{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T00:26:38Z","timestamp":1785803198856,"version":"3.56.0"},"reference-count":56,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T00:00:00Z","timestamp":1760745600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Science Center, Poland","award":["2021\/41\/N\/NZ9\/01195"],"award-info":[{"award-number":["2021\/41\/N\/NZ9\/01195"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>This study explores the synthesis of chlorine-substituted flavanones and their biotechnologically derived glycosides in order to evaluate how structural modifications influence both antimicrobial activity and pharmacokinetic properties, with attention to issues such as solubility and membrane transport. Four chloroflavanones (2\u2032-, 3\u2032-, 4\u2032-, and 6-chloroflavanone) were synthesized and biotransformed using entomopathogenic fungi to obtain glycosylated derivatives. Antimicrobial activity was assessed against five microbial strains, while pharmacokinetic properties were predicted computationally. Results showed that 4\u2032-chloroflavanone demonstrated the strongest antimicrobial activity, particularly against Gram-positive bacteria Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 19433. Most compounds unexpectedly promoted Escherichia coli ATCC 25922 growth, except 4\u2032-chloroflavanone and 3\u2032-chloroflavanone 6-O-\u03b2-D-(4\u2033-O-methyl)-glucopyranoside. Nearly all compounds exhibited antifungal activity against Candida albicans ATCC 10231. Glycosylation generally reduced antimicrobial potency but improved water solubility and in silico predictions indicate markedly reduced blood\u2013brain barrier permeation and potential P-glycoprotein recognition. Selective chlorine substitution combined with biotechnological glycosylation may offer a route to antimicrobial flavonoids with improved aqueous solubility and favorable predicted pharmacokinetics.<\/jats:p>","DOI":"10.3390\/ijms262010138","type":"journal-article","created":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T08:18:54Z","timestamp":1760948334000},"page":"10138","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Fungal Biotransformation of Chloroflavanones and Antimicrobial Activity of Parent Compounds and Derived Products"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9507-0196","authenticated-orcid":false,"given":"Agnieszka","family":"Krawczyk-\u0141ebek","sequence":"first","affiliation":[{"name":"Department of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wroc\u0142aw University of Environmental and Life Sciences, 50-375 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9757-6684","authenticated-orcid":false,"given":"Tomasz","family":"Janeczko","sequence":"additional","affiliation":[{"name":"Department of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wroc\u0142aw University of Environmental and Life Sciences, 50-375 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Barbara","family":"\u017barowska","sequence":"additional","affiliation":[{"name":"Department of Biotechnology and Food Microbiology, Faculty of Biotechnology and Food Science, Wroc\u0142aw University of Environmental and Life Sciences, 51-630 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9259-0161","authenticated-orcid":false,"given":"Edyta","family":"Kostrzewa-Sus\u0142ow","sequence":"additional","affiliation":[{"name":"Department of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wroc\u0142aw University of Environmental and Life Sciences, 50-375 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,10,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"500","DOI":"10.1016\/j.ejmech.2013.04.064","article-title":"Superior Anticancer Activity of Halogenated Chalcones and Flavonols over the Natural Flavonol Quercetin","volume":"65","author":"Dias","year":"2013","journal-title":"Eur. 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