Cladolosides C 4 , D 1 , D 2 , M, M 1 , M 2 , 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.

Eight new triterpene olygoglycosides, cladolosides C ₄ (1), D ₁ (2), D ₂ (3), M (4), M ₁ (5), M ₂ (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 C ₄ (1) contains an uncommon 20,21,22,23,24,25,26,27-octa-norlanostane aglycone. Cladolosides D ₁ (2), D ₂ (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 D ₂ (3), inhibited the colony formation and growth of HT-29 cells at non-cytotoxic concentrations. The highest inhibitory activity was demonstrated by cladoloside M ₁ (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.
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