{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T19:17:41Z","timestamp":1790191061534,"version":"4.1.0"},"reference-count":51,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2024,5,30]],"date-time":"2024-05-30T00:00:00Z","timestamp":1717027200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Direcci\u00f3n General de Investigaci\u00f3n, Innovaci\u00f3n y Emprendimiento (DGIIE) of the Universidad T\u00e9cnica Federico Santa Mar\u00eda","award":["PI_LIR_2020_1"],"award-info":[{"award-number":["PI_LIR_2020_1"]}]},{"name":"Direcci\u00f3n General de Investigaci\u00f3n, Innovaci\u00f3n y Emprendimiento (DGIIE) of the Universidad T\u00e9cnica Federico Santa Mar\u00eda","award":["1130924"],"award-info":[{"award-number":["1130924"]}]},{"DOI":"10.13039\/100009051","name":"ANID","doi-asserted-by":"publisher","award":["PI_LIR_2020_1"],"award-info":[{"award-number":["PI_LIR_2020_1"]}],"id":[{"id":"10.13039\/100009051","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009051","name":"ANID","doi-asserted-by":"publisher","award":["1130924"],"award-info":[{"award-number":["1130924"]}],"id":[{"id":"10.13039\/100009051","id-type":"DOI","asserted-by":"publisher"}]},{"name":"FONDEF IT21I003","award":["PI_LIR_2020_1"],"award-info":[{"award-number":["PI_LIR_2020_1"]}]},{"name":"FONDEF IT21I003","award":["1130924"],"award-info":[{"award-number":["1130924"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Flavonoids are an abundant class of naturally occurring compounds with broad biological activities, but their limited abundance in nature restricts their use in medicines and food additives. Here we present the synthesis and determination of the antibacterial and antioxidant activities of twenty-two structurally related flavonoids (five of which are new) by scientifically validated methods. Flavanones (FV1\u2013FV11) had low inhibitory activity against the bacterial growth of MRSA 97-7. However, FV2 (C5,7,3\u2032,4\u2032 = OH) and FV6 (C5,7 = OH; C4\u2032 = SCH3) had excellent bacterial growth inhibitory activity against Gram-negative E. coli (MIC = 25 \u00b5g\/mL for both), while Chloramphenicol (MIC = 25 \u00b5g\/mL) and FV1 (C5,7,3\u2032 = OCH3; 4\u2032 = OH) showed inhibitory activity against Gram-positive L. monocytogenes (MIC = 25 \u00b5g\/mL). From the flavone series (FO1\u2013FO11), FO2 (C5,7,3\u2032,4\u2032 = OH), FO3 (C5,7,4\u2032 = OH; 3\u2032 = OCH3), and FO5 (C5,7,4\u2032 = OH) showed good inhibitory activity against Gram-positive MRSA 97-7 (MIC = 50, 12, and 50 \u00b5g\/mL, respectively), with FO3 being more active than the positive control Vancomycin (MIC = 25 \u00b5g\/mL). FO10 (C5,7= OH; 4\u2032 = OCH3) showed high inhibitory activity against E. coli and L. monocytogenes (MIC = 25 and 15 \u00b5g\/mL, respectively). These data add significantly to our knowledge of the structural requirements to combat these human pathogens. The positions and number of hydroxyl groups were key to the antibacterial and antioxidant activities.<\/jats:p>","DOI":"10.3390\/ijms25115999","type":"journal-article","created":{"date-parts":[[2024,5,30]],"date-time":"2024-05-30T10:42:34Z","timestamp":1717065754000},"page":"5999","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Antibacterial and Antioxidant Activity of Synthetic Polyoxygenated Flavonoids"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4391-1739","authenticated-orcid":false,"given":"Mauricio Enrique","family":"Osorio-Olivares","sequence":"first","affiliation":[{"name":"Laboratorio de S\u00edntesis Org\u00e1nica, Departamento de Qu\u00edmica, Universidad T\u00e9cnica Federico Santa Mar\u00eda, Valpara\u00edso 2390123, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4184-9815","authenticated-orcid":false,"given":"Yesseny","family":"V\u00e1squez-Mart\u00ednez","sequence":"additional","affiliation":[{"name":"Escuela de Medicina, Facultad de Ciencias M\u00e9dicas, Laboratorio de Virolog\u00eda Molecular y Control de Pat\u00f3genos, Facultad de Qu\u00edmica y Biolog\u00eda, Universidad de Santiago de Chile, Santiago 9170022, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7345-1123","authenticated-orcid":false,"given":"Katy","family":"D\u00edaz","sequence":"additional","affiliation":[{"name":"Laboratorio de Pruebas Biol\u00f3gicas, Departamento de Qu\u00edmica, Universidad T\u00e9cnica Federico Santa Mar\u00eda, Valpara\u00edso 2390123, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Javiera","family":"Canelo","sequence":"additional","affiliation":[{"name":"Escuela de Medicina, Facultad de Ciencias M\u00e9dicas, Laboratorio de Virolog\u00eda Molecular y Control de Pat\u00f3genos, Facultad de Qu\u00edmica y Biolog\u00eda, Universidad de Santiago de Chile, Santiago 9170022, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3980-3081","authenticated-orcid":false,"given":"Lautaro","family":"Taborga","sequence":"additional","affiliation":[{"name":"Laboratorio de Productos Naturales, Departamento de Qu\u00edmica, Universidad T\u00e9cnica Federico Santa Mar\u00eda, Valpara\u00edso 2390123, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4054-7487","authenticated-orcid":false,"given":"Luis","family":"Espinoza-Catal\u00e1n","sequence":"additional","affiliation":[{"name":"Laboratorio de S\u00edntesis Org\u00e1nica, Departamento de Qu\u00edmica, Universidad T\u00e9cnica Federico Santa Mar\u00eda, Valpara\u00edso 2390123, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,5,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Shah, A., and Smith, D.L. 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