Synaptosides A and A1, triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic acid and their cytotoxic activity against tumor cells

J Nat Prod. 2008 Apr;71(4):525-31. doi: 10.1021/np070283+. Epub 2008 Feb 22.

Abstract

Two novel triterpene holostane glycosides, synaptosides A ( 1) and A 1 ( 2), have been isolated from the Vietnamese sea cucumber Synapta maculata (Synaptida, Apodida). Their structures were elucidated by spectroscopic methods (NMR and MS) and chemical transformations. Glycosides 1 and 2 have rare branched pentasaccharide carbohydrate chains featuring a 3- O-methylglucuronic acid residue not previously reported in glycosides from sea cucumbers and a 6- O-sulfated glucose. Glycoside 2 has an oxo group at C-7 and a 8(9)-double bond. All these structural features are unknown in glycosides from sea cucumbers. Glycoside 1 has moderate cytotoxic activity (IC 50 8.6 microg/mL) and glycoside 2 is inactive against HeLa tumor cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Drug Screening Assays, Antitumor
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • HeLa Cells
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Oceans and Seas
  • Sea Cucumbers / chemistry*
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*
  • Vietnam

Substances

  • Antineoplastic Agents
  • Glycosides
  • Triterpenes
  • synaptoside A
  • synaptoside A1