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).
Similar content being viewed by others
References
N. K. Kochetkov and G. P. Smirnova, Adv. Carbohydr. Chem. Biochem., 1986, 44, 387.
G. P. Smirnova, in Progress khimii uglevodov [Progress in the Carbohydrate Chemistry], Ed. I. V. Torgov, Nauka, Moscow, 1985, 126 (in Russian).
G. P. Smirnova, Biologiya morya [Marine Biology], 1987, 3 (in Russian).
M. Inagaki, R. Isobe, and R. Higuchi, Eur. J. Org. Chem., 1999, 771.
S. Kawatake, M. Inagaki, R. Isobe, T. Miyamoto, and R. Higuchi, Chem. Pharm. Bull. (Tokyo), 2002, 50, 1386.
R. Higuchi, S. Matsumoto, M. Fujita, T. Komori, and T. Sasaki, Liebigs Ann., 1994, 545.
G. P. Smirnova, I. S. Glukhoded, and N. K. Kochetkov, Bioorgan. Khim., 1988, 14, 636 [Sov. Bioorg. Chem., 1988, 14, 349 (Engl. Transl.)].
G. Muralikrishna, G. Reuter, J. Peter-Katalinis, H. Egge, F.-G. Hanisch, H.-C. Siebert, and R. Schauer, Carbohydr. Res., 1992, 236, 321.
N. V. Chekareva, G. P. Smirnova, and V. L. Sadovskaya, Bioorgan. Khim., 1996, 22, 62 [Russ. Bioorg. Chem., 1996, 22, 55 (Engl. Transl.)].
G. P. Smirnova, I. S. Glukhoded, and N. K. Kochetkov, Bioorgan. 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, Izv. Akad. Nauk, Ser. Khim., 2000, 156 [Russ. Chem. Bull., 2000, 49, 159 (Engl. Transl.)].
M. Iwamori and Y. Nagai, Biochim. Biophys. Acta, 1981, 665, 214.
I. S. Glukhoded, G. P. Smirnova, and N. K. Kochetkov, Bioorgan. Khim., 1990, 16, 839 [Sov. Bioorg. Chem., 1990, 16, 469 (Engl. Transl.)].
G. P. Smirnova and N. K. Kochetkov, Bioorgan. Khim., 1982, 8, 102 [Sov. Bioorg. Chem., 1982, 8 (Engl. Transl.)].
N. K. Kochetkov, G. P. Smirnova, and I. S. Glukhoded, Biochim. Biophys. Acta, 1982, 712, 650.
G. P. Smirnova, Bioorgan. Khim., 1990, 16, 830 [Sov. Bioorg. Chem., 1990, 16, 462 (Engl. Transl.)].
R. A. Laine and O. J. Renkonen, J. Lipid Res., 1975, 16, 102.
A. Kisis, M. Tsuda, R. J. Kulmacz, W. K. Wilson, and G. J. Schroepfer, Jr., J. Lipid Res., 1995, 36, 787.
G. P. Smirnova and N. K. Kochetkov, Biochim. Biophys. Acta, 1980, 618, 486.
N. K. Kochetkov and G. P. Smirnova, Biochim. Biophys. Acta, 1983, 759, 192.
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. Wiegand, Biochim. Biophys. Acta, 1970, 210, 299.
A. Hara and T. Taketomi, J. Biochem., 1975, 78, 5.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
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
Issue Date:
DOI: https://doi.org/10.1023/B:RUCB.0000011890.59554.d2