Skip to main content
Log in

A rapid method for the preparation of ganglioside Glac2 (GD3)

  • Method
  • Published:
Lipids

Abstract

A method is described for the preparation of ganglioside Glac2 [(II3(NeuAc)2-LacCer, GD3] from cream of bovine milk using liquid-phase extraction with methanol or ethanol followed by anion exchange chromatography. The method is rapid and inexpensive; 1 kg cream, centrifuged from 14–15 L of bovine milk, yields approximately 70 mg of pure ganglioside Glac2. The sialic acid constituent of ganglioside Glac2 isolated from bovine milk cream consists solely of theN-acetylneuraminic acid derivative. The major components of its ceramide consist of octadecasphing-4-enine and the 22∶0 (behenic acid) and 23∶0 fatty acids.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Abbreviations

DEAE:

diethylaminoethyl

I/H/W:

isopropanol/n-hexane/water

TLC:

thin-layer chromatography

References

  1. Wiegandt, H. (1985)New Comprehensive Biochemistry, Vol. 10, pp. 199–260, Elsevier, Amsterdam.

    Google Scholar 

  2. Handa, S., and Burton, R.M. (1969)Lipids 4, 205–209.

    Article  PubMed  CAS  Google Scholar 

  3. Puro, K., and Keränen, A. (1969)Biochim. Biophys. Acta 187, 393–400.

    PubMed  CAS  Google Scholar 

  4. Wiegandt, H., and Bücking, H.W. (1970)Eur J. Biochem. 15, 287–292.

    Article  PubMed  CAS  Google Scholar 

  5. Gielen, W. (1968)Zschr. Naturforsch 23b, 117–118.

    Google Scholar 

  6. Senn, H.-J., Orth, M., Fitzke, E., Wieland, H., and Gerok, W. (1989)Eur. J. Biochem. 181, 657–662.

    Article  PubMed  CAS  Google Scholar 

  7. Keenan, T.W. (1974)Biochim. Biophys. Acta 337, 255–270.

    PubMed  CAS  Google Scholar 

  8. Sariola, H., Aufderheide, E., Bernhard, H., Henke-Fahle, S., Dippold, W., and Ekblom, P. (1988)Cell 54, 235–245.

    Article  PubMed  CAS  Google Scholar 

  9. Portoukalian, J., Zwingelstein, G., Abdul-Malak, N., and Doré, J.-F. (1978)Biochem. Biophys. Res. Comm. 85, 916–920.

    Article  PubMed  CAS  Google Scholar 

  10. Nakamura, O., Iwamori, M., Matsutani, M., and Takakura, K. (1991)Acta Neurochirurgica 109, 34–36.

    Article  PubMed  CAS  Google Scholar 

  11. Ravindranath, M.H., Morton, D.L., and Irie, R.F. (1989)Cancer Res. 49, 3891–3897.

    PubMed  CAS  Google Scholar 

  12. Ritter, G., Boosfeld, E., Calves, M.J., Oettgen, H.F., Old, L.J., and Livingston, P.O. (1990)Immunobiol 182, 32–43.

    CAS  Google Scholar 

  13. Ritter, G., Boosfeld, E., Alduri, R., Calves, M., Oettgen, H.F., Old, L.J., and Livingston, P.O. (1991)Int. J. Cancer 48, 379–385.

    PubMed  CAS  Google Scholar 

  14. Stallcup, W.B., Pytela, R., and Ruoslahti, E. (1989)Developmental Biology 132, 212–229.

    Article  PubMed  CAS  Google Scholar 

  15. Mazurov, A.V., Prokazova, N.V., Mikhailenko, I.A., Mukjin, D.N., Repin, V.S., and Bergelson, L.D. (1988)Biochim. Biophys. Acta 968, 167–171.

    Article  PubMed  CAS  Google Scholar 

  16. Hauttecoeur, B., Sonnino, S., and Ghidoni, R. (1985)Biochim. Biophys. Acta 833, 303–307.

    PubMed  CAS  Google Scholar 

  17. Takamizawa, K., Iwamori, M., Mutai, M.I., and Nagai, Y. (1986)J. Biol. Chem. 261, 5625–5630.

    PubMed  CAS  Google Scholar 

  18. Huang, R.T.C. (1973)Biochim. Biophys. Acta 306, 82–84.

    PubMed  CAS  Google Scholar 

  19. Tettamanti, G., Bonali, F., Marchesini, S., and Zambotti, V. (1973)Biochim. Biophys. Acta 296, 160–170.

    PubMed  CAS  Google Scholar 

  20. Yu, R.K., and Ando, S. (1980)Adv. Exp. Med. Biol. 125, 33–45.

    PubMed  CAS  Google Scholar 

  21. Kuhn, R., and Wiegandt, H. (1964)Zschr. Naturforsch. 19b, 256–257.

    CAS  Google Scholar 

  22. Holm, M., Mansson, J.E., Vanier, M.T., and Svennerholm, L. (1972)Biochim. Biophys. Acta 280, 356–364.

    PubMed  CAS  Google Scholar 

  23. Bouchon, B., Portoukalian, J., Madec, A.M., and Orgiazzi, J.S. (1990)Biochim. Biophys. Acta 1051, 1–5.

    Article  PubMed  CAS  Google Scholar 

  24. Shiraishi, T., Kinter, M.T., Mills, S.E., Lippert, M.C., Boca, G.S., and Young, Jr., W.W. (1988)Biochim. Biophys. Acta 961, 160–169.

    PubMed  CAS  Google Scholar 

  25. Ritter, G., Krause, W., Geyer, R., Stirm, S., and Wiegandt, H. (1987)Arch. Biochem. Biophys. 257, 370–378.

    Article  PubMed  CAS  Google Scholar 

  26. Seifert, H. (1965)Klin. Wochenschrift 44, 469.

    Article  Google Scholar 

  27. Fredman, P., van Holst, H., Collins, V.P., Dellheden, B., and Svennerholm, L. (1993)J. Neurochem. 60, 99–105.

    Article  PubMed  CAS  Google Scholar 

  28. Pukel, C.S., Lloyd, K.O., Travassos, L.R., Dippold, W.G., Oettgen, H.F., and Lloyd, J.O. (1982)J. Exp. Med. 155, 1133–1147.

    Article  PubMed  CAS  Google Scholar 

  29. Nudelman, E., Hakomori, S., Kannagi, R., Levery, S., Yeh, M., Hellstrom, K.E., and Hellstrom, I. (1982)J. Biol. Chem. 257, 12752–12756.

    PubMed  CAS  Google Scholar 

  30. Cheresh, D.A., Harper, J.R., Schulz, G., and Reisfeld, R.A. (1984)Proc. Natl. Acad. Sci. USA 81, 5767–5771.

    Article  PubMed  CAS  Google Scholar 

  31. Cheresh, D.A., Varki, A.P., Varki, N.M., Stallcup, W.B., Levine, J., and Reisfeld, J. (1984)J. Biol. Chem. 259, 7453–7459.

    PubMed  CAS  Google Scholar 

  32. Jennemann, R., Rodden, F., Bauer, B.L., Mennel, H.D., and Wiegandt, H. (1990)Cancer Res. 50, 7444–7449.

    PubMed  CAS  Google Scholar 

  33. Berra, B., Papi, L., Bigozzi, U., Serino, D., Morichi, R., Menonna, P., Repelli, S., Cogliati, T., and Montali, E. (1991)Int. J. Cancer 47, 329–333.

    PubMed  CAS  Google Scholar 

  34. Siddiqui, B., Buehler, J., Degregorio, M.W., and Macher, B.A. (1984)Cancer Res. 44, 5262–5265.

    PubMed  CAS  Google Scholar 

  35. Matsui, E., Ogura, K., and Handa, S. (1987)J. Biochem. 101, 423–432.

    PubMed  CAS  Google Scholar 

  36. Wiegandt, H. (1973)Hoppe-Seyler's Z. Physiol. Chem. 352, 1049–1056.

    Google Scholar 

  37. Ritter, G., Boosfeld, E., Markstein, E., Yu, R.K., Ren, S., Stallcup, W., Oettgen, H.F., Old, L.J., and Livingston, P.O. (1990),Cancer Res. 50, 1403–1410.

    PubMed  CAS  Google Scholar 

  38. Felding-Habermann, B., Jennemann, R., Schmitt, J., and Wiegandt, H. (1986)Eur. J. Biochem. 166 651–658.

    Article  Google Scholar 

  39. Gross, S.K., Williams, M.A., McCluer, M.A., and Varki, A. (1980)J. Neurochem. 34, 1351–1361.

    Article  PubMed  CAS  Google Scholar 

  40. Stainier, D.Y.R., Bilder, D.H., and Gilbert, W. (1991)Developmental Biology 144, 177–188.

    Article  PubMed  CAS  Google Scholar 

  41. Suzuki, Y., Suzuki, N., Michi, H., and Matsumoto, M. (1985)Lipids 20, 588–593.

    Article  PubMed  CAS  Google Scholar 

  42. Hueso, P., Reglero, A., Rodrigo, M., and Cabezas, J.A. (1985)Biol. Chem. Hoppe-Seyler 366, 167–171.

    PubMed  CAS  Google Scholar 

  43. Iwamori, M., and Nagai, Y. (1978)J. Biol. Chem. 253, 8328–8331.

    PubMed  CAS  Google Scholar 

  44. Sparrow, J.R., and Barnstable, C.J. (1988)J. Neurosci. Res. 21, 398–409.

    Article  PubMed  CAS  Google Scholar 

  45. Gregson, N.A., Johnson, A.R., Wheeler, D.F., and Voaden, M.J. (1989)Biochem. Soc. Trans. 17, 222–223.

    CAS  Google Scholar 

  46. Sekine, M., Ariga, T., Miyatake, T., Kase, R., Suzuki, A., and Yamakawa, T. (1985)J. Biochem. 97, 1219–1227.

    PubMed  CAS  Google Scholar 

  47. Levison, St. W., and McCarthy, K.D. (1989)J. Neuroimmunology 24, 223–232.

    Article  CAS  Google Scholar 

  48. Gaver, R.C., and Sweeley, C.C. (1965)J. Am. Oil Chem. Soc. 42, 294–298.

    PubMed  CAS  Google Scholar 

  49. Hanfland, P. (1975)Chem. Phys. Lipids 15, 105–124.

    Article  PubMed  CAS  Google Scholar 

  50. Karlsson, K.-A., and Martensson, E. (1968)Biochim. Biophys. Acta 152, 230–233.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Short hand notations for gangliosides are according to Wiegandt (Ref. 1). Glac2, (II3(NeuAc)2-LacCer) is NeuAcα,8NeuAcα,-3Galβ,4Glcβ,1Cer; Gtet1, (II3NeuAc-Gg4Cer) is Gal\,3GalNAcβ,-4(NeuAcα,3)Galβ,4Glcβ,1Cer.

About this article

Cite this article

Jennemann, R., Wiegandt, H. A rapid method for the preparation of ganglioside Glac2 (GD3). Lipids 29, 365–368 (1994). https://doi.org/10.1007/BF02537191

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02537191

Keywords

Navigation