Abstract
Gangliosides were isolated from the starfishEvasterias echinosoma and their structures were elucidated by chemical and physicochemical methods. Two major gangliosides were found to be disialogangliosides, whose carbohydrate chain is based on the trisaccharide β-N-acylgalactosaminyl-(l→3)-β-galactosyl-(l→4)-β-glucose (acyl is formyl or acetyl), both residue at of 8-O-methyl-N-acetylneuraminic acid being attached to theN-acylgalactosamine residue at positions 3 and 6. The minor components are disialogangliosides with linear carbohydrate chains in which the terminal sialic acid residue is attached to the penultimateN-acetylneuraminic acid residue at positions 4, 8, or 9. The lipid part of the gangliosides consists of sphingenine and unsubstituted fatty acids (mainly, palmitic and stearic acids).
Similar content being viewed by others
References
N. K. Kochetkov and G. P. Smirnova,Adv. Carbohydr. Chem. Biochem., 1986,44, 387.
G. P. Smirnova, inProgress khimii uglevodov [Progress in the Chemistry of Carbohydrates], Ed. I. V. Torgov, Nauka, Moscow, 1985, 126 (in Russian).
G. P. Smirnova,Biologiya morya [Sea Biology], 1987, 3 (in Russian).
N. K. Kochetkov, G. P. Smirnova, and I. S. Glukhoded,Biochim. Biophys. Acta, 1982,712, 650.
G. P. Smirnova, I. S. Glukhoded, and N. K. Kochetkov,Bioorg. Khim., 1988,14, 636 [Sov. Bioorg. Chem., 1988,14, 349 (Engl. Transl.)].
G. Muralikrishna, G. Reuter, J. Peter-Katalinić, H. Egge, F.-G. Hanisch, and R. Schauer,Carbohydr. Res., 1992,236, 321.
N. V. Chekareva, G. P. Smirnova, and V. L. Sadovskaya,Bioorg. Khim., 1996,22, 62 [Russ. Bioorg. Chem., 1996,22, 55 (Engl. Transl.)].
I. G. Zhukova, T. A. Bogdanovskaya, G. P. Smirnova, N. V. Chekareva, and N. K. Kochetkov,Dokl. Akad. Nauk SSSR, 1973,208, 981 [Dokl. Chem., 1973, (Engl. Transl.)].
G. P. Smirnova, I. S. Glukhoded, and N. K. Kochetkov,Bioorg. Khim., 1986,12, 679 [Sov. Bioorg. Chem., 1986,12, 377 (Engl. Transl.)].
G. P. Smirnova, N. K. Kochetkov, and V. L. Sadovskaya,Biochim. Biophys. Acta., 1987,920, 47.
G. P. Smirnova,Bioorg. Khim., 1990,16, 830 [Sov. Bioorg. Chem., 1990,16, 462 (Engl. Transl.)].
M. Garoff, D. R. Bundle, and M. B. Perry,Eur. J. Biochem., 1984,139, 195.
R. A. Laine and O. J. Renkonen,J. Lipid Res., 1975,16, 102.
E. Katzenellenbogen, E. Romanovska, N. A. Kocharova, A. S. Shashkov, Y. A. Knirel, and N. K. Kochetkov,Carbohydr. Res., 1995,273, 187.
M. McNeil, H. Gaylord, and P. J. Brenan,Carbohydr. Res., 1998,177, 185.
E. V. Vinogradov, A. S. Shashkov, Y. A. Knirel, N. K. Kochetkov, N. V. Tochtamysheva, S. F. Averin, O. V. Goncharova, and V. S. Khlebnikov,Carbohydr. Res., 1991,214, 289.
S. Gasa, T. Mitsuyama, and A. Makita,J. Lipid Res., 1983,24, 174.
S. B. Levery, E. H. Holmes, D. D. Harris, and S. Hakomori,Biochemistry, 1992,31, 1069.
L. Svennerholm,Acta Chem. Scand., 1957,24, 604.
V. E. Vaskovsky, E. Y. Kostetsky, V. I. Svetashev, I. G. Zhukova, and G. P. Smirnova,Comp. Biochem. Physiol., 1970,34, 163.
L. Svennerholm,Acta Chem. Scand., 1958,12, 547.
T. Miettinen and I. Takki-Luukkainen,Acta Chem. Scand., 1959,13, 856.
C. C. Winterbourn,J. Neurochem. 1971,18, 1153.
I. Ciucanu and F. Kerek,Carbohydr. Res., 1984,131, 203.
K. Stellner, H. Saito, and S. Hakomori,Arch. Biochem. Biophys., 1973,155, 464.
I. Ishizuka, M. Kloppenburg, and H. Wiegandt,Biochim. Biophys. Acta, 1970,210, 299.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 156–161, January, 2000.
Rights and permissions
About this article
Cite this article
Smirnova, G.P. Gangliosides from the starfishEvasterias echinosoma: identification of a disialoganglioside containing 8-O-methyl-N-acetylneuraminic acid andN-formylgalactosamine. Russ Chem Bull 49, 159–164 (2000). https://doi.org/10.1007/BF02499084
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02499084