Constituents of holothuroidea.9. Isolation and structure of a new ganglioside molecular species from the sea cucumber Holothuria pervicax

Chem Pharm Bull (Tokyo). 2000 Jan;48(1):157-9. doi: 10.1248/cpb.48.157.

Abstract

A new ganglioside molecular species, HPG-7 (1) was obtained from the polar fraction of the chloroform/methanol extract of the sea cucumber, Holothuria pervicax. On the basis of chemical and spectroscopic evidence, the structure of 1 was determined, and the major component was 1-O-[alpha-L-fucopyranosyl-(1-->4)-(N-acetyl-alpha-D-neuraminosyl) - (2-->11)-(N-glycolyl-alpha-D-neuraminosyl)-(2-->4)-(N-acetyl -alpha-D- neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-(2S,3S,4R)-2-[(2R)-2- hydroxytetracosanoylamino]-14-methyl-hexadecane-1,3,4-triol. This is the first report on the isolation and structure elucidation of trisialo-ganglioside from sea cucumber. 1 showed neuritogenic activity toward the rat pheochromocytoma cell line, PC-12 cell.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Carbohydrate Sequence
  • Gangliosides / chemistry
  • Gangliosides / isolation & purification*
  • Gangliosides / pharmacology
  • Gas Chromatography-Mass Spectrometry
  • Methylation
  • Molecular Sequence Data
  • PC12 Cells
  • Rats
  • Sea Cucumbers / chemistry*

Substances

  • Antineoplastic Agents
  • Gangliosides
  • HPG-7 ganglioside