title: Structure and in vitro antitumor activity evaluation of brominated diterpenes from the red alga Sphaerococcus coronopifolius.
abstract: A novel bromoditerpene methyl ketone (1), two new bromoditerpene alcohols featuring a neodolastane (2), and a bromocorodienol skeleton (3), along with 13 previously reported metabolites (4-16) were isolated from the organic extract of Sphaerococcus coronopifolius collected from the rocky coasts of Corfu island in the Ionian Sea. The structures of the new natural products, as well as their relative stereochemistry, were elaborated on the basis of extensive spectral analysis, including 2D NMR experiments. The absolute stereochemistry of metabolite 3 was determined using the modified Mosher's method. The isolated metabolites were evaluated for their antitumoral activity against four human apoptosis-resistant (U373, A549, SKMEL-28, OE21) and two human apoptosis-sensitive (PC-3, LoVo) cancer cell lines with IC(50) in vitro growth inhibitory concentrations in the range 3-100 microM.
authors.affiliation: Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, Panepistimiopolis Zografou, Athens 15771, Greece.
authors.forename: Vangelis
authors.initials: V
authors.lastname: Smyrniotopoulos
authors.forename: Constantinos
authors.initials: C
authors.lastname: Vagias
authors.forename: Céline
authors.initials: C
authors.lastname: Bruyère
authors.forename: Delphine
authors.initials: D
authors.lastname: Lamoral-Theys
authors.forename: Robert
authors.initials: R
authors.lastname: Kiss
authors.forename: Vassilios
authors.initials: V
authors.lastname: Roussis
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D017605:Bromine Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D009369:Neoplasms / Q000188:drug therapy; D000461:Rhodophyta / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D017605:Bromine Compounds; D004224:Diterpenes