title: Anthenosides L-U, Steroidal Glycosides with Unusual Structural Features from the Starfish Anthenea aspera.
abstract: Ten new polyhydroxysteroidal glycosides, anthenosides L-U (1-10), with rare positions of carbohydrate fragment attachments, were isolated from the starfish Anthenea aspera. The structures of 1-10 were established by NMR and ESIMS techniques as well as by chemical transformations. The unoxidized Δ22-24-nor-cholestane (1), (24S)-Δ22-24-methylcholestane (2-5), and Δ22-cholestane (7) side chains of the steroidal aglycons, 3-O-methyl-β-d-galactofuranosyl residue (2, 8), and 5α-cholest-8(14)-ene-3α,7β,16α-trihydroxysteroidal nucleus (9, 10) have not been found previously in starfish polar steroidal compounds. The mixture of glycosides 9 and 10 showed hemolytic activity with an EC50= 8 μM. Compound 4 at a dose of 10 μM exhibited a potential immunomodulatory action, decreasing by 24% the intracellular ROS content in RAW 264.7 murine macrophages, induced by pro-inflammatory endotoxic lipopolysaccharide from E. coli.
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of 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 Eastern Branch of Russian Academy of Sciences , Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Sofiya D
authors.initials: SD
authors.lastname: Kharchenko
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of 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 Eastern Branch of 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 Eastern Branch of 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 Eastern Branch of Russian Academy of Sciences , Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Ekaterina A
authors.initials: EA
authors.lastname: Chingizova
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of 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 Eastern Branch of Russian Academy of Sciences , Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.
authors.forename: Evgeny V
authors.initials: EV
authors.lastname: Evtushenko
authors.affiliation: Severtsov Institute of Ecology and Evolution, Russian Academy of Sciences , Leninskii Pr. 33, 119071 Moscow, Russian Federation.
authors.forename: Tatyana I
authors.initials: TI
authors.lastname: Antokhina
authors.affiliation: Institute of Marine Biochemistry, Vietnam Academy of Science and Technology , 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Chau Van
authors.initials: CV
authors.lastname: Minh
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences , Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russian Federation.|Far Eastern Federal University , Sukhanova Str. 8, 690000 Vladivostok, Russian Federation.
authors.forename: Valentin A
authors.identifier: http://orcid.org/0000-0002-8213-8411
authors.initials: VA
authors.lastname: Stonik
mesh_terms: D000818:Animals; D004926:Escherichia coli; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013215:Starfish / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D006027:Glycosides; D008070:Lipopolysaccharides; D013256:Steroids