Metabolic pathways and physiological and pathological significances of lysolipid phosphate mediators

Journal of Cellular Biochemistry

Volumn 92, Issue 5, 2004, Pages 869-881

  Tokumura, Akira ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Lipid phosphate phosphatase; Lysophosphatidic acid; Lysophosphatidylcholine; Lysophospholipase D; Phospholipase A1; Sphingosine 1 phosphate; Sphingosylphosphorylcholine

Indexed keywords

GLYCEROL; LYSOPHOSPHATIDIC ACID; LYSOPHOSPHOLIPASE; LYSOPHOSPHOLIPID; PHOSPHOLIPASE A; SPHINGOSINE; SPHINGOSINE 1 PHOSPHATE; DRUG DERIVATIVE; SPHINGOSINE 1-PHOSPHATE;

LIPID DEGRADATION; LIPID METABOLISM; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN FUNCTION; PROTEIN LOCALIZATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; REVIEW; SIGNAL TRANSDUCTION; ANIMAL; BLOOD; METABOLISM;

ANIMALS; LYSOPHOSPHOLIPIDS; SPHINGOSINE;

EID: 16644392588     PISSN: 07302312     EISSN: 10974644     Source Type: Journal    
DOI: 10.1002/jcb.20147     Document Type: Review

References (74)

1. Ancellin N, Colmont C, Su J, Li Q, Mittereder N, Chae SS, Stefansson S, Liau G, Hla T. 2002. Extracellular export of sphingosine kinase-1 enzyme. Sphingosine 1-phosphate generation and the induction of angiogenic vascular maturation. J Biol Chem 277:6667-6675.
2. Aoki J, Taira A, Takanezawa Y, Kishi Y, Hama K, Kishimoto T, Mizuno K, Saku K, Taguchi R, Arai H. 2002. Serum lysophosphatidic acid is produced through diverse phospholipase pathways. J Biol Chem 277: 48737-48744.
3. Baker DL, Desiderio DM, Miller DD, Tolley B, Tigyi GJ. 2001. Direct quantitative analysis of lysophosphatidic acid molecular species by stable isotope dilution electrospray ionization liquid chromatography-mass spectrometry. Anal Biochem 292:287-295.
4. Baker DL, Morrison P, Miller B, Riely CA, Tolley B, Westermann AM, Moolenaar W, Tigyi G. 2002. Plasma lysophosphatidic acid concentration and ovarian cancer. JAMA 287:3081-3082.
5. Bollen M, Gijsbers R, Ceulemans H, Stalmans W, Stefan C. 2000. Nucleotide pyrophosphatases/phosphodiesterases on the move. Crit Rev Biochem Mol Biol 35:393-432.
6. Boujaoude LC, Bradshaw-Wilder C, Mao C, Cohn J, Ogretmen B, Hannun YA, Obeid LM. 2001. Cystic fibrosis transmembrane regulator regulates uptake of sphingoid base phosphates and lysophosphatidic acid. Modulation of cellular activity of sphingosine 1-phosphate. J Biol Chem 276:35258-35264.
7. Brauer AU, Savaskan NE, Kühn H, Prehn S, Ninnemann O, Nitsch R. 2003. A new phospholipids phosphatase, PRG-1, is involved in axon growth and regenerative sprouting. Nat Neurosci 6:572-578.
8. Brindley DN. 1993. Hepatic secretion of lysophosphatidylcholine: A novel transport system for polyunsaturated fatty acids and choline. J Nutr Biochem 4:442-449.
9. Brindley DN, English D, Pilquil C, Buri K, Ling ZC. 2002. Lipid phosphate phosphatases regulate signal transduction through glycerolipids and sphingolipids. Biochim Biophys Acta 1582:33-44.
10. Clair T, Aoki J, Koh E, Bandle RW, Nam SW, Ptaszynska MM, Mills GB, Schiffmann E, Liotta LA, Stracke ML. 2003. Autotaxin hydrolyzes sphingosylphosphorylcholine to produce the regulator of migration, sphingosine-1-phosphate. Cancer Res 63:5446-5453.
11. Deutschman DH, Carstens JS, Klepper RL, Smith WS, Page MT, Young TR, Gleason LA, Nakajima N, Sabbadini RA. 2003. Predicting obstructive coronary artery disease with serum sphingosine-1-phosphate. Am Heart J 146:62-68.
12. Edsall LC, Spiegel S. 1999. Enzymatic measurement of sphingosine 1-phosphate. Anal Biochem 272:80-86.
13. Ferry G, Tellier E, Try A, Gres S, Naime I, Simon MF, Rodriguez M, Boucher J, Tack I, Gesta S, Chromarat P, Dieu M, Raes M, Galizzi JP, Valet P, Boutin JA, Saulnier-Blache SJ. 2003. Autotaxin is released from adipocytes, catalyzed lysophosphatidic acid synthesis, and activates preadipocyte proliferation. Up-regulated expression with adipocytes differentiation and obesity. J Biol Chem 278: 18162-18169.
14. Fukushima N, Ishii I, Contos JJ, Weiner JA, Chun J. 2001. Lysophospholipid receptors. Annu Rev Pharmacol Toxicol 41:507-534.
15. Fuss B, Baba H, Phan T, Tuohy VK, Macklin WB. 1997. Phosphodiesterase I, a novel adhesion molecule and/or cytokine involved in oligodendrocyte function. J Neurosci 17:9095-9103.
16. Gaits F, Fourcade O, Le Balle F, Gueguen G, Gaigé B, Gassama-Diagne A, Fauvel J, Salles JP, Mauco G, Simon MF, Chap H. 1997. Lysophosphatidic acid as a phospholipid mediator: Pathways of synthesis. FEBS Lett 410: 54-58.
17. Geng D, Baker DP, Foley SF, Zhou C, Stieglitz K, Roberts MF. 1999. A 20-kDa domain is required for phosphatidic acid-induced allosteric activation of phospholipase D from Streptomyces chromofuscus. Biochim Biophys Acta 1430:234-244.
18. Gijsbers R, Aoki J, Arai H, Bollen M. 2003. The hydrolysis of lysophospholipids and nucleotides by autotaxin (NPP2) involves a single catalytic site. FEBS Lett 538:60-64.
19. Gobeil F, Jr., Bernier SG, Vazquez-Tello A, Brault S, Beauchamp MH, Quiniou C, Marrache AM, Checchin D, Sennlaub F, Hou X, Nader M, Bkaily G, Ribeiro-da-Silva A, Goetzl EJ, Chemtob S. 2003. Modulation of pro-inflammatory gene expression by nuclear lysophosphatidic acid receptor type-1. J Biol Chem 278:38875-38883.
20. Goding JW, Grobben B, Slegers H. 2003. Physiological and pathophysiological functions of the ecto-nucleotide pyrophosphatase/ phosphodiesterase family. Biochim Biophys Acta 1638:1-19.
21. Hama K, Bandoh K, Kakehi Y, Aoki J, Arai H. 2002. Lysophosphatidic acid (LPA) receptors are activated differentially by biological fluids: Possible role of LPA-binding proteins in activation of LPA receptors. FEBS Lett 523:187-192.
22. 1β. J Biol Chem 278:49438-49447.
23. Im DS. 2004. Discovery of new G-protein-coupled receptors for lipid mediators. J Lipid Res 45:410-418.
24. Kim JI, Jo EJ, Lee HY, Cha MS, Min JK, Choi CH, Lee YM, Choi YA, Baek SH, Ryu SH, Lee KS, Kwak JY, Baek YS. 2003. Sphingosine 1-phosphate in amniotic fluid modulates cyclooxygenase-2 expression in human amnion-derived WISH cells. J Biol Chem 278:31731-31736.
25. Kishimoto T, Matsuoka T, Imamura S, Mizuno K. 2003. A novel colorimetric assay for the determination of lysophosphatidic acid in plasma using an enzymatic cycling method. Clin Chim Acta 333:59-67.
26. Lagarde M, Bernoud N, Thies F, Brossard N, Lemaitre-Delaunay D, Croset M, Lagarde M. 2001. Lysophosphatidylcholine as a carrier of docosahexaenoic acid to target tissues. World Rev Nutr Diet 88:173-177.
27. Liliom K, Sun G, Bunemann M, Virag T, Nusser N, Baker DL, Wang DA, Fabian MJ, Brandts B, Bender K, Eikel A, Malik KU, Miller DD, Desidelio DM, Tigyi G, Pott L. 2001. Sphingosylphosphocholine is a naturally occurring lipid mediator in blood plasma: A possible role in regulating cardiac function via sphingolipid receptors. Biochem J 355:189-197.
28. Luquain C, Singh A, Wang L, Natarajan V, Morris AJ. 2003. Role of phospholipase D in agonist-stimulated lysophosphatidic acid synthesis by ovarian cancer cells. J Lipid Res 44:1963-1975.
29. Maebashi M, Yoshinaga K. 1984. Formation of a vasopressor substance in the incubated serum of patients with various hypertensive diseases. Tohoku J Exp Mod 142: 173-182.
30. Malchinkhuu E, Sato K, Muraki T, Ishikawa K, Kuwabara A, Okajima F. 2003. Assessment of the role of sphingosine 1-phosphate and its receptors in high-density lipoprotein-induced stimulation of astroglial cell function. Biochem J 370:817-827.
31. McIntyre TM, Pontsler AV, Silva AR, St Hilaire A, Xu Y, Hinshaw JC, Zimmerman GA, Hama K, Aoki J, Arai H, Prestwich GD. 2003. Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARγ agonist. Proc Natl Acad Sci USA 100:131-136.
32. Mills GB, Moolenaar WH. 2003. The emerging role of lysophosphatidic acid in cancer. Nat Rev Cancer 3:582-591.
33. Min JK, Yoo HS, Lee EY, Lee WJ, Lee YM. 2002. Simultaneous quantitative analysis of sphingoid base 1-phosphates in biological samples by o-phthalaldehyde precolumn derivatization after dephosphorylation with alkaline phosphatase. Anal Biochem 303:167-175.
34. Nakane S, Tokumura A, Waku K, Sugiura T. 2001. Hen egg yolk and white contain high amounts of lysophosphatidic acids, growth factor-like lipids: Distinct molecular species compositions. Lipids 36:413-419.
35. Nakane S, Oka S, Arai S, Waku K, Ishima Y, Tokumura A, Sugiura T. 2002. 2-Arachidonoyl-sn-glycero-3-phosphate, an arachidonic acid-containing lysophosphatidic acid: occurrence and rapid enzymatic conversion to 2-arachidonoyl-sn-glycerol, a cannabinoid receptor ligand, in rat brain. Arch Biochem Biophys 402:51-58.
36. Ohe Y, Ohnishi H, Okazaki H, Tomizawa K, Kobayashi H, Okawa K and Motozaki K. 2003. Characterization of nucleotide pyrophosphatase-5 as an oligomannoside glycoprotein in rat brain. Biochem Biophys Res Commun 308:719-725.
37. Okajima F. 2002. Plasma lipoproteins behave as carriers of extracellular sphingosine 1-phosphate: Is this an atherogenic mediator or an anti-atherogenic mediator? Biochim Biophys Acta 1582:132-137.
38. Prieschl EE, Csonga R, Novotny V, Kikuchi GE, Baumruker T. 1999. The balance between sphingosine and sphingosine-1-phosphate is decisive for mast cell activation after Fcε receptor 1 triggering. J Exp Med 190: 1-8.
39. Rother E, Brandl R, Baker DL, Goyal P, Gebhard H, Tigyi G, Siess W. 2003. Subtype-selective antagonists of lysophosphatidic acid receptors inhibit platelet activation triggered by the lipid core of atherosclerotic plaques. Circulation 108:741-747.
40. Ruwisch L, Schäfer-Korting M, Kleuser B. 2001. An improved high-performance liquid chromatographic method for the determination of sphingosine-1-phosphate in complex biological materials. Naunyn-Schmideberg's Arch Pharmacol 363:358-363.
41. Sano T, Baker D, Virag T, Wada A, Yatomi Y, Kobayashi T, Igarashi Y, Tigyi G. 2002. Multiple mechanisms linked to platelet activation result in lysophosphatidic acid and sphingosine 1-phosphate generation in blood. J Biol Chem 277:21197-21206.
42. Sasagawa T, Okita M, Murakami J, Kato T, Watanabe A. 1999. Abnormal serum lysophospholipids in multiple myeloma patients. Lipids 34:17-21.
43. Saulnier-Blache JS, Girard A, Simon MF, Lafontan M, Valet P. 2000. A simple and highly sensitive radio-enzymatic assay for lysophosphatidic acid quantification. J Lipid Res 41:1947-1951.
44. Sengupta S, Xiao Y, Xu Y. 2003. A novel laminin-induced lysophosphatidic acid autocrine loop in the migration of ovarian cancer cells. FASEB J 17:1570-1572.
45. Siess W. 2002. Athero- and thrombogenic actions of lysophosphatidic acid and sphingosine-1-phosphate. Biochim Biophys Acta 1582:204-215.
46. Simon MF, Rey A, Castan-Laurel L, Gres S, Sibrac D, Valet P, Saulnier-Blache JS. 2002. Expression of ectolipid phosphate phosphohydrolases in 3T3F442A preadipocytes and adipocytes: Involvement in the control of lysophosphatidic acid production. J Biol Chem 277: 23131-23136.
47. Smyth SS, Sciorra VA, Sigal YJ, Pamuklar Z, Wang Z, Xu Y, Prestwich GD, Morris AJ. 2003. Lipid phosphate phosphatases regulate lysophosphatidic acid production and signaling in platelets. Studies using chemical inhibitors of lipid phosphate phosphatase activity. J Biol Chem 278:43214-43223.
48. 1 that produces lysophosphatidic acid. J Biol Chem 277:34254-34263.
49. Stracke M, Krutzsch HC, Unsworth EJ, Årestad A, Cioce V, Schiffmann E, Liotta LA. 1992. Identification, purification, and partial sequence analysis of autotaxin, a novel motility-stimulating protein. J Biol Chem 267:2524-2529.
50. Sugiura T, Waku K. 2000. 2-Arachidonoylglycerol and the cannabinoid receptors. Chem Phys Lipids 108:89-106.
51. Sugiura T, Nakane S, Kishimoto S, Waku K, Yoshioka Y, Tokumura A, Hanahan DJ. 1999. Occurrence of lysophosphatidic acid and its alkyl ether-linked analogs in rat brain and comparison of their biological activities toward cultured neural cells. Biochim Biophys Acta 1440:194-204.
52. Sugiura T, Nakane S, Kishimoto S, Waku K, Yoshioka Y, Tokumura A. 2002. Lysophosphatidic acid, a growth factor-like lipid, in the saliva. J Lipid Res 43:2049-2055.
53. Tigyi G, Parrill AL. 2003. Molecular mechanisms of lysophosphatidic acid action. Prog Lipid Res 42:527-543.
54. Tokumura A. 1995. A family of phospholipid autacoids: Occurrence, metabolism, and bioactions. Prog Lipid Res 34:151-184.
55. Tokumura A. 2002. Physiological and pathophysiological roles of lysophosphatidic acids produced by secretory lysophospholipase D in body fluid. Biochim Biophys Acta 1582:18-25.
56. Tokumura A, Tsutsumi T, Tsukatani H. 1992. Transbilayer movement and metabolic fate of ether-linked phosphatidic acid (1-O-octdecyl-2-acetyl-sn- glycerol 3-phosphate) in guinea pig peritoneal polymorphonuclear leukocytes. J Biol Chem 267:7275-7283.
57. Tokumura A, Miyake M, Yoshimoto O, Shimizu M, Fukuzawa K. 1998. Metal-ion stimulation and inhibition of lysophospholipase D which generates bioactive lysophosphatidic acid in rat plasma. Lipids 33:1009-1015.
58. Tokumura A, Fujimoto H, Yoshimoto O, Nishioka Y, Miyake M, Fukuzawa K. 1999a. Production of lysophosphatidic acid by lysophospholipase D in incubated plasma of spontaneously hypertensive rats and Wistar-Kyoto rats. Life Sci 65:245-253.
59. Tokumura A, Nishioka Y, Yoshimoto O, Shinomiya J, Fukuzawa K. 1999b. Substrate specificity of lysophospholipase D which produces bioactive lysophosphatidic acids in rat plasma. Biochim Biophys Acta 1437:235-245.
60. Tokumura A, Sinomiya J, Kishimoto S, Tanaka T, Kogure K, Sugiura T, Satouchi K, Waku K, Fukuzawa K. 2002a. Human platelets respond differentially to lysophosphatidic acids having a highly unsaturated fatty acyl group and alkyl ether-linked lysophosphatidic acids. Biochem J 365:617-628.
61. Tokumura A, Tominaga K, Yasuda K, Kanzaki H, Kogure K, Fukuzawa K. 2002b. Lack of significant differences in the corrected activity of lysophospholipase D, producer of phospholipid mediator lysophosphatidic acid, in incubated serum from women with and without ovarian tumors. Cancer 94:141-151.
62. Tokumura A, Kanaya Y, Kitahara M, Miyake M, Yoshioka Y, Fukuzawa K. 2002c. Increased formation of lysophosphatidic acids by lysophospholipase D in serum of hypercholesterolemic rabbits. J Lipid Res 43:307-315.
63. Tokumura A, Kanaya Y, Miyake M, Yamano S, Irahara M, Fukuzawa K. 2002d. Increased production of bioactive lysophosphatidic acid by serum lysophospholipase D in human pregnancy. Biol Reprod 67:1386-1392.
64. Tokumura A, Majima E, Kariya Y, Tominaga K, Kogure K, Yasuda K, Fukuzawa K. 2002e. Identification of human plasma lysophospholipase D, a lysophosphatidic acid-producing enzyme, as autotaxin, a multifunctional phosphodiesterase. J Biol Chem 277:39436-39442.
65. Umezu-Goto M, Kishi Y, Taira A, Hama K, Dohmae N, Takio K, Yamori T, Mills GB, Inoue K, Aoki J, Arai H. 2002. Autotaxin has lysophospholipase D activity leading to tumor cell growth and motility by lysophosphatidic acid production. J Cell Biol 158:227-233.
66. Valet P, Pages C, Jeanneton O, Daviaud D, Barbe P, Record M, Saulnier-Blache JS, Lafontan M. 1998. Alpha2-adrenergic receptor-mediated release of lysophosphatidic acid by adipocytes. A paracrine signal for preadipocyte growth. J Clin Invest 101:1431-1438.
67. Xiao YJ, Chen Y, Kennedy AW, Belinson J, Xu Y. 2000. Evaluation of plasma lysophospholipids for diagnostic significance using electrospray ionization mass spectrometry (ESI-MS) analyses. Ann NY Acad Sci 905:242-259.
68. Xiao YJ, Schwartz B, Washington M, Kennedy A, Webster K, Belinson J, Xu Y. 2001. Electrospray ionization mass spectrometry analysis of lysophospholipids in human ascitic fluids: Comparison of the lysophospholipid contents in malignant versus nonmalignant ascitic fluids. Anal Biochem 290:302-313.
69. Xu Y. 2002. Sphingosylphosphorylcholine and lysophosphatidylcholine: G protein-coupled receptors and receptor-mediated signal transduction. Biochim Biophys Acta 1582:81-88.
70. Xu Y, Shen Z, Wiper DW, Wu M, Morton RE, Elson P, Kennedy AW, Belinson J, Markman M, Casey G. 1998. Lysophosphatidic acid as a potential biomarker for ovarian and other gynecological cancers. JAMA 280: 719-723.
71. Xu Y, Xiao Y, Zhu K, Baudhuin LM, Lu J, Hong G, Kim K, Cristina KL, Song L, Williams FS, Elson P, Markman M, Belinson J. 2003. Unfolding the pathophysiological role of bioactive lysophospholipids. Curr Drug Targets Immune Endocr Metabol Disord 3:23-32.
72. Yatomi Y, Ozaki Y, Ohmori T, Igarashi Y. 2001. Sphingosine 1-phosphate: Synthesis and release. Prostaglandins Other Lipid Mediat 64:107-122.
73. Yoon HR, Kim H, Cho SH. 2003. Quantitative analysis of acyl-lysophosphatidic acid in plasma using negative ionization tandem mass spectrometry. J Chromatogr B 788:85-92.
74. Zambonelli C, Roberts MF. 2003. An iron-dependent bacterial phospholipase D reminiscent of purple acid phosphatase. J Biol Chem 278:13706-13711.