Structure and biological action of cladolosides B1, B2, C, C1, C2 and D, six new triterpene glycosides from the sea cucumber Cladolabes schmeltzii

Nat Prod Commun. 2013 Nov;8(11):1527-34.

Abstract

Six new nonsulfated triterpene glycosides, cladolosides B1 (1), B2 (2), C (3), C1 (4), C2 (5) and D (6) and known holotoxin A1 (7) have been isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of the glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. Glycosides 1 and 2 have pentasaccharide branched carbohydrate moieties and differ from each other by the aglycone structures. Compounds 3-6 are hexaosides; 3-5 contain identical carbohydrate moieties with two terminal 3-O-methylglucose residues and glucose as the fifth sugar unit and differ from each other in the structures of their aglycones. Cladoloside D (6) has a new variant of carbohydrate chain with xylose and glucose residues as fifth and sixth monosaccharides, correspondingly. All of the substances demonstrated rather strong cytotoxic and hemolytic effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Glycosides / chemistry*
  • Glycosides / pharmacology
  • Molecular Structure
  • Sea Cucumbers / chemistry*
  • Structure-Activity Relationship
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology

Substances

  • Glycosides
  • Triterpenes