Abstract
Among cellular molecules, lipids constitute an important group of macromolecules classified according to their chemical structure and function. Characterization of the entire lipidome is a great challenge, not only due to the structural diversity of lipids but also large number of species. Phospholipids play a key structural and functional role in biological membranes since the phospholipid bilayer serves as a platform for proteins involved in cell signaling, and phospholipids support key metabolic cellular processes. The identification and quantification of phospholipids and products of their metabolism biological material requires the use of sensitive analytical techniques. Lipidomic analysis requires a number of steps, including extraction from a biological matrix, classifying by derivatization, and ending with the analysis of the data obtained. However, these analyses enable the identification of the molecular mechanisms mediated by phospholipids and indicate their metabolites as potential disease biomarkers. This chapter indicates the advantages and disadvantages of various modern analytical approaches, mainly based on the combination of chromatographic techniques with mass spectrometry, currently used to characterize phospholipids and their metabolites resulting from peroxidation (α, β-unsaturated aldehydes and isoprostanes) and enzymatic oxidation of fatty acids (endocannabinoids and eicosanoids). Moreover, tips and pitfalls of the classical quantitative and large-scale analyses are also discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Lydic, T. A., & Goo, Y.-H. (2018). Lipidomics unveils the complexity of the lipidome in metabolic diseases. Clinical and Translational Medicine, 7(1), 4.
Li, M., Yang, L., Bai, Y., & Liu, H. (2014). Analytical methods in lipidomics and their applications. Analytical Chemistry, 86, 161–175.
Wang, M., Wang, C., & Han, X. (2017). Selection of internal standards for accurate quantification of complex lipid species in biological extracts by electrospray ionization mass spectrometry-what, how and why? Mass Spectrometry Reviews, 36(6), 693–714.
Ayala, A., Muñoz, M. F., & Argüelles, S. (2014). Lipid peroxidation: Production, metabolism, and signaling mechanisms of malondialdehyde and 4-hydroxy-2-nonenal. Oxidative Medicine and Cellular Longevity, 2014, 360438.
Girotti, A. W., & Korytowski, W. (2016). Reactions of singlet oxygen with membrane lipids: Lipid hydroperoxide generation, translocation, reductive turnover, and signaling activity. In S. Nonell & C. Flors (Eds.), Singlet oxygen: Applications in biosciences and nanosciences (Vol. 1, pp. 409–430). RSC Publishing.
Łuczaj, W., Moniuszko, A., Jarocka-Karpowicz, I., et al. (2016). Tick-borne encephalitis – Lipid peroxidation and its consequences. Scandinavian Journal of Clinical and Laboratory Investigation, 76(1), 1–9.
Łuczaj, W., Gindzienska-Sieskiewicz, E., Jarocka-Karpowicz, I., et al. (2016). The onset of lipid peroxidation in rheumatoid arthritis: Consequences and monitoring. Free Radical Research, 50, 304–313.
Galano, J. M., Lee, Y. Y., Oger, C., et al. (2017). Isoprostanes, neuroprostanes and phytoprostanes: An overview of 25 years of research in chemistry and biology. Progress in Lipid Research, 68, 83–108.
Chanda, D., Neumann, D., & Glatz, J. F. C. (2019). The endocannabinoid system: Overview of an emerging multi-faceted therapeutic target. Prostaglandins, Leukotrienes, and Essential Fatty Acids, 140, 51–56.
Mouchlis, V. D., & Dennis, E. A. (2019). Phospholipase A2 catalysis and lipid mediator lipidomics. Biochimica et Biophysica Acta – Molecular and Cell Biology of Lipids, 1864, 766–771.
Bystrická, Z., & Ďuračková, Z. (2016). Gas chromatography determination of fatty acids in the human erythrocyte membranes – A review. Prostaglandins, Leukotrienes, and Essential Fatty Acids, 115, 35–40.
Dołowy, M., & Pyka, A. (2015). Chromatographic methods in the separation of long-chain mono- and polyunsaturated fatty acids. Journal of Chemistry, 2015(120830), 1–20.
Vale, G., Martin, S. A., Mitsche, M. A., et al. (2019). Three phase liquid extraction (3PLE) – A simple, and fast method for lipidomic workflows. Journal of Lipid Research, 60(3), 694–706.
Bylda, C., Thiele, R., Kobold, U., & Volmer, D. A. (2014). Recent advances in sample preparation techniques to overcome difficulties encountered during quantitative analysis of small molecules from biofluids using LC-MS/MS. Analyst, 139, 2265–2276.
Breil, C., Vian, M. A., Zemb, T., et al. (2017). “Bligh and Dyer” and Folch methods for solid–liquid–liquid extraction of lipids from microorganisms. Comprehension of solvatation mechanisms and towards substitution with alternative solvents. International Journal of Molecular Sciences, 18(4), pii: E708.
Burla, B., Arita, M., & Arita, M. (2018). MS-based lipidomics of human blood plasma:A community-initiated position paper to develop accepted guidelines. Journal of Lipid Research, 59, 2001–2017.
Zivkovic, A. M., Wiest, M. M., Nguyen, U. T., et al. (2009). Effects of sample handling and storage on quantitative lipid analysis in human serum. Metabolomics, 5(4), 507–516.
Deranieh, R. M., Joshi, A. S., & Greenberg, M. L. (2013). Thin-layer chromatography of phospholipids. In D. Rapaport & J. M. Herrmann (Eds.), Membrane biogenesis. Methods and protocols (pp. 21–27). Humana Press.
Johnston, M. R., & Sobhi, H. F. (2017). Advances in fatty acid analysis for clinical investigation and diagnosis using GC/MS methodology. Journal of Biochemistry and Analytical Studies, 3(1), 1–11.
Wang, M., Wang, C., Han, R. H., & Han, X. (2016). Novel advances in shotgun lipidomics for biology and medicine. Progress in Lipid Research, 61, 83–108.
Berry, K. A. Z., Barkley, R. M., Berry, J. J., et al. (2016). Tandem mass spectrometry in combination with product ion mobility for the identification of phospholipids. Analytical Chemistry, 89(1), 916–921.
Pulfer, M., & Murphy, R. C. (2003). Electrospray mass spectrometry of phospholipids. Mass Spectrometry Reviews, 22(5), 332–364.
Tsoukalas, D., Alegakis, A. K., Fragkiadaki, P., et al. (2018). Application of metabolomics part II: Focus on fatty acids and their metabolites in healthy adults. International Journal of Molecular Medicine, 43(1), 1–10.
Christinat, N., Morin-Rivron, D., & Masoodi, M. (2016). High-throughput quantitative lipidomics analysis of nonesterified fatty acids in human plasma. Journal of Proteome Research, 15, 2228–2235.
Mok, H. J., Lee, J. W., Bandu, R., et al. (2016). A rapid and sensitive profiling of free fatty acids using liquid chromatography electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) after chemical derivatization. RSC Advances, 6, 32130–32139.
Seeley, J. V., & Seeley, S. K. (2013). Multidimensional gas chromatography: Fundamental advances and new applications. Analytical Chemistry, 85, 557–578.
Hancu, G., Tero-Vescan, A., Filip, C., & Rusu, A. (2018). Capillary electrophoresis in the enantioseparation of modern antidepressants: An overview. Biomedical Chromatography, 32(11), e4335.
Barrera, G., Pizzimenti, S., Daga, M., et al. (2018). Lipid peroxidation-derived aldehydes, 4-hydroxynonenal and malondialdehyde in aging-related disorders. Antioxidants, 7(8), pii: E102.
Łuczaj, W., Domingues, P., Domingues, M. R., et al. (2017). Phospholipidomic analysis reveals changes in sphingomyelin and lysophosphatidylcholine profiles in plasma from patients with neuroborreliosis. Lipids, 52, 93–98.
Jadoon, S., & Malik, A. (2018). A comprehensive review article on isoprostanes as biological markers. Biochemical Pharmacology, 7(246), 1–8.
Sousa, B. C., Pitt, A. R., & Spickett, C. M. (2017). Chemistry and analysis of HNE and other prominent carbonyl-containing lipid oxidation compounds. Free Radical Biology & Medicine, 111, 294–308.
Spickett, C. M., Wiswedel, I., Siems, W., et al. (2010). Advances in methods for the determination of biologically relevant lipid peroxidation products. Free Radical Research, 44(10), 1172–1202.
Zelzer, S., Mangge, H., Oberreither, R., et al. (2015). Oxidative stress: Determination of 4-hydroxy-2-nonenal by gas chromatography/mass spectrometry in human and rat plasma. Free Radical Research, 49(10), 1233–1238.
Tsikas, D., Rothmann, S., Schneider, J. Y., et al. (2017). Simultaneous GC-MS/MS measurement of malondialdehyde and 4-hydroxy-2-nonenal in human plasma: Effects of long-term L-arginine administration. Analytical Biochemistry, 524, 31–44.
Spickett, C. M. (2013). The lipid peroxidation product 4-hydroxy-2-nonenal: Advances in chemistry and analysis. Redox Biology, 1, 145–152.
Domijan, A. M., Ralić, J., Radić, B. S., et al. (2015). Quantification of malondialdehyde by HPLC-FL–application to various biological samples. Biomedical Chromatography, 29(1), 41–46.
Kuda, O. (2017). Bioactive metabolites of docosahexaenoic acid. Biochimie, 136, 12–20.
Marchioni, C., de Souza, I. D., Acquaro, V. R., et al. (2018). Recent advances in LC-MS/MS methods to determine endocannabinoids in biological samples: Application in neurodegenerative diseases. Analytica Chimica Acta, 1044, 12–28.
Luque-Córdoba, D., Calderón-Santiago, M., Luque de Castro, M. D., & Priego-Capote, F. (2018). Study of sample preparation for determination of endocannabinoids and analogous compounds in human serum by LC-MS/MS in MRM mode. Talanta, 185, 602–610.
Zoerner, A. A., Gutzki, F. M., Batkai, S., et al. (2011). Quantification of endocannabinoids in biological systems by chromatography and mass spectrometry: A comprehensive review from an analytical and biological perspective. Biochimica et Biophysica Acta, 1811(11), 706–723.
Wu, J., Gouveia-Figueira, S., Domellöf, M., et al. (2016). Oxylipins, endocannabinoids, and related compounds in human milk: Levels and effects of storage conditions. Prostaglandins & Other Lipid Mediators, 122, 28–36.
Sergi, M., Battista, N., Montesano, C., et al. (2013). Determination of the two major endocannabinoids in human plasma by μ-SPE followed by HPLC-MS/MS. Analytical and Bioanalytical Chemistry, 405, 785–793.
Thakare, R., Chhonker, Y. S., Gautam, N., et al. (2018). Simultaneous LC-MS/MS analysis of eicosanoids and related metabolites in human serum, sputum and BALF. Biomedical Chromatography, 32(3), 1–27.
Liakh, I., Pakiet, A., Sledzinski, T., & Mika, A. (2019). Modern methods of sample preparation for the analysis of oxylipins in biological samples. Molecules, 25, 24–31.
Kendall, A. C., Pilkington, S. M., Massey, K. A., et al. (2015). Distribution of bioactive lipid mediators in human skin. The Journal of Investigative Dermatology, 135(6), 1510–1520.
Gandhi, A. S., Budac, D., Khayrullina, T., et al. (2017). Quantitative analysis of lipids: A higher-throughput LC-MS/MS-based method and its comparison to ELISA. Future Science OA, 3(1), FSO157.
Puppolo, M., Varma, D., & Jansen, S. A. (2014). A review of analytical methods for eicosanoids in brain tissue. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 964, 50–64.
Chhonker, Y. S., Bala, V., & Murry, D. J. (2018). Quantification of eicosanoids and their metabolites in biological matrices: A review. Bioanalysis, 10(24), 2027–2046.
O’Donnell, V. B., Maskrey, B., & Taylor, G. W. (2009). Eicosanoids: Generation and detection in mammalian cells. In B. Larijani, R. Woscholski, & C. A. Rosser (Eds.), Lipid signaling protocols (pp. 1–19). Humana Press.
Deems, R., Buczynski, M. W., Bowers-Gentry, R., et al. (2007). Detection and quantitation of eicosanoids via high performance liquid chromatography-electrospray ionization-mass spectrometry. Methods in Enzymology, 432, 59–82.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Section Editor information
Rights and permissions
Copyright information
© 2022 Springer Nature Switzerland AG
About this entry
Cite this entry
Łuczaj, W., Biernacki, M., Jarocka-Karpowicz, I., Skrzydlewska, E. (2022). Analytical Approaches to Assessment of Phospholipid Metabolism in Physiology and Pathology. In: Buszewski, B., Baranowska, I. (eds) Handbook of Bioanalytics. Springer, Cham. https://doi.org/10.1007/978-3-030-95660-8_6
Download citation
DOI: https://doi.org/10.1007/978-3-030-95660-8_6
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-95659-2
Online ISBN: 978-3-030-95660-8
eBook Packages: Chemistry and Materials ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics