Isolation and structure of a monomethylated ganglioside possessing neuritogenic activity from the ovary of the sea urchin Diadema setosum.
A new monomethylated ganglioside, DSG-A (3), was obtained, together with four known gangliosides, compounds (1, 2, 4, 5), from the lipid fraction of the chloroform/methanol extract of the ovary of the sea urchin Diadema setosum. The structures of the new ganglioside was determined on the basis of chemical and spectroscopic evidence to be 1-O-[9-O-methyl-(N-acetyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (3). The ceramide moiety of 3 was composed of C18-phytosphingosine base, and 2-hydroxy and nonhydroxylated fatty acid units. These gangliosides showed neuritogenic activity toward the rat pheochromocytoma cell line PC-12 in the presence of nerve growth factor, in which compound 3 showed the most potent activity.
Yamada
Koji
K
Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Tanabe
Kaoru
K
Miyamoto
Tomofumi
T
Kusumoto
Toshihide
T
Inagaki
Masanori
M
Higuchi
Ryuichi
R
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D049109:Cell Proliferation / Q000187:drug effects; D005260:Female; D005732:Gangliosides / Q000737:chemistry / Q000494:pharmacology*; D008401:Gas Chromatography-Mass Spectrometry; D000432:Methanol / Q000737:chemistry; D008745:Methylation; D008969:Molecular Sequence Data; D016501:Neurites / Q000187:drug effects*; D010053:Ovary / Q000737:chemistry*; D016716:PC12 Cells; D051381:Rats; D012617:Sea Urchins; D012997:Solvents; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared
C529729:1-O-(9-O-methyl-(N-acetyl-alpha-D-neuraminosyl)-(2-6)-beta-D-glucopyranosyl)ceramide; D005732:Gangliosides; D012997:Solvents; D000432:Methanol