Constituents of Holothuroidea, 18. Isolation and structure of biologically active disialo- and trisialo-gangliosides from the sea cucumber Cucumaria echinata.
Three new disialo- and trisialo-gangliosides, CEG-6 (6), CEG-8 (8), and CEG-9 (9), were obtained, together with one known ganglioside, HLG-3 (7), from the lipid fraction of the chloroform/methanol extract of the sea cucumber Cucumaria echinata. The structures of the new gangliosides were determined on the basis of chemical and spectroscopic evidence to be 1-O-[alpha-L-fucopyranosyl-(1-->11)-(N-glycolyl-alpha-D-neuraminosyl)-(2-->4)-(N-acetyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (6) and 1-O-[(N-glycolyl-D-neuraminosyl)-(2-->11)-(N-glycolyl-D-neuraminosyl)-(2-->4)-(N-acetyl-D-neuraminosyl)-(2-->6)-D-glucopyranosyl]-ceramide (8, 9). The ceramide moieties of each compound were composed of an homogeneous sphingosine or phytosphingosine base and heterogeneous 2-hydroxy or nonhydroxylated fatty acid units. These gangliosides showed neuritogenic activity toward the rat pheochromocytoma cell line PC-12 in the presence of nerve growth factor.
Kisa
Fumiaki
F
Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Fukuoka 812-8582, Japan.
Yamada
Koji
K
Miyamoto
Tomofumi
T
Inagaki
Masanori
M
Higuchi
Ryuichi
R
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002470:Cell Survival / Q000187:drug effects; D048016:Cucumaria / Q000737:chemistry*; D005732:Gangliosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D047332:Holothuria / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008969:Molecular Sequence Data; D009414:Nerve Growth Factors / Q000737:chemistry; D016501:Neurites / Q000187:drug effects; D016716:PC12 Cells; D051381:Rats; D012015:Reference Standards; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D005732:Gangliosides; D009414:Nerve Growth Factors