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Structure of gangliosides from gonads of the starfish Evasterias retifera

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Abstract

Mono- and disialogangliosides were isolated from gonads of the starfish Evasterias retifera. Their structures were elucidated using chemical methods, GC-MS analysis, and enzymatic hydrolysis with neuraminidase. The monosialoganglioside has the structure 8-O-Me-Neu5Gc-α2→3-GalNAc-β1→3-Gal-β1→4-Glc-β1→1-Cer, while the disialoganglioside contains an additional Neu5Ac residue which glycosylates GalNAc in position 6. The lipid moieties of both gangliosides contain phytosphingosine (mainly C18:0) and two types of fatty acids, unsubstituted (mainly C16:0 and C18:0) and α-hydroxy acids (mainly α-hydroxy-C16:0).

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References

  1. N. K. Kochetkov and G. P. Smirnova, Adv. Carbohydr. Chem. Biochem., 1986, 44, 387.

    Google Scholar 

  2. G. P. Smirnova, in Progress khimii uglevodov [Progress in the Carbohydrate Chemistry], Ed. I. V. Torgov, Nauka, Moscow, 1985, 126 (in Russian).

    Google Scholar 

  3. G. P. Smirnova, Biologiya morya [Marine Biology], 1987, 3 (in Russian).

  4. M. Inagaki, R. Isobe, and R. Higuchi, Eur. J. Org. Chem., 1999, 771.

  5. S. Kawatake, M. Inagaki, R. Isobe, T. Miyamoto, and R. Higuchi, Chem. Pharm. Bull. (Tokyo), 2002, 50, 1386.

    Google Scholar 

  6. R. Higuchi, S. Matsumoto, M. Fujita, T. Komori, and T. Sasaki, Liebigs Ann., 1994, 545.

  7. G. P. Smirnova, I. S. Glukhoded, and N. K. Kochetkov, Bioorgan. Khim., 1988, 14, 636 [Sov. Bioorg. Chem., 1988, 14, 349 (Engl. Transl.)].

    Google Scholar 

  8. G. Muralikrishna, G. Reuter, J. Peter-Katalinis, H. Egge, F.-G. Hanisch, H.-C. Siebert, and R. Schauer, Carbohydr. Res., 1992, 236, 321.

    Google Scholar 

  9. N. V. Chekareva, G. P. Smirnova, and V. L. Sadovskaya, Bioorgan. Khim., 1996, 22, 62 [Russ. Bioorg. Chem., 1996, 22, 55 (Engl. Transl.)].

    Google Scholar 

  10. G. P. Smirnova, I. S. Glukhoded, and N. K. Kochetkov, Bioorgan. Khim., 1986, 12, 679 [Sov. Bioorg. Chem., 1986, 12, 377 (Engl. Transl.)].

    Google Scholar 

  11. G. P. Smirnova, N. K. Kochetkov, and V. L. Sadovskaya, Biochim. Biophys. Acta, 1987, 920, 47.

    Google Scholar 

  12. G. P. Smirnova, Izv. Akad. Nauk, Ser. Khim., 2000, 156 [Russ. Chem. Bull., 2000, 49, 159 (Engl. Transl.)].

  13. M. Iwamori and Y. Nagai, Biochim. Biophys. Acta, 1981, 665, 214.

    Google Scholar 

  14. I. S. Glukhoded, G. P. Smirnova, and N. K. Kochetkov, Bioorgan. Khim., 1990, 16, 839 [Sov. Bioorg. Chem., 1990, 16, 469 (Engl. Transl.)].

    Google Scholar 

  15. G. P. Smirnova and N. K. Kochetkov, Bioorgan. Khim., 1982, 8, 102 [Sov. Bioorg. Chem., 1982, 8 (Engl. Transl.)].

    Google Scholar 

  16. N. K. Kochetkov, G. P. Smirnova, and I. S. Glukhoded, Biochim. Biophys. Acta, 1982, 712, 650.

    Google Scholar 

  17. G. P. Smirnova, Bioorgan. Khim., 1990, 16, 830 [Sov. Bioorg. Chem., 1990, 16, 462 (Engl. Transl.)].

    Google Scholar 

  18. R. A. Laine and O. J. Renkonen, J. Lipid Res., 1975, 16, 102.

    Google Scholar 

  19. A. Kisis, M. Tsuda, R. J. Kulmacz, W. K. Wilson, and G. J. Schroepfer, Jr., J. Lipid Res., 1995, 36, 787.

    Google Scholar 

  20. G. P. Smirnova and N. K. Kochetkov, Biochim. Biophys. Acta, 1980, 618, 486.

    Google Scholar 

  21. N. K. Kochetkov and G. P. Smirnova, Biochim. Biophys. Acta, 1983, 759, 192.

    Google Scholar 

  22. L. Svennerholm, Acta Chem. Scand., 1957, 24, 604.

    Google Scholar 

  23. V. E. Vaskovsky, E. Y. Kostetsky, V. I. Svetashev, I. G. Zhukova, and G. P. Smirnova, Comp. Biochem. Physiol., 1970, 34, 163.

    Google Scholar 

  24. L. Svennerholm, Acta Chem. Scand., 1958, 12, 547.

    Google Scholar 

  25. T. Miettinen and I. Takki-Luukkainen, Acta Chem. Scand., 1959, 13, 856.

    Google Scholar 

  26. C. C. Winterbourn, J. Neurochem. 1971, 18, 1153.

    Google Scholar 

  27. I. Ciucanu and F. Kerek, Carbohydr. Res., 1984, 131, 203.

    Google Scholar 

  28. K. Stellner, H. Saito, and S. Hakomori, Arch. Biochem. Biophys., 1973, 155, 464.

    Google Scholar 

  29. I. Ishizuka, M. Kloppenburg, and H. Wiegand, Biochim. Biophys. Acta, 1970, 210, 299.

    Google Scholar 

  30. A. Hara and T. Taketomi, J. Biochem., 1975, 78, 5.

    Google Scholar 

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Smirnova, G.P. Structure of gangliosides from gonads of the starfish Evasterias retifera . Russian Chemical Bulletin 52, 2270–2275 (2003). https://doi.org/10.1023/B:RUCB.0000011890.59554.d2

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