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ECB-ART-40624
J Nat Prod 2008 Apr 01;714:525-31. doi: 10.1021/np070283+.
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Synaptosides A and A1, triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic acid and their cytotoxic activity against tumor cells.

Avilov SA , Silchenko AS , Antonov AS , Kalinin VI , Kalinovsky AI , Smirnov AV , Dmitrenok PS , Evtushenko EV , Fedorov SN , Savina AS , Shubina LK , Stonik VA .


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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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Genes referenced: LOC100887844