HPLC-ESI-IT-MS/MS Analysis and Biological Activity of Triterpene Glycosides from the Colombian Marine Sponge Ectyoplasia ferox

Abstract

The marine sponge Ectyoplasia ferox produces antipredatory and allelopathic triterpenoid glycosides as part of its chemical defense repertoire against predators, competitors, and fouling organisms. These molecules are responsible for the pharmacological potential found in the glycosides present in this species. In order to observe the glycochemical diversity present in E. ferox, a liquid chromatography coupled to a tandem mass spectrometry approach to analyse a complex polar fraction of this marine sponge was performed. This gave valuable information for about twenty-five compounds three of which have been previously reported and another three which were found to be composed of known aglycones. Furthermore, a group of four urabosides, sharing two uncommon substitutions with carboxyl groups at C-4 on the terpenoid core, were identified by a characteristic fragmentation pattern. The oxidized aglycones present in this group of saponins can promote instability, making the purification process difficult. Cytotoxicity, cell cycle modulation, a cell cloning efficiency assay, as well as its hemolytic activity were evaluated. The cytotoxic activity was about IC50 40 µg/mL on Jurkat and CHO-k1 cell lines without exhibiting hemolysis. Discussion on this bioactivity suggests the scanning of other biological models would be worthwhile.

Environmentally benign antifouling potentials of triterpene-glycosides from Streptomyces fradiae: a mangrove isolate

“…Perusal of the literature showed the pharmaceutical importance of triterpene-glycosides in the crude/puried extract of several marine and terrestrial organisms through FT-IR spectroscopy and other spectral analysis. [58][59][60] Fig. 6 Anti-molluscicidal activity of the crude extract of S. fradiae RMS-MSU and copper sulphate (CuSO 4 ) against the marine limpet P. vulgate.…”

Triterpene and Steroid Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities

“…They have obtained valuable information about the presence of 25 compounds including three that were previously reported and three which are a combination of known aglycones and different carbohydrate chains. The saponins mixture revealed a significant cytotoxic effect on the CHO-k1 and Jurkat cell lines, as was found by the MTT test [ 61 ].…”

“…In order to estimate of the diversity of triterpene glycosides in the same collection of E. ferox , the authors used an metabolomic approach and applied the HPLC-ESI-IT-MS/MS method [ 61 ]. They have obtained valuable information about the presence of 25 compounds including three that were previously reported and three which are a combination of known aglycones and different carbohydrate chains.…”

Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

“…Triterpene glycosides are the most abundant secondary metabolites in terrestrial plants and sea cucumbers. Marine triterpene glycosides are the predominant secondary metabolites of holothurians and are suggested to be responsible for their general cytotoxicity (Zhang et al, 2006a , b , c , d ; Kim and Himaya, 2012 ; Colorado-Ríos et al, 2013 ). Last 20 years more than 100 new triterpene glycosides were isolated.…”