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

• Published in: Marine Drugs
• Main Authors: Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andrijaschenko, Roman S. Popov, Ekaterina A. Chingizova, Vladimir I. Kalinin, Pavel S. Dmitrenok
• Format: Article in Journal/Newspaper
• Language: English
• Published: MDPI AG 2021
• Subjects: Psolus chitonoides; triterpene glycosides; chitonoidosides; sea cucumber; cytotoxic activity; Biology (General); QH301-705.5; Bering Island
• Online Access: https://doi.org/10.3390/md19120696; https://doaj.org/article/7f92866902d74e16b3a8980617a7961c

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.