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J. Biochem, 1990, Vol. 107, No. 6 868-871
© 1990 Japanese Biochemical Society

research-article

Characterization of Ganglioside GM4 Lactones Isolated from the Whale Brain

Takashi Terabayashi, Tadao Ogawa and Yasuhiro Kawanishi

Laboratory of Biochemistry, Department of Chemistry, Kitasato University Kitasato, Sagamihara, Kanagawa 228

Two novel ganglioside lactones were isolated from the brain of Bryde's whale (Balaenoptera edeni) and scharacterized. These gangliosides migrated above GM4 and were designated M4-1 and M4-2 in the order of location from the bottom of the TLC plate. These gangliosides were converted to GM4 by mild alkali treatment. Although M4-1 and M4-2 contained 1 mol each of N-acetylneuraminic acid and galactose, they behaved as neutral lipids on ion-exchange chromatography. Inner ester linkages were found in these gangliosides by secondary ion mass spectrometry and infrared spectroscopy. Two dimensional J-correlated proton NMR spectra revealed that an inner ester linkage was formed in M4-1 between the sialic acid carboxyl group and the C-4 hydroxyl group of the galactosyl residue and another inner ester linkage was formed in M4-2 between the sialic acid carboxyl group and the C-2 hydroxyl group of galactose.


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