Constituents of Holothuroidea, 17. Isolation and structure of biologically active monosialo-gangliosides from the sea cucumber Cucumaria echinata

Chem Pharm Bull (Tokyo). 2006 Jul;54(7):982-7. doi: 10.1248/cpb.54.982.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chloroform / chemistry
  • Cucumaria / chemistry*
  • Gangliosides / analysis
  • Gangliosides / chemistry*
  • Gangliosides / classification*
  • Gangliosides / isolation & purification
  • Gangliosides / pharmacology
  • Gas Chromatography-Mass Spectrometry
  • Holothuria / chemistry*
  • Methanol / chemistry
  • Molecular Structure
  • Neurites / drug effects
  • PC12 Cells
  • Rats
  • Solvents / chemistry

Substances

  • Gangliosides
  • Solvents
  • sialogangliosides
  • Chloroform
  • Methanol