Abstract
Sea cucumbers produce numerous compounds with a wide range of chemical structural diversity. Among these, saponins are the most diverse and include sulfated, non-sulfated, acetylated and methylated congeners with different aglycone and sugar moieties. In this study, MALDI and ESI tandem mass spectrometry, in the positive ion mode, were used to elucidate the structure of new saponins extracted from the viscera of H. lessoni. Fragmentation of the aglycone provided structural information on the presence of the acetyl group. The presence of the O-acetyl group was confirmed by observing the mass transition of 60 u corresponding to the loss of a molecule of acetic acid. Ion fingerprints from the glycosidic cleavage provided information on the mass of the aglycone (core), and the sequence and type of monosaccharides that constitute the sugar moiety. The tandem mass spectra of the saponin precursor ions [M + Na]+ provided a wealth of detailed structural information on the glycosidic bond cleavages. As a result, and in conjunction with existing literature, we characterized the structure of five new acetylated saponins, Lessoniosides A–E, along with two non-acetylated saponins Lessoniosides F and G at m/z 1477.7, which are promising candidates for future drug development. The presented strategy allows a rapid, reliable and complete analysis of native saponins.
Highlights
Sea cucumbers belonging to the class Holothuroidea of the Echinodermata phylum are marine invertebrates that produce a range of compounds that have the potential to be used in agriculture, and as pharmaceuticals, nutraceuticals and cosmeceuticals [1,2].Saponins are the most important characteristic and abundant secondary metabolites in this species [3].Sea cucumber saponins exert a wide range of medicinal and pharmacological properties
We reported the isolation and purification of several saponins from the viscera of sea cucumber species, H. lessoni, using ethanolic extraction, followed by solvent partition, HPCPC
Sodium ions were introduced to the samples before conducting the MS analysis, ensuring all saponins observed in the positive ion mode were predominantly singly charged sodium adducts [M + Na]+; triterpene glycosides have a high affinity to alkali cations
Summary
Sea cucumbers belonging to the class Holothuroidea of the Echinodermata phylum are marine invertebrates that produce a range of compounds that have the potential to be used in agriculture, and as pharmaceuticals, nutraceuticals and cosmeceuticals [1,2]. Sea cucumber saponins share common saponin features, their aglycones, called sapogenins or genins, are significantly different from those reported in the plant kingdom [1]. These amphipathic compounds generally possess a triterpene or steroid backbone or aglycone (hydrophilic, lipid-soluble) connected glycosidically to a saccharide moiety (hydrophilic, water-soluble) [3,4,5]. A series of unusual non-holostane triterpene glycoside have been reported from sea cucumbers, belonging to order Dendrochirotida, which have a shortened side chain, and no lactone function. We expect that the results of this project will transform the value of the viscera of sea cucumbers into sources of high value products, important to human health and industry
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