Cladolosides C4, D1, D2, M, M1, M2, N and Q, new triterpene glycosides with diverse carbohydrate chains from sea cucumber Cladolabes schmeltzii. An uncommon 20,21,22,23,24,25,26,27-okta-nor-lanostane aglycone. The synergism of inhibitory action of non-toxic dose of the glycosides and radioactive irradiation on colony formation of HT-29 cancer cells.

Abstract

Eight new triterpene olygoglycosides, cladolosides C4 (1), D1 (2), D2 (3), M (4), M1 (5), M2 (6), N (7) and Q (8), were isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Sclerodactylidae, Dendrochirotida). Structures of these glycosides were elucidated by 2D NMR spectroscopy and HR ESI mass spectrometry. A novel hexasaccharide carbohydrate chain having xylose residues as the first, second and third sugars was found in the glycoside 7. Cladoloside C4 (1) contains an uncommon 20,21,22,23,24,25,26,27-octa-norlanostane aglycone. Cladolosides D1 (2), D2 (3) and Q (8) were new representatives of the hexaosides with a non-methylated terminal sugar unit in the "upper" half-chain. Cytotoxic activities of the isolated compounds against ascite form of mouse Ehrlich carcinoma cells, mouse erythrocytes and human colorectal adenocarcinoma HT-29 cells were examined and their structure-activity relationships were analyzed. In addition, the majority of tested compounds, except for cladoloside D2 (3), inhibited the colony formation and growth of HT-29 cells at non-cytotoxic concentrations. The highest inhibitory activity was demonstrated by cladoloside M1 (5). Moreover, synergism of effects of radioactive irradiation and non-toxic dose of compounds 1-8 decreasing the number of colonies of HT-29 cells was observed. Cladoloside N (7) was the most active and increased the inhibitory effect from radiation by 75%. The biosynthetic transformations of the aglycones are discussed.

• Authors: Alexandra S Silchenko, Anatoly I Kalinovsky, Sergey A Avilov, Pelageya V Andryjaschenko, Pavel S Dmitrenok, Ekaterina A Yurchenko, Svetlana P Ermakova, Olesya S Malyarenko, Igor Yu Dolmatov, Vladimir I Kalinin
• Journal: Carbohydrate research (Carbohydr Res) Vol. 468 Pg. 36-44 (Oct 2018) ISSN: 1873-426X [Electronic] Netherlands
• PMID: 30121417 (Publication Type: Journal Article)
• Copyright: Copyright © 2018 Elsevier Ltd. All rights reserved.

Chemical References

• Glycosides
• Triterpenes

Topics

• Animals
• Dose-Response Relationship, Drug
• Glycosides (chemistry)
• HT29 Cells
• Humans
• Radiobiology
• Sea Cucumbers (chemistry)
• Structure-Activity Relationship
• Triterpenes (chemistry, pharmacology)