Abstract
Three new triterpene glycosides, named ulososide F (1), urabosides A (2) and B (3), together with the previously reported ulososide A (4), were isolated from the Caribbean marine sponge Ectyoplasia ferox. Their structures were elucidated using extensive interpretation of 1D and 2D-NMR data, as well as HRESIMS. The aglycon of all compounds is a rare 30-norlonastane and the sugar residues were identified after acid hydrolysis and GC analyses. Cytotoxicities of the isolated compounds were evaluated against Jurkat and CHO cell lines by a MTT in vitro assay as well as a hemolysis assay. Unexpectedly, all these saponin derivatives showed very low activity in our bioassays.
Highlights
Secondary metabolites play critical roles in the chemical defense systems of many marine organisms and they are frequently involved in the organization of benthic communities
The methanol fraction was further subjected to repeated HPLC purifications yielding the new ulososide F (1) and urabosides A (2) and B (3), together with the known compound uloloside A (4)
Glycoside terpenoids belonging to the same taxon show characteristic structural features that were found to be independent of the collection site and season
Summary
Secondary metabolites play critical roles in the chemical defense systems of many marine organisms and they are frequently involved in the organization of benthic communities. Ectyoplasia ferox (Duchassaing & Michelotti, 1864) (Poecilosclerida, Raspailiidae) was selected for a full chemical study due to its high abundance in the Urabá Gulf, our region of interest This species has been described at sites in the Northern part of the Caribbean, like Florida or even the Bahamas, and our chemical study will shed light on some possible differences in the secondary metabolome induced by geographical and/or environmental factors. Triterpenoid saponins, named ectyoplasides and feroxosides, were identified as major chemical components of this species [9,10], but polar lipids were reported [11,12,13] These compounds were suggested to possess ecological roles, and to have pharmaceutical potential. We report the results of our chemical study on a specimen of Ectyoplasia ferox collected in the Urabá Gulf (Colombia) and the isolation and structure elucidation of four triterpenoid saponins 1–4 which clearly differ from the previously isolated ectyoplasides and feroxosides (Figure 1)
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