Identification of N-acylphosphatidylserine molecules in eukaryotic cells

Biochemistry

Volumn 46, Issue 50, 2007, Pages 14500-14513

  Guan, Ziqiang ^a   Li, Shengrong ^b   Smith, Dale C ^b   Shaw, Walter A ^b   Raetz, Christian R H ^a  

^a DUKE UNIVERSITY MEDICAL CENTER   (United States)

^b Avanti Polar Lipids Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EUKARYOTIC CELLS; FATTY ACYL CHAINS; MOLECULAR SPECIES; POLYUNSATURATED SPECIES;

BRAIN; CHAIN LENGTH; COLUMN CHROMATOGRAPHY; COMPLEXATION; MASS SPECTROMETRY; RATS;

MOLECULAR BIOLOGY;

AMIDE; ARACHIDONIC ACID DERIVATIVE; ARACHIDONOYLSERINE; CELLULOSE; GLYCEROL; LIPID; PHOSPHATIDYLSERINE; PHOSPHOLIPASE D; SERINE DERIVATIVE; UNCLASSIFIED DRUG;

ACCURACY; ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; ENZYME DEGRADATION; EUKARYOTIC CELL; LIPID ANALYSIS; LIPID BRAIN LEVEL; LIPOGENESIS; LIQUID CHROMATOGRAPHY; MACROPHAGE; MASS SPECTROMETRY; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN STRUCTURE; TANDEM MASS SPECTROMETRY; TUMOR CELL; YEAST;

ANIMALS; BRAIN; CHROMATOGRAPHY, ION EXCHANGE; CHROMATOGRAPHY, LIQUID; EUKARYOTIC CELLS; FATTY ACIDS; LIPIDS; MASS SPECTROMETRY; MICE; MOLECULAR STRUCTURE; PHOSPHATIDYLSERINES; PHOSPHOLIPASE D; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SWINE; TANDEM MASS SPECTROMETRY;

BOVINAE; ESCHERICHIA COLI; EUKARYOTA; SUIDAE;

EID: 37249062581     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi701907g     Document Type: Article

References (41)

1. Fahy, E., Subramaniam, S., Brown, H. A., Glass, C. K., Merrill, A. H., Jr., Murphy, R. C., Raetz, C. R. H., Russell, D. W., Seyama, Y., Shaw, W., Shimizu, T., Spener, F., van Meer, G., VanNieuwenhze, M. S., White, S. H., Witztum, J. L., and Dennis, E. A. (2005) A comprehensive classification system for lipids, J. Lipid Res. 46, 839-862.
2. Dennis, E. A., Brown, H. A., Deems, R., Glass, C. K., Merrill, A. H., Murphy, R. C., Raetz, C. R. H., Shaw, W., Subramaniam, S., Russell, D. W., van Nieuwenhze, M., White, S. H., Witztum, J. L., and Wooley, J. (2005) The LIPID MAPS approach to lipidomics, in Functional Lipidomics (Feng, L., and Prestwich, G. D., Eds.) pp 1-15, CRC Press/Taylor and Francis Group, Boca Raton, FL.
3. Raetz, C. R. H. (1986) Molecular genetics of membrane phospholipid synthesis, Annu. Rev. Genet. 20, 253-295.
4. Zoeller, R. A., Wightman, P. D., Anderson, M. S., and Raetz, C. R. H. (1987) Accumulation of lysophosphatidylinositol in RAW 264.7 macrophage tumor cells stimulated by lipid A precursors, J. Biol. Chem. 262, 17212-17220.
5. Riley, M., Abe, T., Arnaud, M. B., Berlyn, M. K., Blattner, F. R., Chaudhuri, R. R., Glasner, J. D., Horiuchi, T., Keseler, I. M., Kosuge, T., Mori, H., Perna, N. T., Plunkett, G., III, Rudd, K. E., Serres, M. H., Thomas, G. H., Thomson, N. R., Wishart, D., and Wanner, B. L. (2006) Escherichia coli K-12: a cooperatively developed annotation snapshot-2005, Nucleic Acids Res. 34, 1-9.
6. Murphy, R. C., Fiedler, J., and Hevko, J. (2001) Analysis of nonvolatile lipids by mass spectrometry, Chem. Rev. 101, 479-526.
7. Han, X., Yang, J., Cheng, H., Ye, H., and Gross, R. W. (2004) Toward fingerprinting cellular lipidomes directly from biological samples by two-dimensional electrospray ionization mass spectrometry, Anal. Biochem. 330, 317-331.
8. Fenn, J. B., Mann, M., Meng, C. K., Wong, S. F., and Whitehouse, C. M. (1989) Electrospray ionization for mass spectrometry of large biomolecules, Science 246, 64-71.
9. Karas, M., and Hillenkamp, F. (1988) Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons, Anal. Chem. 60, 2299-2301.
10. Pulfer, M., and Murphy, R. C. (2003) Electrospray mass spectrometry of phospholipids, Mass. Spectrom. Rev. 22, 332-364.
11. Ivanova, P. T., Cerda, B. A., Horn, D. M., Cohen, J. S., McLafferty, F. W., and Brown, H. A. (2001) Electrospray ionization mass spectrometry analysis of changes in phospholipids in RBL-2H3 mastocytoma cells during degranulation, Proc. Natl. Acad. Sci. U.S.A. 98, 7152-7157.
12. Guan, Z., Breazeale, S. D., and Raetz, C. R. H. (2005) Extraction and identification by mass spectrometry of undecaprenyl diphosphate-MurNAc- pentapeptide-GlcNAc from Escherichia coli, Anal. Biochem. 345, 336-339.
13. Donohue, T. J., Cain, B. D., and Kaplan, S. (1982) Purification and characterization of an N-acylphosphatidylserine from Rhodopseudomonas sphaeroides, Biochemistry 21, 2765-2773.
14. Schmid, P. C., Kumar, V. V., Weis, B. K., and Schmid, H. H. O. (1991) Phosphatidyl-Tris rather than N-acylphosphatidylserine is synthesized by Rhodopseudomonas sphaeroides grown in Tris-containing media, Biochemistry 30, 1746-1751.
15. Milman, G., Maor, Y., Abu-Lafi, S., Horowitz, M., Gallily, R., Batkai, S., Mo, F. M., Offertaler, L., Pacher, P., Kunos, G., and Mechoulam, R. (2006) N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties, Proc. Natl. Acad. Sci. U.S.A. 103, 2428-2433.
16. McKinney, M. K., and Cravatt, B. F. (2005) Structure and function of fatty acid amide hydrolase, Annu. Rev. Biochem. 74, 411-432.
17. Cravatt, B. F., and Lichtman, A. H. (2004) The endogenous cannabinoid system and its role in nociceptive behavior, J. Neurobiol. 61, 149-160.
18. Leung, D., Saghatelian, A., Simon, G. M., and Cravatt, B. F. (2006) Inactivation of N-acyl phosphatidylethanolamine phospholipase D reveals multiple mechanisms for the biosynthesis of endocannabinoids, Biochemistry 45, 4720-4726.
19. Wang, C., Wilson, W. A., Moore, S. D., Mace, B. E., Maeda, N., Schmechel, D. E., and Sullivan, P. M. (2005) Human apoE4-targeted replacement mice display synaptic deficits in the absence of neuropathology, Neurobiol. Dis. 18, 390-398.
20. Dulbecco, R., and Vogt, M. (1954) Plaque formation and isolation of pure lines with poliomyelitis viruses, J. Exp. Med. 99, 167-182.
21. Bligh, E. G., and Dyer, J. J. (1959) A rapid method of total lipid extraction and purification, Can. J. Biochem. Physiol. 37, 911-917.
22. Raetz, C. R. H., and Kennedy, E. P. (1973) Function of cytidine diphosphate-diglyceride and deoxycytidine diphosphate-diglyceride in the biogenesis of membrane lipids in Escherichia coli, J. Biol. Chem. 248, 1098-1105.
23. 3 in Escherichia coli K12. Detection of 4-amino-4-deoxy- L-arabinose, phosphoethanolamine and palmitate, J. Biol. Chem. 274, 18503-18514.
24. 2-lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4, J. Lipid Res. 47, 1097-1111.
25. Radika, K., and Raetz, C. R. H. (1988) Purification and properties of lipid A disaccharide synthase of Escherichia coli, J. Biol. Chem. 263, 14859-14867.
26. Hsu, F. F., and Turk, J. (2000) Charge-remote and charge-driven fragmentation processes in diacyl glycerophosphoethanolamine upon low-energy collisional activation: a mechanistic proposal, J. Am. Soc. Mass Spectrom. 11, 892-899.
27. Hsu, F. F., and Turk, J. (2005) Studies on phosphatidylserine by tandem quadrupole and multiple stage quadrupole ion-trap mass spectrometry with electrospray ionization: structural characterization and the fragmentation processes, J. Am. Soc. Mass Spectrom. 16, 1510-1522.
28. Nelson, G. J. (1970) Studies on the lipids of sheep red blood cells. IV. The identification of a new phospholipid. N-acyl phosphatidyl serine, Biochem. Biophys. Res. Commun. 38, 261-265.
29. Epps, D. E., Natarajan, V., Schmid, P. C., and Schmid, H. O. (1980) Accumulation of N-acylethanolamine glycerophospholipids in infarcted myocardium, Biochim. Biophys. Acta 618, 420-430.
30. Natarajan, V., Reddy, P. V., Schmid, P. C., and Schmid, H. H. (1982) N-Acylation of ethanolamine phospholipids in canine myocardium, Biochim. Biophys. Acta 712, 342-355.
31. Reddy, P. V., Natarajan, V., Schmid, P. C., and Schmid, H. H. (1983) N-Acylation of dog heart ethanolamine phospholipids by transacylase activity. Biochim. Biophys. Acta 750, 472-480.
32. Natarajan, V., Schmid, P. C., Reddy, P. V., Zuzarte-Augustin, M. L., and Schmid, H. H. O. (1983) Biosynthesis of N-acylethanolamine phospholipids by dog brain preparations. J. Neurochem. 41, 1303-1312.
33. Simon, G. M., and Cravatt, B. F. (2006) Endocannabinoid biosynthesis proceeding through glycerophospho-N-acyl ethanolamine and a role for alpha/beta-hydrolase 4 in this pathway, J. Biol. Chem. 281, 26465-26472.
34. Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor, Science 258, 1946-1949.
35. Calignano, A., La Rana, G., Giuffrida, A., and Piomelli, D. (1998) Control of pain initiation by endogenous cannabinoids, Nature 394, 277-281.
36. Lambert, D. M., Vandevoorde, S., Jonsson, K. O., and Fowler, C. J. (2002) The palmitoylethanolamide family: a new class of anti-inflammatory agents?, Curr. Med. Chem. 9, 663-674.
37. Di Marzo, V., Goparaju, S. K., Wang, L., Liu, J., Batkai, S., Jarai, Z., Fezza, F., Miura, G. I., Palmiter, R. D., Sugiura, T., and Kunos, G. (2001) Leptin-regulated endocannabinoids are involved in maintaining food intake, Nature 410, 822-825.
38. Maccarrone, M., Pauselli, R., Di Rienzo, M., and Finazzi-Agro, A. (2002) Binding, degradation and apoptotic activity of stearoylethanol amide in rat C6 glioma cells, Biochem. J. 366, 137-144.
39. Sun, Y. X., Tsuboi, K., Okamoto, Y., Tonai, T., Murakami, M., Kudo, I., and Ueda, N. (2004) Biosynthesis of anandamide and N-palmitoylethanolamine by sequential actions of phospholipase A2 and lysophospholipase D, Biochem. J. 380, 749-756.
40. Kuge, O., and Nishijima, M. (1997) Phosphatidylserine synthase I and II of mammalian cells, Biochim. Biophys. Acta 1348, 151-156.
41. Stone, S. J., and Vance, J. E. (1999) Cloning and expression of murine liver phosphatidylserine synthase (PSS)-2: differential regulation of phospholipid metabolism by PSS1 and PSS2, Biochem. J. 342 (Pt 1), 57-64.