title: Cystoseira usneoides: A Brown Alga Rich in Antioxidant and Anti-inflammatory Meroditerpenoids.
abstract: Twelve new meroditerpenoids, 1-12, along with eight known compounds, have been isolated from the brown alga Cystoseira usneoides collected off the coast of Tarifa (Spain). The structures of the new metabolites have been established by spectroscopic techniques. All of the new compounds consist of a toluhydroquinone-derived nucleus linked to a regular diterpenoid moiety, which can either be acyclic or contain an ether ring. Most structural diversity arises from the presence of different oxygenated functionalities and unsaturations along the two terminal isoprenoid units of the diterpene backbone. Twelve of the isolated meroditerpenes have been tested in antioxidant assays. All of them have shown radical-scavenging activity. The most active compounds were cystodiones G (1) and H (2), 11-hydroxyamentadione (15), and amentadione (16), which exhibited antioxidant activities in the range of 77-87% that of the Trolox standard. In anti-inflammatory assays, cystodiones G (1) and M (6), cystone C (9), 11-hydroxyamentadione (15), and amentadione (16) showed significant activity as inhibitors of the production of the proinflammatory cytokine TNF-α in LPS-stimulated THP-1 human macrophages.
authors: Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz , 11510 Puerto Real (Cádiz), Spain.
authors: Carolina
authors: C
authors: de los Reyes
authors: Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz , 11510 Puerto Real (Cádiz), Spain.
authors: María J
authors: MJ
authors: Ortega
authors: Departamento de Farmacología, Facultad de Farmacia, Universidad de Sevilla , 41012 Sevilla, Spain.|Department of Biology, Faculty of Sciences, University Abdelmalek Essâadi , 93030 Tetouan, Morocco.
authors: Hanaa
authors: H
authors: Zbakh
authors: Departamento de Farmacología, Facultad de Farmacia, Universidad de Sevilla , 41012 Sevilla, Spain.
authors: Virginia
authors: V
authors: Motilva
authors: Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz , 11510 Puerto Real (Cádiz), Spain.
authors: Eva
authors: E
authors: Zubía
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000459:Phaeophyceae / Q000737:chemistry*; D010936:Plant Extracts / Q000494:pharmacology; D013030:Spain; D013729:Terpenes / Q000737:chemistry; D014409:Tumor Necrosis Factor-alpha
chemical_list: D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D004224:Diterpenes; D008070:Lipopolysaccharides; D010936:Plant Extracts; D013729:Terpenes; D014409:Tumor Necrosis Factor-alpha; C041060:cystone