{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T04:36:15Z","timestamp":1775190975076,"version":"3.50.1"},"reference-count":35,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2012,12,10]],"date-time":"2012-12-10T00:00:00Z","timestamp":1355097600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Purified phlorotannin extracts from four brown seaweeds (Cystoseira nodicaulis (Withering) M. Roberts, Cystoseira tamariscifolia (Hudson) Papenfuss, Cystoseira usneoides (Linnaeus) M. Roberts and Fucus spiralis Linnaeus), were characterized by HPLC-DAD-ESI-MSn. Fucophloroethol, fucodiphloroethol, fucotriphloroethol, 7-phloroeckol, phlorofucofuroeckol and bieckol\/dieckol were identified. The antioxidant activity and the hyaluronidase (HAase) inhibitory capacity exhibited by the extracts were also assessed. A correlation between the extracts activity and their chemical composition was established. F. spiralis, the species presenting higher molecular weight phlorotannins, generally displayed the strongest lipid peroxidation inhibitory activity (IC50 = 2.32 mg\/mL dry weight) and the strongest HAase inhibitory capacity (IC50 = 0.73 mg\/mL dry weight). As for superoxide radical scavenging, C. nodicaulis was the most efficient species (IC50 = 0.93 mg\/mL dry weight), followed by F. spiralis (IC50 = 1.30 mg\/mL dry weight). These results show that purified phlorotannin extracts have potent capabilities for preventing and slowing down the skin aging process, which is mainly associated with free radical damage and with the reduction of hyaluronic acid concentration, characteristic of the process.<\/jats:p>","DOI":"10.3390\/md10122766","type":"journal-article","created":{"date-parts":[[2012,12,10]],"date-time":"2012-12-10T11:03:00Z","timestamp":1355137380000},"page":"2766-2781","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":208,"title":["Phlorotannin Extracts from Fucales Characterized by HPLC-DAD-ESI-MSn: Approaches to Hyaluronidase Inhibitory Capacity and Antioxidant Properties"],"prefix":"10.3390","volume":"10","author":[{"given":"Federico","family":"Ferreres","sequence":"first","affiliation":[{"name":"Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS (CSIC), P.O. Box 164, 30100 Campus University Espinardo, Murcia, Spain"}]},{"given":"Graciliana","family":"Lopes","sequence":"additional","affiliation":[{"name":"REQUIMTE\/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, no. 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7646-0386","authenticated-orcid":false,"given":"Angel","family":"Gil-Izquierdo","sequence":"additional","affiliation":[{"name":"Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS (CSIC), P.O. Box 164, 30100 Campus University Espinardo, Murcia, Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9764-3920","authenticated-orcid":false,"given":"Paula","family":"Andrade","sequence":"additional","affiliation":[{"name":"REQUIMTE\/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, no. 228, 4050-313 Porto, Portugal"}]},{"given":"Carla","family":"Sousa","sequence":"additional","affiliation":[{"name":"REQUIMTE\/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, no. 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4849-8840","authenticated-orcid":false,"given":"Teresa","family":"Mouga","sequence":"additional","affiliation":[{"name":"GIRM\u2014Marine Resources Research Group, School of Tourism and Maritime Technology, Polytechnic Institute of Leiria, Santu\u00e1rio N.\u00aa Sra. Dos Rem\u00e9dios, Apartado 126, 2524-909 Peniche, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0740-4396","authenticated-orcid":false,"given":"Patr\u00edcia","family":"Valent\u00e3o","sequence":"additional","affiliation":[{"name":"REQUIMTE\/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, no. 228, 4050-313 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2012,12,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1016\/j.phymed.2003.10.009","article-title":"Effects of the aqueous extract of Bryothamnion triquetrum on chemical hypoxia and aglycemia-induced damage in GT1\u20137 mouse hypothalamic immortalized cells","volume":"13","author":"Fallarero","year":"2006","journal-title":"Phytomedicine"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"e31145","DOI":"10.1371\/journal.pone.0031145","article-title":"Can phlorotannins purified extracts constitute a novel pharmacological alternative for microbial infections with associated inflammatory conditions?","volume":"7","author":"Lopes","year":"2012","journal-title":"PLoS One"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1016\/j.etap.2011.09.004","article-title":"Potential pharmacological applications of polyphenolic derivatives from marine brown algae","volume":"32","author":"Thomas","year":"2011","journal-title":"Environ. Toxicol. Pharmacol."},{"key":"ref_4","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_5","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1002\/pca.1210","article-title":"Phenolic compounds in the brown seaweed Ascophyllum nodosum: Distribution and radical-scavenging activities","volume":"21","author":"Audibert","year":"2010","journal-title":"Phytochem. Anal."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1326","DOI":"10.1021\/jf204112f","article-title":"Phlorotannins from brown algae (Fucus vesiculosus) inhibited the formation of advanced glycation endproducts by scavenging reactive carbonyls","volume":"60","author":"Liu","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2219","DOI":"10.1016\/j.procbio.2011.09.015","article-title":"Phlorotannins as bioactive agents from brown algae","volume":"46","author":"Li","year":"2011","journal-title":"Process Biochem."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"McClintock, J.B., and Baker, B.J. (2001). Marine Chemical Ecology, CRC Press.","DOI":"10.1201\/9781420036602"},{"key":"ref_9","unstructured":"Round, F.E., and Chapman, D.J. (1986). Progress in Phycological Research, Biopress."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1631\/jzus.B0820185","article-title":"Anti-allergic effects of ethanol extracts from brown seaweeds","volume":"10","author":"Samee","year":"2009","journal-title":"J. Zhejiang Univ. Sci. B"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"703","DOI":"10.1046\/j.1365-2621.2002.00603.x","article-title":"Inhibitory activity of brown algal phlorotannins against hyaluronidase","volume":"37","author":"Shibata","year":"2002","journal-title":"Int. J. Food Sci. Technol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1007\/s10811-007-9254-8","article-title":"Antioxidant activities of phlorotannins isolated from Japanese Laminariaceae","volume":"20","author":"Shibata","year":"2008","journal-title":"J. Appl. Phycol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1016\/S0753-3322(99)80087-0","article-title":"Skin antioxidants: Their role in aging and in oxidative stress\u2014New approaches for their evaluation","volume":"53","author":"Kohen","year":"1999","journal-title":"Biomed. Pharmacother."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2565","DOI":"10.1038\/sj.jid.5700340","article-title":"Oxidative stress in the pathogenesis of skin disease","volume":"126","author":"Bickers","year":"2006","journal-title":"J. Invest. Dermatol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"64","DOI":"10.1016\/j.phymed.2011.10.003","article-title":"Bioactive compounds from natural resources against skin aging","volume":"19","author":"Muckerjee","year":"2011","journal-title":"Phytomedicine"},{"key":"ref_16","first-page":"1","article-title":"Skin elasticity and sea polyphenols","volume":"1","author":"Hwang","year":"2010","journal-title":"Seanol Sci. Centre Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1080\/01932690801934653","article-title":"Inhibitory effects of triphlorethol-A on MMP-1 induced by oxidative stress in human keratinocytes via ERK and AP-1 inhibition","volume":"71","author":"Kang","year":"2008","journal-title":"J. Toxicol. Environ. Health A"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3483","DOI":"10.1021\/jf900820x","article-title":"Isolation and identification of phlorotannins from Ecklonia stolonifera with antioxidant and anti-inflammatory properties","volume":"57","author":"Kim","year":"2009","journal-title":"J. Agric. Food Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"889","DOI":"10.1093\/jac\/dkf222","article-title":"Bactericidal activity of phlorotannins from the brown alga Ecklonia kurome","volume":"50","author":"Nagayama","year":"2002","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_20","first-page":"347","article-title":"Co-occurrence and antioxidant activities of fucol and fucophlorethol classes of polymeric phenols in Fucus spiralis","volume":"49","author":"Florian","year":"2006","journal-title":"Bot. Mar."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1115","DOI":"10.1016\/0031-9422(75)85198-3","article-title":"Bifuhalol und diphlorethol aus Cystoseira tamariscifolia","volume":"14","author":"Glombitza","year":"1975","journal-title":"Phytochemistry"},{"key":"ref_22","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_23","doi-asserted-by":"crossref","first-page":"680","DOI":"10.1007\/s00300-005-0735-4","article-title":"Variation in phlorotannin content within two species of brown macroalgae (Desmarestia anceps and D. menziesii) from the Western Antarctic Peninsula","volume":"28","author":"Fairhead","year":"2005","journal-title":"Polar Biol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1273","DOI":"10.1007\/BF02266965","article-title":"A new assay for quantifying brown algal phlorotannins and comparisons to previous methods","volume":"22","author":"Stern","year":"1996","journal-title":"J. Chem. Ecol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"547","DOI":"10.1002\/pca.2354","article-title":"Profiling phlorotannins in brown macroalgae by Liquid Chromatography-High Resolution Mass Spectrometry","volume":"23","author":"Steevensz","year":"2012","journal-title":"Phytochem. Anal."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1016\/j.phytochem.2009.10.020","article-title":"In vitro chemoprotective potential of fucophlorethols from the brown alga  Fucus vesiculosus L. by anti-oxidant activity and inhibition of selected cytochrome P450 enzymes","volume":"71","author":"Parys","year":"2012","journal-title":"Phytochemistry"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1417","DOI":"10.1016\/S0031-9422(97)00499-8","article-title":"Fucophlorethols from the brown algae Sargassum spinuligerum and Cystophora torulosa","volume":"46","author":"Glombitza","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2807","DOI":"10.1271\/bbb.60417","article-title":"Isolation of a new anti-allergic phlorotannin, phlorofucofuroeckol-B, from an edible brown alga Eisenia arborea","volume":"70","author":"Sugiura","year":"2006","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"693","DOI":"10.1016\/j.foodchem.2009.03.025","article-title":"Antioxidant and antitumoural activities of some Phaeophyta from Britany coasts","volume":"116","author":"Zubia","year":"2009","journal-title":"Food Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4205","DOI":"10.1021\/jf072740y","article-title":"Tronchuda cabbage (Brassica oleracea L. var. costata DC): Scavenger of reactive nitrogen species","volume":"56","author":"Sousa","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"595","DOI":"10.3136\/fstr.14.595","article-title":"Radical scavenging and hyaluronidase inhibitory activities of phlorotannins from the edible brown alga Eisenia arborea","volume":"14","author":"Sugiura","year":"2008","journal-title":"Food Sci. Technol. Res."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2841","DOI":"10.1016\/j.fct.2009.09.004","article-title":"Ficus carica L.: Metabolic and biological screening","volume":"47","author":"Oliveira","year":"2009","journal-title":"Food Chem. Toxicol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1016\/S0168-9452(02)00332-1","article-title":"Antioxidant activity and free radical scavenging capacity between Korean medicinal plants and flavonoids by assay-guided comparison","volume":"163","author":"Choi","year":"2002","journal-title":"Plant Sci."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Taniguchi, N., and Gutteridge, J.M.C. (2000). Experimental Protocols for Reactive Oxygen and Nitrogen Species, Press Inc.","DOI":"10.1093\/oso\/9780198506683.001.0001"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/S0304-3835(98)00196-7","article-title":"Quantitation of hyaluronidases by the Morgan-Elson reaction: Comparison of the enzyme activities in the plasma of tumor patients and healthy volunteers","volume":"131","author":"Muckenschnabela","year":"1998","journal-title":"Cancer Lett."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/10\/12\/2766\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:54:09Z","timestamp":1760219649000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/10\/12\/2766"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,12,10]]},"references-count":35,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2012,12]]}},"alternative-id":["md10122766"],"URL":"https:\/\/doi.org\/10.3390\/md10122766","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,12,10]]}}}