Constituents of Crinoidea. 3. Isolation and structure of a glycosyl inositolphosphoceramide-type ganglioside with neuritogenic activity from the feather star Comanthus japonica

Chem Pharm Bull (Tokyo). 2004 Sep;52(9):1140-2. doi: 10.1248/cpb.52.1140.

Abstract

A glycosyl inositolphosphoceramide-type ganglioside, CJP4, was obtained from the polar lipid fraction of the chloroform/methanol extract of the feather star Comanthus japonica. The structure of this ganglioside has been determined on the basis of chemical and spectroscopic evidence to be 9-O-methyl-(N-glycolyl-alpha-D-neuraminosyl)-(2-->11)-9-O-methyl-(N-glycolyl-alpha-D-neuraminosyl)-(2-->11)-9-O-methyl-(N-glycolyl-alpha-D-neuraminosyl)-(2-->3)-inositolphosphoceramide, which contains C(16)-sphingosine and C(22:0)-, C(24:0)-fatty acid. This is the first report on the isolation and structural elucidation of a trisialo-glycosyl inositolphosphoceramide-type ganglioside. Moreover, CJP4 exhibited neuritogenic activity toward the rat pheochromocytoma PC12 cells in the presence of nerve growth factor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Ceramides / chemistry
  • Ceramides / isolation & purification*
  • Ceramides / pharmacology
  • Glycosphingolipids / chemistry
  • Glycosphingolipids / isolation & purification*
  • Glycosphingolipids / pharmacology
  • Molecular Structure
  • Nerve Growth Factors / chemistry
  • Nerve Growth Factors / isolation & purification*
  • Nerve Growth Factors / pharmacology
  • Rats
  • Starfish / chemistry*

Substances

  • 9-O-MGN-MGN-MGN-IPCA
  • Ceramides
  • Glycosphingolipids
  • Nerve Growth Factors