Two-Dimensional ³¹P,¹H NMR Spectroscopic Profiling of Phospholipids in Cheese and Fish

Abstract

Phospholipids (PLs) comprise an important lipid class in food because of their technological use as emulsifiers and their nutritional value. This study used one-dimensional (31)P NMR and two-dimensional (2D) (31)P,(1)H COSY NMR spectroscopy for the determination of the PL composition of cheese and fish after liquid-liquid enrichment. This extraction step enabled the identification of 10 PLs in cheese and 9 PLs in fish by 2D (31)P,(1)H NMR. Variations in the (31)P shifts indicated differences in the fatty acids attached to the individual PLs. The total PL content in cheese fat and fish oil ranged from 0.3 to 0.4% and from 5 to 12%, respectively. Phosphatidylcholine was the most prominent PL in both matrices (up to 65%). Minor PLs (limit of detection = 4 nmol, i.e. 500 μL of an 8 μM solution) were identified in forms of phosphatidic acid, lysophosphatidic acid, and phosphatidylglycerol. Specific cross couplings and (1)H fine structures in the 2D (31)P,(1)H NMR spectra proved to be valuable for the assignment and verification of known and uncommon PLs in the samples.

In vitro anti-atherogenic properties of traditional Greek cheese lipid fractions

“…Phospholipids, such as PE and PC, have been identified in various dairy products (Contarini and Povolo 2013;Kaffarnik et al 2013). The TLC polar lipid fractions of the cheese samples of the present study, which exhibited potent biological activity, were found to have similar R f values to those of SM, PC and PE.…”

Nuclear Magnetic Resonance (NMR) Spectroscopy in Food Science: A Comprehensive Review

“…NMR has the ability to serve as an invaluable tool for the compositional analysis of foods, not only due to its ability to provide important information for structural elucidation, but also for its quantitative nature. NMR has been effectively used for the analysis of several classes of compounds including lipids (Dais & Hatzakis, ; Monakhova & Diehl, , ; Siddiqui et al., ; Tsiafoulis et al., ), carbohydrates (Kazalaki et al., ; Merkx, Hong, Ermacora, & van, ; Singh, Kumar, Srivastava, Deepak, & Singh, ; Spraul et al., , ), amino acids (Belton et al., ), alcohols (Hatzakis, Archavlis, & Dais, ; Nilsson et al., ), organic acids (Berregi, del Campo, Caracena, & Miranda, ), polyphenols (Agiomyrgianaki & Dais, , ; Charisiadis, Exarchou, Troganis, & Gerothanassis, ), vitamins (Ackermann et al., ; Dais et al., ; Shumilina, Ciampa, Capozzi, Rustad, & Dikiy, ; Vaysse et al., ), terpenes (Dais, Plessel, Williamson, & Hatzakis, ), phospholipids (Hatzakis, Koidis, Boskou, & Dais, ; Kaffarnik, Ehlers, Gröbner, Schleucher, & Vetter, ), colorants (Englert, ; Scotter, ; Venkatachalam et al., ; Berké, Chèze, Vercauteren, & Deffieux, ), and contaminants (Lachenmeier et al., ) in a variety of foods, such as oils (Dais & Hatzakis, ; Siddiqui et al., ), beverages (Kidrič, ; Ryu, Koda, Miyaka, & Tanokura, ; Santos, Fonseca, Lião, Alcantara, & Barison, ; Zurriarrain et al., 2015), meats (García‐García et al., ), dairy products (Gangwar, Singh, & Deepak, ; Hu, Furihata, Ito‐Ishida, Kaminogawa, & Tanokura, ; Maher & Rochfort, ; Murgia, Mele, & Monduzzi, ; Scano et al., ; Tociu et al., ), and infant formula (Zhao et al., ). For the structural characterization of various food components, the application of 2D techniques is often required.…”

Seafood Phospholipids: Extraction Efficiency and Phosphorous Nuclear Magnetic Resonance Spectroscopy (31P NMR) Profiles

“…Total PL content plus PL profiles were determined using phosphorous nuclear magnetic resonance ( 31 P NMR). This technique is being increasingly used on its own, or in conjunction with hydrogen nuclear magnetic resonance ( 1 H NMR) and carbon nuclear magnetic resonance ( 31 C NMR), for both qualitative and quantitative analyses of PL in diverse biological matrixes, including fish oil (Kaffarnik, Ehlers, Gröbner, Schleucher, & Vetter, 2013;Li, Yang, Bai, & Liu, 2013;Siddiqui et al, 2003;Williamson & Hatzakis, 2017).…”