Constituents of Holothuroidea, 18. Isolation and structure of biologically active disialo- and trisialo-gangliosides from the sea cucumber Cucumaria echinata

Chem Pharm Bull (Tokyo). 2006 Sep;54(9):1293-8. doi: 10.1248/cpb.54.1293.

Abstract

Three new disialo- and trisialo-gangliosides, CEG-6 (6), CEG-8 (8), and CEG-9 (9), were obtained, together with one known ganglioside, HLG-3 (7), 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-[alpha-L-fucopyranosyl-(1-->11)-(N-glycolyl-alpha-D-neuraminosyl)-(2-->4)-(N-acetyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (6) and 1-O-[(N-glycolyl-D-neuraminosyl)-(2-->11)-(N-glycolyl-D-neuraminosyl)-(2-->4)-(N-acetyl-D-neuraminosyl)-(2-->6)-D-glucopyranosyl]-ceramide (8, 9). The ceramide moieties of each compound were composed of an homogeneous sphingosine or phytosphingosine base and heterogeneous 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
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cell Survival / drug effects
  • Cucumaria / chemistry*
  • Gangliosides* / chemical synthesis
  • Gangliosides* / chemistry
  • Gangliosides* / pharmacology
  • Holothuria / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Sequence Data
  • Nerve Growth Factors / chemistry
  • Neurites / drug effects
  • PC12 Cells
  • Rats
  • Reference Standards
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Gangliosides
  • Nerve Growth Factors