{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,28]],"date-time":"2026-04-28T17:24:08Z","timestamp":1777397048876,"version":"3.51.4"},"reference-count":69,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2020,9,20]],"date-time":"2020-09-20T00:00:00Z","timestamp":1600560000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Due to their large spectrum of bioactive properties, much attention has recently been drawn to phlorotannins\u2014i.e., phenolic compounds characteristic from brown macroalgae. This study aimed to evaluate the antioxidant and anti-inflammatory properties of F. vesiculosus phlorotannin extracts and purified fractions. Overall, the crude extract and its ethyl acetate fraction (EtOAc) showed good radical scavenging activity, particularly towards nitric oxide (NO\u2022). Subsequent subfractions of EtOAc (F1 to F9) with different molecular weights were then shown to inhibit lipopolysaccharide-induced NO\u2022 production in macrophages, with stronger effects being observed for fractions of lower MWs. Of the three intracellular markers analyzed, inducible NO\u2022 synthase showed the highest sensitivity to almost all the phlorotannin-rich samples, followed by interleukin 1\u03b2 and cyclooxygenase 2, which was only inhibited by F2. Furthermore, this subfraction inhibited the phosphorylation and degradation of inhibitory protein \u03baB\u03b1, thus preventing the activation of NF-\u03baB and blocking the inflammatory cascade at the transcriptional level. This sample was characterized by the presence of a major compound with a deprotonated molecular ion at m\/z 507 with a fragmentation pattern coherent with that of a phlorotannin derivative. Overall, this work unveiled some of the mechanistic aspects behind the anti-inflammatory capacity of phlorotannins from F. vesiculosus, endorsing its use as a possible natural source of anti-inflammatory compounds.<\/jats:p>","DOI":"10.3390\/ijms21186897","type":"journal-article","created":{"date-parts":[[2020,9,20]],"date-time":"2020-09-20T21:20:28Z","timestamp":1600636828000},"page":"6897","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":66,"title":["Phlorotannins from Fucus vesiculosus: Modulation of Inflammatory Response by Blocking NF-\u03baB Signaling Pathway"],"prefix":"10.3390","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6571-7975","authenticated-orcid":false,"given":"Marcelo D.","family":"Catarino","sequence":"first","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"given":"Ana","family":"Silva","sequence":"additional","affiliation":[{"name":"CNC.IBILI, Faculty of Pharmacy, University of Coimbra, Health Sciences Campus, 3000-548 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9846-6754","authenticated-orcid":false,"given":"Maria T.","family":"Cruz","sequence":"additional","affiliation":[{"name":"CNC.IBILI, Faculty of Pharmacy, University of Coimbra, Health Sciences Campus, 3000-548 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9318-9732","authenticated-orcid":false,"given":"Nuno","family":"Mateus","sequence":"additional","affiliation":[{"name":"REQUIMTE\/LAQV, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur M.S.","family":"Silva","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7882-737X","authenticated-orcid":false,"given":"Susana M.","family":"Cardoso","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2020,9,20]]},"reference":[{"key":"ref_1","unstructured":"GBIF Secretariat (2020, January 21). GBIF Backbone Taxonomy-Fucus vesiculosus L.. Available online: https:\/\/doi.org\/10.15468\/dl.r83ttf."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Catarino, M.D., Silva, A.M.S., and Cardoso, S.M. (2018). Phycochemical Constituents and Biological Activities of Fucus spp.. Mar. Drugs, 16.","DOI":"10.3390\/md16080249"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Catarino, D.M., Silva, M.A., and Cardoso, M.S. (2017). Fucaceae: A Source of Bioactive Phlorotannins. Int. J. Mol. Sci., 18.","DOI":"10.3390\/ijms18061327"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"558","DOI":"10.1039\/b600518g","article-title":"Phloroglucinol compounds of natural origin","volume":"23","author":"Bharate","year":"2006","journal-title":"Nat. Prod. Rep."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Ummat, V., Tiwari, B.K., Jaiswal, A.K., Condon, K., Garcia-Vaquero, M., O\u2019Doherty, J., O\u2019Donnell, C., and Rajauria, G. (2020). Optimisation of ultrasound frequency, extraction time and solvent for the recovery of polyphenols, phlorotannins and associated antioxidant activity from brown seaweeds. Mar. Drugs.","DOI":"10.3390\/md18050250"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"115","DOI":"10.5530\/fra.2017.1.17","article-title":"Effects of extraction conditions over the phlorotannin content and antioxidant activity of extract from brown algae Sargassum serratum","volume":"7","author":"Boi","year":"2017","journal-title":"Free Radic. Antioxid."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.foodchem.2015.06.098","article-title":"Considerations on the use of enzyme-assisted extraction in combination with pressurized liquids to recover bioactive compounds from algae","volume":"192","author":"Montero","year":"2016","journal-title":"Food Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1045","DOI":"10.1007\/s00343-013-2321-x","article-title":"Optimization of the microwave-assisted extraction of phlorotannins from Saccharina japonica Aresch and evaluation of the inhibitory effects of phlorotannin-containing extracts on HepG2 cancer cells","volume":"31","author":"He","year":"2013","journal-title":"Chin. J. Oceanol. Limnol."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Obluchinskaya, E.D., Daurtseva, A.V., Pozharitskaya, O.N., Flisyuk, E.V., and Shikov, A.N. (2019). Natural Deep Eutectic Solvents as Alternatives for Extracting Phlorotannins from Brown Algae. Pharm. Chem. J.","DOI":"10.1007\/s11094-019-01987-0"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Heavisides, E., Rouger, C., Reichel, A.F., Ulrich, C., Wenzel-Storjohann, A., Sebens, S., and Tasdemir, D. (2018). Seasonal variations in the metabolome and bioactivity profile of fucus vesiculosus extracted by an optimised, pressurised liquid extraction protocol. Mar. Drugs.","DOI":"10.3390\/md16120503"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"V\u00e1zquez-Rodr\u00edguez, B., Guti\u00e9rrez-Uribe, J.A., Antunes-Ricardo, M., Santos-Zea, L., and Cruz-Su\u00e1rez, L.E. (2020). Ultrasound-assisted extraction of phlorotannins and polysaccharides from Silvetia compressa (Phaeophyceae). J. Appl. Phycol.","DOI":"10.1007\/s10811-019-02013-2"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"326","DOI":"10.1002\/pca.986","article-title":"High-performance liquid chromatographic analysis of phlorotannins from the brown alga Fucus vesiculosus","volume":"18","author":"Koivikko","year":"2007","journal-title":"Phytochem. Anal."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1007\/s10886-005-0984-2","article-title":"Contents of soluble, cell-wall-bound and exuded phlorotannins in the brown alga Fucus vesiculosus, with implications on their ecological functions","volume":"31","author":"Koivikko","year":"2005","journal-title":"J. Chem. Ecol."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Catarino, M., Silva, A., Mateus, N., and Cardoso, S. (2019). Optimization of Phlorotannins Extraction from Fucus vesiculosus and Evaluation of Their Potential to Prevent Metabolic Disorders. Mar. Drugs, 17.","DOI":"10.3390\/md17030162"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"5874","DOI":"10.1021\/jf3003653","article-title":"Antioxidant capacities of phlorotannins extracted from the brown algae Fucus vesiculosus","volume":"60","author":"Wang","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.jembe.2011.01.002","article-title":"Distribution and radical scavenging activity of phenols in Ascophyllum nodosum (Phaeophyceae)","volume":"399","author":"Breton","year":"2011","journal-title":"J. Exp. Mar. Bio. Ecol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2766","DOI":"10.3390\/md10122766","article-title":"Phlorotannin extracts from fucales characterized by HPLC-DAD-ESI-MSn: Approaches to hyaluronidase inhibitory capacity and antioxidant properties","volume":"10","author":"Ferreres","year":"2012","journal-title":"Mar. Drugs"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"460","DOI":"10.1016\/j.intimp.2014.09.019","article-title":"8,8\u2032-Bieckol, isolated from edible brown algae, exerts its anti-inflammatory effects through inhibition of NF-\u03baB signaling and ROS production in LPS-stimulated macrophages","volume":"23","author":"Yang","year":"2014","journal-title":"Int. Immunopharmacol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/j.intimp.2014.06.009","article-title":"Hemeoxygenase 1 partly mediates the anti-inflammatory effect of dieckol in lipopolysaccharide stimulated murine macrophages","volume":"22","author":"Yayeh","year":"2014","journal-title":"Int. Immunopharmacol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"9120","DOI":"10.1021\/jf3022018","article-title":"Anti-inflammatory activities of an ethanol extract of Ecklonia stolonifera in lipopolysaccharide-stimulated RAW 264.7 murine macrophage cells","volume":"60","author":"Lee","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1146\/annurev-ecolsys-040212-092530","article-title":"Inflammation: Mechanisms, Costs, and Natural Variation","volume":"43","author":"Ashley","year":"2012","journal-title":"Annu. Rev. Ecol. Evol. Syst."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"771","DOI":"10.1016\/j.cell.2010.03.006","article-title":"Inflammation 2010: New adventures of an old flame","volume":"140","author":"Medzhitov","year":"2010","journal-title":"Cell"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/B978-0-444-63602-7.00003-5","article-title":"The anti-inflammatory potential of flavonoids: Mechanistic aspects","volume":"Vol. 48","year":"2016","journal-title":"Studies in Natural Products Chemistry"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"775","DOI":"10.1016\/j.bbagrm.2010.05.004","article-title":"Inhibiting NF-\u03baB activation by small molecules as a therapeutic strategy","volume":"1799","author":"Gupta","year":"2010","journal-title":"Biochim. Biophys. Acta-Gene Regul. Mech."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Serasanambati, M., and Chilakapati, S.R. (2016). Function of Nuclear Factor Kappa B (NF-kB) in Human Diseases-A Review. South. Indian J. Biol. Sci.","DOI":"10.22205\/sijbs\/2016\/v2\/i4\/103443"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Phasanasophon, K., and Kim, S.M. (2019). Anti-inflammatory activity of the phlorotannin trifuhalol A using LPS-stimulated RAW264.7 cells through NF-\u03baB and MAPK main signaling pathways. Nat. Prod. Commun.","DOI":"10.1177\/1934578X19849798"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2019","DOI":"10.1016\/j.jff.2013.08.010","article-title":"The anti-inflammatory effects of phlorotannins from Eisenia arborea on mouse ear edema by inflammatory inducers","volume":"5","author":"Sugiura","year":"2013","journal-title":"J. Funct. Foods"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1016\/B978-0-12-387669-0.00008-9","article-title":"Medicinal effects of phlorotannins from marine brown algae","volume":"Vol. 64","author":"Kim","year":"2011","journal-title":"Advances in Food and Nutrition Research"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.algal.2017.09.009","article-title":"Phlorotannin extracts from Fucales: Marine polyphenols as bioregulators engaged in inflammation-related mediators and enzymes","volume":"28","author":"Barbosa","year":"2017","journal-title":"Algal Res."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Lopes, G., Sousa, C., Silva, L.R., Pinto, E., Andrade, P.B., Bernardo, J., Mouga, T., and Valent\u00e3o, P. (2012). Can phlorotannins purified extracts constitute a novel pharmacological alternative for microbial infections with associated inflammatory conditions?. PLoS ONE, 7.","DOI":"10.1371\/journal.pone.0031145"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"7773","DOI":"10.1021\/jf8007053","article-title":"Toxicity and antioxidant activity in vitro and in vivo of two Fucus vesiculosus extracts","volume":"56","author":"Poquet","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3355","DOI":"10.1039\/C7FO00881C","article-title":"Antioxidant and anti-inflammatory activities of Geranium robertianum L. decoctions","volume":"8","author":"Catarino","year":"2017","journal-title":"Food Funct."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1016\/j.foodchem.2009.02.041","article-title":"Total phenolic compounds, radical scavenging and metal chelation of extracts from Icelandic seaweeds","volume":"116","author":"Wang","year":"2009","journal-title":"Food Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1016\/j.fct.2007.10.028","article-title":"Protective capacities of certain spices against peroxynitrite-mediated biomolecular damage","volume":"46","author":"Ho","year":"2008","journal-title":"Food Chem. Toxicol."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Huang, D., Ou, B., Hampsch-Woodill, M., Flanagan, J.A., and Prior, R.L. (2002). High-throughput assay of oxygen radical absorbance capacity (ORAC) using a multichannel liquid handling system coupled with a microplate fluorescence reader in 96-well format. J. Agric. Food Chem.","DOI":"10.1021\/jf0201529"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"914","DOI":"10.1016\/j.foodchem.2010.07.019","article-title":"Type 2 diabetes-related bioactivities of coffee: Assessment of antioxidant activity, NF-\u03baB inhibition, and stimulation of glucose uptake","volume":"124","author":"Chu","year":"2011","journal-title":"Food Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3143","DOI":"10.1007\/s10811-019-01816-7","article-title":"Phlorotannins from Fucales: Potential to control hyperglycemia and diabetes-related vascular complications","volume":"31","author":"Lopes","year":"2019","journal-title":"J. Appl. Phycol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"105","DOI":"10.2174\/1568026615666141209144506","article-title":"Antioxidant Capacities of Flavones and Benefits in Oxidative-Stress Related Diseases","volume":"15","author":"Catarino","year":"2015","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1416","DOI":"10.1016\/j.bcp.2007.11.023","article-title":"Structure-activity relationship of coumarin derivatives on xanthine oxidase-inhibiting and free radical-scavenging activities","volume":"75","author":"Lin","year":"2008","journal-title":"Biochem. Pharmacol."},{"key":"ref_40","first-page":"1215","article-title":"Assessment of the spatial variability of phenolic contents and associated bioactivities in the invasive alga Sargassum muticum sampled along its European range from Norway to Portugal","volume":"26","author":"Tanniou","year":"2014","journal-title":"J. Appl. Phycol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"396","DOI":"10.1016\/j.jff.2015.03.049","article-title":"Alaskan seaweeds lower inflammation in RAW 264.7 macrophages and decrease lipid accumulation in 3T3-L1 adipocytes","volume":"15","author":"Kellogg","year":"2015","journal-title":"J. Funct. Foods"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2234","DOI":"10.1007\/s12010-012-9761-1","article-title":"Antioxidant, anti-inflammatory, and anti-senescence activities of a phlorotannin-rich natural extract from Brown Seaweed Ascophyllum nodosum","volume":"167","author":"Dutot","year":"2012","journal-title":"Appl. Biochem. Biotechnol."},{"key":"ref_43","first-page":"1","article-title":"Silver-zeolite combined to polyphenol-rich extracts of Ascophyllum nodosum: Potential active role in prevention of periodontal diseases","volume":"9","author":"Cillard","year":"2014","journal-title":"PLoS ONE"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1016\/j.ifset.2016.07.027","article-title":"A comparison of the effects of an Ascophyllum nodosum ethanol extract and its molecular weight fractions on the inflammatory immune gene expression in-vitro and ex-vivo","volume":"37","author":"Bahar","year":"2016","journal-title":"Innov. Food Sci. Emerg. Technol."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Masters, S.L., Simon, A., Aksentijevich, I., and Kastner, D.L. (2009). Horror Autoinflammaticus: The Molecular Pathophysiology of Autoinflammatory Disease. Annu. Rev. Immunol.","DOI":"10.1146\/annurev.immunol.25.022106.141627"},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Rudolphi, K., Gerwin, N., Verzijl, N., van der Kraan, P., and van den Berg, W. (2003). Pralnacasan, an inhibitor of interleukin-1\u03b2 converting enzyme, reduces joint damage in two murine models of osteoarthritis. Osteoarthr. Cartil.","DOI":"10.1016\/S1063-4584(03)00153-5"},{"key":"ref_47","unstructured":"Callejas, N.A., Castrillo, A., Bosc\u00e1, L., and Mart\u00edn-Sanz, P. (1999). Inhibition of prostaglandin synthesis up-regulates cyclooxygenase-2 induced by lipopolysaccharide and peroxisomal proliferators. J. Pharmacol. Exp. Ther."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1016\/j.intimp.2012.08.021","article-title":"Anti-inflammatory effects of phlorofucofuroeckol B-rich ethyl acetate fraction obtained from Myagropsis myagroides on lipopolysaccharide-stimulated RAW 264.7 cells and mouse edema","volume":"14","author":"Joung","year":"2012","journal-title":"Int. Immunopharmacol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"46","DOI":"10.2527\/jas.53944","article-title":"Extracts of brown seaweeds can attenuate the bacterial lipopolysaccharide-induced pro-inflammatory response in the porcine colon ex vivo","volume":"90","author":"Bahar","year":"2012","journal-title":"J. Anim. Sci."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1016\/j.ifset.2016.04.014","article-title":"A cold water extract of Fucus vesiculosus inhibits lipopolysaccharide (LPS) induced pro-inflammatory responses in the porcine colon ex-vivo model","volume":"37","author":"Bahar","year":"2016","journal-title":"Innov. Food Sci. Emerg. Technol."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Pautz, A., Art, J., Hahn, S., Nowag, S., Voss, C., and Kleinert, H. (2010). Regulation of the expression of inducible nitric oxide synthase. Nitric Oxide-Biol. Chem.","DOI":"10.1016\/j.niox.2010.04.007"},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Wei, R., Lee, M.S., Lee, B., Oh, C.W., Choi, C.G., and Kim, H.R. (2016). Isolation and identification of anti-inflammatory compounds from ethyl acetate fraction of Ecklonia stolonifera and their anti-inflammatory action. J. Appl. Phycol.","DOI":"10.1007\/s10811-016-0847-y"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"410","DOI":"10.1016\/j.fct.2008.11.041","article-title":"Ecklonia cava ethanolic extracts inhibit lipopolysaccharide-induced cyclooxygenase-2 and inducible nitric oxide synthase expression in BV2 microglia via the MAP kinase and NF-\u03baB pathways","volume":"47","author":"Jung","year":"2008","journal-title":"Food Chem. Toxicol."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"570","DOI":"10.1021\/acs.jafc.5b04482","article-title":"Protective Effect of Brown Alga Phlorotannins against Hyper-inflammatory Responses in Lipopolysaccharide-Induced Sepsis Models","volume":"64","author":"Yang","year":"2016","journal-title":"J. Agric. Food Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1111\/jfbc.12312","article-title":"Eckol from Eisenia bicyclis inhibits inflammation through the Akt\/NF-\u03baB signaling in Propionibacterium acnes-induced human keratinocyte Hacat cells","volume":"41","author":"Eom","year":"2017","journal-title":"J. Food Biochem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1789","DOI":"10.1016\/j.tiv.2011.09.012","article-title":"Phlorofucofuroeckol A inhibits the LPS-stimulated iNOS and COX-2 expressions in macrophages via inhibition of NF-\u03baB, Akt, and p38 MAPK","volume":"25","author":"Kim","year":"2011","journal-title":"Toxicol. Vitr."},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Joe, M.J., Kim, S.N., Choi, H.Y., Shin, W.S., Park, G.M., Kang, D.W., and Yong, K.K. (2006). The inhibitory effects of eckol and dieckol from Ecklonia stolonifera on the expression of matrix metalloproteinase-1 in human dermal fibroblasts. Biol. Pharm. Bull.","DOI":"10.1248\/bpb.29.1735"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1113","DOI":"10.1007\/s10068-013-0191-9","article-title":"Anti-inflammatory activity of ethanolic extract of Sargassum sagamianum in RAW 264.7 cells","volume":"22","author":"Kim","year":"2013","journal-title":"Food Sci. Biotechnol."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"137","DOI":"10.3109\/08820139.2014.942459","article-title":"Anti-inflammatory effects of ethanolic extract from Sargassum horneri (Turner) C. Agardh on lipopolysaccharide-stimulated macrophage activation via NF-\u03baB pathway regulation","volume":"44","author":"Kim","year":"2015","journal-title":"Immunol. Invest."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/j.algal.2017.11.025","article-title":"Profiling phlorotannins from Fucus spp. of the Northern Portuguese coastline: Chemical approach by HPLC-DAD-ESI\/MSnand UPLC-ESI-QTOF\/MS","volume":"29","author":"Lopes","year":"2018","journal-title":"Algal Res."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"904","DOI":"10.1016\/j.foodchem.2017.08.032","article-title":"Structure dependent antioxidant capacity of phlorotannins from Icelandic Fucus vesiculosus by UHPLC-DAD-ECD-QTOFMS","volume":"240","author":"Hermund","year":"2018","journal-title":"Food Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"979","DOI":"10.1016\/j.foodres.2017.03.043","article-title":"Phenolic compounds from three brown seaweed species using LC-DAD\u2013ESI-MS\/MS","volume":"99","author":"Munekata","year":"2017","journal-title":"Food Res. Int."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1016\/j.chroma.2015.07.053","article-title":"Anti-proliferative activity and chemical characterization by comprehensive two-dimensional liquid chromatography coupled to mass spectrometry of phlorotannins from the brown macroalga Sargassum muticum collected on North-Atlantic coasts","volume":"1428","author":"Montero","year":"2016","journal-title":"J. Chromatogr. A"},{"key":"ref_64","doi-asserted-by":"crossref","unstructured":"Mezghani, S., Csupor, D., Bourguiba, I., Hohmann, J., Amri, M., and Bouaziz, M. (2016). Characterization of Phenolic Compounds of Ulva rigida (Chlorophycae) and Its Antioxidant Activity. Eur. J. Med. Plants.","DOI":"10.9734\/EJMP\/2016\/22935"},{"key":"ref_65","doi-asserted-by":"crossref","unstructured":"Kim, H.H., Kim, H.S., Ko, J.Y., Kim, C.Y., Lee, J.H., and Jeon, Y.J. (2016). A single-step isolation of useful antioxidant compounds from Ishige okamurae by using centrifugal partition chromatography. Fish. Aquat. Sci.","DOI":"10.1186\/s41240-016-0023-y"},{"key":"ref_66","unstructured":"Heo, S.J., Kim, J.P., Jung, W.K., Lee, N.H., Kang, H.S., Jun, E.M., Park, S.H., Kang, S.M., Lee, Y.J., and Park, P.J. (2008). Identification of chemical structure and free radical scavenging activity of diphlorethohydroxycarmalol isolated from a brown alga, Ishige okamurae. J. Microbiol. Biotechnol."},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Pereira, O., Catarino, M., Afonso, A., Silva, A., and Cardoso, S. (2018). Salvia elegans, Salvia greggii and Salvia officinalis Decoctions: Antioxidant Activities and Inhibition of Carbohydrate and Lipid Metabolic Enzymes. Molecules, 23.","DOI":"10.3390\/molecules23123169"},{"key":"ref_68","unstructured":"Barbosa, J.M. (2016). Prepara\u00e7\u00e3o e Avalia\u00e7\u00e3o da Atividade Anti-Inflamat\u00f3ria de novos Derivados Polifen\u00f3licos Glicosilados. [Master\u2019s Thesis, Faculty of Pharmacy, University of Coimbra]."},{"key":"ref_69","doi-asserted-by":"crossref","unstructured":"Jamalzadeh, L., Ghafoori, H., Sariri, R., Rabuti, H., Nasirzade, J., Hasani, H., and Aghamaali, M.R. (2016). Cytotoxic Effects of Some Common Organic Solvents on MCF-7, RAW-264.7 and Human Umbilical Vein Endothelial Cells. Avicenna J. Med. Biochem.","DOI":"10.17795\/ajmb-33453"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/21\/18\/6897\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:11:48Z","timestamp":1760177508000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/21\/18\/6897"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,9,20]]},"references-count":69,"journal-issue":{"issue":"18","published-online":{"date-parts":[[2020,9]]}},"alternative-id":["ijms21186897"],"URL":"https:\/\/doi.org\/10.3390\/ijms21186897","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,9,20]]}}}