Constituents of Crinoidea. 3. Isolation and structure of a glycosyl inositolphosphoceramide-type ganglioside with neuritogenic activity from the feather star Comanthus japonica.
A glycosyl inositolphosphoceramide-type ganglioside, CJP4, was obtained from the polar lipid fraction of the chloroform/methanol extract of the feather star Comanthus japonica. The structure of this ganglioside has been determined on the basis of chemical and spectroscopic evidence to be 9-O-methyl-(N-glycolyl-alpha-D-neuraminosyl)-(2-->11)-9-O-methyl-(N-glycolyl-alpha-D-neuraminosyl)-(2-->11)-9-O-methyl-(N-glycolyl-alpha-D-neuraminosyl)-(2-->3)-inositolphosphoceramide, which contains C(16)-sphingosine and C(22:0)-, C(24:0)-fatty acid. This is the first report on the isolation and structural elucidation of a trisialo-glycosyl inositolphosphoceramide-type ganglioside. Moreover, CJP4 exhibited neuritogenic activity toward the rat pheochromocytoma PC12 cells in the presence of nerve growth factor.
Arao
Kazuyoshi
K
Faculty of Pharmaceutical Sciences, Kyushu University, Hitashi-ku, Fukuoka 812-8582, Japan.
Inagaki
Masanori
M
Miyamoto
Tomofumi
T
Higuchi
Ryuichi
R
D000818:Animals; D045744:Cell Line, Tumor; D002518:Ceramides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006028:Glycosphingolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D009414:Nerve Growth Factors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051381:Rats; D013215:Starfish / Q000737:chemistry*
C496430:9-O-MGN-MGN-MGN-IPCA; D002518:Ceramides; D006028:Glycosphingolipids; D009414:Nerve Growth Factors