{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,30]],"date-time":"2026-03-30T22:37:38Z","timestamp":1774910258030,"version":"3.50.1"},"reference-count":42,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2020,6,16]],"date-time":"2020-06-16T00:00:00Z","timestamp":1592265600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["PTDC\/SAU-PUB\/28736\/2017 , UIDB\/04423\/2020 and UIDP\/04423\/2020"],"award-info":[{"award-number":["PTDC\/SAU-PUB\/28736\/2017 , UIDB\/04423\/2020 and UIDP\/04423\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Antioxidants have long been used in the cosmetic industry to prevent skin photoaging, which is mediated by oxidative stress, making the search for new antioxidant compounds highly desirable in this field. Naturally occurring xanthones are polyphenolic compounds that can be found in microorganisms, fungi, lichens, and some higher plants. This class of polyphenols has a privileged scaffold that grants them several biological activities. We have previously identified simple oxygenated xanthones as promising antioxidants and disclosed as hit, 1,2-dihydroxyxanthone (1). Herein, we synthesized and studied the potential of xanthones with different polyoxygenated patterns as skin antiphotoaging ingredients. In the DPPH antioxidant assay, two newly synthesized derivatives showed IC50 values in the same range as ascorbic acid. The synthesized xanthones were discovered to be excellent tyrosinase inhibitors and weak to moderate collagenase and elastase inhibitors but no activity was revealed against hyaluronidase. Their metal-chelating effect (FeCl3 and CuCl2) as well as their stability at different pH values were characterized to understand their potential to be used as future cosmetic active agents. Among the synthesized polyoxygenated xanthones, 1,2-dihydroxyxanthone (1) was reinforced as the most promising, exhibiting a dual ability to protect the skin against UV damage by combining antioxidant\/metal-chelating properties with UV-filter capacity and revealed to be more stable in the pH range that is close to the pH of the skin. Lastly, the phototoxicity of 1,2-dihydroxyxanthone (1) was evaluated in a human keratinocyte cell line and no phototoxicity was observed in the concentration range tested.<\/jats:p>","DOI":"10.3390\/molecules25122782","type":"journal-article","created":{"date-parts":[[2020,6,18]],"date-time":"2020-06-18T12:21:46Z","timestamp":1592482906000},"page":"2782","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4077-6060","authenticated-orcid":false,"given":"Diana I. S. P.","family":"Resende","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"},{"name":"CIIMAR-Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"given":"Mariana C.","family":"Almeida","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"},{"name":"CIIMAR-Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"given":"Bruna","family":"Maciel","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Tecnologia Farmac\u00eautica, Departamento do Medicamento, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6650-5285","authenticated-orcid":false,"given":"Helena","family":"Carmo","sequence":"additional","affiliation":[{"name":"UCIBIO, REQUIMTE, Laborat\u00f3rio de Toxicologia, Departamento de Ci\u00eancias Biol\u00f3gicas, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"}]},{"given":"Jos\u00e9","family":"Sousa Lobo","sequence":"additional","affiliation":[{"name":"UCIBIO\/REQUIMTE, MedTec-Laborat\u00f3rio de Tecnologia Farmac\u00eautica, Departamento de Ci\u00eancias do Medicamento, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"}]},{"given":"Carlotta","family":"Dal Pozzo","sequence":"additional","affiliation":[{"name":"University of Ferrara, Dept. of Life Sciences and Biotechnology, Via Fossato di Mortara 17\/1944121 Ferrara, Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9314-8669","authenticated-orcid":false,"given":"Sara M.","family":"Cravo","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"},{"name":"CIIMAR-Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0706-8505","authenticated-orcid":false,"given":"Gon\u00e7alo P.","family":"Rosa","sequence":"additional","affiliation":[{"name":"cE3c\u2013Centre for Ecology, Evolution and Environmental Changes \/ Azorean Biodiversity Group, 9500-321 Ponta Delgada, Portugal"},{"name":"Faculdade de Ci\u00eancias e Tecnologia, Universidade dos A\u00e7ores, 9500-321 Ponta Delgada, Portugal"}]},{"given":"Aida","family":"Kane-Pag\u00e8s","sequence":"additional","affiliation":[{"name":"Faculdade de Ci\u00eancias e Tecnologia, Universidade dos A\u00e7ores, 9500-321 Ponta Delgada, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5797-8913","authenticated-orcid":false,"given":"Maria","family":"do Carmo Barreto","sequence":"additional","affiliation":[{"name":"cE3c\u2013Centre for Ecology, Evolution and Environmental Changes \/ Azorean Biodiversity Group, 9500-321 Ponta Delgada, Portugal"},{"name":"Faculdade de Ci\u00eancias e Tecnologia, Universidade dos A\u00e7ores, 9500-321 Ponta Delgada, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1498-048X","authenticated-orcid":false,"given":"Isabel F","family":"Almeida","sequence":"additional","affiliation":[{"name":"UCIBIO\/REQUIMTE, MedTec-Laborat\u00f3rio de Tecnologia Farmac\u00eautica, Departamento de Ci\u00eancias do Medicamento, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5397-4672","authenticated-orcid":false,"given":"Maria Em\u00edlia","family":"de Sousa","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"},{"name":"CIIMAR-Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4676-1409","authenticated-orcid":false,"given":"Madalena M. M.","family":"Pinto","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, 4050-313 Porto, Portugal"},{"name":"CIIMAR-Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental, Avenida General Norton de Matos, S\/N, 4450-208 Matosinhos, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2020,6,16]]},"reference":[{"key":"ref_1","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. Investig. Dermatol."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Dunaway, S., Odin, R., Zhou, L., Ji, L., Zhang, Y., and Kadekaro, A.L. (2018). Natural Antioxidants: Multiple Mechanisms to Protect Skin From Solar Radiation. Front. 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