{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T00:17:31Z","timestamp":1789690651286,"version":"4.0.1"},"reference-count":69,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2021,5,22]],"date-time":"2021-05-22T00:00:00Z","timestamp":1621641600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100007194","name":"Universidad de Santiago de Chile","doi-asserted-by":"publisher","award":["DICYT-USACH 021901VM"],"award-info":[{"award-number":["DICYT-USACH 021901VM"]}],"id":[{"id":"10.13039\/100007194","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100007194","name":"Universidad de Santiago de Chile","doi-asserted-by":"publisher","award":["DICYT-USACH 021641MC"],"award-info":[{"award-number":["DICYT-USACH 021641MC"]}],"id":[{"id":"10.13039\/100007194","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100009068","name":"Consejo Nacional de Innovaci\u00f3n, Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["1130924"],"award-info":[{"award-number":["1130924"]}],"id":[{"id":"10.13039\/501100009068","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Prenylated flavonoids are an important class of naturally occurring flavonoids with important biological activity, but their low abundance in nature limits their application in medicines. Here, we showed the hemisynthesis and the determination of various biological activities of seven prenylated flavonoids, named 7\u201313, with an emphasis on antimicrobial ones. Compounds 9, 11, and 12 showed inhibitory activity against human pathogenic fungi. Compounds 11, 12 (flavanones) and 13 (isoflavone) were the most active against clinical isolated Staphylococcus aureus MRSA, showing that structural requirements as prenylation at position C-6 or C-8 and OH at positions C-5, 7, and 4\u2032 are key to the antibacterial activity. The combination of 11 or 12 with commercial antibiotics synergistically enhanced the antibacterial activity of vancomycin, ciprofloxacin, and methicillin in a factor of 10 to 100 times against drug-resistant bacteria. Compound 11 combined with ciprofloxacin was able to decrease the levels of ROS generated by ciprofloxacin. According to docking results of S enantiomer of 11 with ATP-binding cassette transporter showed the most favorable binding energy; however, more studies are needed to support this result.<\/jats:p>","DOI":"10.3390\/ijms22115472","type":"journal-article","created":{"date-parts":[[2021,5,23]],"date-time":"2021-05-23T23:58:05Z","timestamp":1621814285000},"page":"5472","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study"],"prefix":"10.3390","volume":"22","author":[{"given":"Mauricio","family":"Osorio","sequence":"first","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"}]},{"given":"Marcela","family":"Carvajal","sequence":"additional","affiliation":[{"name":"Centro de Biotecnolog\u00eda CB-DAL, Universidad T\u00e9cnica Federico Santa Mar\u00eda, Valpara\u00edso 2390136, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alejandra","family":"Vergara","sequence":"additional","affiliation":[{"name":"Centro de Biotecnolog\u00eda CB-DAL, Universidad T\u00e9cnica Federico Santa Mar\u00eda, Valpara\u00edso 2390136, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Estefania","family":"Butassi","sequence":"additional","affiliation":[{"name":"Farmacognosia, Facultad de Ciencias Bioqu\u00edmicas y Farmac\u00e9uticas, Universidad Nacional de Rosario, Suipacha 531, Rosario 2000, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Susana","family":"Zacchino","sequence":"additional","affiliation":[{"name":"Farmacognosia, Facultad de Ciencias Bioqu\u00edmicas y Farmac\u00e9uticas, Universidad Nacional de Rosario, Suipacha 531, Rosario 2000, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carolina","family":"Mascayano","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias del Ambiente, Facultad de Qu\u00edmica y Biolog\u00eda, Universidad de Santiago de Chile, Santiago 9170022, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6268-1118","authenticated-orcid":false,"given":"Margarita","family":"Montoya","sequence":"additional","affiliation":[{"name":"Laboratorio Bioqu\u00edmica Celular, Departamento de Biolog\u00eda, Facultad de Qu\u00edmica y Biolog\u00eda, Universidad de Santiago de Chile, Santiago 9170022, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sophia","family":"Mej\u00edas","sequence":"additional","affiliation":[{"name":"Laboratorio Bioqu\u00edmica Celular, Departamento de Biolog\u00eda, Facultad de Qu\u00edmica y Biolog\u00eda, Universidad de Santiago de Chile, Santiago 9170022, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marcelo Cortez-San","family":"Mart\u00edn","sequence":"additional","affiliation":[{"name":"Laboratorio de Virolog\u00eda Molecular y Control de Pat\u00f3genos, Departamento de Biolog\u00eda, Facultad de Qu\u00edmica y Biolog\u00eda, Universidad de Santiago de Chile, Santiago 9170022, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yesseny","family":"V\u00e1squez-Mart\u00ednez","sequence":"additional","affiliation":[{"name":"Programa Centro de Investigaciones Biom\u00e9dicas Aplicadas, Escuela de Medicina, Facultad de Ciencias M\u00e9dicas, Universidad de Santiago de Chile, Santiago 9170022, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,5,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1007\/s12272-011-0206-0","article-title":"In vitro sortase A inhibitory and antimicrobial activity of flavonoids isolated from the roots of Sophora flavescens","volume":"34","author":"Oh","year":"2011","journal-title":"Arch. 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