title: Anti-inflammatory potential of monogalactosyl diacylglycerols and a monoacylglycerol from the edible brown seaweed Fucus spiralis Linnaeus.
abstract: A monoacylglycerol (1) and a 1:1 mixture of two monogalactosyl diacylglycerols (MGDGs) (2 and 3) were isolated from the brown seaweed Fucus spiralis Linnaeus. The structures were elucidated by spectroscopic means (NMR and MS) and by comparison with the literature. Compound 1 was composed of a glycerol moiety linked to oleic acid (C18:1 Ω9). Compounds 2 and 3 contained a glycerol moiety linked to a galactose unit and eicosapentaenoic acid (C20:5 Ω3) combined with octadecatetraenoic acid (C18:4 Ω3) or linolenic acid (C18:3 Ω3), respectively. The isolated compounds were tested for their cytotoxic and anti-inflammatory activity in RAW 264.7 macrophage cells. All of them inhibited NO production at non-cytotoxic concentrations. The fraction consisting of compounds 2 and 3, in a ratio of 1:1, was slightly more effective than compound 1 (IC₅₀ of 60.06 and 65.70 µg/mL, respectively). To our knowledge, this is the first report of these compounds from F. spiralis and on their anti-inflammatory capacity.
authors.affiliation: REQUIMTE/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal. gracilianalps@gmail.com.
authors.forename: Graciliana
authors.initials: G
authors.lastname: Lopes
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, Universitätsstraße 1, Düsseldorf 40225, Germany. georgios.daletos@uni-duesseldorf.de.
authors.forename: Georgios
authors.initials: G
authors.lastname: Daletos
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, Universitätsstraße 1, Düsseldorf 40225, Germany. proksch@uni-duesseldorf.de.
authors.forename: Peter
authors.initials: P
authors.lastname: Proksch
authors.affiliation: REQUIMTE/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal. pandrade@ff.up.pt.
authors.forename: Paula B
authors.initials: PB
authors.lastname: Andrade
authors.affiliation: REQUIMTE/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal. valentao@ff.up.pt.
authors.forename: Patrícia
authors.initials: P
authors.lastname: Valentão
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004396:Coloring Agents; D003907:Dexamethasone / Q000494:pharmacology; D004075:Diglycerides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000494:pharmacology; D044645:Fucus / Q000737:chemistry*; D005989:Glycerides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007202:Indicators and Reagents; D007770:L-Lactate Dehydrogenase / Q000378:metabolism; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D009569:Nitric Oxide / Q000037:antagonists & inhibitors; D012015:Reference Standards; D021241:Spectrometry, Mass, Electrospray Ionization; D013778:Tetrazolium Salts; D013844:Thiazoles
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D004396:Coloring Agents; D004075:Diglycerides; D004791:Enzyme Inhibitors; D005989:Glycerides; D007202:Indicators and Reagents; D008070:Lipopolysaccharides; D013778:Tetrazolium Salts; D013844:Thiazoles; D009569:Nitric Oxide; D003907:Dexamethasone; D007770:L-Lactate Dehydrogenase; C022616:thiazolyl blue