title: Marine polyprenylated hydroquinones, quinones, and chromenols with inhibitory effects on leukotriene formation.
abstract: A series of polyprenylated hydroquinones, quinones, and chromenols were isolated from the extracts of the marine sponge Ircinia spinosula and the brown alga Taonia atomaria, which gave rise to the constituents 1-4 and 5-8, respectively. Compounds 1, 2, 6, and 7 are new natural products, which were fully characterized. Their anti-inflammatory activities in terms of leukotriene formation were evaluated in an in vitro assay with pork leukocytes. The new hydroxylated compound, 2'-[28-hydroxy]heptaprenyl-1',4'-hydroquinone (= 2-[(2E,6E,10E,14E,18Z,22E)-19-(hydroxymethyl)-3,7,11,15,23,27-hexamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl]benzene-1,4-diol; 1), the known tetraprenyl benzoquinone sargaquinone (5), and the known polyprenyl chromenols 3 and 4 exhibited the highest anti-inflammatory activities, with IC50 values of 1.9-9.4 microM (Table 3). Potential structure-activity relationships (SAR) are discussed.
authors.affiliation: School of Pharmacy, Department of Pharmacognosy and Chemistry of Natural Products, University of Athens, Panepistimiopolis Zografou, Athens, Greece.
authors.forename: Leto-A
authors.initials: LA
authors.lastname: Tziveleka
authors.forename: Dennis
authors.initials: D
authors.lastname: Abatis
authors.forename: Kerstin
authors.initials: K
authors.lastname: Paulus
authors.forename: Rudolf
authors.initials: R
authors.lastname: Bauer
authors.forename: Constantinos
authors.initials: C
authors.lastname: Vagias
authors.forename: Vassilios
authors.initials: V
authors.lastname: Roussis
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry* / Q000494:pharmacology; D006873:Hydroquinones / Q000737:chemistry* / Q000494:pharmacology; D007962:Leukocytes / Q000187:drug effects / Q000378:metabolism; D015289:Leukotrienes / Q000378:metabolism*; D016859:Lipoxygenase Inhibitors; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry* / Q000494:pharmacology; D013552:Swine
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D001578:Benzopyrans; D006873:Hydroquinones; D015289:Leukotrienes; D016859:Lipoxygenase Inhibitors; D011809:Quinones