Abstract
The saponin composition of a specimen of black sea cucumber, Holothuria atra collected in the Persian Gulf was studied by a combined approach including LC-MS/MS, Molecular Networking, pure compound isolation, and NMR spectroscopy. The saponin composition of Holothuria atra turned out to be more complex than previously reported. The most abundant saponins in the extract (1–4) were isolated and characterized by 1D- and 2D-NMR experiments. Compound 1 was identified as a new triterpene glycoside saponin, holothurin A5. The side chain of the new saponin 1, unprecedented among triterpene glycosides, is characterized by an electrophilic enone function, which can undergo slow water or methanol addition under neutral conditions. The cytotoxic activity of compounds 1–4, evaluated on the human cervix carcinoma HeLa cell line, was remarkable, with IC50 values ranging from 1.2 to 2.5 µg/mL.
Highlights
Holothurians are marine echinoderms commonly referred to as sea cucumbers
To evaluate the whole content of saponins, the BuOH extract was subjected to LC-MS and LCLC-MS/MS analysis on an LTQ-Orbitrap instrument using the pentafluorophenyl (PFP) stationary
The analysis was performed in the negative-ion mode, because because it is known that almost all the saponins from H. atra contain a sulfated sugar and are it is known that almost all the saponins from H. atra contain a sulfated sugar and are anionic anionic in solution
Summary
Holothurians are marine echinoderms commonly referred to as sea cucumbers. Holothurians have been attracting increasing interest for their high content of secondary metabolites with manifold potential applications, especially in the pharmaceutical field [2]. It has been reported that sea cucumbers extracts may act as anticoagulant agents and inhibitors of hyperlipidemia [9,10]. In addition to their pharmacological activities, secondary metabolites from holothurians are attractive for their possible applications in the nutraceutical and cosmeceutical fields [11,12,13]
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