glycerophospholipids

Summary

Summary: Derivatives of phosphatidic acid in which the hydrophobic regions are composed of two fatty acids and a polar alcohol is joined to the C-3 position of glycerol through a phosphodiester bond. They are named according to their polar head groups, such as phosphatidylcholine and phosphatidylethanolamine.

Top Publications

  1. Kihara A, Igarashi Y. Cross talk between sphingolipids and glycerophospholipids in the establishment of plasma membrane asymmetry. Mol Biol Cell. 2004;15:4949-59 pubmed
    b>Glycerophospholipids and sphingolipids are distributed asymmetrically between the two leaflets of the lipid bilayer...
  2. Ellis S, Wu C, Deeley J, Zhu X, Truscott R, in het Panhuis M, et al. Imaging of human lens lipids by desorption electrospray ionization mass spectrometry. J Am Soc Mass Spectrom. 2010;21:2095-104 pubmed publisher
    ..lens is distinct from most other tissues in that it is high in dihydrosphingomyelin and the most abundant glycerophospholipids in the lens are unusual 1-O-alkyl-ether linked phosphatidylethanolamines and phosphatidylserines...
  3. Welti S, Fraterman S, D Angelo I, Wilm M, Scheffzek K. The sec14 homology module of neurofibromin binds cellular glycerophospholipids: mass spectrometry and structure of a lipid complex. J Mol Biol. 2007;366:551-62 pubmed
    ..Ion intensities of initial phospholipids and exchanged deuterated analogues bound by the protein module allow the quantitative analysis of differences in the exchange activity under various conditions. ..
  4. Frisardi V, Panza F, Seripa D, Farooqui T, Farooqui A. Glycerophospholipids and glycerophospholipid-derived lipid mediators: a complex meshwork in Alzheimer's disease pathology. Prog Lipid Res. 2011;50:313-30 pubmed publisher
    ..Neural membranes contain several classes of glycerophospholipids (GPs), that not only constitute their backbone but also provide the membrane with a suitable environment, ..
  5. Myers D, Ivanova P, Milne S, Brown H. Quantitative analysis of glycerophospholipids by LC-MS: acquisition, data handling, and interpretation. Biochim Biophys Acta. 2011;1811:748-57 pubmed publisher
    ..b>Glycerophospholipids present a significant challenge in this regard, given the headgroup diversity, large number of possible ..
  6. Aradottir S, Seidl S, Wurst F, Jonsson B, Alling C. Phosphatidylethanol in human organs and blood: a study on autopsy material and influences by storage conditions. Alcohol Clin Exp Res. 2004;28:1718-23 pubmed
    ..Blood samples that contain ethanol can be stored refrigerated for up to 72 hr or frozen in liquid nitrogen and stored at -80 degrees C without affecting PEth levels. ..
  7. Kallio H, Yang B, Peippo P, Tahvonen R, Pan R. Triacylglycerols, glycerophospholipids, tocopherols, and tocotrienols in berries and seeds of two subspecies (ssp. sinensis and mongolica) of Sea Buckthorn (Hippophaë rhamnoides). J Agric Food Chem. 2002;50:3004-9 pubmed
    ..were compared in terms of triacylglycerols, glycerophospholipids, tocopherols, and tocotrienols. The berries of ssp. mongolica contained less oleic acid (4.6 vs 20...
  8. Rouzer C, Ivanova P, Byrne M, Milne S, Marnett L, Brown H. Lipid profiling reveals arachidonate deficiency in RAW264.7 cells: Structural and functional implications. Biochemistry. 2006;45:14795-808 pubmed
    b>Glycerophospholipids containing arachidonic acid (20:4) serve as the precursors for an array of biologically active lipid mediators, most of which are produced by macrophages...
  9. Pomorski T, Menon A. Lipid flippases and their biological functions. Cell Mol Life Sci. 2006;63:2908-21 pubmed
    ..This review summarizes recent progress on the identification and characterization of the various flippases and the demonstration of their biological functions...

More Information

Publications62

  1. Klingler M, Klem S, Demmelmair H, Koletzko B. Comparison of the incorporation of orally administered DHA into plasma, erythrocyte and cheek cell glycerophospholipids. Br J Nutr. 2013;109:962-8 pubmed publisher
    ..The DHA increases in cheek cell, plasma and erythrocyte glycerophospholipids are compared...
  2. Mimoun M, Coste T, Lebacq J, Lebecque P, Wallemacq P, Leal T, et al. Increased tissue arachidonic acid and reduced linoleic acid in a mouse model of cystic fibrosis are reversed by supplemental glycerophospholipids enriched in docosahexaenoic acid. J Nutr. 2009;139:2358-64 pubmed publisher
    An imbalance in (n-6)/(n-3) PUFA has been reported in cystic fibrosis (CF) patients. Glycerophospholipids enriched in docosahexaenoic acid (GPL-DHA) have been shown to regulate the (n-6)/(n-3) fatty acid ratio in the elderly...
  3. Rappley I, Myers D, Milne S, Ivanova P, LaVoie M, Brown H, et al. Lipidomic profiling in mouse brain reveals differences between ages and genders, with smaller changes associated with alpha-synuclein genotype. J Neurochem. 2009;111:15-25 pubmed publisher
    ..Our results provide a detailed and systematic characterization of brain phospholipid composition in mice and identify age-related changes relevant both to Parkinson's disease and to normal aging. ..
  4. Guan X, Riezman I, Wenk M, Riezman H. Yeast lipid analysis and quantification by mass spectrometry. Methods Enzymol. 2010;470:369-91 pubmed publisher
    ..The methods to identify and quantify yeast glycerophospholipids and sphingolipids involve electrospray ionization mass spectrometry using fragmentation to characterize the ..
  5. Aradottir S, Moller K, Alling C. Phosphatidylethanol formation and degradation in human and rat blood. Alcohol Alcohol. 2004;39:8-13 pubmed
    ..Human blood seems to be particular in its ability to synthesize PEth and to maintain a stable level of PEth due to the lack of degrading activity. ..
  6. Klingler M, Demmelmair H, Koletzko B, Glaser C. Fatty acid status determination by cheek cell sampling combined with methanol-based ultrasound extraction of glycerophospholipids. Lipids. 2011;46:981-90 pubmed publisher
    ..We developed a sensitive method for the analysis of fatty acids in cheek cell glycerophospholipids, which includes significant improvements of cell sampling, non-chromatographic isolation of ..
  7. Sanyal S, Frank C, Menon A. Distinct flippases translocate glycerophospholipids and oligosaccharide diphosphate dolichols across the endoplasmic reticulum. Biochemistry. 2008;47:7937-46 pubmed publisher
  8. Ejsing C, Duchoslav E, Sampaio J, Simons K, Bonner R, Thiele C, et al. Automated identification and quantification of glycerophospholipid molecular species by multiple precursor ion scanning. Anal Chem. 2006;78:6202-14 pubmed
    ..lipid standards with diheptadecanoyl (17:0/17:0) fatty acid moieties, representing six common classes of glycerophospholipids. The automated analysis of total lipid extracts was powered by a robotic nanoflow ion source and produced ..
  9. Kainu V, Hermansson M, Somerharju P. Electrospray ionization mass spectrometry and exogenous heavy isotope-labeled lipid species provide detailed information on aminophospholipid acyl chain remodeling. J Biol Chem. 2008;283:3676-87 pubmed
    ..the approach described here provides highly detailed information on remodeling of exogenously added (amino)glycerophospholipids and should thus be very helpful when elucidating the proteins and processes maintaining molecular species ..
  10. Ivanova P, Milne S, Byrne M, Xiang Y, Brown H. Glycerophospholipid identification and quantitation by electrospray ionization mass spectrometry. Methods Enzymol. 2007;432:21-57 pubmed
    b>Glycerophospholipids are the structural building blocks of the cellular membrane...
  11. Ivanova P, Milne S, Brown H. Identification of atypical ether-linked glycerophospholipid species in macrophages by mass spectrometry. J Lipid Res. 2010;51:1581-90 pubmed publisher
    ..A comprehensive qualitative analysis of glycerophospholipids from different macrophage cells was conducted...
  12. Shindou H, Shimizu T. Acyl-CoA:lysophospholipid acyltransferases. J Biol Chem. 2009;284:1-5 pubmed publisher
    Cell membranes contain several classes of glycerophospholipids, which have numerous structural and functional roles in the cells...
  13. Sun T, Pawlowski S, Johnson M. Highly efficient microscale purification of glycerophospholipids by microfluidic cell lysis and lipid extraction for lipidomics profiling. Anal Chem. 2011;83:6628-34 pubmed publisher
    ..article presents a novel method for small-scale lipidomics of bacterial cells by integrating extraction of glycerophospholipids on a microchip with a nanoelectrospray ionization quadrupole time-of-flight tandem mass spectrometer (..
  14. Hsu F, Turk J. Structural characterization of unsaturated glycerophospholipids by multiple-stage linear ion-trap mass spectrometry with electrospray ionization. J Am Soc Mass Spectrom. 2008;19:1681-91 pubmed publisher
    Structural elucidation of glycerophospholipids (GPLs), including the polar head group, the position of double-bond(s) along the fatty acyl substituents, and the positions of acyl groups on the glycerol backbone, using multiple-stage liner ..
  15. Hermansson M, Hokynar K, Somerharju P. Mechanisms of glycerophospholipid homeostasis in mammalian cells. Prog Lipid Res. 2011;50:240-57 pubmed publisher
    ..Here, we review the key features of the processes contributing to phospholipid homeostasis in mammalian cells, with a particular emphasis on the regulation and coordination of biosynthesis and degradation. ..
  16. Aradottir S, Lundqvist C, Alling C. Phosphatidylethanol in rat organs after ethanol exposure. Alcohol Clin Exp Res. 2002;26:514-8 pubmed
    ..PEth is formed in most organs of rats exposed to ethanol acutely or chronically. Variations in PEth level and rates of PEth formation and PEth degradation are organ specific. ..
  17. Rouzer C, Ivanova P, Byrne M, Brown H, Marnett L. Lipid profiling reveals glycerophospholipid remodeling in zymosan-stimulated macrophages. Biochemistry. 2007;46:6026-42 pubmed
    ..lipid profiling by mass spectrometry provides comparative data on the relative distribution of individual glycerophospholipids within each of the major classes...
  18. Tomcala A, Tollarova M, Overgaard J, Simek P, Kostal V. Seasonal acquisition of chill tolerance and restructuring of membrane glycerophospholipids in an overwintering insect: triggering by low temperature, desiccation and diapause progression. J Exp Biol. 2006;209:4102-14 pubmed
    ..Other features of autumnal acclimatization, i.e. depression of supercooling capacity and accumulation of polyhydric alcohols, were also triggered solely by low temperatures. ..
  19. Chang Q, Gummadi S, Menon A. Chemical modification identifies two populations of glycerophospholipid flippase in rat liver ER. Biochemistry. 2004;43:10710-8 pubmed
    Transbilayer flipping of glycerophospholipids in the endoplasmic reticulum (ER) is a key feature of membrane biogenesis. Flipping appears to be an ATP-independent, bidirectional process facilitated by specific proteins or flippases...
  20. Su H, McClarty G, Dong F, Hatch G, Pan Z, Zhong G. Activation of Raf/MEK/ERK/cPLA2 signaling pathway is essential for chlamydial acquisition of host glycerophospholipids. J Biol Chem. 2004;279:9409-16 pubmed
    ..activation of the host Raf-MEK-ERK-cPLA2 signaling cascade is required for the chlamydial uptake of host glycerophospholipids. Both the MAP kinase pathway (Ras/Raf/MEK/ERK) and Ca(2+)-dependent cytosolic phospholipase A2 (cPLA2) were ..
  21. Kita Y, Ohto T, Uozumi N, Shimizu T. Biochemical properties and pathophysiological roles of cytosolic phospholipase A2s. Biochim Biophys Acta. 2006;1761:1317-22 pubmed
    Phospholipase A(2) (PLA(2)) (EC 3.1.1.4) catalyzes hydrolysis of the sn-2 ester bond of glycerophospholipids. The enzyme is essential for the production of two classes of lipid mediators, fatty acid metabolites and lysophospholipid-..
  22. Glaser C, Demmelmair H, Koletzko B. High-throughput analysis of fatty acid composition of plasma glycerophospholipids. J Lipid Res. 2010;51:216-21 pubmed publisher
    ..We developed a high-throughput method for the analysis of FAs in plasma glycerophospholipids (GPs) with increased sensitivity...
  23. Benghezal M, Roubaty C, Veepuri V, Knudsen J, Conzelmann A. SLC1 and SLC4 encode partially redundant acyl-coenzyme A 1-acylglycerol-3-phosphate O-acyltransferases of budding yeast. J Biol Chem. 2007;282:30845-55 pubmed
    Phosphatidic acid is the intermediate, from which all glycerophospholipids are synthesized...
  24. Fonteh A, Chiang J, Cipolla M, Hale J, Diallo F, Chirino A, et al. Alterations in cerebrospinal fluid glycerophospholipids and phospholipase A2 activity in Alzheimer's disease. J Lipid Res. 2013;54:2884-97 pubmed publisher
    Our aim is to study selected cerebrospinal fluid (CSF) glycerophospholipids (GP) that are important in brain pathophysiology...
  25. Deeley J, Thomas M, Truscott R, Mitchell T, Blanksby S. Identification of abundant alkyl ether glycerophospholipids in the human lens by tandem mass spectrometry techniques. Anal Chem. 2009;81:1920-30 pubmed publisher
    Previous studies have shown that the human lens contains glycerophospholipids with ether linkages...
  26. Li D, Weisinger H, Weisinger R, Mathai M, Armitage J, Vingrys A, et al. Omega 6 to omega 3 fatty acid imbalance early in life leads to persistent reductions in DHA levels in glycerophospholipids in rat hypothalamus even after long-term omega 3 fatty acid repletion. Prostaglandins Leukot Essent Fatty Acids. 2006;74:391-9 pubmed
    ..The increased ALA and reduced DHA proportions in the animals re-fed ALA in later life are consistent with a dysfunction or down-regulation of the conversion of ALA to 18:4n-3 by the delta-6 desaturase. ..
  27. Sawamura N, Morishima Kawashima M, Waki H, Kobayashi K, Kuramochi T, Frosch M, et al. Mutant presenilin 2 transgenic mice. A large increase in the levels of Abeta 42 is presumably associated with the low density membrane domain that contains decreased levels of glycerophospholipids and sphingomyelin. J Biol Chem. 2000;275:27901-8 pubmed
    ..mutant PS2 transgenic mice contained remarkably increased levels of Abeta42 and significantly low levels of glycerophospholipids and sphingomyelin...
  28. Larsen A, Uran S, Jacobsen P, Skotland T. Collision-induced dissociation of glycero phospholipids using electrospray ion-trap mass spectrometry. Rapid Commun Mass Spectrom. 2001;15:2393-8 pubmed
    ..J. Chromatogr. B 2001; 758: 265). ..
  29. Blom T, Koivusalo M, Kuismanen E, Kostiainen R, Somerharju P, Ikonen E. Mass spectrometric analysis reveals an increase in plasma membrane polyunsaturated phospholipid species upon cellular cholesterol loading. Biochemistry. 2001;40:14635-44 pubmed
    ..We suggest that remodeling of phospholipids toward higher unsaturation may serve as both an acute and a long-term adaptive mechanism in human cellular membranes against cholesterol excess. ..
  30. Varga A, Hansson P, Johnson G, Alling C. Normalization rate and cellular localization of phosphatidylethanol in whole blood from chronic alcoholics. Clin Chim Acta. 2000;299:141-50 pubmed
    ..001) with the one-compartment elimination model. The half-life was calculated as 4.0+/-0.7 days. A weak significance (P<0.05) was observed in the correlation of PEth at day 1 and half-life values of the same subjects. ..
  31. Queiroz A, Medina Cleghorn D, Marjanovic O, Nomura D, Riley L. Comparative metabolic profiling of mce1 operon mutant vs wild-type Mycobacterium tuberculosis strains. Pathog Dis. 2015;73:ftv066 pubmed publisher
    ..These lipids included decreased levels of saccharolipids and glycerophospholipids, and increased levels of alpha-, methoxy- and keto mycolic acids (MA), and hydroxyphthioceranic acid...
  32. Fruhwirth G, Hermetter A. Mediation of apoptosis by oxidized phospholipids. Subcell Biochem. 2008;49:351-67 pubmed publisher
    Free radical-mediated oxidation of (poly)unsaturated glycerophospholipids in membranes and lipoproteins leads to the formation of a plethora of products...
  33. Lee S, Cheung See Kit M, Williams T, Yamout N, Zufferey R. The glycosomal alkyl-dihydroxyacetonephosphate synthase TbADS is essential for the synthesis of ether glycerophospholipids in procyclic trypanosomes. Exp Parasitol. 2018;185:71-78 pubmed publisher
    b>Glycerophospholipids are the main constituents of the biological membranes in Trypanosoma brucei, which causes sleeping sickness in humans...
  34. Taves J, Rastedt D, Canine J, Mork D, Wallert M, Provost J. Sodium hydrogen exchanger and phospholipase D are required for alpha1-adrenergic receptor stimulation of metalloproteinase-9 and cellular invasion in CCL39 fibroblasts. Arch Biochem Biophys. 2008;477:60-6 pubmed publisher
    ..This work describes for the first time a PE-induced relationship between NHE1 and MMP-9 and a new potential mechanism by which NHE1 could promote tumor formation and metastasis. ..
  35. Lario S, Ramírez Lázaro M, Sanjuán Herráez D, Brunet Vega A, Pericay C, Gombau L, et al. Plasma sample based analysis of gastric cancer progression using targeted metabolomics. Sci Rep. 2017;7:17774 pubmed publisher
    ..A panel of 208 metabolites including acylcarnitines, amino acids and biogenic amines, sphingolipids, glycerophospholipids, hexoses, and tryptophan and phenylalanine metabolites were quantified using two complementary quantitative ..
  36. Merino Ramos T, Vázquez Calvo Ã, Casas J, Sobrino F, Saiz J, Martín Acebes M. Modification of the Host Cell Lipid Metabolism Induced by Hypolipidemic Drugs Targeting the Acetyl Coenzyme A Carboxylase Impairs West Nile Virus Replication. Antimicrob Agents Chemother. 2016;60:307-15 pubmed publisher
    ..the cellular content of multiple lipids, including those directly implicated in the flavivirus life cycle (glycerophospholipids, sphingolipids, and cholesterol)...
  37. Jeong H, Park J, Jun Y, Lee C. Crystal structures of Mmm1 and Mdm12-Mmm1 reveal mechanistic insight into phospholipid trafficking at ER-mitochondria contact sites. Proc Natl Acad Sci U S A. 2017;114:E9502-E9511 pubmed publisher
    ..surface on the SMP domain not only mediates ER membrane docking but also results in preferential binding to glycerophospholipids such as phosphatidylcholine (PC), phosphatidic acid (PA), phosphatidylglycerol (PG), and phosphatidylserine ..
  38. Zimmer J, Doyle D. Phospholipid requirement and pH optimum for the in vitro enzymatic activity of the E. coli P-type ATPase ZntA. Biochim Biophys Acta. 2006;1758:645-52 pubmed
    ..The present study describes how the E. coli ZntA P-type ATPase can be stabilized and functionally activated in a detergent solubilized system. ..
  39. Li S, Sullivan N, Rouphael N, Yu T, Banton S, Maddur M, et al. Metabolic Phenotypes of Response to Vaccination in Humans. Cell. 2017;169:862-877.e17 pubmed publisher
    ..Networks associated with inositol phosphate, glycerophospholipids, and sterol metabolism are tightly coupled with immunity...
  40. Kirov H, Schwarzer M, Neugebauer S, Faerber G, Diab M, Doenst T. Metabolomic profiling in patients undergoing Off-Pump or On-Pump coronary artery bypass surgery. BMC Cardiovasc Disord. 2017;17:93 pubmed publisher
    ..We assessed five analyte classes (41 acylcarnitines, 14 amino acids, 92 glycerophospholipids, 15 sphingolipids, sugars, lactate) using a mass-spectrometry-based kit (Biocrates AbsoluteIDQ® p150) in ..
  41. Rasmussen J, Hermetter A. Chemical synthesis of fluorescent glycero- and sphingolipids. Prog Lipid Res. 2008;47:436-60 pubmed publisher
  42. Yamashita A, Hayashi Y, Matsumoto N, Nemoto Sasaki Y, Koizumi T, Inagaki Y, et al. Coenzyme-A-Independent Transacylation System; Possible Involvement of Phospholipase A2 in Transacylation. Biology (Basel). 2017;6: pubmed publisher
    ..ether-linked lysophospholipids, is involved in the enrichment of arachidonic acid in alkyl ether-linked glycerophospholipids, and is critical for the metabolism of eicosanoids and platelet-activating factor...
  43. Tan C, Ho C, Heng S, Wu J, Tan B, Ng Y, et al. Clinacanthus nutans Extracts Modulate Epigenetic Link to Cytosolic Phospholipase A2 Expression in SH-SY5Y Cells and Primary Cortical Neurons. Neuromolecular Med. 2016;18:441-52 pubmed publisher
    ..doi: 10.1007/s12035-015-9314-z , 2015). This enzyme catalyzes the release of arachidonic acid from glycerophospholipids, and formation of pro-inflammatory eicosanoids or toxic lipid peroxidation products such as 4-..
  44. Martel J, Wu C, Hung C, Wong T, Cheng A, Cheng M, et al. Fatty acids and small organic compounds bind to mineralo-organic nanoparticles derived from human body fluids as revealed by metabolomic analysis. Nanoscale. 2016;8:5537-45 pubmed publisher
    ..A wide range of organic compounds is identified, including fatty acids, glycerophospholipids, amino acids, sugars, and amides...
  45. Sargis R, Subbaiah P. Trans unsaturated fatty acids are less oxidizable than cis unsaturated fatty acids and protect endogenous lipids from oxidation in lipoproteins and lipid bilayers. Biochemistry. 2003;42:11533-43 pubmed
    ..These studies show that dietary trans unsaturated fatty acids decrease the rate of lipid peroxidation, an effect that may mitigate the atherogenic effect of these fatty acids. ..
  46. Wurst F, Yegles M, Alling C, Aradottir S, Dierkes J, Wiesbeck G, et al. Measurement of direct ethanol metabolites in a case of a former driving under the influence (DUI) of alcohol offender, now claiming abstinence. Int J Legal Med. 2008;122:235-9 pubmed publisher
    ..A careful individual interpretation of the results for the different markers, however, is an absolute necessity. ..
  47. Hines K, Herron J, Xu L. Assessment of altered lipid homeostasis by HILIC-ion mobility-mass spectrometry-based lipidomics. J Lipid Res. 2017;58:809-819 pubmed publisher
    ..Main lipid categories such as glycerolipids, sphingolipids, and glycerophospholipids are separated on the basis of their lipid backbones in the IM dimension, whereas subclasses of each ..
  48. Zellmer S. Evidence for the hydrolysis of topical applied liposomal lipids in human stratum corneum. Cell Mol Biol Lett. 2002;7:272 pubmed
  49. Briolay A, Jaafar R, Nemoz G, Bessueille L. Myogenic differentiation and lipid-raft composition of L6 skeletal muscle cells are modulated by PUFAs. Biochim Biophys Acta. 2013;1828:602-13 pubmed publisher
    ..The cholesterol to glycerophospholipids ratio decreased during differentiation, both in total (TM) and detergent-resistant membranes (DRM)...
  50. Wang L, Wang X, Li Y, Hou Y, Sun F, Zhou S, et al. Plasma lipid profiling and diagnostic biomarkers for oral squamous cell carcinoma. Oncotarget. 2017;8:92324-92332 pubmed publisher
    ..Differentially expressed lipids were categorized as glycerophospholipids and sphingolipids...
  51. Dinis Oliveira R. Oxidative and Non-Oxidative Metabolomics of Ethanol. Curr Drug Metab. 2016;17:327-35 pubmed
    ..It is expected that knowing the metabolomics of ethanol may provide additional insights to better understand the toxicological effects and the variability of dose response. ..
  52. Yang L, Gordon V, Mishra A, Som A, Purdy K, Davis M, et al. Synthetic antimicrobial oligomers induce a composition-dependent topological transition in membranes. J Am Chem Soc. 2007;129:12141-7 pubmed
  53. Chong C, Lin T, Chang C, Yang Y, Tsai M, Yu Y, et al. Micellar electrokinetic chromatography profiles of human high-density lipoprotein phospholipids. Electrophoresis. 2011;32:1241-51 pubmed publisher
    ..Interestingly, at absorbance 234 nm, distinctively different MEKC profiles were observed for the three HDL phospholipids. ..