title: Structures and biological activities of cladolosides C3, E1, E2, F1, F2, G, H1 and H2, eight triterpene glycosides from the sea cucumber Cladolabes schmeltzii with one known and four new carbohydrate chains.
abstract: Eight new nonsulfated triterpene glycosides, cladolosides C3(1), E1(2), E2(3), F1(4), F2(5), G(6), H1(7) and H2(8) have been isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida) collected in the Vietnamese shallow waters. The structures of the glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. Glycosides 2, 3, 4, and 5 have pentasaccharide branched carbohydrate moieties and differ from each other by monosaccharide compositions and aglycone structures. At that, glycosides 2 and 3 contain three xylose, one 3-O-methyl-glucose and one quinovose residues, while glycosides 4 and 5 have two quinovose, two xylose and one 3-O-methyl-glucose residues. Compounds 1 and 6-8 are hexaosides differing from each other by aglycone structures and by the fifth monosaccharide residue, which proved to be glucose in cladoloside C3(1), xylose in cladoloside G(6) and quinovose in cladolosides H1(7) and H2(8). The presence of quinovose residue in the fifth position, as in 4, 5, 7 and 8 has never been earlier found in carbohydrate chains of triterpene glycosides from sea cucumbers. The carbohydrate chains with xylose in the fifth position of pentaosides and hexaosides are also very unusual for holothurious glycosides. All the substances demonstrate strong or moderate cytotoxic and hemolytic effects with hexaosides being more active than the corresponding pentaosides. Peculiarities of the biosynthesis and biochemical evolution of glycosides of this type are discussed.
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, Russian Federation.
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, Russian Federation.
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, Russian Federation.
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, Russian Federation.
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, Russian Federation.
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, Russian Federation.
authors.forename: Ekaterina A
authors.initials: EA
authors.lastname: Yurchenko
authors.affiliation: A.V. Zhirmunsky Institute of Marine Biology, Far Eastern Branch of the Russian Academy of Sciences, Palchevsky St. 17, 690041, Vladivostok, Russian Federation; Far Eastern Federal University, Sukhanova St. 8, 690950, Vladivostok, Russian Federation.
authors.forename: Igor Yu
authors.initials: IY
authors.lastname: Dolmatov
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, Russian Federation. Electronic address: kalininv@piboc.dvo.ru.
authors.forename: Vladimir I
authors.initials: VI
authors.lastname: Kalinin
mesh_terms: D000818:Animals; D001769:Blood / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D006027:Glycosides / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D051379:Mice; D015394:Molecular Structure; D012616:Sea Cucumbers / Q000737:chemistry*; D013154:Spleen / Q000166:cytology / Q000187:drug effects; D014315:Triterpenes / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D006027:Glycosides; D014315:Triterpenes
keywords: Cladolabes schmeltzii; Cytotoxic activity; NMR; Triterpene glycosides