Characterization of Ganglioside GM4 Lactones Isolated from the Whale Brain

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 mi...

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Bibliographic Details
Published in:Journal of biochemistry (Tokyo) 1990-06, Vol.107 (6), p.868-871
Main Authors: Terabayashi, Takashi, Ogawa, Tadao, Kawanishi, Yasuhiro
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Animals
Biological and medical sciences
Brain Chemistry
Carbohydrates
Cetacea - metabolism
Chemical Phenomena
Chemistry
Chromatography, Thin Layer
Fundamental and applied biological sciences. Psychology
Gangliosides - isolation & purification
Gangliosides - metabolism
Heterosides
Magnetic Resonance Spectroscopy
Mass Spectrometry
Other biological molecules
Whales - metabolism
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Summary: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.
ISSN:0021-924X
1756-2651
DOI:10.1093/oxfordjournals.jbchem.a123140