Cytotoxicity on human cancer cells of ophidiacerebrosides isolated from the African starfish Narcissia canariensis

Mar Drugs. 2010 Dec 22;8(12):2988-98. doi: 10.3390/md8122988.

Abstract

The starfish Narcissia canariensis harvested from the coasts off Dakar, Senegal, was investigated for glycolipids (GL). This report deals with the isolation, characterization and biological activity of a fraction F13-3 separated from the GL mixture and selected according to its ability to inhibit KB cell proliferation after 72 hours of treatment. Firstly, a GL mixture F13 was obtained that accounted for 1.36% of starfish biomass (dry weight) and 0.36% of total lipids. The fraction F13-3 obtained from F13 contained three homologous GL identified as peracetylated derivatives on the basis of chemical and spectroscopic evidence. These contained a β-glucopyranoside as sugar head, a 9-methyl-branched 4,8,10-triunsaturated long-chain aminoalcohol as sphingoid base and amide-linked 2-hydroxy fatty acid chains. The majority (63%) had an amide-linked 2-hydroxydocosanoic acid chain and was identified as the ophidiacerebroside-C, firstly isolated from the starfish Ophidiaster ophidiamus. The minor components of F13-3 differed by one more or one less methylene group, and corresponded to ophidiacerebroside-B and -D. We found that F13-3 displayed an interesting cytotoxic activity over 24 hours on various adherent human cancerous cell lines (multiple myeloma, colorectal adenocarcinoma and glioblastoma multiforme) with an IC(50) of around 20 μM.

Keywords: Narcissia canariensis; glycosylceramides; human cancer cell lines; in vitro anticancerous activity; starfish.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects*
  • Cell Survival / drug effects
  • Cerebrosides / chemistry
  • Cerebrosides / isolation & purification
  • Cerebrosides / pharmacology*
  • Glioblastoma / drug therapy*
  • Glycolipids / chemistry
  • Glycolipids / isolation & purification
  • Glycolipids / pharmacology
  • Glycosphingolipids / chemistry
  • Glycosphingolipids / isolation & purification
  • Glycosphingolipids / pharmacology
  • HCT116 Cells
  • Humans
  • KB Cells
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Senegal
  • Starfish / chemistry*

Substances

  • Antineoplastic Agents
  • Cerebrosides
  • Glycolipids
  • Glycosphingolipids