Abstract
Four new triterpene disulfated glycosides, chitonoidosides E1 (1), F (2), G (3), and H (4), were isolated from the Far-Eastern sea cucumber Psolus chitonoides and collected near Bering Island (Commander Islands) at depths of 100–150 m. Among them there are two hexaosides (1 and 3), differing from each other by the terminal (sixth) sugar residue, one pentaoside (4) and one tetraoside (2), characterized by a glycoside architecture of oligosaccharide chains with shortened bottom semi-chains, which is uncommon for sea cucumbers. Some additional distinctive structural features inherent in 1–4 were also found: the aglycone of a recently discovered new type, with 18(20)-ether bond and lacking a lactone in chitonoidoside G (3), glycoside 3-O-methylxylose residue in chitonoidoside E1 (1), which is rarely detected in sea cucumbers, and sulfated by uncommon position 4 terminal 3-O-methylglucose in chitonoidosides F (2) and H (4). The hemolytic activities of compounds 1–4 and chitonoidoside E against human erythrocytes and their cytotoxic action against the human cancer cell lines, adenocarcinoma HeLa, colorectal adenocarcinoma DLD-1, and monocytes THP-1, were studied. The glycoside with hexasaccharide chains (1, 3 and chitonoidoside E) were the most active against erythrocytes. A similar tendency was observed for the cytotoxicity against adenocarcinoma HeLa cells, but the demonstrated effects were moderate. The monocyte THP-1 cell line and erythrocytes were comparably sensitive to the action of the glycosides, but the activity of chitonoidosides E and E1 (1) significantly differed from that of 3 in relation to THP-1 cells. A tetraoside with a shortened bottom semi-chain, chitonoidoside F (2), displayed the weakest membranolytic effect in the series.
Highlights
Triterpene glycosides are characteristic secondary metabolites of the sea cucumbers
Extensive studies on glycosides provide significant information on the exploration of chemical diversity, properties and biological activity of a huge collection of natural products, which are a valuable and promising resource of new drugs and medicines [1,2,3,4,5,6,7,8]. The interest in these compounds is driven by their taxonomic specificity [9,10,11] as well as the possibility of reconstructing the sequences of the biosynthetic transformations of aglycones and carbohydrate chains during biosynthesis [12,13] and of defining the peculiarities of «structure-activity relationships» based on knowledge about their structural diversity [14]
The continuation of the research into triterpene glycosides from the sea cucumber Psolus chitonoides resulted in the isolation of four previously unknown chitonoidosides E1 (1), F (2), G (3) and H (4)
Summary
Extensive studies on glycosides provide significant information on the exploration of chemical diversity, properties and biological activity of a huge collection of natural products, which are a valuable and promising resource of new drugs and medicines [1,2,3,4,5,6,7,8] The interest in these compounds is driven by their taxonomic specificity [9,10,11] as well as the possibility of reconstructing the sequences of the biosynthetic transformations of aglycones and carbohydrate chains during biosynthesis [12,13] and of defining the peculiarities of «structure-activity relationships» based on knowledge about their structural diversity [14]. 5.03 d (8.0) 3.87 t (8.0) 3.98 t (9.3) 3.49 t (9.3) 3.67 dd (6.2; 9.3) 1.61 d (6.2)
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
