title: Four New Steroidal Glycosides, Protolinckiosides A - D, from the Starfish Protoreaster lincki.
abstract: Four new steroidal glycosides, protolinckiosides A - D (1 - 4, resp.), were isolated along with four previously known glycosides, 5 - 8, from the MeOH/EtOH extract of the starfish Protoreaster lincki. The structures of 1 - 4 were elucidated by extensive NMR and ESI-MS techniques as (3β,4β,5α,6β,7α,15α,16β,25S)-4,6,7,8,15,16,26-heptahydroxycholestan-3-yl 2-O-methyl-β-d-xylopyranoside (1), (3β,5α,6β,15α,24S)-3,5,6,8,15-pentahydroxycholestan-24-yl α-l-arabinofuranoside (2), sodium (3β,6β,15α,16β,24R)-29-(β-d-galactofuranosyloxy)-6,8,16-trihydroxy-3-[(2-O-methyl-β-d-xylopyranosyl)oxy]stigmast-4-en-15-yl sulfate (3), and sodium (3β,6β,15α,16β,22E,24R)-28-(β-d-galactofuranosyloxy)-6,8,16-trihydroxy-3-[(2-O-methyl-β-d-xylopyranosyl)oxy]ergosta-4,22-dien-15-yl sulfate (4). The unsubstituted β-d-galactofuranose residue at C(28) or C(29) of the side chains was found in starfish steroidal glycosides for the first time. Compounds 1 - 4 significantly decreased the intracellular reactive oxygen species (ROS) content in RAW 264.7 murine macrophages at induction by proinflammatory endotoxic lipopolysaccharide (LPS) from E. coli.
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, 690022, Russia.
authors.forename: Timofey V
authors.initials: TV
authors.lastname: Malyarenko
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, 690022, Russia. kicha@piboc.dvo.ru.
authors.forename: Alla A
authors.initials: AA
authors.lastname: Kicha
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, 690022, Russia.
authors.forename: Anatoly I
authors.initials: AI
authors.lastname: Kalinovsky
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, 690022, Russia.
authors.forename: Natalia V
authors.initials: NV
authors.lastname: Ivanchina
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, 690022, Russia.
authors.forename: Roman S
authors.initials: RS
authors.lastname: Popov
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, 690022, Russia.
authors.forename: Evgeny A
authors.initials: EA
authors.lastname: Pislyagin
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, 690022, Russia.
authors.forename: Ekaterina S
authors.initials: ES
authors.lastname: Menchinskaya
authors.affiliation: Centre for Marine Biodiversity, University of Kerala, Kariavattom, Thiruvananthapuram 695581, Kerala, India.|Kerala University of Fisheries and Ocean Studies, Kochi 682506, Kerala, India.
authors.forename: Krishna Pillai
authors.initials: KP
authors.lastname: Padmakumar
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, 690022, Russia. stonik@piboc.dvo.ru.
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
mesh_terms: D000818:Animals; D002460:Cell Line; D004305:Dose-Response Relationship, Drug; D004447:Echinodermata / Q000737:chemistry*; D004926:Escherichia coli / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D017382:Reactive Oxygen Species / Q000378:metabolism; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D006027:Glycosides; D008070:Lipopolysaccharides; D017382:Reactive Oxygen Species; D013256:Steroids
keywords: Cytotoxic activity; Glycosides; Lysosomal activity; Protolinckiosides A - D; Protoreaster lincki; Starfish; Steroids