Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota

K. Yamada, R. Matsubara, M. Kaneko, Tomofumi Miyamoto, R. Higuchi

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

Three ganglioside molecular species, HLG-1 (1), HLG-2 (2), and HLG-3 (3) have been obtained from the lipid fraction of the chloroform/methanol extract of the sea cucumber Holothuria leucospilota. The structures of these gangliosides have been determined, on the basis of chemical and spectroscopic evidence, as 1-O-[(N-gly colyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (1), 1-O-[(N-glycolyl-α-D-neuraminosyl)-(2→4) (N-acetyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl] -ceramide (2) and 1-O-[α-L-fucopyranosyl-(1→11)-(N-glycolyl-α-D-neuraminosyl) -(2→4)-(N-acetyl-α-D-neuraminosyl)-(2→6) -β-D-glucopyranosyl]-ceramide (3). The ceramide moieties were composed of heterogeneous phytosphingosine, sphingosine and 2-hydroxy fatty acid units. Compounds 2 and 3 represent new ganglioside molecular species. These three ganglioside molecular species showed neuritogenic activity toward the rat pheochromocytoma cell line, PC-12 cell, in the presence of NGF (nerve growth factor).

Original languageEnglish
Pages (from-to)447-452
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume49
Issue number4
DOIs
Publication statusPublished - May 5 2001

Fingerprint

Holothuria
Sea Cucumbers
Gangliosides
Ceramides
phytosphingosine
Hydroxy Acids
Sphingosine
PC12 Cells
Nerve Growth Factor
Chloroform
Methanol
Rats
Fatty Acids
Cells
Lipids

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota. / Yamada, K.; Matsubara, R.; Kaneko, M.; Miyamoto, Tomofumi; Higuchi, R.

In: Chemical and Pharmaceutical Bulletin, Vol. 49, No. 4, 05.05.2001, p. 447-452.

Research output: Contribution to journalArticle

@article{1072570764094ef48eaa4e4b0ccbda19,
title = "Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota",
abstract = "Three ganglioside molecular species, HLG-1 (1), HLG-2 (2), and HLG-3 (3) have been obtained from the lipid fraction of the chloroform/methanol extract of the sea cucumber Holothuria leucospilota. The structures of these gangliosides have been determined, on the basis of chemical and spectroscopic evidence, as 1-O-[(N-gly colyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (1), 1-O-[(N-glycolyl-α-D-neuraminosyl)-(2→4) (N-acetyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl] -ceramide (2) and 1-O-[α-L-fucopyranosyl-(1→11)-(N-glycolyl-α-D-neuraminosyl) -(2→4)-(N-acetyl-α-D-neuraminosyl)-(2→6) -β-D-glucopyranosyl]-ceramide (3). The ceramide moieties were composed of heterogeneous phytosphingosine, sphingosine and 2-hydroxy fatty acid units. Compounds 2 and 3 represent new ganglioside molecular species. These three ganglioside molecular species showed neuritogenic activity toward the rat pheochromocytoma cell line, PC-12 cell, in the presence of NGF (nerve growth factor).",
author = "K. Yamada and R. Matsubara and M. Kaneko and Tomofumi Miyamoto and R. Higuchi",
year = "2001",
month = "5",
day = "5",
doi = "10.1248/cpb.49.447",
language = "English",
volume = "49",
pages = "447--452",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "The Pharmaceutical Society of Japan",
number = "4",

}

TY - JOUR

T1 - Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota

AU - Yamada, K.

AU - Matsubara, R.

AU - Kaneko, M.

AU - Miyamoto, Tomofumi

AU - Higuchi, R.

PY - 2001/5/5

Y1 - 2001/5/5

N2 - Three ganglioside molecular species, HLG-1 (1), HLG-2 (2), and HLG-3 (3) have been obtained from the lipid fraction of the chloroform/methanol extract of the sea cucumber Holothuria leucospilota. The structures of these gangliosides have been determined, on the basis of chemical and spectroscopic evidence, as 1-O-[(N-gly colyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (1), 1-O-[(N-glycolyl-α-D-neuraminosyl)-(2→4) (N-acetyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl] -ceramide (2) and 1-O-[α-L-fucopyranosyl-(1→11)-(N-glycolyl-α-D-neuraminosyl) -(2→4)-(N-acetyl-α-D-neuraminosyl)-(2→6) -β-D-glucopyranosyl]-ceramide (3). The ceramide moieties were composed of heterogeneous phytosphingosine, sphingosine and 2-hydroxy fatty acid units. Compounds 2 and 3 represent new ganglioside molecular species. These three ganglioside molecular species showed neuritogenic activity toward the rat pheochromocytoma cell line, PC-12 cell, in the presence of NGF (nerve growth factor).

AB - Three ganglioside molecular species, HLG-1 (1), HLG-2 (2), and HLG-3 (3) have been obtained from the lipid fraction of the chloroform/methanol extract of the sea cucumber Holothuria leucospilota. The structures of these gangliosides have been determined, on the basis of chemical and spectroscopic evidence, as 1-O-[(N-gly colyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (1), 1-O-[(N-glycolyl-α-D-neuraminosyl)-(2→4) (N-acetyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl] -ceramide (2) and 1-O-[α-L-fucopyranosyl-(1→11)-(N-glycolyl-α-D-neuraminosyl) -(2→4)-(N-acetyl-α-D-neuraminosyl)-(2→6) -β-D-glucopyranosyl]-ceramide (3). The ceramide moieties were composed of heterogeneous phytosphingosine, sphingosine and 2-hydroxy fatty acid units. Compounds 2 and 3 represent new ganglioside molecular species. These three ganglioside molecular species showed neuritogenic activity toward the rat pheochromocytoma cell line, PC-12 cell, in the presence of NGF (nerve growth factor).

UR - http://www.scopus.com/inward/record.url?scp=0035064620&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035064620&partnerID=8YFLogxK

U2 - 10.1248/cpb.49.447

DO - 10.1248/cpb.49.447

M3 - Article

C2 - 11310672

AN - SCOPUS:0035064620

VL - 49

SP - 447

EP - 452

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 4

ER -