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

Chem Pharm Bull (Tokyo). 2001 Apr;49(4):447-52. doi: 10.1248/cpb.49.447.

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-glycolyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (1), 1-O-[(N-glycolyl-alpha-D-neuraminosyl)-(2-->4)-(N-acetyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (2) and 1-O-[alpha-L-fucopyranosyl-(1-->11)-(N-glycolyl-alpha-D-neuraminosyl)-neuraminosyl)-(2-->4)-(N-aetyl-alpha-D-neuraminosyl)-(2-->6)-beta-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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbohydrate Sequence
  • Chromatography, Thin Layer
  • Disaccharides / chemistry
  • Echinodermata / chemistry*
  • Gangliosides / isolation & purification
  • Gangliosides / pharmacology*
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Conformation
  • Molecular Sequence Data
  • Nerve Regeneration / drug effects*
  • Neurites / drug effects
  • PC12 Cells
  • Rats
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • 1-O-((N-glycolylneuraminosyl)-(2-4)-(N-acetylneuraminosyl)-(2-6)glucopyranosyl)ceramide
  • 1-O-((N-glycolylneuraminosyl)-(2-6)-glucopyranosyl)ceramide
  • 1-O-((fucopyranosyl-(1-11)-(N-glycolylneuraminosyl)neuraminosyl)-(2-4)-(N-aetylneuraminosyl)-(2-6)-glucopyranosyl)ceramide
  • Disaccharides
  • Gangliosides