Lysophospholipids: Potential markers of diseases and infertility?

Mini-Reviews in Medicinal Chemistry

Volumn 12, Issue 1, 2012, Pages 74-86

  Fuchs, B ^a   Muller K ^b   Paasch, U ^a   Schiller, J ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b LEIBNIZ INSTITUTE FOR ZOO AND WILDLIFE RESEARCH   (Germany)

Author keywords

Disease Markers; Inflammation; Lysophosphatidylcholine; Lysophospholipids; Phospholipase; Phospholipids; Reactive Oxygen Species; Spermatozoa

Indexed keywords

CERAMIDE; DIACYLGLYCEROL; FLAVONOID; G PROTEIN COUPLED RECEPTOR; HYDROGEN PEROXIDE; HYDROXYL RADICAL; HYPOCHLOROUS ACID; LYSOPHOSPHATIDYLCHOLINE; LYSOPHOSPHOLIPID; MYELOPEROXIDASE; OLEIC ACID; PHOSPHATIDIC ACID; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHATIDYLGLYCEROL; PHOSPHATIDYLINOSITOL; PHOSPHATIDYLSERINE; PHOSPHOLIPASE; PHOSPHOLIPASE A1; PHOSPHOLIPASE A2; POLYPHOSPHOINOSITIDE; PROSTAGLANDIN; QUERCETIN; REACTIVE OXYGEN METABOLITE; SPHINGOMYELIN; SPHINGOSINE 1 PHOSPHATE RECEPTOR;

ASTHMA; ATHEROSCLEROSIS; CHEMICAL ANALYSIS; DIABETES MELLITUS; ELECTRON SPIN RESONANCE; ENDOMETRIOSIS; ENZYME ACTIVITY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; FLUORESCENCE SPECTROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYPERLIPIDEMIA; IN VITRO STUDY; IN VIVO STUDY; INFERTILITY; INFLAMMATORY DISEASE; MASS SPECTROMETRY; NEOPLASM; NEUTROPHIL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PSORIASIS; RADIOACTIVITY; REVIEW; RHEUMATOID ARTHRITIS; RHINITIS; SEPSIS; SPERMATOZOON; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROSCOPY;

ATHEROSCLEROSIS; BIOLOGICAL MARKERS; FEMALE; HUMANS; INFERTILITY; INFLAMMATION; LYSOPHOSPHATIDYLCHOLINES; LYSOPHOSPHOLIPIDS; MALE; MOLECULAR DIAGNOSTIC TECHNIQUES; NEOPLASMS; SIGNAL TRANSDUCTION;

EID: 84855829714     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/138955712798868931     Document Type: Review

References (93)

1. Fuchs, B.; Schiller, J. Lysophospholipids: their generation, physiological role and detection. Are they important disease markers? Mini.-Rev. Med. Chem., 2009, 9, 368-378.
2. Larsson, K.; Sato, K.; Tiberg, F. Lipids: Structure, Physical Properties and Functionality, 1st ed.; The Oily Press Lipid Library: Bridgwater, 2006.
3. Billich, A.; Baumruker, T. Sphingolipid metabolizing enzymes as novel therapeutic targets. Subcell. Biochem., 2008, 49, 487-522.
4. Wymann, M.P.; Schneiter, R. Lipid signalling in disease. Nat. Rev. Mol. Cell. Biol., 2008, 9, 162-176.
5. Arab, L.; Akbar, J. Biomarkers and the measurement of fatty acids. Public Health Nutr., 2002, 5, 865-871.
6. 2: its usefulness in laboratory diagnostics. Crit. Rev. Clin. Lab. Sci., 1999, 36, 65-163.
7. Hu, J.S.; Li, Y.B.; Wang, J.W.; Sun, L.; Zhang, G.J. Mechanism of lysophosphatidylcholine-induced lysosome destabilization. J. Membr. Biol., 2007, 215, 27-35.
8. 2 superfamily and its group numbering system. Biochim. Biophys. Acta., 2006, 1761, 1246-1259.
9. 31P NMR and MALDI-TOF MS. Clin. Biochem., 2005, 38, 925-933.
10. Matsumoto, T.; Kobayashi, T.; Kamata, K. Role of lysophosphatidylcholine (LPC) in atherosclerosis. Curr. Med. Chem., 2007, 14, 3209-3220.
11. Ford, D.A.; Lipid oxidation by hypochlorous acid: chlorinated lipids in atherosclerosis and myocardial ischemia. Clin. Lipidol., 2010, 5, 835-852.
12. Schiller, J.; Fuchs, B.; Arnhold, J.; Arnold, K. Contribution of reactive oxygen species to cartilage degradation in rheumatic diseases: molecular pathways, diagnosis and potential therapeutic strategies. Curr. Med. Chem., 2003, 10, 2123-2145.
13. Wu, J.; Teuber, K.; Eibisch, M.; Fuchs, B.; Schiller, J. Chlorinated and brominated phosphatidylcholines are generated under the influence of the Fenton reagent at low pH-a MALDI-TOF MS study. Chem. Phys. Lipids, 2011, 164, 1-8.
14. Fuchs, B.; Schober, C.; Richter, G.; Nimptsch, A.; Süß, R.; Schiller, J. The reactions between HOCl and differently saturated phospholipids: Physiological relevance, products and methods of evaluation. Mini-Rev. Org. Chem., 2008, 5, 254-261.
15. Halliwell B. Phagocyte-derived reactive species: salvation or suicide? Trends Biochem. Sci., 2006, 31, 509-515.
16. 2 in vascular disease: mediators of endothelial dysfunction and atherosclerosis. Med. Sci. Monit., 2006, 12, RA5-16.
17. Arnhold, J.; Osipov, A.N.; Spalteholz, H.; Panasenko, O.M.; Schiller, J. Effects of hypochlorous acid on unsaturated phosphatidylcholines. Free Radic. Biol. Med., 2001, 31, 1111-1119.
18. Arnhold, J.; Osipov, A.N.; Spalteholz, H.; Panasenko, O.M.; Schiller, J. Formation of lysophospholipids from unsaturated phosphatidylcholines under the influence of hypochlorous acid. Biochim. Biophys. Acta, 2002, 1572, 91-100.
19. Choi, J.; Zhang, W.; Gu, X.; Chen, X.; Hong, L.; Laird, J.M.; Salomon, R.G. Lysophosphatidylcholine is generated by spontaneous deacylation of oxidized phospholipids. Chem. Res. Toxicol., 2011, 24, 111-118.
20. Hernández-Caselles, T.; Villalaín, J.; Gómez-Fernández, J.C. Stability of liposomes on long term storage. J. Pharm. Pharmacol., 1990, 42, 397-400.
21. Richter, G.; Schober, C.; Süß, R.; Fuchs, B.; Birkemeyer, C.; Schiller J. Comparison of the positive and negative ion electrospray ionization and matrix-assisted laser desorption ionization-time-offlight mass spectra of the reaction products of phosphatidylethanolamines and hypochlorous acid. Anal. Biochem., 2008, 376, 157-159.
22. 2 but not by hypochlorous acid. Bioorg. Chem., 2009, 37, 202-210.
23. 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, 2021-2041.
24. Reynolds, L.J.; Washburn, W.N.; Deems, R.A.; Dennis, E.A. Assay strategies and methods for phospholipases. Methods Enzymol. 1991, 197, 3-23.
25. Aarsman, A.J.; van Deenen, L.L.M.; van den Bosch, H. Studies on lysophospholipases: VII. Synthesis of acylthioester analogs of lysolecithin and their use in a continuous spectrophotometric assay for lysophospholipases, a method with potential applicability to other lipolytic enzymes. Bioorg. Chem., 1976, 5, 241-253.
26. Rawyler, A.; Siegenthaler, P.A. A single and continuous spectrophotometric assay for various lipolytic enzymes, using natural, non-labelled lipid substrates. Biochim. Biophys. Acta, 1989, 1004, 337-344.
27. Morrot, G.; Hervé, P.; Zachowski, A.; Fellmann, P.; Devaux, P.F. Aminophospholipid translocase of human erythrocytes: phospholipid substrate specificity and effect of cholesterol. Biochemistry, 1989, 28, 3456-3462.
28. Müller, K.; Pomorski, T.; Müller, P.; Herrmann, A. In: Advances in Experimental Medicine and Biology-The Fate of the Male Germ Cell; Ivell & Holstein, Eds.; Plenum Press: New York, 1997; Vol 424, pp. 243-244.
29. Devaux, P.F.; Fellmann, P.; Hervé, P. Investigation on lipid asymmetry using lipid probes: comparison between spin-labeled lipids and fluorescent lipids. Chem. Phys. Lipids, 2002, 116, 115-1134.
30. Clejan, S. HPLC analytical methods for the separation of molecular species of fatty acids in diacylglycerol and cellular phospholipids. Methods Mol. Biol., 1998, 105, 255-274.
31. Fuchs, B.; Süß, R.; Teuber, K.; Eibisch, M.; Schiller, J. Lipid analysis by thin-layer chromatography-A review of the current state. J. Chromatogr. A, 2011, 1218, 2754-2774.
32. Hostetler, K.Y.; Gardner, M.F.; Aldern, K.A. Assay of phospholipases C and D in presence of other lipid hydrolases. Methods Enzymol., 1991, 197, 125-134.
33. 2 and 1-alkylglycerophosphocholine acetyltransferase activities in stimulated alveolar macrophages by HPLC analysis of NBD-labeled ether lipids. Chem. Phys. Lipids, 1996, 79, 29-37.
34. van den Bosch, H.; Aarsman, A.J. A review on methods of phospholipase A determination. Agents Actions, 1979, 9, 382-389.
35. Welsh, C.J.; Schmeichel, K. Assays for investigations of signal transduction mechanisms involving phospholipase D: mass measurements of phosphatidate, phosphatidylethanol, and diacylglycerol in cultured cells. Anal. Biochem., 1991, 192, 281-292.
36. 2 by capillary electrophoresis. J. Chromatogr. A, 1999, 853, 285-293.
37. Catz, S.D.; Sterin-Speziale, N.B. Bradykinin stimulates phosphoinositide turnover and phospholipase C but not phospholipase D and NADPH oxidase in human neutrophils. J. Leukoc. Biol., 1996, 59, 591-597.
38. 31P NMR spectroscopy of phospholipids: From micelles to membranes. Curr. Anal. Chem., 2007, 3, 283-301.
39. Fuchs, B.; Süß, R.; Schiller, J. An update of MALDI-TOF mass spectrometry in lipid research. Prog. Lipid Res., 2010, 49, 450-475.
40. Fuchs, B.; Arnold, K.; Schiller, J. In: Encyclopedia of Analytical Chemistry; Meyers, Ed.; John Wiley & Sons Ltd.: Chichester, 2008; Vol 1, pp. 1-39.
41. 2 using fast atom bombardment mass spectrometry. Bioorg. Med. Chem. Lett., 1999, 9, 337-340.
42. Liebisch, G.; Drobnik, W.; Lieser, B.; Schmitz, G. High-throughput quantification of lysophosphatidylcholine by electrospray ionization tandem mass spectrometry. Clin. Chem., 2002, 48, 2217-2224.
43. Pulfer, M.; Murphy, R.C. Electrospray mass spectrometry of phospholipids. Mass Spectrom. Rev., 2003, 22, 332-364.
44. Liebisch, G.; Schmitz, G. Quantification of lysophosphatidylcholine species by high-throughput electrospray ionization tandem mass spectrometry (ESI-MS/MS). Methods Mol. Biol., 2009, 580, 29-37.
45. 2. Anal. Biochem., 2002, 308, 61-70.
46. Petković, M.; Schiller, J.; Müller, J.; Müller, M.; Arnold, K.; Arnhold, J. The signal-to-noise ratio as the measure for the quantification of lysophospholipids by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. Analyst, 2001, 126, 1042-1050.
47. Hong, C.-W.; Song, D.-K. Immunomodulatory actions of lysophosphatidylcholine. Biomol. Therapeut., 2008, 16, 69-76.
48. 2 inhibition and neutralization of free radicals by antioxidants-A new role as anti-inflammatory molecule. Curr. Top. Med. Chem., 2007, 7, 765-777.
49. Messner, M.C.; Albert, C.J.; McHowat, J.; Ford, D.A. Identification of lysophosphatidylcholine-chlorohydrin in human atherosclerotic lesions. Lipids, 2008, 43, 243-249.
50. Rivera, R.; Chun, J. Biological effects of lysophospholipids. Rev. Physiol. Biochem. Pharmacol., 2008, 160, 25-46.
51. Gardell, S.E.; Dubin, A.E.; Chun, J. Emerging medicinal roles for lysophospholipid signaling. Trends Mol. Med., 2006, 12, 65-75.
52. Meyer zu Heringdorf, D.; Jakobs K.H. Lysophospholipid receptors: Signalling, pharmacology and regulation by lysophospholipid metabolism. Biochim. Biophys. Acta, 2007, 1768, 923-940.
53. Tabata, K.; Baba, K.; Shiraishi, A.; Ito, M.; Fujita, N. The orphan GPCR GPR87 was deorphanized and shown to be a lysophosphatidic acid receptor. Biochem. Biophys. Res. Commun., 2007, 363, 861-866.
54. Pasternack, S.M.; von Kügelgen, I.; Aboud, K.A.; Lee, Y.A.; Rüschendorf, F.; Voss, K.; Hillmer, A.M.; Molderings, G.J.; Franz, T.; Ramirez, A.; Nürnberg, P.; Nöthen, M.M.; Betz, R.C. G protein-coupled receptor P2Y5 and its ligand LPA are involved in maintenance of human hair growth. Nat Genet., 2008, 40, 329-334.
55. Chun, J.; Goetzl, E.J.; Hla, T.; Igarashi, Y.; Lynch, K.R.; Moolenaar, W.; Pyne, S.; Tigyi, G. International Union of Pharmacology. IV. Lysophospholipid receptor nomenclature. Pharmacol. Rev., 2002, 54, 265-269.
56. Noguchi, K.; Ishii, S.; Shimizu, T. Identification of p2y9/GPR23 as a novel G proteincoupled receptor for lysophosphatidic acid, structurally distant from the Edg family. J. Biol. Chem., 2003, 278, 25600-25606.
57. Im, D.S. New intercellular lipid mediators and their GPCRs: an update. Prostaglandins Other Lipid Mediat., 2009, 89, 53-56.
58. Müller, J.; Petković, M.; Schiller, J.; Arnold, K.; Reichl, S.; Arnhold, J. Effects of lysophospholipids on the generation of reactive oxygen species by fMLP-and PMA-stimulated human neutrophils. Luminescence, 2002, 17, 141-149.
59. Lin, P.; Welch, E.J.; Gao, X.P.; Malik, A.B.; Ye, R.D. Lysophosphatidylcholine modulates neutrophil oxidant production through elevation of cyclic AMP. J. Immunol., 2005, 174, 2981-2989.
60. Frasch, S.C.; Zemski-Berry, K.; Murphy, R.C.; Borregaard, N.; Henson, P.M.; Bratton, D.L. Lysophospholipids of different classes mobilize neutrophil secretory vesicles and induce redundant signaling through G2A. J. Immunol., 2007, 178, 6540-6548.
61. Englberger, W.; Bitter-Suermann, D.; Hadding, U. Influence of lysophospholipids and PAF on the oxidative burst of PMNL. Int. J. Immunopharmacol., 1987, 9, 275-282.
62. Yan, J.J.; Jung, J.S.; Lee, J.E.; Lee, J.; Huh, S.O.; Kim, H.S.; Jung, K.C.; Cho, J.Y.; Nam, J.S.; Suh, H.W.; Kim, Y.H.; Song, D.K. Therapeutic effects of lysophosphatidylcholine in experimental sepsis. Nat. Med., 2004, 10, 161-167.
63. Zurgil, N.; Afrimzon, E.; Shafran, Y.; Shovman, O.; Gilburd, B.; Brikman, H.; Shoenfeld, Y.; Deutsch, M. Lymphocyte resistance to lysophosphatidylcholine mediated apoptosis in atherosclerosis. Atherosclerosis, 2007, 190, 73-83.
64. Birgbauer, E.; Chun, J. New developments in the biological functions of lysophospholipids. Cell. Mol. Life Sci., 2006, 63, 2695-2701.
65. Tome, M.E.; Lutz, N.W.; Briehl, M.M. Overexpression of catalase or Bcl-2 delays or prevents alterations in phospholipid metabolism during glucocorticoid-induced apoptosis in WEHI7.2 cells. Biochim. Biophys. Acta, 2003, 1642, 149-162.
66. Ye, X. Lysophospholipid signaling in the function and pathology of the reproductive system. Hum. Reprod. Update, 2008, 14, 519-536.
67. Xie, D.; Annex, B.H.; Donatucci, C.F. Growth factors for therapeutic angiogenesis in hypercholesterolemic erectile dysfunction. Asian J. Androl., 2008, 10, 23-27.
68. Mah, P.M.; Wittert, G.A. Obesity and testicular function. Mol. Cell. Endocrinol., 2010, 316, 180-186.
69. Ehrenwald, E.; Parks, J.E.; Foote, R.H. Cholesterol efflux from bovine sperm. I. Induction of the acrosome reaction with lysophosphatidylcholine after reducing sperm cholesterol. Gamete Res. 1988, 20, 145-157.
70. Meizel, S. The importance of hydrolytic enzymes to an exocytotic event, the mammalian sperm acrosome reaction. Biol. Rev. Camb. Philos. Soc., 1984, 59, 125-157.
71. Roldan, E.R.S. Role of phospholipases during sperm acrosomal exocytosis. Front. Biosci., 1998, 3, 1109-1119
72. Roldan, E.R.; Shi, Q.X. Sperm phospholipases and acrosomal exocytosis. Front. Biosci. 2007, 12, 89-104.
73. 2 is released during sperm acrosome reaction and controls fertility outcome in mice. J. Clin. Invest., 2010, 120, 1415-1428.
74. 2 in sperm-zona pellucida interaction. Mol. Reprod. Dev., 1999, 53, 68-76.
75. Bansal, A.K.; Bilaspuri, G.S. Impacts of oxidative stress and antioxidants on semen functions. Vet. Med. Int. 2010, Sep 7 2010, pii: 686137.
76. O'Flaherty, C.; Breininger, E.; Beorlegui, N.; Beconi, M.T. Acrosome reaction in bovine spermatozoa: role of reactive oxygen species and lactate dehydrogenase C4. Biochim. Biophys. Acta, 2005, 1726, 96-101.
77. Glander, H.-J.; Schiller, J.; Süß, R.; Paasch, U.; Grunewald, S.; Arnhold, J. Deterioration of spermatozoal plasma membrane is associated with an increase of sperm lyso-phosphatidylcholines. Andrologia, 2002, 34, 360-366.
78. Grunewald, S.; Baumann, T.; Paasch, U.; Glander, H.-J. Capacitation and acrosome reaction in nonapoptotic human spermatozoa. Ann. N. Y. Acad. Sci., 2006, 1090, 138-146.
79. Nichi, M.; Goovaerts, I.G.; Cortada, C.N.; Barnabe, V.H.; De Clercq, J.B.; Bols, P.E. Roles of lipid peroxidation and cytoplasmic droplets on in vitro fertilization capacity of sperm collected from bovine epididymides stored at 4 and 34 degrees C. Theriogenology, 2007, 67, 334-340.
80. Fuchs, B.; Müller, K.; Göritz, F.; Blottner, S.; Schiller, J. Characteristic oxidation products of choline plasmalogens are detectable in cattle and roe deer spermatozoa by MALDI-TOF mass spectrometry. Lipids, 2007, 42, 991-998.
81. Ngwenya, B.Z.; Yamamoto, N. Activation of peritoneal macrophages by lysophosphatidylcholine. Biochim. Biophys. Acta, 1985, 839, 9-15.
82. Ryborg, A.K.; Deleuran, B.; Sogaard, H.; Kragballe, K. Intracutaneous injection of lysophosphatidylcholine induces skin inflammation and accumulation of leukocytes. Acta Derm. Venereol., 2000, 80, 242-246.
83. Stiko, A.; Regnström, J.; Shah, P.K.; Cercek, B.; Nilsson, J. Active oxygen species and lysophosphatidylcholine are involved in oxidized low density lipoprotein activation of smooth muscle cell DNA synthesis. Arterioscler. Thromb. Vasc. Biol., 1996, 16, 194-200.
84. Kishimoto, T.; Soda, Y.; Matsuyama, Y.; Mizuno, K. An enzymatic assay for lysophosphatidylcholine concentration in human serum and plasma. Clin. Biochem., 2002, 35, 411-416.
85. 2 and lysophosphatidylcholine in the coronary circulation: association with early coronary atherosclerosis and endothelial dysfunction in humans. Circulation, 2007, 115, 2715-2721.
86. 2 and effects of simvastatin treatment. Atherosclerosis, 2008, 196, 931-936.
87. Okita, M.; Gaudette, D.C.; Mills, G.B.; Holub, B.J. Elevated levels and altered fatty acid composition of plasma lysophosphatidylcholine (lysoPC) in ovarian cancer patients. Int. J. Cancer, 1997, 71, 31-34.
88. 2 activity and plasma lysophosphatidylcholine levels in asthma and rhinitis and their relationship to airway sensitivity to histamine. Am. Rev. Respir. Dis., 1990, 142, 157-161.
89. Drobnik, W.; Liebisch, G.; Audebert, F.X.; Fröhlich, D.; Glück, T.; Vogel, P.; Rothe, G.; Schmitz, G. Plasma ceramide and lysophosphatidylcholine inversely correlate with mortality in sepsis patients. J. Lipid Res., 2003, 44, 754-761.
90. Zhang, B.; Fan, P.; Shimoji, E.; Itabe, H.; Miura, S.; Uehara, Y.; Matsunaga, A.; Saku, K. Modulating effects of cholesterol feeding and simvastatin treatment on plateletactivating factor acetylhydrolase activity and lysophosphatidylcholine concentration. Atherosclerosis, 2006, 186, 291-301.
91. Murphy, A.A.; Santanam, N.; Morales, A.J.; Parthasarathy, S. Lysophosphatidyl choline, a chemotactic factor for monocytes/Tlymphocytes is elevated in endometriosis. J. Clin. Endocrinol. Metab., 1998, 83, 2110-2113.
92. Ryborg, A.K.; Grøn, B.; Kragballe, K. Increased lysophosphatidylcholine content in lesional psoriatic skin. Br. J. Dermatol., 1995, 133, 398-402.
93. 2 by quercetin. Inflammation, 1993, 17, 573-582.