plasmalogens

Summary

Summary: GLYCEROPHOSPHOLIPIDS in which one of the two acyl chains is attached to glycerol with an ether alkenyl linkage instead of an ester as with the other glycerophospholipids.

Top Publications

  1. Favreliere S, Barrier L, Durand G, Chalon S, Tallineau C. Chronic dietary n-3 polyunsaturated fatty acids deficiency affects the fatty acid composition of plasmenylethanolamine and phosphatidylethanolamine differently in rat frontal cortex, striatum, and cerebellum. Lipids. 1998;33:401-7 pubmed
    ..However, by retaining 22:6n-3, striatum PmE could be most resilient. ..
  2. Zoeller R, Lake A, Nagan N, Gaposchkin D, Legner M, Lieberthal W. Plasmalogens as endogenous antioxidants: somatic cell mutants reveal the importance of the vinyl ether. Biochem J. 1999;338 ( Pt 3):769-76 pubmed
    ..double bond as a crucial element in cellular protection under these conditions and support the hypothesis that plasmalogens, through the vinyl ether, act as antioxidants to protect cells against ROS...
  3. Wood P, Smith T, Lane N, Khan M, Ehrmantraut G, Goodenowe D. Oral bioavailability of the ether lipid plasmalogen precursor, PPI-1011, in the rabbit: a new therapeutic strategy for Alzheimer's disease. Lipids Health Dis. 2011;10:227 pubmed publisher
    Docosahexaenoic acid (DHA) and DHA-containing ethanolamine plasmalogens (PlsEtn) are decreased in the brain, liver and the circulation in Alzheimer's disease...
  4. Goldfine H. The appearance, disappearance and reappearance of plasmalogens in evolution. Prog Lipid Res. 2010;49:493-8 pubmed publisher
    b>Plasmalogens, 1-O-alk-1'-enyl 2-acyl glycerol phospholipids and glycolipids, seem to have evolved first in anaerobic bacteria, but they did not persist when facultative and aerobic species appeared after the concentration of oxygen ..
  5. Brites P, Motley A, Gressens P, Mooyer P, Ploegaert I, Everts V, et al. Impaired neuronal migration and endochondral ossification in Pex7 knockout mice: a model for rhizomelic chondrodysplasia punctata. Hum Mol Genet. 2003;12:2255-67 pubmed
    ..e. a severe depletion of plasmalogens, impaired alpha-oxidation of phytanic acid and impaired beta-oxidation of very-long-chain fatty acids...
  6. Maeba R, Ueta N. Ethanolamine plasmalogen and cholesterol reduce the total membrane oxidizability measured by the oxygen uptake method. Biochem Biophys Res Commun. 2003;302:265-70 pubmed
    ..Alpha-tocopherol only prolonged an induction period dose-dependently in the present oxidizing system, suggesting a novel antioxidant mechanism of ethanolamine plasmalogens besides the action of scavenging radicals.
  7. Smith R, Lespi P, Di Luca M, Bustos C, Marra F, de Alaniz M, et al. A reliable biomarker derived from plasmalogens to evaluate malignancy and metastatic capacity of human cancers. Lipids. 2008;43:79-89 pubmed
    ..Analyses of fatty acyl chains from ethanolamine-containing plasmalogens provided a reliable tumor marker that correlated with high Se and linearity with metastases spreading...
  8. Maeba R, Maeda T, Kinoshita M, Takao K, Takenaka H, Kusano J, et al. Plasmalogens in human serum positively correlate with high- density lipoprotein and decrease with aging. J Atheroscler Thromb. 2007;14:12-8 pubmed
    The objective of the present study was to propose plasmalogens as a beneficial factor in human plasma by showing a highly positive correlation with high-density lipoprotein (HDL) and a significant reduction with aging...
  9. Brites P, Waterham H, Wanders R. Functions and biosynthesis of plasmalogens in health and disease. Biochim Biophys Acta. 2004;1636:219-31 pubmed
    b>Plasmalogens (1-O-alk-1'-enyl-2-acyl glycerophospholipids) constitute a special class of phospholipids characterized by the presence of a vinyl-ether bond at the sn-1 position...

More Information

Publications62

  1. Han X, Holtzman D, McKeel D. Plasmalogen deficiency in early Alzheimer's disease subjects and in animal models: molecular characterization using electrospray ionization mass spectrometry. J Neurochem. 2001;77:1168-80 pubmed
  2. Vance J. Lipoproteins secreted by cultured rat hepatocytes contain the antioxidant 1-alk-1-enyl-2-acylglycerophosphoethanolamine. Biochim Biophys Acta. 1990;1045:128-34 pubmed
    ..P. et al. (1984) Proc. Natl. Acad. Sci. USA 81, 3883-3887). Thus, the presence of plasmalogen as part of newly secreted lipoprotein particles may prevent their oxidation and subsequent uptake by macrophages. ..
  3. Latorre E, Collado M, Fernandez I, Aragonés M, Catalán R. Signaling events mediating activation of brain ethanolamine plasmalogen hydrolysis by ceramide. Eur J Biochem. 2003;270:36-46 pubmed
    ..We have previously demonstrated that endogenous ceramide modifies the metabolism of brain ethanolamine plasmalogens. The mechanism involved was studied...
  4. Favreliere S, Perault M, Huguet F, De Javel D, Bertrand N, Piriou A, et al. DHA-enriched phospholipid diets modulate age-related alterations in rat hippocampus. Neurobiol Aging. 2003;24:233-43 pubmed
    ..Our results show that supplementation with DHA-enriched egg PL can enhance Ach release and correct PUFA composition. ..
  5. Lessig J, Fuchs B. Plasmalogens in biological systems: their role in oxidative processes in biological membranes, their contribution to pathological processes and aging and plasmalogen analysis. Curr Med Chem. 2009;16:2021-41 pubmed
    b>Plasmalogens are a specific glycerophospholipid class containing a vinyl ether moiety at the sn-1-position of the glycerol backbone...
  6. Murthy M, Hamilton J, Greiner R, Moriguchi T, Salem N, Kim H. Differential effects of n-3 fatty acid deficiency on phospholipid molecular species composition in the rat hippocampus. J Lipid Res. 2002;43:611-7 pubmed
    ..led to a reduction of 22:6n-3 molecular species in phosphatidylcholine (PC), phosphatidylethanolamine (PE), PE-plasmalogens (PLE), and phosphatidylserine (PS) by 70-80%...
  7. Khan M, Singh J, Singh I. Plasmalogen deficiency in cerebral adrenoleukodystrophy and its modulation by lovastatin. J Neurochem. 2008;106:1766-79 pubmed publisher
    ..In summary, this study reports that altered metabolism of PlsEtn and ROS in cALD may be corrected by lovastatin treatment...
  8. Skaff O, Pattison D, Davies M. The vinyl ether linkages of plasmalogens are favored targets for myeloperoxidase-derived oxidants: a kinetic study. Biochemistry. 2008;47:8237-45 pubmed publisher
    b>Plasmalogens, which contain a vinyl ether bond, are major phospholipids of the plasma membranes of endothelial and vascular smooth muscle cells and cardiac myocytes...
  9. Mawatari S, Yunoki K, Sugiyama M, Fujino T. Simultaneous preparation of purified plasmalogens and sphingomyelin in human erythrocytes with phospholipase A1 from Aspergillus orizae. Biosci Biotechnol Biochem. 2009;73:2621-5 pubmed
    A method for the simultaneous purification of plasmalogens and sphingomyelin (SM) in human erythrocytes is described. Treatment of total lipids with n-hexane/acetone (1:1 v/v) resulted in selective precipitation of SM...
  10. Berdyshev E. Mass spectrometry of fatty aldehydes. Biochim Biophys Acta. 2011;1811:680-93 pubmed publisher
    ..This review provides an overview of current GC/MS and LC/MS approaches of fatty aldehyde analysis as well as discusses technical challenges standing in the way of free fatty aldehyde quantitation. ..
  11. Albert C, Thukkani A, Heuertz R, Slungaard A, Hazen S, Ford D. Eosinophil peroxidase-derived reactive brominating species target the vinyl ether bond of plasmalogens generating a novel chemoattractant, alpha-bromo fatty aldehyde. J Biol Chem. 2003;278:8942-50 pubmed
    b>Plasmalogens are a subclass of glycerophospholipids that are enriched in the plasma membrane of many mammalian cells. The vinyl ether bond of plasmalogens renders them susceptible to oxidation...
  12. Viola A, Confort Gouny S, Ranjeva J, Chabrol B, Raybaud C, Vintila F, et al. MR imaging and MR spectroscopy in rhizomelic chondrodysplasia punctata. AJNR Am J Neuroradiol. 2002;23:480-3 pubmed
    ..The importance of these metabolic anomalies is correlated to the deficiency in plasmalogen biosynthesis...
  13. Pettegrew J, Panchalingam K, Levine J, McClure R, Gershon S, Yao J. Chronic myo-inositol increases rat brain phosphatidylethanolamine plasmalogen. Biol Psychiatry. 2001;49:444-53 pubmed
    ..The observed alteration in the PtdEtn-Plas/PtdEtn ratio could provide insights into the therapeutic effect of myo-inositol in affective disorders. ..
  14. Braverman N, Zhang R, Chen L, Nimmo G, Scheper S, Tran T, et al. A Pex7 hypomorphic mouse model for plasmalogen deficiency affecting the lens and skeleton. Mol Genet Metab. 2010;99:408-16 pubmed publisher
    ..The pathology results from a deficiency of plasmalogens, a critical class of ether phospholipids whose functions are largely unknown...
  15. Farooqui A. Studies on plasmalogen-selective phospholipase A2 in brain. Mol Neurobiol. 2010;41:267-73 pubmed publisher
    ..It is proposed that accumulation of ceramide and increased expression of cytokines may be responsible for the stimulation of PlsEtn-PLA(2) in Alzheimer disease. ..
  16. Wood P, Mankidy R, Ritchie S, Heath D, Wood J, Flax J, et al. Circulating plasmalogen levels and Alzheimer Disease Assessment Scale-Cognitive scores in Alzheimer patients. J Psychiatry Neurosci. 2010;35:59-62 pubmed
    b>Plasmalogens, which are key structural phospholipids in brain membranes, are decreased in the brain and serum of patients with Alzheimer disease (AD)...
  17. Wood P, Khan M, Smith T, Ehrmantraut G, Jin W, Cui W, et al. In vitro and in vivo plasmalogen replacement evaluations in rhizomelic chrondrodysplasia punctata and Pelizaeus-Merzbacher disease using PPI-1011, an ether lipid plasmalogen precursor. Lipids Health Dis. 2011;10:182 pubmed publisher
    ..b>Plasmalogens (ether glycerophosphoethanolamine lipids) are decreased in these genetic disorders...
  18. Brites P, Ferreira A, da Silva T, Sousa V, Malheiro A, Duran M, et al. Alkyl-glycerol rescues plasmalogen levels and pathology of ether-phospholipid deficient mice. PLoS ONE. 2011;6:e28539 pubmed publisher
    A deficiency of plasmalogens, caused by impaired peroxisomal metabolism affects normal development and multiple organs in adulthood...
  19. Styger R, Wiesmann U, Honegger U. Plasmalogen content and beta-adrenoceptor signalling in fibroblasts from patients with Zellweger syndrome. Effects of hexadecylglycerol. Biochim Biophys Acta. 2002;1585:39-43 pubmed
    ..b>Plasmalogens are part of the membrane lipid composition...
  20. Wanders R, Waterham H. Peroxisomal disorders: the single peroxisomal enzyme deficiencies. Biochim Biophys Acta. 2006;1763:1707-20 pubmed
  21. Andre A, Juaneda P, Sebedio J, Chardigny J. Plasmalogen metabolism-related enzymes in rat brain during aging: influence of n-3 fatty acid intake. Biochimie. 2006;88:103-11 pubmed
    b>Plasmalogens (Pls) are phospholipids containing a vinyl-ether bond at the sn-1 position of the glycerol backbone. They represent between 1/2 and 2/3 of the ethanolamine phospholipids in the brain...
  22. Han X. Lipid alterations in the earliest clinically recognizable stage of Alzheimer's disease: implication of the role of lipids in the pathogenesis of Alzheimer's disease. Curr Alzheimer Res. 2005;2:65-77 pubmed
    ..Collectively, this review will provide an overview of the lipid alterations in Alzheimer's disease and the relationship of these lipid alterations with the development of AD pathogenesis. ..
  23. Engelmann B. Plasmalogens: targets for oxidants and major lipophilic antioxidants. Biochem Soc Trans. 2004;32:147-50 pubmed
    ..Here, previous results on the role of plasmalogens in lipid oxidation are evaluated on the basis of criteria required for an antioxidant...
  24. Guan Z, Johnston N, Aygun Sunar S, Daldal F, Raetz C, Goldfine H. Structural characterization of the polar lipids of Clostridium novyi NT. Further evidence for a novel anaerobic biosynthetic pathway to plasmalogens. Biochim Biophys Acta. 2011;1811:186-93 pubmed publisher
    ..PG and amino acyl PG were present in both the diacyl and alk-1'-enyl acyl (plasmalogen) forms and cardiolipin plasmalogens were found to contain one or two alk-1'-enyl chains...
  25. Braverman N, Moser A. Functions of plasmalogen lipids in health and disease. Biochim Biophys Acta. 2012;1822:1442-52 pubmed publisher
    b>Plasmalogens are a unique class of membrane glycerophospholipids containing a fatty alcohol with a vinyl-ether bond at the sn-1 position, and enriched in polyunsaturated fatty acids at the sn-2 position of the glycerol backbone...
  26. Wood P, Khan M, Smith T, Goodenowe D. Cellular diamine levels in cancer chemoprevention: modulation by ibuprofen and membrane plasmalogens. Lipids Health Dis. 2011;10:214 pubmed publisher
    ..In this regard, we examined the effects of membrane plasmalogens and ibuprofen on regulation of cellular levels of diamines, polyamine mediators that are augmented in cancer ..
  27. Grimm M, Grösgen S, Riemenschneider M, Tanila H, Grimm H, Hartmann T. From brain to food: analysis of phosphatidylcholins, lyso-phosphatidylcholins and phosphatidylcholin-plasmalogens derivates in Alzheimer's disease human post mortem brains and mice model via mass spectrometry. J Chromatogr A. 2011;1218:7713-22 pubmed publisher
    ..Additionally, we show that the method applied with multiple reaction monitoring (MRM) used for this study is suitable for semi quantitative analysis of small amounts (10 ?l) of brain tissue. ..
  28. Igarashi M, Ma K, Gao F, Kim H, Rapoport S, Rao J. Disturbed choline plasmalogen and phospholipid fatty acid concentrations in Alzheimer's disease prefrontal cortex. J Alzheimers Dis. 2011;24:507-17 pubmed publisher
    ..These lipid changes, which suggest extensive membrane remodeling, may contribute to membrane instability and synaptic loss in AD and reflect neuroinflammation. ..
  29. Pike L, Han X, Chung K, Gross R. Lipid rafts are enriched in arachidonic acid and plasmenylethanolamine and their composition is independent of caveolin-1 expression: a quantitative electrospray ionization/mass spectrometric analysis. Biochemistry. 2002;41:2075-88 pubmed
    ..In addition, these detergent-resistant membranes were not enriched in arachidonic acid-containing ethanolamine plasmalogens. These data provide insight into the structure of lipid rafts and identify potential new roles for these ..
  30. Gorgas K, Teigler A, Komljenovic D, Just W. The ether lipid-deficient mouse: tracking down plasmalogen functions. Biochim Biophys Acta. 2006;1763:1511-26 pubmed
    ..properties as well as physiological functions of major mammalian ether-linked glycerolipids, including plasmalogens were reviewed...
  31. Dragonas C, Bertsch T, Sieber C, Brosche T. Plasmalogens as a marker of elevated systemic oxidative stress in Parkinson's disease. Clin Chem Lab Med. 2009;47:894-7 pubmed publisher
  32. Gaposchkin D, Farber H, Zoeller R. On the importance of plasmalogen status in stimulated arachidonic acid release in the macrophage cell line RAW 264.7. Biochim Biophys Acta. 2008;1781:213-9 pubmed publisher
    We examined the dependence of stimulated arachidonic acid release on plasmalogens using the murine, macrophage cell line 264.7 and two plasmalogen-deficient variants, RAW.12 and RAW.108...
  33. Kuczynski B, Reo N. Evidence that plasmalogen is protective against oxidative stress in the rat brain. Neurochem Res. 2006;31:639-56 pubmed
    ..Our data suggest a high basal [PlsEtn], or the capacity to synthesize new ethanolamine lipids (particularly PlsEtn) may protect against PH(3) toxicity...
  34. Zemski Berry K, Murphy R. Electrospray ionization tandem mass spectrometry of glycerophosphoethanolamine plasmalogen phospholipids. J Am Soc Mass Spectrom. 2004;15:1499-508 pubmed
    ..ion mode electrospray tandem mass spectrometry to study the collision-induced dissociation of various GPEtn plasmalogens present in the phospholipid membranes of human neutrophils...
  35. Gootjes J, Mooijer P, Dekker C, Barth P, Poll The B, Waterham H, et al. Biochemical markers predicting survival in peroxisome biogenesis disorders. Neurology. 2002;59:1746-9 pubmed
    ..Combination of both markers gives an even better prediction. These results contribute to the management of patients with PBD. ..
  36. Munn N, Arnio E, Liu D, Zoeller R, Liscum L. Deficiency in ethanolamine plasmalogen leads to altered cholesterol transport. J Lipid Res. 2003;44:182-92 pubmed
    b>Plasmalogens are a major sub-class of ethanolamine and choline phospholipids in which the sn-1 position has a long chain fatty alcohol attached through a vinyl ether bond...
  37. Rodemer C, Thai T, Brugger B, Kaercher T, Werner H, Nave K, et al. Inactivation of ether lipid biosynthesis causes male infertility, defects in eye development and optic nerve hypoplasia in mice. Hum Mol Genet. 2003;12:1881-95 pubmed
    Although known for almost 80 years, the physiological role of plasmalogens (PLs), the major mammalian ether lipids (ELs), is still enigmatic...
  38. Wallner S, Schmitz G. Plasmalogens the neglected regulatory and scavenging lipid species. Chem Phys Lipids. 2011;164:573-89 pubmed publisher
    b>Plasmalogens are a class of phospholipids carrying a vinyl ether bond in sn-1 and an ester bond in sn-2 position of the glycerol backbone...
  39. Steinberg S, Dodt G, Raymond G, Braverman N, Moser A, Moser H. Peroxisome biogenesis disorders. Biochim Biophys Acta. 2006;1763:1733-48 pubmed
    ..Studies of the cellular and molecular defects in PBD patients have contributed significantly to our understanding of the role of each PEX gene in peroxisome assembly...
  40. Ullen A, Fauler G, Köfeler H, Waltl S, Nusshold C, Bernhart E, et al. Mouse brain plasmalogens are targets for hypochlorous acid-mediated modification in vitro and in vivo. Free Radic Biol Med. 2010;49:1655-65 pubmed publisher
    b>Plasmalogens, 1-O-alk-1'-enyl-2-acyl-sn-glycerophospholipids, are significant constituents of cellular membranes and are essential for normal brain development...
  41. Acar N, Berdeaux O, Juaneda P, Gregoire S, Cabaret S, Joffre C, et al. Red blood cell plasmalogens and docosahexaenoic acid are independently reduced in primary open-angle glaucoma. Exp Eye Res. 2009;89:840-53 pubmed publisher
    ..lipid entities that may affect the membrane physiology, namely, polyunsaturated fatty acids (PUFAs) and plasmalogens, are modified in POAG and whether these potential variations are related to the stage of glaucoma...
  42. Stenvinkel P, Diczfalusy U, Lindholm B, Heimburger O. Phospholipid plasmalogen, a surrogate marker of oxidative stress, is associated with increased cardiovascular mortality in patients on renal replacement therapy. Nephrol Dial Transplant. 2004;19:972-6 pubmed
    ..However, it is not well established that increased oxidative stress predicts cardiovascular mortality in ESRD. Plasmalogens, a group of phospholipids with a vinyl ether bond in the sn-1 position, are considered to be sensitive markers ..
  43. Magnusson C, Haraldsson G. Ether lipids. Chem Phys Lipids. 2011;164:315-40 pubmed publisher
    ..It was accomplished by a highly convergent five step process. ..
  44. Fabelo N, Martin V, Santpere G, Marin R, Torrent L, Ferrer I, et al. Severe alterations in lipid composition of frontal cortex lipid rafts from Parkinson's disease and incidental Parkinson's disease. Mol Med. 2011;17:1107-18 pubmed publisher
    ..The findings correlate with abnormal lipid raft signaling and cognitive decline observed during the development of these neurodegenerative disorders. ..
  45. Thai T, Rodemer C, Jauch A, Hunziker A, Moser A, Gorgas K, et al. Impaired membrane traffic in defective ether lipid biosynthesis. Hum Mol Genet. 2001;10:127-36 pubmed
    ..localized to peroxisomes and hence some peroxisomal disorders are characterized by a severe deficiency of plasmalogens, the main ether lipids in humans...
  46. Lessig J, Fuchs B. HOCl-mediated glycerophosphocholine and glycerophosphoethanolamine generation from plasmalogens in phospholipid mixtures. Lipids. 2010;45:37-51 pubmed publisher
    Many mammalian tissues and cells contain, in addition to (diacyl) phospholipids, considerable amounts of plasmalogens, which may function as important antioxidants...
  47. Kaddurah Daouk R, McEvoy J, Baillie R, Zhu H, K Yao J, Nimgaonkar V, et al. Impaired plasmalogens in patients with schizophrenia. Psychiatry Res. 2012;198:347-52 pubmed publisher
    b>Plasmalogens are a subclass of glycerophospholipids and ubiquitous constituents of cellular membranes and serum lipoproteins. Several neurological disorders show decreased level of plasmogens...
  48. Mitchell T, Buffenstein R, Hulbert A. Membrane phospholipid composition may contribute to exceptional longevity of the naked mole-rat (Heterocephalus glaber): a comparative study using shotgun lipidomics. Exp Gerontol. 2007;42:1053-62 pubmed
    ..Vinyl ether-linked phospholipids (plasmalogens) are higher in naked mole-rat tissues than in mice...
  49. da Silva T, Sousa V, Malheiro A, Brites P. The importance of ether-phospholipids: a view from the perspective of mouse models. Biochim Biophys Acta. 2012;1822:1501-8 pubmed publisher
    ..b>Plasmalogens are the most abundant form of alkenyl-glycerophospholipids, and their synthesis requires functional peroxisomes...
  50. Katafuchi T, Ifuku M, Mawatari S, Noda M, Miake K, Sugiyama M, et al. Effects of plasmalogens on systemic lipopolysaccharide-induced glial activation and ?-amyloid accumulation in adult mice. Ann N Y Acad Sci. 2012;1262:85-92 pubmed publisher
    ..b>Plasmalogens (Pls) are glycerophospholipids constituting cellular membranes and play significant roles in membrane fluidity ..
  51. Wu L, Pfeiffer D, Calhoon E, Madiai F, Marcucci G, Liu S, et al. Purification, identification, and cloning of lysoplasmalogenase, the enzyme that catalyzes hydrolysis of the vinyl ether bond of lysoplasmalogen. J Biol Chem. 2011;286:24916-30 pubmed publisher
    ..Overexpression of TMEM86b in HEK 293T cells resulted in decreased levels of plasmalogens, suggesting that the enzyme may be important in regulating plasmalogen levels in animal cells.
  52. Farooqui A, Horrocks L. Plasmalogens, phospholipase A2, and docosahexaenoic acid turnover in brain tissue. J Mol Neurosci. 2001;16:263-72; discussion 279-84 pubmed
    b>Plasmalogens are glycerophospholipids of neural membranes containing vinyl ether bonds. Their synthetic pathway is located in peroxisomes and endoplasmic reticulum...
  53. Nagy K, Brahmbhatt V, Berdeaux O, Bretillon L, Destaillats F, Acar N. Comparative study of serine-plasmalogens in human retina and optic nerve: identification of atypical species with odd carbon chains. J Lipid Res. 2012;53:776-83 pubmed publisher
    ..b>Plasmalogens (vinyl-ether bearing phospholipids) are commonly found in the forms of phosphatidylcholine and ..