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Six new nonsulfated triterpene glycosides, cladolosides B 1 (1), B 2 (2), C (3), C 1 (4), C 2 (5) and D (6) and known holotoxin A 1 (7) have been isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of the glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. Glycosides 1 and 2 have pentasaccharide branched carbohydrate moieties and differ from each other by the aglycone structures. Compounds 3–6 are hexaosides; 3–5 contain identical carbohydrate moieties with two terminal 3- O-methylglucose residues and glucose as the fifth sugar unit and differ from each other in the structures of their aglycones. Cladoloside D (6) has a new variant of carbohydrate chain with xylose and glucose residues as fifth and sixth monosaccharides, correspondingly. All of the substances demonstrated rather strong cytotoxic and hemolytic effects.

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Structure and Biological Action of Cladolosides B1, B2, C, C1, C2 and D, Six New Triterpene Glycosides from the Sea Cucumber Cladolabes schmeltzii