Gangliosides from the eggs of the sea urchin, Anthocidaris crassispina.
NeuGc alpha 2-6Glc beta 1-1Cer (M5 ganglioside) and HSO3-8NeuGc alpha 2-6Glc beta 1-1Cer (T1 ganglioside) were purified by column chromatographies with DEAE-Sephadex A-25 and silicic acid from the eggs of the sea urchin, Anthocidaris crassispina. Their chemical structures were determined by gas-liquid chromatography, methylation analysis, enzymatic hydrolysis, negative-ion fast atom bombardment mass spectrometry, and proton nuclear magnetic resonance spectroscopy. Long-chain base compositions of both gangliosides were almost identical: all the long-chain bases were phytosphingosines, and C18-phytosphingosine accounted for more than 95% of them. Fatty acid compositions were also very similar: the main fatty acids were 22:1, 23:1, 24:1, and their 2-hydroxylated forms, and the 2-hydroxy fatty acids amounted to 65.3 and 74.3% of the fatty acids in M5 and T1 gangliosides, respectively. Proton nuclear magnetic resonance spectroscopic study revealed a downfield-shifted H8 proton signal of NeuGc residue in T1 ganglioside, in agreement with the presence of sulfate ester at the C8 position.
Kubo
H
H
Department of Life Science, Faculty of Science, Tokyo Institute of Technology.
Irie
A
A
Inagaki
F
F
Hoshi
M
M
D000818:Animals; D002241:Carbohydrates / Q000032:analysis; D002518:Ceramides / Q000032:analysis; D002848:Chromatography, DEAE-Cellulose; D002849:Chromatography, Gas; D005227:Fatty Acids / Q000032:analysis; D005732:Gangliosides / Q000032:analysis*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D009439:Neuraminidase; D010063:Ovum / Q000737:chemistry*; D012617:Sea Urchins / Q000378:metabolism*; D012794:Sialic Acids / Q000032:analysis; D012997:Solvents; D013055:Spectrophotometry, Infrared
D002241:Carbohydrates; D002518:Ceramides; D005227:Fatty Acids; D005732:Gangliosides; D012794:Sialic Acids; D012997:Solvents; C066423:ganglioside T1; C066422:ganglioside M5; D009439:Neuraminidase