A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities

Bioorg Med Chem. 2021 Jul 1:41:116188. doi: 10.1016/j.bmc.2021.116188. Epub 2021 Apr 30.

Abstract

Our continuing search for marine bioactive secondary metabolites led to the screening of crude extracts of sea cucumbers by the model of Pyricularia oryzae. A new sulfated triterpene glycoside, coloquadranoside A (1), together with four known triterpene glycosides, philinopside A, B, E and pentactaside B (2-5) were isolated from the sea cucumber Colochirus quadrangularis, and their structures were elucidated using extensive spectroscope analysis (ESI-MS, 1D and 2D NMR) and chemical methods. Coloquadranoside A possesses a 16-acetyloxy group in the holostane-type triterpene aglycone with a 7(8)-double bond, a double bond (25,26) at its side chain, and two β-d-xylose in the carbohydrate chain. Coloquadranoside A exhibits in vitro some antifungus, considerable cytotoxicity (IC50 of 0.46-2.03 μM) against eight human tumor cell lines, in vivo antitumor, and immunomodulatory activity.

Keywords: Bioactivity; Colochirus quadrangularis; Coloquadranoside A; Sea cucumber; Triterpene glycoside.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Glycosides / chemistry*
  • Humans
  • Immunomodulation / drug effects*
  • Mice
  • Mice, Nude
  • Molecular Structure
  • Neoplasms, Experimental
  • Saponins / chemistry
  • Sea Cucumbers / chemistry*
  • Triterpenes / chemistry*

Substances

  • 16-(acetyloxy)-18-oxo-18,20-epoxylanosta-7,24-dien-3-yl 3-O-methylglucopyranosyl-(1-3)-xylopyranosyl-(1-4)-6-deoxy-2-O-sulfonatoglucopyranosyl-(1-2)-4-O-sulfonatoxylopyranoside
  • Antifungal Agents
  • Antineoplastic Agents
  • Glycosides
  • Philinopside E
  • Saponins
  • Triterpenes
  • philinopside A