Constituents of Holothuroidea, 17. Isolation and structure of biologically active monosialo-gangliosides from the sea cucumber Cucumaria echinata.
Three new monosialo-gangliosides, CEG-3 (3), CEG-4 (4), and CEG-5 (5), were obtained, together with two known gangliosides, SJG-1 (1) and CG-1 (2), 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-[4-O-acetyl-alpha-L-fucopyranosyl-(1-->11)-(N-glycolyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (3) and 1-O-[alpha-L-fucopyranosyl-(1-->11)-(N-glycolyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (4, 5). The ceramide moieties of each compound were composed of heterogeneous sphingosine or phytosphingosine bases, and 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; Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.
Yamada
Koji
K
Miyamoto
Tomofumi
T
Inagaki
Masanori
M
Higuchi
Ryuichi
R
D000818:Animals; D002725:Chloroform / Q000737:chemistry; D048016:Cucumaria / Q000737:chemistry*; D005732:Gangliosides / Q000032:analysis / Q000737:chemistry* / Q000145:classification* / Q000302:isolation & purification / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D047332:Holothuria / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D016501:Neurites / Q000187:drug effects; D016716:PC12 Cells; D051381:Rats; D012997:Solvents / Q000737:chemistry
D005732:Gangliosides; D012997:Solvents; C025447:sialogangliosides; D002725:Chloroform; D000432:Methanol