Structural characterization of gangliosides isolated from mullet milt using electrospray ionization-tandem mass spectrometry

Glycobiology

Volumn 9, Issue 10, 1999, Pages 985-993

  Zhu, Junhua ^a   Li, Yu Teh ^b   Li, Su Chen ^b   Cole, Richard B ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b TULANE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Electrospray; Gangliosides; Mullet milt; Tandem mass spectrometry

Indexed keywords

CARBOXYLIC ACID; CERAMIDE; CHLORIDE ION; GANGLIOSIDE; GANGLIOSIDE GM3; LACTONE; PERIODATE; SIALIDASE; SODIUM ION;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FISH; HYDROLYSIS; IONIZATION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

ANIMALS; CARBOHYDRATE SEQUENCE; CERAMIDES; G(M3) GANGLIOSIDE; GANGLIOSIDES; MALE; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PERCIFORMES;

EID: 0032825119     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/9.10.985     Document Type: Article

References (59)

1. Angel, A.S. and Nilsson, B. (1990) Linkage positions in glycoconjugates by periodate oxidation and fast atom bombardment mass spectrometry. Methods Enzymol., 193, 587.
2. + ions. J. Am. Soc. Mass Spectrom., 3, 260-263.
3. Chan, S. and Reinhold, V.N. (1994) Detailed structural characterization of lipid A: electrospray ionization coupled with tandem mass spectrometry. Anal. Biochem., 218, 63-73.
4. Cole, R.B. and Harrata, A.K. (1992) Charge state distribution and discharge suppression in negative ion electrospray mass spectrometry using chlorinated solvent. Rapid Commun. Mass Spectrom., 6, 536-539.
5. Cole, R.B. ed. (1997) Electrospray Ionization Mass Spectrometry: Fundamentals, Instrumentation & Applications. John Wiley & Sons, New York, pp. 1-137.
6. Costello, C.E. and Vath, J.E. (1990) Tandem mass spectrometry of glycolipids. Methods Enzymol., 193, 738-768.
7. Culling, C.F.A. and Reid, P.E. (1982) Histochem of sialic scids. In Schauer, R. (ed.), Sialic Acids: Chemistry, Metabolism and Function. Springer-Verlag, New York.
8. DeGasperi, R., Koerner, T.A.W., Quarles, R.H., Ilyas, Amjad, A., Ishikawa, Y., Li, S.-C. and Li, Y.-T. (1987) Isolation and characterization of ganglisoides with hybrid neolacto-ganglio-type sugar chains. J. Biol. Chem., 262, 17149-17155.
9. Edelman, G.M. (1976) Surface modulation in cell recognition and cell growth, Science, 192, 218-226.
10. Edelman, G.M. (1984) Cell adhesion and morphogenesis: the regulator hypothesis. Proc. Natl. Acad. Sci. USA, 81, 1460-1464.
11. Egge, H. and Peter-Katalinic, J. (1987) Fast atom bombardment mass spectrometry for structural elucidation of glycoconjugates. Mass Spectrom. Rev., 6, 331-393.
12. Egge, H., Peter-Katalinic, J., Karas, M. and Stahl, B. (1991) The use of fast atom bombardment and laser desorption mass spectrometry. Pure Applied Chem., 63, 491-498.
13. Evans, J.E. and McCluer, R.H. (1971) Synthesis and characterization of sialosyllactosylceramide inner ester. Fed. Proc., 30, 1133 (abstract).
14. 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.
15. Fish, R.G. (1996) Role of gangliosides in tumor progression: a molecular target for cancer therapy. Med. Hypotheses, 46, 140-144.
16. Folch, J., Lee, M. and Sloan-Stanley, G.H. (1957) A simple method for the isolation and purification of total lipids from animal species. J. Biol. Chem., 226, 497-509.
17. Fredman, P. (1994) Gangliosides associated with primary brain tumors and their expression in cell lines established from these tumors. Prog. Brain Res., 101, 225-240.
18. Gross, S., Williams, M.A. and McCluer, R.H. (1980) Alkali-labile, sodium borohydride-reducible ganglioside sialic acid residues in brain. J. Neurochem., 34, 1351-1361.
19. Hakomori, S. and Saito, T. (1969) Isolation and characterization of a glycosphingolipid having a new sialic acid. Biochemistry, 8, 5082-5088.
20. Hakomori, S.I. (1984) Glycosphingolipids as differentiation-dependent, tumor-assisted markers and as regulators of cell proliferation. Trends Biochem. Sci., 9, 453-458.
21. Hakomori, S.I. (1990) Bifunctional role of gangliosides. J. Biol. Chem., 265, 18713-18716.
22. Handa, S. and Nakamura, K. (1984) Modification of sialic acid carboxyl group of ganglioside. J. Biochem., 95, 1323-1329.
23. Harris, G. and MacWilliams, I.C. (1954) A dipping technique for revealing sugars on paper chromatograms. Chem. Ind., 249.
24. Haverkamp, J., Schauer, R., Wember, M., Kamerling, J.P. and Vliegenthart, J.F.G. (1975) Synthesis of 9-O-acetyl and 4,9-di-O-acetyl derivatives of the methyl ester of N-acetyl-beta-neuraminic acid methylglycoside. Their use as models in periodate oxidation studies. Z. Physiol. Chem., 356, 1575-1583.
25. Hirabayashi, Y., Li, Y.-T. and Li, S.-C. (1983) Occurrence of a new hematoside in the kidney of guinea pig. FEBS Lett., 161, 127-130.
26. li, T., Ohashi, Y. and Nagai, Y. (1995) Structural elucidation of underivatized gangliosides by electrospray-ionization tandem mass spectrometry (ESIMS/ MS). Carbohydr. Res., 273, 27-40.
27. Iwamori, M. and Nagai, Y. (1978) A new Chromatographic approach to the resolution of individual gangliosides. Gangliosides mapping. Biochim. Biophys. Acta, 528, 257-267.
28. Jensen, N.J., Tomer, K.B. and Gross, M.L. (1985) Collisional activation decomposition mass spectra for locating double bonds in polyunsaturated fatty acids. Anal. Chem., 57, 2018-2021.
29. Kamerling, J.P. and Vliegenthart, J.F.G. (1982) Gas/liquid chromatography/mass spectrometry. In Schauer, R. (ed.), Sialic Acids: Chemistry, Metabolism and Function. Springer-Verlag, New York.
30. Kamerling, J.P., Schauer, R., Shukla, A.K., Stoll, S., van Halbeek, H. and Vliegenthart, J.F.G. (1987) Migration of O-acetyl groups in N, O-acetylneuraminic acids. Eur. J. Biochem., 162, 601-607.
31. Karlsson, K.A. (1989) Animal glycosphingolipids as membrane attachment sites for bacteria. Annu. Rev. Biochem., 58, 309-350.
32. Kawashima, I., Kotani, M., Ozawa, H., Suzuki, M. and Tai, T. (1994) Generation of monoclonal antibodies specific for ganglioside lactones: evidence of the expression of lactone on human melanoma cells. Int. J. Cancer, 58, 263-268.
33. Ledeen, R.W. and Salsman, K. (1970) Fatty acids and long chain base composition of adrenal medulla gangliosides. Lipids, 5, 751-756.
34. Ledeen, R. (1985) Gangliosides of neurons. Trends Neurosci., 8, 169-174.
35. Li, S.-C., Serizawa, S., Li, Y.-T., Nakamura, K. and Handa, S. (1984) Effect of modification of sialic acid on enzymic hydrolysis of gangliosides GM1 and GM2. J. Biol. Chem., 259, 5409-5410.
36. Li, S.-C., DeGasperi, R., Muldrey, J.E. and Li, Y.-T. (1986) A unique glycosphingolipid-splitting enzyme (ceramide-glycanase from leech) cleaves the linkage between the oligosaccharide and the ceramide. Biochem. Biophys. Res. Commun., 141, 346-352.
37. Li, Y.-T., Hirabayashi, Y., DeGasperi, R., Yu, R.K., Ariga, T., Koerner, T.A.W. and Li, S.-C. (1984) Isolation and Characterization of novel phytosphingosine-containing GM2 ganglioside from mullet roe (Mugil cephalus). J. Biol. Chem., 259, 8980-8985.
38. Manzi, A.E., Dell, A., Azadi, P. and Varki, A. (1990) Studies of naturally occurring modifications of sialic acids by fast-atom bombardment-mass spectrometry. J. Biol. Chem., 265, 8094-8107.
39. McCluer, R.H. and Evans, J.E. (1972) Ganglioside inner esters. Adv. Exp. Med. Biol., 19, 95.
40. Morton, D.L., Ravindranath, M.H. and Irie, R.F. (1994) Tumor gangliosides as targets for active specific immunotherapy of melanoma in man. Prog. Brain Res., 101, 251-275.
41. Nagai, Y. and Iwamori, M. (1980) Brain and thymus gangliosides: their molecular diversity and its biological implications and a dynamic annular model for their function in all surface membranes. Mol. Cell Biochem., 29, 81-90.
42. Nores, G.A., Dohi, T., Taniguchi, M. and Hakomori, S. (1987) Density-dependent recognition of cell surface GM3 by a certain anti-melanoma antibody and GM3 lactone as a possible immunogen: requirements for tumor-associated antigen and immunogen. J. Immunol., 139, 3171-3176.
43. Reinhold, B.B., Chan, S.-Y., Chan, S. and Reinhold, V.N. (1994) Profiling glycosphingolipid structural detail: periodate oxidation, electrospray, collision-induced decomposition and tandem mass spectrometry. Organic Mass Spectrom., 29, 736-746.
44. Riboni, L., Sonnino, S., Acquotti, D., Malesci, A., Ghidoni, R., Egge, H., Mingrino, S. and. Tettamanti, G. (1986) Natural occurrence of ganglioside lactones. J. Biol. Chem., 261, 8514-8519.
45. Schauer, R. (1982) Sialic Acids: Chemistry, Metabolism and Function. Cell Biology Monographs, Vol. 10. Springer, Berlin.
46. Schengrund, C.L. (1995) Evidence that molecules on the surface of one cell can adhere to the oligosaccharide position of gangliosides on the surface of another cell. Biol Signals, 4, 1-13.
47. Singh, B.N., Costello, C.E. and Beach, D.H. (1990) Structures of glycophosphosphingolipids of. Tritrichomonas Foetus: a novel glycophosphosphingolipid. Arch. Biochim. Biophys., 286, 409-418.
48. 2+-dependent carbohydrate association through ion spray mass spectrometry. J. Am. Chem. Soc., 115, 2877.
49. Stroud, M.R., Handa, K., Salyan, M.E.K., Ito, K., Levery, S.B., Hamomori, S., Reinhold, B.B. and Reinhold, V.N. (1996) Monosialogangliosides of human myelogenous leukemia HL-60 cells and normal human leukocytes. 2. Characterization of E-selection binding fractions and structural. Requirements for physiological binding to E-selection. Biochemistry, 35, 770-778.
50. Suzuki, Y. (1994) Gangliosides as influenza virus receptor, variation of influenza viruses and their recognition of the receptor sialo-sugar chains. Prog. Lipid Res., 33, 429-457.
51. Svennerholm, L., Bostrom, K., Fredman, P., Mansson, J.E., Rosengren, B. and Rynmark, B.M. (1989) Human brain gangliosides: developmental changes from early fetal stages to advanced ages. Biochim. Biophys. Acta, 105, 109-117.
52. 3-sulfate and identification of their lyso-compounds by delayed extraction matrix-assisted laser desorption ionization time-of-flight mass spectrometry. Biochem. Biophys. Res. Commun., 224, 462-467.
53. Terabayashi, T., Ogawa, T. and Kawanishi, Y. (1990) Characterization of ganglioside GM4 lactone isolated from the whale brain. J. Biochem., 107, 868-871.
54. Tsuji, S., Kojima, N. and Hitoshi, S. (1996) New evidence for the occurrence of a glycolipid-mediated signal transduction system. J. Lipid. Mediators Cell Signalling, 14, 289-294.
55. Troy, F.A. II (1992) Polysialylation - from bacteria to brain. Glycobiology, 2, 5-23.
56. Varki, A. (1992) Diversity in sialic acids. Glycobiology, 2, 25-40.
57. Yachida, Y., Tsuchihashi, K. and Gasa, S. (1996) Characterization of novel mono-O-acetylated GM3s containing 9-O-acetyl sialic acid and 6-O-acetyl galactose in equine erythrocytes. Glycoconjugates J., 13, 225-233.
58. Yu, R.K. and Ledeen, R.W. (1970) Gas-liquid Chromatographic assay of lipid-bound sialic acid: measurement of gangliosides in brain of several species. J. Lipid Res., 11, 506-516.
59. Yu, R.K., Koerner, T.A.W., Ando, S. Yohe, H.C. and Presregard, J.H. (1985) High-resolution proton NMR studies of ganglioside GM3 lactone. J. Biochem., 98, 1367-1373.