title: Cytotoxic Glycosylated Fatty Acid Amides from a Stelletta sp. Marine Sponge.
abstract: We have discovered new glycosylated fatty acid amides, stellettosides, from a Stelletta sp. marine sponge. They were detected through LC-MS analysis of the extract combined with the cytotoxicity assay of the prefractionated sample. Their planar structures were determined by analyses of the NMR and tandem FABMS data. Stellettosides A1 and A2 (1 and 2) as well as stellettosides B1-B4 (3-6) were obtained as inseparable mixtures. Careful analysis of the NMR and tandem FABMS data of each mixture, along with comparison of the tandem FABMS data with that of a synthetic model compound, permitted us to assign the structure of the constituents in the mixture. The absolute configuration of the monosaccharide unit was determined by LC-MS after chiral derivatization. The relative configurations of the vicinal oxygenated methines in the fatty acid chains were assigned by the (1)H NMR data of the isopropylidene derivative. The mixture of stellettosides B1-B4 (3-6) exhibit moderate cytotoxic activity against HeLa cells with an IC50 value of 9 μM, whereas the mixture of stellettosides A1 and A2 (1 and 2) was not active at a concentration of 10 μM.
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
authors.forename: Victoria
authors.initials: V
authors.lastname: Peddie
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
authors.forename: Kentaro
authors.initials: K
authors.lastname: Takada
authors.affiliation: Graduate School of Medical and Dental Sciences, Niigata University , Niigata 951-8510, Japan.
authors.forename: Shujiro
authors.initials: S
authors.lastname: Okuda
authors.affiliation: Sugashima Marine Biological Laboratory, Nagoya University , Mie 517-0004, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Ise
authors.affiliation: Graduate School of Fisheries Science and Environmental Studies, Nagasaki University , Nagasaki 852-8521, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Morii
authors.affiliation: Graduate School of Fisheries Science and Environmental Studies, Nagasaki University , Nagasaki 852-8521, Japan.
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Yamawaki
authors.affiliation: Graduate School of Fisheries Science and Environmental Studies, Nagasaki University , Nagasaki 852-8521, Japan.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Takatani
authors.affiliation: Graduate School of Fisheries Science and Environmental Studies, Nagasaki University , Nagasaki 852-8521, Japan.
authors.forename: Osamu
authors.initials: O
authors.lastname: Arakawa
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
authors.forename: Shigeru
authors.initials: S
authors.lastname: Okada
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
authors.forename: Shigeki
authors.initials: S
authors.lastname: Matsunaga
mesh_terms: D000577:Amides; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006017:Glycolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006031:Glycosylation; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D006017:Glycolipids; C000605885:stellettoside A1; C000605886:stellettoside A2