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The incorporation of chlorine atoms and glucosyl moieties may influence their bioavailability, bioactivity, and pharmacological potential. In this study, 2\u2032-chloroflavone, 3\u2032-chloroflavone, 4\u2032-chloroflavone, and 6-chloroflavone were synthesized and biotransformed using entomopathogenic fungi cultures (\n                    <jats:italic>Isaria fumosorosea<\/jats:italic>\n                    KCH J2 and\n                    <jats:italic>Beauveria bassiana<\/jats:italic>\n                    KCH J1.5) to obtain novel glycosylated derivatives. Pharmacokinetic properties and drug-likeness were predicted using cheminformatics tools. Antimicrobial activity was evaluated against several microbial strains.\n                    <jats:italic>Enterococcus faecalis<\/jats:italic>\n                    ATCC 19433 showed complete growth inhibition with 4\u2032-chloroflavone and 6-chloroflavone, while 2\u2032-chloroflavone and 3\u2032-chloroflavone significantly inhibited its growth. Flavonoid glycosides and flavone demonstrated lower efficacy.\n                    <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    ATCC 29213 was completely or strongly inhibited by all tested compounds.\n                    <jats:italic>Lactobacillus acidophilus<\/jats:italic>\n                    ATCC 4356 was moderately inhibited by flavonoid aglycones and slightly inhibited by glycosides.\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    ATCC 25922 was most effectively inhibited by 4\u2032-chloroflavone and 6-chloroflavone, followed by 2\u2032-chloroflavone and 3\u2032-chloroflavone, with flavone and glycosides showing lower activity.\n                    <jats:italic>Candida albicans<\/jats:italic>\n                    ATCC 1023 exhibited high sensitivity to all compounds. Overall, chlorinated flavones demonstrated greater antimicrobial activity than non-chlorinated counterparts, with aglycones being more effective than glycosylated derivatives. The position of the chlorine atom significantly influences antimicrobial activity.\n                  <\/jats:p>","DOI":"10.1038\/s41598-025-11079-7","type":"journal-article","created":{"date-parts":[[2025,7,16]],"date-time":"2025-07-16T16:10:48Z","timestamp":1752682248000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Antimicrobial activity of new glycoside derivatives of chloroflavones obtained by fungal biotransformation"],"prefix":"10.1038","volume":"15","author":[{"given":"Agnieszka","family":"Krawczyk-\u0141ebek","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Barbara","family":"\u017barowska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomasz","family":"Janeczko","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Edyta","family":"Kostrzewa-Sus\u0142ow","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2025,7,16]]},"reference":[{"key":"11079_CR1","doi-asserted-by":"publisher","unstructured":"Martins, B. 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