title: Cyclic Steroid Glycosides from the Starfish Echinaster luzonicus: Structures and Immunomodulatory Activities.
abstract: Five new steroid glycosides, luzonicosides B-E (2-5), belonging to a rare structure group of marine glycosides, containing carbohydrate moieties incorporated into a macrocycle, and a related open carbohydrate chain steroid glycoside, luzonicoside F (6), were isolated from the starfish Echinaster luzonicus along with the previously known cyclic steroid glycoside luzonicoside A (1). The structures of compounds 2-6 were established by extensive NMR and ESIMS techniques as well as chemical transformations. Luzonicoside A (1) at concentrations of 0.01-0.1 μM was shown to be potent in lysosomal activity stimulation, intracellular ROS level elevation, and NO synthesis up-regulation in RAW 264.7 murine macrophages. Luzonicoside D (4) was less active in these biotests.
authors.affiliation: †G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Alla A
authors.initials: AA
authors.lastname: Kicha
authors.affiliation: †G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 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 East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Timofey V
authors.initials: TV
authors.lastname: Malyarenko
authors.affiliation: †G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Natalia V
authors.initials: NV
authors.lastname: Ivanchina
authors.affiliation: †G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 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 East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Ekaterina S
authors.initials: ES
authors.lastname: Menchinskaya
authors.affiliation: †G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Ekaterina A
authors.initials: EA
authors.lastname: Yurchenko
authors.affiliation: †G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Evgeny A
authors.initials: EA
authors.lastname: Pislyagin
authors.affiliation: †G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Dmitry L
authors.initials: DL
authors.lastname: Aminin
authors.affiliation: ‡Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Hanoi, Vietnam.
authors.forename: Trinh T T
authors.initials: TT
authors.lastname: Huong
authors.affiliation: ‡Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Hanoi, Vietnam.
authors.forename: Pham Quoc
authors.initials: PQ
authors.lastname: Long
authors.affiliation: †G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
mesh_terms: D000818:Animals; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007155:Immunologic Factors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D017382:Reactive Oxygen Species / Q000032:analysis; D013215:Starfish / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D006027:Glycosides; D007155:Immunologic Factors; D017382:Reactive Oxygen Species; D013256:Steroids; D009569:Nitric Oxide