Microscale analysis of glycosphingolipids from Schistosoma mansoni cercariae

Journal of Carbohydrate Chemistry

Volumn 30, Issue 4-6, 2011, Pages 233-248

  Frank, Sandra ^a   Geyer, Hildegard ^a   Geyer, Rudolf ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

Ceramide analysis; Fatty acids; Glycosphingolipids; Mass spectrometry; Sphingoid bases

Indexed keywords

SCHISTOSOMA MANSONI; SPHINGOIDEA; VERMES;

EID: 84855762227     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328303.2011.600490     Document Type: Article

References (32)

1. Hakomori, S. I. Structure and function of glycosphingolipids and sphingolipids: recollections and future trends. Biochim. Biophys. Acta 2008, 1780, 325-346.
2. Lopez, P. H.; Schnaar, R. L. Gangliosides in cell recognition and membrane protein regulation. Curr. Opin. Struct. Biol. 2009, 19, 549-557.
3. Todeschini, A. R.; Hakomori, S. I. Functional role of glycosphingolipids and gangliosides in control of cell adhesion, motility, and growth, through glycosynaptic microdomains. Biochim. Biophys. Acta 2008, 1780, 421-433.
4. van Die, I.; van Stijn, C. M.; Geyer, H.; Geyer, R. Structural and functional analysis of glycosphingolipids of Schistosoma mansoni. Methods Enzymol. 2010, 480, 117-140.
5. van Stijn, C. M.; Meyer, S.; van den Broek, M.; Bruijns, S. C.; van Kooyk, Y.; Geyer, R.; van Die, I. Schistosoma mansoni worm glycolipids induce an inflammatory phenotype in human dendritic cells by cooperation of TLR4 and DC-SIGN. Mol. Immunol. 2010, 47, 1544-1552.
6. Lochnit, G.; Geyer, R.; Heinz, E.; Rietschel, E. T.; Zähringer, U.; Müthing, J. Chemical biology and biomedicine: glycolipids and glycosphingolipids. In Glycoscience: Chemistry and Biological Chemistry. Fraser-Reid, B., Tatsuta, B. K., Thiem, J., Eds.; Springer-Verlag Heidelberg, 2001, Vol. III, 2183-2252.
7. Schnaar, R. L. Isolation of glycosphingolipids. Methods Enzymol. 1994, 230, 348-370. (Pubitemid 24080144)
8. Karlsson, K. A. Sphingolipid long chain bases. Lipids 1970, 5, 878-891.
9. Karlsson, K. A. On the chemistry and occurrence of sphingolipid long-chain bases. Chem. Phys. Lipids 1970, 5, 6-43.
10. Makita, A.; Taniguchi, N. Glycosphingolipids. In Glycolipids. Wiegandt, H., Ed.; Elsevier: Amsterdam, 1985, 1-99.
11. Müthing, J.; Distler, U. Advances on the compositional analysis of glycosphingolipids combining thin-layer chromatography with mass spectrometry. Mass Spectrom. Rev. 2010, 29, 425-479.
12. Levery, S. B. Glycosphingolipid structural analysis and glycosphingolipidomics. Methods Enzymol. 2005, 405, 300-369. (Pubitemid 43081964)
13. Müthing, J. Analyses of glycosphingolipids by high-performance liquid chromatography. Methods Enzymol. 2000, 312, 45-64.
14. Meisen, I.; Mormann, M.; Müthing, J. Thin-layer chromatography, overlay technique and mass spectrometry: a versatile triad advancing glycosphingolipidomics. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 2011, in press.
15. Curatolo, W.; Jungalwala, F. B. Phase behavior of galactocerebrosides from bovine brain. Biochemistry 1985, 24, 6608-6613. (Pubitemid 16207139)
16. Kurita, T.; Izu, H.; Sano, M.; Ito, M.; Kato, I. Enhancement of hydrolytic activity of sphingolipid ceramide N-deacylase in the aqueous-organic biphasic system. J. Lipid Res. 2000, 41, 846-851. (Pubitemid 30314141)
17. Merrill, A. H. Jr.; Sullards, M. C.; Allegood, J. C.; Kelly, S.; Wang, E. Sphingolipidomics: high-throughput, structure-specific, and quantitative analysis of sphingolipids by liquid chromatography tandem mass spectrometry. Methods 2005, 36, 207-224. (Pubitemid 40726151)
18. Domon, B.; Costello, C. A systematic nomenclature for carbohydrate fragmentation in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate J. 1988, 5, 253-257.
19. Wuhrer, M.; Dennis, R. D.; Doenhoff, M. J.; Geyer, R. Stage-associated expression of ceramide structures in glycosphingolipids from the human trematode parasite Schistosoma mansoni. Biochim. Biophys. Acta 2000, 1524, 155-161.
20. Wuhrer, M.; Dennis, R. D.; Doenhoff, M. J.; Lochnit, G.; Geyer, R. Schistosoma mansoni cercarial glycolipids are dominated by Lewis X and pseudo-Lewis Y structures. Glycobiology 2000, 10, 89-101. (Pubitemid 30122203)
21. Harvey, D. J.; Mattu, T. S.; Wormald, M. R.; Royle, L.; Dwek, R. A.; Rudd, P. M. "Internal residue loss": rearrangements occurring during the fragmentation of carbohydrates derivatized at the reducing terminus. Anal. Chem. 2002, 74, 734-740. (Pubitemid 34160538)
22. Wuhrer, M.; Balog, C. I.; Catalina, M. I.; Jones, F. M.; Schramm, G.; Haas, H.; Doenhoff, M. J.; Dunne, D. W.; Deelder, A. M.; Hokke, C. H. IPSE/alpha-1, a major secretory glycoprotein antigen from schistosome eggs, expresses the Lewis X motif on coredifucosylated N-glycans. FEBS J. 2006, 273, 2276-2292.
23. Kannagi, R.; Nudelman, E.; Hakomori, S. Possible role of ceramide in defining structure and function of membrane glycolipids. Proc. Natl. Acad. Sci. USA. 1982, 79, 3470-3474. (Pubitemid 12011386)
24. Anumula, K. R. Quantitative determination of monosaccharides in glycoproteins by high-performance liquid chromatography with highly sensitive fluorescence detection. Anal. Biochem. 1994, 220, 275-283. (Pubitemid 24261169)
25. Wuhrer, M.; Dennis, R. D.; Doenhoff, M. J.; Bickle, Q.; Lochnit, G.; Geyer, R. Immunochemical characterisation of Schistosoma mansoni glycolipid antigens. Mol. Biochem. Parasitol. 1999, 103, 155-169. (Pubitemid 29469770)
26. Wuhrer, M.; Kantelhardt, S. R.; Dennis, R. D.; Doenhoff, M. J.; Lochnit, G.; Geyer, R. Characterization of glycosphingolipids from Schistosoma mansoni eggs carrying Fuc (alpha1-3) GalNAc-, GalNAc (beta1-4) [Fuc (alpha1-3)]GlcNAc- and Gal (beta1-4) [Fuc (alpha1-3)]GlcNAc-(Lewis X) terminal structures. Eur. J. Biochem. 2002, 269, 481-493. (Pubitemid 34128005)
27. Maass, K.; Ranzinger, R.; Geyer, H.; von der Lieth, C. W.; Geyer, R. "Glycopeakfinder" - de novo composition analysis of glycoconjugates. Proteomics 2007, 7, 4435-4444.
28. Ceroni, A.; Maass, K.; Geyer, H.; Geyer, R.; Dell, A.; Haslam, S. M. GlycoWorkbench: a tool for the computer-assisted annotation of mass spectra of glycans. J. Pro-teome Res. 2008, 7, 1650-1659.
29. Gaver, R. C.; Sweeley, C. C. Methods for methanolysis of sphingolipids and direct determination of long-chain bases by gas chromatography. J. Am. Oil Chem. Soc. 1965, 42, 294-298.
30. Wuhrer, M.; Berkefeld, C.; Dennis, R. D.; Idris, M. A.; Geyer, R. The liver flukes Fasciola gigantica and Fasciola hepatica express the leucocyte cluster of differentiation marker CD77 (globotriaosylceramide) in their tegument. Biol. Chem. 2001, 382, 195-207. (Pubitemid 32243928)
31. Brouwers, J. F.; Smeenk, I. M.; van Golde, L. M.; Tielens, A. G. The incorporation, modification and turnover of fatty acids in adult Schistosoma mansoni. Mol. Biochem. Parasitol. 1997, 88, 175-185. (Pubitemid 27346828)
32. Olling, A.; Breimer, M. E.; Peltomaa, E.; Samuelsson, B. E.; Ghardashkhani, S. Electrospray ionization and collision-induced dissociation time-of-flight mass spectrometry of neutral glycosphingolipids. Rapid Commun. Mass Spectrom. 1998, 12, 637-645. (Pubitemid 28222707)