{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T21:40:10Z","timestamp":1761514810107,"version":"build-2065373602"},"reference-count":47,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2021,9,4]],"date-time":"2021-09-04T00:00:00Z","timestamp":1630713600000},"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\/QUI-COL\/32351\/2017","CEECIND\/00466\/2017","ROTEIRO\/0031\/2013-PINFRA\/22161\/2016"],"award-info":[{"award-number":["PTDC\/QUI-COL\/32351\/2017","CEECIND\/00466\/2017","ROTEIRO\/0031\/2013-PINFRA\/22161\/2016"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["MEX\/Ref. 288188"],"award-info":[{"award-number":["MEX\/Ref. 288188"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Flavylium-based compounds in their acidic and cationic form bring color to aqueous solutions, while under slightly acidic or neutral conditions they commonly bring discoloration. Selective host-guest complexation between water-soluble p-sulfonatocalix[n]arenes (SCn) macrocycles and the flavylium cationic species can increase the stability of the colored form, expanding its domain over the pH scale. The association constants between SCn and the cationic (acid) and neutral basic forms of flavylium-based compounds were determined through UV-Vis host-guest titrations at different pH values. The affinity of the hosts for synthetic chromophore was found to be higher than for a natural anthocyanin (Oenin). The higher affinity of SC4 for the synthetic flavylium was confirmed by 1H NMR showing a preferential interaction of the flavylium phenyl ring with the host cavity. In contrast with its synthetic counterpart, the flavylium substitution pattern in the anthocyanin seems to limit the inclusion of the guest in the host\u2019s binding pocket. In this case, the higher affinity was observed for the octamer (SC8) likely due to its larger cavity and higher number of negatively charged sulfonate groups.<\/jats:p>","DOI":"10.3390\/molecules26175389","type":"journal-article","created":{"date-parts":[[2021,9,6]],"date-time":"2021-09-06T13:18:26Z","timestamp":1630934306000},"page":"5389","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Anthocyanin Color Stabilization by Host-Guest Complexation with p-Sulfonatocalix[n]arenes"],"prefix":"10.3390","volume":"26","author":[{"given":"Johan","family":"Mendoza","sequence":"first","affiliation":[{"name":"LAQV\u2014REQUIMTE, Departamento de Qu\u00edmica, Faculdade de Ci\u00eancias e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2226-0404","authenticated-orcid":false,"given":"Luis","family":"Cruz","sequence":"additional","affiliation":[{"name":"LAQV\u2014REQUIMTE, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal"}]},{"given":"Victor de","family":"Freitas","sequence":"additional","affiliation":[{"name":"LAQV\u2014REQUIMTE, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8529-6848","authenticated-orcid":false,"given":"Fernando","family":"Pina","sequence":"additional","affiliation":[{"name":"LAQV\u2014REQUIMTE, Departamento de Qu\u00edmica, Faculdade de Ci\u00eancias e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0121-3695","authenticated-orcid":false,"given":"Nuno","family":"Bas\u00edlio","sequence":"additional","affiliation":[{"name":"LAQV\u2014REQUIMTE, Departamento de Qu\u00edmica, Faculdade de Ci\u00eancias e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2021,9,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1361779","DOI":"10.1080\/16546628.2017.1361779","article-title":"Anthocyanidins and anthocyanins: Colored pigments as food, pharmaceutical ingredients, and the potential health benefits","volume":"61","author":"Khoo","year":"2017","journal-title":"J. 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