Isolation and structure of a monomethylated ganglioside possessing neuritogenic activity from the ovary of the sea urchin Diadema setosum

Chem Pharm Bull (Tokyo). 2008 May;56(5):734-7. doi: 10.1248/cpb.56.734.

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-alpha-D-neuraminosyl)-(2-->6)-beta-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cell Proliferation / drug effects
  • Female
  • Gangliosides / chemistry
  • Gangliosides / pharmacology*
  • Gas Chromatography-Mass Spectrometry
  • Methanol / chemistry
  • Methylation
  • Molecular Sequence Data
  • Neurites / drug effects*
  • Ovary / chemistry*
  • PC12 Cells
  • Rats
  • Sea Urchins
  • Solvents
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Spectroscopy, Fourier Transform Infrared

Substances

  • 1-O-(9-O-methyl-(N-acetyl-alpha-D-neuraminosyl)-(2-6)-beta-D-glucopyranosyl)ceramide
  • Gangliosides
  • Solvents
  • Methanol