title: Antiproliferative activity and absolute configuration of zonaquinone acetate from the Jamaican alga Stypopodium zonale.
abstract: The chemical investigation of specimens of the Jamaican brown alga Stypopodium zonale led to the isolation of a cytotoxic compound, zonaquinone acetate (1), along with known compounds flabellinone, not previously identified in S. zonale, stypoldione, 5',7'-dihydroxy-2'-pentadecylchromone and sargaol. The structures of the metabolites were established by analysis of the spectral data including 1D and 2D NMR experiments while the stereochemistry of 1 was assessed by VCD measurements. Cytotoxic activity was reported in vitro for 1 against breast cancer and colon cancer cell lines at IC(50) values of 19.22-21.62 μM and 17.11-18.35 μM respectively, comparing favorably with standard treatments tamoxifen (17.22-17.32 μM) and fluorouracil (27.03-31.48 μM). When tested with liver cancer cells (Hep G2), no activity was observed. Weak antioxidant activity was observed with 1 but sargaol exhibited high activity.
authors.affiliation: Department of Chemistry, University of the West Indies, Mona Campus, Mona, Kingston 7, Kingston, Jamaica.
authors.forename: Najair
authors.initials: N
authors.lastname: Penicooke
authors.forename: Kemil
authors.initials: K
authors.lastname: Walford
authors.forename: Simone
authors.initials: S
authors.lastname: Badal
authors.forename: Rupika
authors.initials: R
authors.lastname: Delgoda
authors.forename: Lawrence A D
authors.initials: LA
authors.lastname: Williams
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
authors.forename: Bárbara
authors.initials: B
authors.lastname: Gordillo-Román
authors.forename: Winklet
authors.initials: W
authors.lastname: Gallimore
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004224:Diterpenes / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D000459:Phaeophyceae / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; D013729:Terpenes; C561788:sargaol