title: Synaptosides A and A1, triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic acid and their cytotoxic activity against tumor cells.
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.
authors.affiliation: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russian Federation.
authors.forename: Sergey A
authors.initials: SA
authors.lastname: Avilov
authors.forename: Alexandra S
authors.initials: AS
authors.lastname: Silchenko
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Antonov
authors.forename: Vladimir I
authors.initials: VI
authors.lastname: Kalinin
authors.forename: Anatoly I
authors.initials: AI
authors.lastname: Kalinovsky
authors.forename: Alexey V
authors.initials: AV
authors.lastname: Smirnov
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Dmitrenok
authors.forename: Evgeny V
authors.initials: EV
authors.lastname: Evtushenko
authors.forename: Sergey N
authors.initials: SN
authors.lastname: Fedorov
authors.forename: Alexandra S
authors.initials: AS
authors.lastname: Savina
authors.forename: Larisa K
authors.initials: LK
authors.lastname: Shubina
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D009792:Oceans and Seas; D012616:Sea Cucumbers / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D014744:Vietnam
chemical_list: D000970:Antineoplastic Agents; D006027:Glycosides; D014315:Triterpenes; C529461:synaptoside A; C529462:synaptoside A1