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Mar Drugs
2022 May 30;206:. doi: 10.3390/md20060369.
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Structures and Biologic Activity of Chitonoidosides I, J, K, K1 and L-Triterpene Di-, Tri- and Tetrasulfated Hexaosides from the Sea Cucumber Psolus chitonoides.
Silchenko AS
,
Avilov SA
,
Andrijaschenko PV
,
Popov RS
,
Chingizova EA
,
Dmitrenok PS
,
Kalinovsky AI
,
Rasin AB
,
Kalinin VI
.
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Five new triterpene di-, tri- and tetrasulfated hexaosides (chitonoidosides I (1), J (2), K (3), K1 (4) and L (5)) were isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near Bering Island (Commander Islands) from a depth of 100-150 m. The structural variability of the glycosides concerned both the aglycones (with 7(8)- or 9(11)-double bonds) and carbohydrate chains differing from each other by the third sugar residue (Xyl or sulfated by C-6 Glc) and/or by the fourth-terminal in the bottom semi-chain-residue (Glc or sulfated by C-6 MeGlc) as well as by the positions of a sulfate group at C-4 or C-6 in the sixth-terminal in the upper semi-chain-residue (MeGlc). Hemolytic activities of these compounds 1-5 against human erythrocytes as well as cytotoxicity against human cancer cell lines, HeLa, DLD-1 and HL-60, were studied. The hexaosides, chitonoidosides K (3) and L (5) with four sulfate groups, were the most active against tumor cells in all the tests. Noticeably, the sulfate group at C-4 of MeGlc6 did not decrease the membranolytic effect of 5 as compared with 3, having the sulfate group at C-6 of MeGlc6. Erythrocytes were, as usual, more sensitive to the action of the studied glycosides than cancer cells, although the sensitivity of leukemia promyeloblast HL-60 cells was higher than that of other tumor cells. The glycosides 1 and 2 demonstrated some weaker action in relation to DLD-1 cells than against other tumor cell lines. Chitonoidoside K1 (4) with a hydroxyl at C 25 of the aglycone was not active in all the tests. The metabolic network formed by the carbohydrate chains of all the glycosides isolated from P. chitonoides as well as the aglycones biosynthetic transformations during their biosynthesis are discussed and illustrated with schemes.
Figure 1. Chemical structures of glycosides isolated from Psolus chitonoides: 1—chitonoidoside I; 2—chitonoidoside J; 3—chitonoidoside K; 4—chitonoidoside K1; and 5—chitonoidoside L.
Figure 2. Combinatorial library for the glycosides of P. chitonoides.
Figure 3. Biosynthetic network of carbohydrate chains of the glycosides isolated from P. chitonoides. Red indicates main steps of transformations and blue indicates the alternative path of biosynthetic modifications.
Figure 4. Biosynthesis of the aglycones of the glycosides isolated from P. chitonoides.
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