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While anthocyanins, a group of flavonoids, exhibit promising anticancer potential, their structure\u2013activity relationship and adjuvant properties in TNBC remain underexplored. This study evaluated the anti\u2010proliferative effects of five structurally distinct anthocyani(di)ns\u2014cyanidin\u20103\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010glucoside (C3G), delphinidin\u20103\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010glucoside (D3G), delphinidin\u20103\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010rutinoside (D3R), malvidin\u20103\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010glucoside (M3G), and luteolinidin (LT)\u2014on mesenchymal TNBC cells. Combination assays of docetaxel (DT), a first\u2010line chemotherapeutic agent, with the most potent anthocyani(di)ns were conducted with TNBC and MCF\u201012A non\u2010cancerous cells. Trihydroxylated anthocyanins (D3G and D3R), particularly those with a monosaccharide at C3, demonstrated the strongest anti\u2010proliferative effects, reducing MDA\u2010MB\u2010231 cell proliferation by 95% and 70%, respectively, at 400\u2009\u03bcM (IC\n                    <jats:sub>50<\/jats:sub>\n                    : 253.28 and 341.33\u2009\u03bcM) without affecting MCF\u201012A cells. These were followed by 3\u2010deoxy (LT), dihydroxylated (C3G), and O\u2010methylated (M3G) anthocyani(di)ns. In Hs 578T mesenchymal TNBC cells, the trihydroxylated anthocyanins tested also induced strong anti\u2010proliferative effects. Synergistic effects (combination index &lt;\u20090.9) were observed for binary (D3G\u2009+\u2009DT or D3R\u2009+\u2009DT) and ternary (D3G\u2009+\u2009D3R\u2009+\u2009DT) combinations, reducing DT concentrations by up to 37\u2010fold and anthocyanin concentrations by up to 21.9\u2010fold to achieve similar inhibition. The ternary combination was the most effective, requiring the lowest concentrations of DT and anthocyanins. These results underscore the critical role of the ortho\u2010trihydroxylated structure in the anti\u2010proliferative effects of anthocyani(di)ns, highlighting trihydroxylated anthocyanins as promising adjuvants in TNBC treatment, with the potential to lower DT dosage, minimize side effects, delay resistance, and reduce treatment costs while maintaining efficacy.\n                  <\/jats:p>","DOI":"10.1002\/biof.70052","type":"journal-article","created":{"date-parts":[[2025,11,19]],"date-time":"2025-11-19T06:55:18Z","timestamp":1763535318000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Trihydroxylated Anthocyanins Potentiate Effects of Docetaxel in Mesenchymal Triple Negative Breast Cancer Cells"],"prefix":"10.1002","volume":"51","author":[{"given":"Mafalda","family":"Ribeiro","sequence":"first","affiliation":[{"name":"LAQV\/REQUIMTE, Laboratory of Bromatology and Hydrology, Department of Chemical Sciences, Faculty of Pharmacy University of Porto  Porto Portugal"},{"name":"LAQV\/REQUIMTE, Faculty of Nutrition and Food Sciences University of Porto  Porto Portugal"},{"name":"LAQV\/REQUIMTE, Laboratory of Pharmacology, Department of Drug Sciences, Faculty of Pharmacy University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miguel A.","family":"Faria","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Laboratory of Bromatology and Hydrology, Department of Chemical Sciences, Faculty of Pharmacy University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Vojtek","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Laboratory of Pharmacology, Department of Drug Sciences, Faculty of Pharmacy University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4668-9360","authenticated-orcid":false,"given":"Carmen","family":"Diniz","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Laboratory of Pharmacology, Department of Drug Sciences, Faculty of Pharmacy University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Isabel M. P. L. V. O.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Laboratory of Bromatology and Hydrology, Department of Chemical Sciences, Faculty of Pharmacy University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olga","family":"Viegas","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Faculty of Nutrition and Food Sciences University of Porto  Porto Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,11,18]]},"reference":[{"key":"e_1_2_10_2_1","volume-title":"Global Cancer Observatory: Cancer Today","author":"Ferlay J.","year":"2024"},{"key":"e_1_2_10_3_1","volume-title":"Global Cancer Observatory: Cancer Tomorrow","author":"Ferlay J.","year":"2024"},{"issue":"9","key":"e_1_2_10_4_1","first-page":"1864","article-title":"Breast Cancer Molecular Subtypes: From TNBC to QNBC","volume":"6","author":"Hon J. 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