New Trends in Ganglioside Chemistry

  • Sandro Sonnino
  • Riccardo Ghidoni
  • Giuliano Gazzotti
  • Domenico Acquotti
  • Guido Tettamanti
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 228)


Gangliosides are normal components of the plasma membrane of vertebrate cells1,2 and are particularly abundant in the nervous system.1,3 Their concentration at the level of the cortex grey matter is about one-tenth that of total phospholipids4. They are asymmetrically located in the outer lipid layer of the membrane5,6 and exhibit strong amphiphilic properties.3,4 Gangliosides are glycosphingolipids constituted of a hydrophilic sialic acid-containing oligosaccharide and a hydrophobic ceramide portion, linked together by a glycosidic linkage.1,3 The oligosaccharide portion protrudes from the outer membrane surface and the ceramide moiety is inserted into the lipid core of the membrane.1,3 Gangliosides occur in nature in a large number of different species. The number and chemical features of sialic acid, and the number, type, and sequence of the individual sugars of the neutral oligosaccharide core are the basis for a wide variety of chemical structures.1,3,7 Moreover, a ganglioside with a homogenous oligosaccharide portion can be a mixture of several molecular species differing in their ceramide composition (fatty acid of different hydrocarbon chain length, with or without double bonds or hydroxyl groups; long chain bases of different chain length, with or without double bonds).1,3


High Performance Liquid Chromatography Sialic Acid Reversed Phase High Performance Liquid Chromatography Phase High Performance Liquid Chromatography Fatty Acid Moiety 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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  1. 1.
    R.W. Ledeen and R.D. Yu, in: “Research Methods in Neurochemistry”, N. Marks and R. Roonight, eds., Plenum Publishing Corp., N.Y., 371–410 (1978).Google Scholar
  2. 2.
    R. Ghidoni, S. Sonnino, V. Chigorno, A. Malesci and G. Tettamanti, in “Ganglioside structure, function and biomedical potential”, R.W. Ledeen, R.K. Yu, M.M. Rapport and K. Suzuki, eds., Plenum Publishing Corp., N.Y., 307–318 (1984).Google Scholar
  3. 3.
    H. Wiegandt, Adv. Neurochem, 4:149–223 (1982).CrossRefGoogle Scholar
  4. 4.
    G. Tettamanti, A. Preti, B. Cestaro, M. Masserini, S. Sonnino and R. Ghidoni, ACS Symp. Ser., 128:321–343 (1980).CrossRefGoogle Scholar
  5. 5.
    C.G. Gahmberg and S.-I. Hakomori, J. Biol. Chem., 248:4311–4317 (1973).PubMedGoogle Scholar
  6. 6.
    T.L. Steck and G. Dawson, J. Biol. Chem., 24 9:2135–2142 (1974).Google Scholar
  7. 7.
    S. Ando, Neurochem. Int., 5:507–537 (1983).PubMedCrossRefGoogle Scholar
  8. 8.
    S.-I. Hakomori, Ann. Rev. Biochem., 50:733–764 (1981).PubMedCrossRefGoogle Scholar
  9. 9.
    R.O. Brady and P.H. Fishman, Adv. Enzymol., 50:303–323 (1979).PubMedGoogle Scholar
  10. 10.
    G. Tettamanti, S. Sonnino, R. Ghidoni, M. Masserini and B. Venerando, in: “Physics of Amphiphiles: Micelles, Vesicles and Microemulsion”, M. Corti and V. Degiorgio, eds., XC Corso, Soc. Italiana di Fisica, Bologna, Italy, 607–636 (1985).Google Scholar
  11. 11.
    C.G. Gahmberg and S.-I. Hakomori, Biochem. Biophys. Res. Comm., 59:283–291 (1974).PubMedCrossRefGoogle Scholar
  12. 12.
    C.G. Gahmberg and S.-I. Hakomori, J. Biol. Chem., 250:2438–2446 (1975).PubMedGoogle Scholar
  13. 13.
    Y. Kishimoto, S. Yahara and J. Podulso, in: “Biochemistry of Cell Surface Glycolipids”, C.C. Sweely, ed., Am. Chem. Soc. Monogr., 10–23 (1980).Google Scholar
  14. 14.
    S.-I. Hakomori and R. Kannagi, JNCI, 71:231–251 (1973).Google Scholar
  15. 15.
    E. Nudelman, S.-I. Hakomori, R. Kannagi, S. Levery, M.Y. Yeh, K.E. Hellstrom and I. Hellstrom, J. Biol. Chem., 257:12752–12756 (1982).PubMedGoogle Scholar
  16. 16.
    R. Schauer, Adv. Carbohydr. Chem. Biochem., 40:131–234 (1982).PubMedCrossRefGoogle Scholar
  17. 17.
    IUPAC-IUB Commission on Biochemical Nomenclature, Lipids, 12:455–475 (1977).CrossRefGoogle Scholar
  18. 18.
    L. Svennerholm, J. Lipid Res., 5:145–156 (1964).PubMedGoogle Scholar
  19. 19.
    S. Sonnino, R. Ghidoni, V. Chigorno, M. Masserini and G. Tettamanti, Anal. Biochem., 128:104–114 (1983).PubMedCrossRefGoogle Scholar
  20. 20.
    M.C. Byrne, R.W. Ledeen, F.J. Roisen, G. Yorke and J.R. Sclafani, J. Neurochem., 41:1214–1222 (1983).PubMedCrossRefGoogle Scholar
  21. 21.
    G. Tettamanti, F. Bonali, S. Marchesini, V. Zambotti, Biochim. Biophys. Acta, 296:160–170 (1973).PubMedGoogle Scholar
  22. 22.
    R. Ghidoni, S. Sonnino, G. Tettamanti, N. Baumann, G. Reuter and R. Schauer, J. Biol. Chem., 255:6990–6995 (1980).PubMedGoogle Scholar
  23. 23.
    M. Iwamori and Y. Nagai, Biochim. Biophys. Acta, 528:257–267 (1978).PubMedGoogle Scholar
  24. 24.
    S.K. Kundu and D.D. Scott, J. Chromatog., 232:19–27 (1982).CrossRefGoogle Scholar
  25. 25.
    R.H. McCluer and J.E. Evans, J. Lipid Res., 14:611–617 (1983).Google Scholar
  26. 26.
    G. Gazzotti, R. Ghidoni and S. Sonnino, Tenth Meeting of the International Society for Neurochemistry, Supplement to J. Neurochem, 44.Google Scholar
  27. 27.
    S. Sonnino, R. Ghidoni, G. Gazzotti, G. Kirschner, G. Galli and G. Tettamanti, J. Lipid Res., 25:620–629 (1984).PubMedGoogle Scholar
  28. 28.
    G. Gazzotti, S. Sonnino, R. Ghidoni, G. Kirschner and G. Tettamanti, J. Neurosc. Res., 12:179–197 (1984).CrossRefGoogle Scholar
  29. 29.
    G. Gazzotti, S. Sonnino, R. Ghidoni, P. Orlando and G. Tettamanti, Glycoconjugate J., 1:111–121 (1984).CrossRefGoogle Scholar
  30. 30.
    G. Gazzotti, S. Sonnino and R. Ghidoni, J. Chromat., 315:395–400 (1984).CrossRefGoogle Scholar
  31. 31.
    S. Nevenhofer, G. Schwarzmann, H. Egge and K. Sandoff, Biochemistry, 24:525–532 (1985).CrossRefGoogle Scholar
  32. 32.
    S. Sonnino, G. Kirschner, R. Ghidoni, D. Acquotti and G. Tettamanti, J. Lipid Res., 26:248–257 (1985).PubMedGoogle Scholar
  33. 33.
    K. Obata, M. Olde and S. Handa, Nature, 266:359–371 (1977).CrossRefGoogle Scholar
  34. 34.
    J.I. Morgan and N. Seifert, J. Supramol. Struct., 10:1111–124 (1979).CrossRefGoogle Scholar
  35. 35.
    F.G. Roisen, H. Bartfeld, R. Nagele and G. Yorke, Science, 214:577–578 (1981).PubMedCrossRefGoogle Scholar
  36. 36.
    A. Leon, L. Facci, G. Toffano, S. Sonnino and G. Tettamanti, J. Neurochem., 37:350–357 (1981).PubMedCrossRefGoogle Scholar
  37. 37.
    L. Facci, A. Leon, G. Toffano, S. Sonnino, R. Ghidoni and G. Tettamanti, J. Neurochem., 42:299–305 (1984).PubMedCrossRefGoogle Scholar
  38. 38.
    R. Ghidoni, S. Sonnino, V. Chigorno, B. Venerando and G. Tettamanti, Biochem. J., 213:321–329 (1983).PubMedGoogle Scholar
  39. 39.
    S. Souderfeld, E. Conzelman, G. Schwarzmann, J. Burg, U. Himerichs and K. Sandhoff, Eur. J. Biochem., 149:247–255 (1985).CrossRefGoogle Scholar
  40. 40.
    E.M. Kolodny, R.O. Brady, J.M. Quirk, J. Kanfer, J. Lipid Res., 11:144–149 (1970).PubMedGoogle Scholar
  41. 41.
    J.F. Tallman, P.M. Fishman and R.C.Menneberry, Arch. Biochem. Biophys., 182:556–562 (1977).PubMedCrossRefGoogle Scholar
  42. 42.
    Y. Suzuki and K. Suzuki, J. Lipid Res., 13:687–690 (1972).PubMedGoogle Scholar
  43. 43.
    P. Orlando, G. Cocciante, G. Ippolito, P. Massari, S. Roberti and G. Tettamanti, Pharmacol. Res. Comm., 11:759–773 (1979).CrossRefGoogle Scholar
  44. 44.
    R. Ghidoni, G. Tettamanti and V. Zambotti, Biochem. Exp. Biol., 13:61–69 (1977).PubMedGoogle Scholar
  45. 45.
    A. Novak, J.A. Lowden, Y.L. Gravel and L.S. Wolfe, J. Lipid Res.,20:678–681 (1979).PubMedGoogle Scholar
  46. 46.
    K.C. Leskawa, S. Dasgupta, J.L. Chien and E.L. Hogan, Anal. Biochem., 140:172–177 (1984).PubMedCrossRefGoogle Scholar
  47. 47.
    R.W. Veh, A.P. Corfield, M. Sander, R. Schauer, Biochim. Biophys. Acta, 486:145–160 (1977).Google Scholar
  48. 48.
    G. Schwarzmann, Biochim. Biophys. Acta, 529:106–114 (1978).PubMedGoogle Scholar
  49. 49.
    J. Schraven, C. Cap, G. Nowoczek, K. Sandhoff, Anal. Biochem., 78:333–339 (1977).PubMedCrossRefGoogle Scholar
  50. 50.
    R. Ghidoni, S. Sonnino, M. Masserini, P. Orlando and G. Tettamanti, J. Lipid Res., 22:1286–1295 (1981).PubMedGoogle Scholar
  51. 51.
    T.A.W. Koerner, J.H. Prestegard, P.C. Demou and R.K. Yu, Biochemistry, 22:2676–2687 (1983).PubMedCrossRefGoogle Scholar
  52. 52.
    D. Burn, V. Petron and G.O. Westan, Tetrahedron Lett., 9:14–15 (1960).CrossRefGoogle Scholar
  53. 53.
    V. Chigorno, M. Pitto, G. Cardace, D. Acquotti, G. Kirschner, S. Sonnino, R. Ghidoni and G. Tettamanti, Glycoconjugate J., 2:279–292 (1985).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1988

Authors and Affiliations

  • Sandro Sonnino
    • 1
  • Riccardo Ghidoni
    • 1
  • Giuliano Gazzotti
    • 1
  • Domenico Acquotti
    • 1
  • Guido Tettamanti
    • 1
  1. 1.Study Center for the Functional Biochemistry of Brain Lipids Department of Biological ChemistryThe Medical School University of MilanMilanItaly

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