Homochiral Asymmetric Triacylglycerol Isomers in Egg Yolk

Nagai, Toshiharu; Ishikawa, Kinya; Yoshinaga, Kazuaki; Yoshida, Akihiko; Beppu, Fumiaki; Gotoh, Naohiro

doi:10.5650/jos.ess17128

Cited by 11 publications

(5 citation statements)

References 25 publications

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“…2A, 2B. In consistent with previous reports 24) , these neutral lipid classes were rich in monounsaturated and polyunsaturated fatty acids (PUFA) . For DG, the predominant molecules were DG (18:1_18:1) and DG (18:1_18:2) , which was in accordance with the major molecular species in TG.…”

Section: Lipid Molecular Species Analysissupporting

confidence: 90%

Characterization and Comparison of Lipid Profiles of Selected Chicken Eggs Based on Lipidomics Approach

Zhao

2023

J. Oleo Sci.

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IntroductionChicken eggs are a favorite food and the major consumed eggs worldwide 1) . They contain numerous nutritional components, such as proteins, lipids, minerals, amino acids, and vitamins 1) . Currently, many studies have confirmed that the nutrient profiles of eggs could be modified by different hen breeds 2) , feeds 3) , and husbandry systems (free range or indoor) 2) . In China s market, there are various types of chicken eggs available with different origins, quality and also retail prices. For instance, Yunan Nixi chicken eggs, being an unique eggs in the Yunnan area with the chicken name derived from that of the Nixi Township in Shangri-La, are usually sold at a 5-fold higher price than the ordinary eggs. In addition, silky fowl s eggs are another high priced chicken eggs in China have a long eating history and have been credited with famous medicinal and health-promoting properties 4) . Determine the detailed nutritional characteristics of different chicken eggs will provide references for the evaluation of quality and commercial value of the eggs.Lipids are one of the most important nutrients of chicken eggs that are present in egg yolk (65％ dry weight percentage) and include approximately 62％ triacylglycerol (TG) , 33％ phospholipid (PL) , and less than 5％ cholesterol 5) .

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Section: Lipid Molecular Species Analysissupporting

confidence: 90%

Characterization and Comparison of Lipid Profiles of Selected Chicken Eggs Based on Lipidomics Approach

Zhao

2023

J. Oleo Sci.

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“…For example, the decreasing TG (18:0/18:1/22:5) (FC = 0.729643) in T30 may be converted to TG (18:0/18:1/22:4) (FC = 1.49), allowing the yolk system to become a thermally stable state. In addition, the compositions in saturated fatty acid and high abundance of TG will greatly affect the overall nutritional and physicochemical properties of the egg yolk 35 . Furthermore, after storage, the fatty acyl C18:1, oleic acid, tended to be the main constituent of TG, reported previously for its anti‐inflammatory activity through the activation of pathways involving various immune competent cells 36 .…”

Section: Resultsmentioning

confidence: 87%

“…In addition, the compositions in saturated fatty acid and high abundance of TG will greatly affect the overall nutritional and physicochemical properties of the egg yolk. 35 Furthermore, after storage, the fatty acyl C18:1, oleic acid, tended to be the main constituent of TG, reported previously for its anti-inflammatory activity through the activation of pathways involving various immune competent cells. 36 The nutritional value of eggs handled under different conditions will vary depending on the fatty acid composition and TG abundance in the egg yolk.…”

Section: Specific Lipid Profiles Induced By Storagementioning

confidence: 77%

UHPLC‐Q‐Orbitrap‐based untargeted lipidomics reveals the variation of yolk lipids during egg storage

et al. 2022

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BACKGROUND Egg yolk is recognized for its excellent nutritional benefit and economic value; however, egg is a perishable food, potentially losing quality if not handled properly between the time from farm production to consumption. Knowledge of the changes of yolk lipid composition under an extreme storage condition close to vitelline membrane breaking, which results in an inedible condition for shelf‐eggs, remains incomplete. Considering the complexity of yolk lipids, the architectural features of yolk lipids at high‐temperature storage (30°C for 10 days versus fresh) were classified through lipidomics. RESULTS This strategy yielded 1508 features within the lipid database coupled with 74 significantly different lipids (P < 0.05, fold change > 1.2 or < 0.83), mainly triglycerides, phospholipids, and sphingolipids. Most of them were decreased after storage; for example, triglycerides were assumed to play a role as a ‘buffer’ to maintain the system stability during storage by balancing fatty acid saturation, which strongly reduces the egg edible value for humans. Furthermore, phospholipids, especially the highly unsaturated phosphatidylcholine, decreased significantly and were suggested to be the primary cause for the variation in yolk emulsifying properties and flavor. CONCLUSION Altogether, these results deriving from oxidation and lipolysis reactions enhance our understanding of lipid transformation and the biochemical mechanisms, at the molecular level, of the deteriorative process of the egg yolk. These findings may lay the foundation for identifying processes, including some modifications of the lipid composition of rations fed to laying hens, aiming to improve the long‐term shelf‐stability of shell eggs and egg products. © 2022 Society of Chemical Industry.

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“…On the other hand, CHIRALCEL OD-RH column recognized the difference between saturated and unsaturated fatty acids at the sn-1 and 3 positions of the pair of TAG enantiomers; sn-PPO/sn-OPP, sn-OOP/sn-POO, and sn-PPL/sn-LPP and separated these pairs into each enantiomer peak for the first time. Moreover, the combination of the RP HPLC and chiral HPLC enabled the quantification of naturally occurring TAG positional isomers and enantiomers [14][15][16]. However, the use of two kinds of separation modes made the analysis procedure complicated and the analysis time very long.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous Quantification of Mixed-Acid Triacylglycerol Positional Isomers and Enantiomers in Palm Oil and Lard by Chiral High-Performance Liquid Chromatography Coupled with Mass Spectrometry

Nagai¹,

Kinoshita

Kasamatsu³

et al. 2020

Symmetry

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Palm oil and lard are edible fats which are rich in palmitic (P) and oleic acids (O). In this study, triacylglycerol (TAG) positional isomers (symmetric and asymmetric isomers) and enantiomers (asymmetric isomers) in palm oil and lard were quantified simultaneously by using liquid chromatography/mass spectrometry. The CHIRALPAK IF-3 column used in our previous study recognized the difference of TAG isomers consisting of P and O in palm oil and lard, separated sn-OPP/sn-PPO/sn-POP and sn-OPO/sn-OOP/sn-POO into each isomer peak, and enabled the quantification of these TAG isomers with good recovery (95–120%). Although sn-POP and sn-OPO were the major TAGs in palm oil and lard, a comparison of the abundance ratios of TAG enantiomers such as sn-PPO/sn-OPP and sn-OOP/sn-POO revealed that there were slightly more TAG enantiomers with O at the sn-1 position and P at the sn-3 position in palm oil and P at the sn-1 position and O at the sn-3 position in lard. These results were consistent with previous reports for the positional distribution of fatty acids of palm oil and lard. This is the first study that has enabled all TAG isomers consisting of P and O in natural oils and fats to be individually quantified by mass spectrometry.

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Homochiral Asymmetric Triacylglycerol Isomers in Egg Yolk

Cited by 11 publications

References 25 publications

Characterization and Comparison of Lipid Profiles of Selected Chicken Eggs Based on Lipidomics Approach

Characterization and Comparison of Lipid Profiles of Selected Chicken Eggs Based on Lipidomics Approach

UHPLC‐Q‐Orbitrap‐based untargeted lipidomics reveals the variation of yolk lipids during egg storage

Simultaneous Quantification of Mixed-Acid Triacylglycerol Positional Isomers and Enantiomers in Palm Oil and Lard by Chiral High-Performance Liquid Chromatography Coupled with Mass Spectrometry

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