Synaptosides A and A₁, Triterpene Glycosides from the Sea Cucumber Synapta maculata Containing 3-O-Methylglucuronic Acid and Their Cytotoxic Activity against Tumor Cells

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Abstract

Two novel triterpene holostane glycosides, synaptosides A ( 1) and A 1 ( 2), have been isolated from the Vietnamese sea cucumber Synapta maculata (Synaptida, Apodida). Their structures were elucidated by spectroscopic methods (NMR and MS) and chemical transformations. Glycosides 1 and 2 have rare branched pentasaccharide carbohydrate chains featuring a 3- O-methylglucuronic acid residue not previously reported in glycosides from sea cucumbers and a 6- O-sulfated glucose. Glycoside 2 has an oxo group at C-7 and a 8(9)-double bond. All these structural features are unknown in glycosides from sea cucumbers. Glycoside 1 has moderate cytotoxic activity (IC 50 8.6 microg/mL) and glycoside 2 is inactive against HeLa tumor cells.

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