Assignment of mono‐ and polyunsaturated fatty acids in lipids of tissues and body fluids

Willker, Wieland; Leibfritz, Dieter

doi:10.1002/(sici)1097-458x(199806)36:13<s79::aid-omr294>3.3.co;2-q

Cited by 23 publications

(33 citation statements)

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“…1D NMR spectra were acquired at RT using a rotor-synchronized Carr-Purcell-Meibom-Gill (CPMG) pulse sequence [90 • -(τ -180 • −τ ) n -acquisition] with a T 2 filter to suppress broad NMR resonances and the following settings: 5 kHz sample spinning speed, 256 transients, 5 s recycle delay. Rotor-synchronized 2D TOC-SY NMR experiments were performed with 41.8 ms mixing time at 2.25 kHz sampling and more sensitive (phase-sensitive) 2D HSQC 1 H-13 C NMR spectra were acquired at 5 kHz [10].The metabolite resonances and 2D HRMAS NMR cross peaks were assigned according to published chemical shift values [11,12]. After HRMAS NMR analysis, samples were fixed in formalin and embedded in paraffin, then 5-µm sections were stained with hematoxylin-eosin and subjected to histopathological analysis.…”

Section: Methodsmentioning

confidence: 75%

“…2b). Cross peaks for n-3 would have had chemical shifts that were very close to those for n-6, but also one at 2.09/20.88 ppm (Fω-1( -1)) [12] which was absent in our NMR spectra (Figs. 2b and 3).…”

Section: Resultsmentioning

confidence: 89%

“…2a. Protons arising from the molecular sequences CH=CH-CH 2 -CH=CH (5.3 ppm), CH=CH-CH 2 -CH=CH (2.8 ppm), CH=CH-CH 2 -CH 2 (2.1 ppm) and CH=CH-CH 2 -CH 2 This NMR pattern provides clear evidence that the 2.8 ppm diagonal peak originated from one or more PUFA species [12]. Further, 2D 1 H and 13 C correlated GE-HSQC NMR spectra indicated that the 2.8 ppm signal in the 1D NMR spectra arose solely from n-6 species [12], and there were no indications of the presence of n-3 species, the relevant NMR cross peaks showing the following 1 H/ 13 C chemical shifts: 2.79/26.06 ppm ( − CH 2 − ), 2.07/26.17 ppm ( -1 (H8,14)), 2.30/34.15 ppm (Fα(γ -chain)), 2.30/35.50 ppm (Fα(β-chain)), 1.61/25.50+25.30 ppm (Fβ), 1.30/32.37 ppm (Fω-3( -2)H15, 0.89/14.22 ppm (Fω(γ &β − chain)) ( Fig.…”

Section: Resultsmentioning

confidence: 99%

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Detection of polyunsaturated omega-6 fatty acid in human malignant prostate tissue by 1D and 2D high-resolution magic angle spinning NMR spectroscopy

Stenman

Hauksson

Gröbner

et al. 2009

Magn Reson Mater Phy

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Section: Methodsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

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Detection of polyunsaturated omega-6 fatty acid in human malignant prostate tissue by 1D and 2D high-resolution magic angle spinning NMR spectroscopy

Stenman

Hauksson

Gröbner

et al. 2009

Magn Reson Mater Phy

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“…Cross-peaks are seen between the J-coupled protons in a spin network and each carbon involved in this network. The HSQC-TOCSY method has so far been used to analyze the positional distribution of unsaturated chains in triacylglycerol model compounds [32] and to correlate carbon signals with the adjacent allylic protons of unsaturated fatty acids [36,37]. As an example, Fig.…”

Section: C-nmr Spectramentioning

confidence: 99%

High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

Hatzakis

Agiomyrgianaki

Kostidis

et al. 2011

J Americ Oil Chem Soc

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Multinuclear ( 1 H, 13 C, 31 P) and multidimensional NMR spectroscopy was employed for the analysis of diacylglycerol (DAG) oil and the quantification of its acylglycerols and acyl chains composition. A number of gradient selected two dimensional NMR techniques (TOCSY, HSQC-DEPT, HSQC-TOCSY, and HMBC) facilitated the assignment of the complex one dimensional 1 H-and 13 C-NMR spectra. In several cases, the aforementioned 2D-NMR techniques offered solid proof of earlier assignments based on chemical shift changes induced by the presence and relative positions of double bonds within the acyl chains. Integration of the appropriate signals in the NMR spectra of the three nuclei allowed the determination of DAG oil composition, which was found to be within the limits accepted for this oil, namely 1-monoacylglycerols 0.40-0.60%; 2-monoacylglycerols 0.40-0.50%; 1,3-diacylglycerols 57-62%; 1,2-diacylglycerols 28-32%; triacylglycerols 9-11%; saturated fatty acids 3-5%; oleic acid 37-45%; linoleic acid 49-53%; and linolenic acid 5-6.5%; tocopherols 0.24-0.27%. The compositional results obtained from the NMR spectra of the three nuclei were compared and discussed in terms of repeatability and ease of performance.

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“…2). NMR studies employing heteronuclear techniques (primarily 1 H-13 C HSQC) for the study of hepatic lipid composition in rodents have reported that this region is dominated by the 20:4, 22:6, 18:2, and 18:1 fatty acids (Willker and Leibfritz 1998). Previous studies in rats have shown that the fatty acid composition of PC primarily contains some combination of these fatty acids (with the exception of 22:6).…”

Section: Lipid Metabolite Profiles Of Fathead Minnow Livermentioning

confidence: 99%

Profiling lipid metabolites yields unique information on sex- and time-dependent responses of fathead minnows (Pimephales promelas) exposed to 17α-ethynylestradiol

et al. 2008

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Alterations in hepatic lipid profiles of fathead minnows (FHM) exposed to the synthetic estrogen 17a-ethynylestradiol (EE2) were determined using 1 H-NMR spectroscopy-based metabolite profiling. The exposures were conducted using either 10 ng/l or 100 ng/l EE2 via a continuous flow water delivery system. Livers were collected at 1, 4, and 8 days of the exposure and 8 days after the chemical was removed from the water (i.e. an 8 day depuration). The exposure resulted in a number of sex-specific changes in lipid profiles that were also highly time dependent. Those metabolites most affected by exposure included phosphatidylcholine, diglycerides, triglycerides and cholesterol. In addition, changes in the length and degree of unsaturation of hepatic fatty acids were observed. Lipid profiles in plasma for fish collected on the 4th day of exposure were also analyzed in order to provide further insights into changes observed in hepatic metabolite changes. Using validated partial least-squares discriminant analysis (PLS-DA), the response trajectories of the male liver lipid profiles at both exposure concentrations were compared. This analysis indicated that the males exposed to the low concentration of EE2 (10 ng/l) were largely able to recover from the exposure once the chemical was removed from the water. Conversely, the males exposed to the high concentration (100 ng/l) did not appear to recover from the exposure despite the 8 day depuration.

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Assignment of mono‐ and polyunsaturated fatty acids in lipids of tissues and body fluids

Cited by 23 publications

References 0 publications

Detection of polyunsaturated omega-6 fatty acid in human malignant prostate tissue by 1D and 2D high-resolution magic angle spinning NMR spectroscopy

Detection of polyunsaturated omega-6 fatty acid in human malignant prostate tissue by 1D and 2D high-resolution magic angle spinning NMR spectroscopy

High‐Resolution NMR Spectroscopy: An Alternative Fast Tool for Qualitative and Quantitative Analysis of Diacylglycerol (DAG) Oil

Profiling lipid metabolites yields unique information on sex- and time-dependent responses of fathead minnows (Pimephales promelas) exposed to 17α-ethynylestradiol

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