered Integrated molecular Orbital and molecular Mechanics (ONIOM) calculations.

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“…Conjugated linoleic acids (CLAs) have been extensively investigated using 1 H- and 13 C-NMR [ 6 , 18 , 19 , 20 , 21 , 22 ]. NOESY experiments, and the analyses of spin–spin coupling constants were utilized to identify the geometric configurations of the double bonds [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

DFT Calculations of 1H- and 13C-NMR Chemical Shifts of Geometric Isomers of Conjugated Linoleic Acid (18:2 ω-7) and Model Compounds in Solution

et al. 2020

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A density functional theory (DFT) study of the 1H- and 13C-NMR chemical shifts of the geometric isomers of 18:2 ω-7 conjugated linoleic acid (CLA) and nine model compounds is presented, using five functionals and two basis sets. The results are compared with available experimental data from solution high resolution nuclear magnetic resonance (NMR). The experimental 1H chemical shifts exhibit highly diagnostic resonances due to the olefinic protons of the conjugated double bonds. The “inside” olefinic protons of the conjugated double bonds are deshielded than those of the “outside” protons. Furthermore, in the cis/trans isomers, the signals of the cis bonds are more deshielded than those of the trans bonds. These regularities of the experimental 1H chemical shifts of the olefinic protons of the conjugated double bonds are reproduced very accurately for the lowest energy DFT optimized single conformer, for all functionals and basis sets used. The other low energy conformers have negligible effects on the computational 1H-NMR chemical shifts. We conclude that proton NMR chemical shifts are more discriminating than carbon, and DFT calculations can provide a valuable tool for (i) the accurate prediction of 1H-NMR chemical shifts even with less demanding functionals and basis sets; (ii) the unequivocal identification of geometric isomerism of CLAs that occur in nature, and (iii) to derive high resolution structures in solution.

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NMR-Based Μetabolomics of the Lipid Fraction of Organic and Conventional Bovine Milk

Cited by 38 publications

References 66 publications

NMR Lipid Profile of Milk from Alpine Goats with Supplemented Hempseed and Linseed Diets

NMR Lipid Profile of Milk from Alpine Goats with Supplemented Hempseed and Linseed Diets

NMR and Computational Studies as Analytical and High-Resolution Structural Tool for Complex Hydroperoxides and Diastereomeric Endo-Hydroperoxides of Fatty Acids in Solution-Exemplified by Methyl Linolenate

DFT Calculations of 1H- and 13C-NMR Chemical Shifts of Geometric Isomers of Conjugated Linoleic Acid (18:2 ω-7) and Model Compounds in Solution

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