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Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H.

Alexandra S SilchenkoAnatoly I KalinovskySergey A AvilovPelageya V AndrijaschenkoRoman S PopovEkaterina A ChingizovaVladimir I KalininPavel S Dmitrienok
Published in: Marine drugs (2021)
Four new triterpene disulfated glycosides, chitonoidosides E 1 ( 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 E 1 ( 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 E 1 ( 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.
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