title: Structures and Biogenesis of Fallaxosides D₄, D₅, D₆ and D₇, Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax.
abstract: Four new trisulfated triterpene glycosides, fallaxosides D₄ (1), D₅ (2), D₆ (3) and D₇ (4) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The structures of the glycosides have been elucidated by 2D NMR spectroscopy and HRESIMS. All the glycosides have the lanostane aglycones of a rare non-holostane type with 7(8)-, 8(9)- or 9(11)-double bonds, one or two hydroxyl groups occupying unusual positions in the polycyclic nucleus and shortened or normal side chains. The pentasaccharide carbohydrate moieties of 1-4 have three sulfate groups. The cytotoxic activity of glycosides 1-4 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied.
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia. sialexandra@mail.ru.
authors.forename: Alexandra S
authors.initials: AS
authors.lastname: Silchenko
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia. kaaniv@piboc.dvo.ru.
authors.forename: Anatoly I
authors.initials: AI
authors.lastname: Kalinovsky
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia. Avilov-1957@mail.ru.
authors.forename: Sergey A
authors.initials: SA
authors.lastname: Avilov
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia. pandriyashchenko@inbox.ru.
authors.forename: Pelageya V
authors.initials: PV
authors.lastname: Andryjaschenko
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia. paveldmt@piboc.dvo.ru.
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Dmitrenok
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia. kalininv@piboc.dvo.ru.
authors.forename: Vladimir I
authors.initials: VI
authors.lastname: Kalinin
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia. martyyas@mail.ru.
authors.forename: Ekaterina A
authors.initials: EA
authors.lastname: Chingizova
authors.affiliation: P.P. Shirshov Institute of Oceanology of the Russian Academy of Sciences, Nakhimovsky Pr., 36, 117997 Moscow, Russia. kirill.minin569@gmail.com.
authors.forename: Kirill V
authors.initials: KV
authors.lastname: Minin
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia. stonik@piboc.dvo.ru.
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
mesh_terms: D000818:Animals; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D048016:Cucumaria / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry* / Q000494:pharmacology*; D006461:Hemolysis / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D006027:Glycosides; D014315:Triterpenes
keywords: Cucumaria fallax; fallaxosides; non-holostane glycosides; sea cucumbers; triterpene glycosides