{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T14:52:38Z","timestamp":1790952758795,"version":"4.1.0"},"reference-count":64,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2019,11,27]],"date-time":"2019-11-27T00:00:00Z","timestamp":1574812800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100005357","name":"Agent\u00fara na Podporu V\u00fdskumu a V\u00fdvoja","doi-asserted-by":"publisher","award":["APVV-15-0079"],"award-info":[{"award-number":["APVV-15-0079"]}],"id":[{"id":"10.13039\/501100005357","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006109","name":"VEGA","doi-asserted-by":"publisher","award":["1\/0686\/17"],"award-info":[{"award-number":["1\/0686\/17"]}],"id":[{"id":"10.13039\/501100006109","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Researchers Supporting Project","award":["RSP-2019\/59"],"award-info":[{"award-number":["RSP-2019\/59"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The beneficial effects of polyphenols, predominantly in the context of oxidative stress-related diseases such as cancer, cardiovascular diseases and neurological conditions including Alzheimer\u2019s and Parkinson\u2019s diseases, have been documented by a number of papers and reviews. The antioxidant\/prooxidant properties of phenolic compounds are related mainly to the number and positions of hydroxyl groups and to their redox metal (Cu, Fe) chelating capacity. In this work we studied structurally distinct phenolic molecules such as myricetin, morin, 3\u2032,4\u2032-dihydroxy-flavone, taxifolin and 4-hydroxycoumarin, either alone or as interacting with Cu2+ ions. EPR and UV-Vis spectroscopy confirmed that the effective binding of cupric ions to phenolic compounds requires the presence of the 3-OH and 4-CO groups on the flavonoid C ring and unsaturated C2-C3 bond of the C-ring, which permits through-conjugation with the B-ring. An ABTS assay revealed that radical scavenging activities of phenolic compounds are related to their number of hydroxyl groups, planarity of the molecular skeleton, extent of delocalization and they decrease in the order: myricetin &gt; morin &gt; 3\u2032,4\u2032-dihydroxyflavone ~ 4-hydroxy coumarin &gt; taxifolin. Absorption titrations indicate that copper ions can modulate the DNA binding affinity of flavonoids via the formation of their Cu-chelates. Gel electrophoresis measurements indicated that the protective effect of the phenolic compounds decreases in the order: 3\u2032,4\u2032-dihydroxyflavone &gt; 4-OH coumarin &gt; morin &gt; taxifolin ~ myricetin. This can be explained by the fact that myricetin, taxifolin and morin form stable Cu(II) complexes capable of causing DNA damage via interaction with DNA and ROS formation via the Fenton reaction. Application of ROS scavengers revealed the formation of singlet oxygen, superoxide and hydroxyl radicals and their concerted synergistic effect on the DNA. The overall results suggest that the most pronounced DNA damage has been observed for flavonoids containing higher number of hydroxyl groups (including 3-OH group of the C ring), such as myricetin (six hydroxyl groups), morin and taxifolin (five hydroxyl groups) in the presence of Cu(II) ions. The proposed mechanism of action by which Cu(II) complexes of myricetin, morin and taxifolin interact with DNA predispose these substances to act as potential anticancer agents. The anticancer activity of phenolic compounds can be explained by their moderate prooxidant properties, which can boost ROS formation and kill cancer cells. Alternatively, slight prooxidant properties may activate antioxidant systems, including antioxidant enzymes and low molecular antioxidants such as glutathione and thus act as preventive anticancer agents.<\/jats:p>","DOI":"10.3390\/molecules24234335","type":"journal-article","created":{"date-parts":[[2019,11,27]],"date-time":"2019-11-27T03:55:51Z","timestamp":1574826951000},"page":"4335","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":165,"title":["A Switch between Antioxidant and Prooxidant Properties of the Phenolic Compounds Myricetin, Morin, 3\u2032,4\u2032-Dihydroxyflavone, Taxifolin and 4-Hydroxy-Coumarin in the Presence of Copper(II) Ions: A Spectroscopic, Absorption Titration and DNA Damage Study"],"prefix":"10.3390","volume":"24","author":[{"given":"Klaudia","family":"Jomov\u00e1","sequence":"first","affiliation":[{"name":"Department of Chemistry, Constantine the Philosopher University in Nitra, 949 74 Nitra, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lenka","family":"Hudecova","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Constantine the Philosopher University in Nitra, 949 74 Nitra, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Lauro","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Constantine the Philosopher University in Nitra, 949 74 Nitra, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miriama","family":"Simunkova","sequence":"additional","affiliation":[{"name":"Faculty Chemical and Food Technology, Slovak University of Technology, 812 37 Bratislava, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saleh H.","family":"Alwasel","sequence":"additional","affiliation":[{"name":"King Saud University, Zoology Department, College of Science, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ibrahim M.","family":"Alhazza","sequence":"additional","affiliation":[{"name":"King Saud University, Zoology Department, College of Science, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marian","family":"Valko","sequence":"additional","affiliation":[{"name":"Faculty Chemical and Food Technology, Slovak University of Technology, 812 37 Bratislava, Slovakia"},{"name":"King Saud University, Zoology Department, College of Science, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,11,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"329","DOI":"10.1016\/j.arr.2012.01.006","article-title":"Natural polyphenols against neurodegenerative disorders: Potentials and pitfalls","volume":"11","author":"Ebrahimi","year":"2012","journal-title":"Ageing Res. 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