Triterpene glycosides from Antarctic sea cucumbers. 2. Structure of Achlioniceosides A(1), A(2), and A(3) from the sea cucumber Achlionice violaecuspidata (=Rhipidothuria racowitzai)

J Nat Prod. 2009 Jan;72(1):33-8. doi: 10.1021/np800469v.

Abstract

Three new triterpene glycosides, achlioniceosides A(1) (1), A(2) (2), and A(3) (3), have been isolated from the Antarctic sea cucumber Achlionice violaecuspidata. The glycoside structures were elucidated using extensive NMR spectroscopic analysis including one-dimensional (1)H and (13)C spectra, (1)H-(1)H-COSY, HMBC, HMQC, and NOESY and mass spectrometry. Gycosides 1-3 are disulfated pentaosides that are branched at the first xylose residue. The sulfates are attached to C-6 of the glucose residues. Glycosides 1-3 are the first triterpene glycosides isolated from a sea cucumber belonging to the order Elasipodida.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antarctic Regions
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sea Cucumbers / chemistry*
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*

Substances

  • Glycosides
  • Triterpenes
  • achlioniceoside A(1)
  • achlioniceoside A(2)
  • achlioniceoside A(3)