Abstract
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-α-D-neuraminosyl)- (2→6)-β-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.
| Original language | English |
|---|---|
| Pages (from-to) | 734-738 |
| Number of pages | 5 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 56 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - May 19 2008 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
- Drug Discovery
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Isolation and structure of a monomethylated ganglioside possessing neuritogenic activity from the ovary of the sea urchin Diadema setosum. / Yamada, Koji; Tanabe, Kaoru; Miyamoto, Tomofumi; Kusumoto, Toshihide; Inagaki, Masanori; Higuchi, Ryuichi.
In: Chemical and Pharmaceutical Bulletin, Vol. 56, No. 5, 19.05.2008, p. 734-738.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Isolation and structure of a monomethylated ganglioside possessing neuritogenic activity from the ovary of the sea urchin Diadema setosum
AU - Yamada, Koji
AU - Tanabe, Kaoru
AU - Miyamoto, Tomofumi
AU - Kusumoto, Toshihide
AU - Inagaki, Masanori
AU - Higuchi, Ryuichi
PY - 2008/5/19
Y1 - 2008/5/19
N2 - 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-α-D-neuraminosyl)- (2→6)-β-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.
AB - 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-α-D-neuraminosyl)- (2→6)-β-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.
UR - http://www.scopus.com/inward/record.url?scp=43449134112&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=43449134112&partnerID=8YFLogxK
U2 - 10.1248/cpb.56.734
DO - 10.1248/cpb.56.734
M3 - Article
C2 - 18451570
AN - SCOPUS:43449134112
VL - 56
SP - 734
EP - 738
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 5
ER -