Free accessResearch articleFirst published online 2011-8
Structure of Cucumariosides H 5,H 6,H 7 and H 8,Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix and Unprecedented Aglycone with 16,22-Epoxy-group
Four new triterpene glycosides cucumariosides H5 (1), H6 (2), H7 (3) and H8 (4) along with the known cucumarioside H (5) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. The structures of glycosides 1–4 were elucidated on the basis of spectral data (2D NMR and MS). Glycosides 1–4 belong to the group of cucumariosides H, having branched rare pentasaccharide carbohydrate moieties with one sulfate group and 3-O-methyl-D-xylose as a terminal monosaccharide unit. Glycosides 1–3 and 5 differ from each other in structures of side chains of the aglycones, while cucumarioside H8 (4) has a novel aglycone with unprecedented 16(22)-epoxy-group, never found in the sea cucumbers glycosides. Glycosides 1–3, and 5 were cytotoxic against mouse lymphocytes and hemolytic against mouse erythrocytes. Glycoside 2 was less active in comparison with others.
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