{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,18]],"date-time":"2026-07-18T03:56:44Z","timestamp":1784347004230,"version":"3.55.0"},"reference-count":62,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2024,7,24]],"date-time":"2024-07-24T00:00:00Z","timestamp":1721779200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>This study aimed to explore the capacity of immobilized lipases on the acetylation of six aglycon flavonoids, namely myricetin, quercetin, luteolin, naringenin, fisetin and morin. For this purpose, lipase B from Candida antarctica (CaLB) and lipase from Thermomyces lanuginosus (TLL) were immobilized onto the surface of ZnOFe nanoparticles derived from an aqueous olive leaf extract. Various factors affecting the conversion of substrates and the formation of monoesterified and diesterified products, such as the amount of biocatalyst and the molar ratio of the substrates and reaction solvents were investigated. Both CaLB and TLL-ZnOFe achieved 100% conversion yield of naringenin to naringenin acetate after 72 h of reaction time, while TLL-ZnOFe achieved higher conversion yields of quercetin, morin and fisetin (73, 85 and 72% respectively). Notably, CaLB-ZnOFe displayed significantly lower conversion yields for morin compared with TLL-ZnOFe. Molecular docking analysis was used to elucidate this discrepancy, and it was revealed that the position of the hydroxyl groups of the B ring on morin introduced hindrances on the active site of CaLB. Finally, selected flavonoid esters showed significantly higher antimicrobial activity compared with the original compound. This work indicated that these lipase-based nanobiocatalysts can be successfully applied to produce lipophilic derivatives of aglycon flavonoids with improved antimicrobial activity.<\/jats:p>","DOI":"10.3390\/biom14080897","type":"journal-article","created":{"date-parts":[[2024,7,24]],"date-time":"2024-07-24T15:47:32Z","timestamp":1721836052000},"page":"897","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["A Study on the Regioselective Acetylation of Flavonoid Aglycons Catalyzed by Immobilized Lipases"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0717-712X","authenticated-orcid":false,"given":"Angelos","family":"Papanikolaou","sequence":"first","affiliation":[{"name":"Laboratory of Biotechnology, Department of Biological Applications and Technology, University of Ioannina, 45110 Ioannina, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4043-4060","authenticated-orcid":false,"given":"Alexandra V.","family":"Chatzikonstantinou","sequence":"additional","affiliation":[{"name":"Laboratory of Biotechnology, Department of Biological Applications and Technology, University of Ioannina, 45110 Ioannina, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3958-6830","authenticated-orcid":false,"given":"Renia","family":"Fotiadou","sequence":"additional","affiliation":[{"name":"Laboratory of Biotechnology, Department of Biological Applications and Technology, University of Ioannina, 45110 Ioannina, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-3278-7461","authenticated-orcid":false,"given":"Aliki","family":"Tsakni","sequence":"additional","affiliation":[{"name":"Department of Food Science and Technology, University of West Attica, 12243 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dimitra","family":"Houhoula","sequence":"additional","affiliation":[{"name":"Department of Food Science and Technology, University of West Attica, 12243 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Angeliki C.","family":"Polydera","sequence":"additional","affiliation":[{"name":"Laboratory of Biotechnology, Department of Biological Applications and Technology, University of Ioannina, 45110 Ioannina, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5811-368X","authenticated-orcid":false,"given":"Ioannis V.","family":"Pavlidis","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Crete, Voutes University Campus, 70013 Heraklion, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8196-4885","authenticated-orcid":false,"given":"Haralambos","family":"Stamatis","sequence":"additional","affiliation":[{"name":"Laboratory of Biotechnology, Department of Biological Applications and Technology, University of Ioannina, 45110 Ioannina, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,7,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"e47","DOI":"10.1017\/jns.2016.41","article-title":"Flavonoids: An Overview","volume":"5","author":"Panche","year":"2016","journal-title":"J. Nutr. Sci."},{"key":"ref_2","first-page":"7","article-title":"Biocatalytic Synthesis of Flavonoid Esters by Lipases and Their Biological Benefits","volume":"83","author":"Franco","year":"2017","journal-title":"Planta Med."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Verma, M.L., Sharma, S., Saini, R., Rani, V., and Kushwaha, R. (2020). Chapter 3- Bioflavonoids: Synthesis, functions and biotechnological applications. Biotechnological Production of Bioactive Compounds, Elsevier.","DOI":"10.1016\/B978-0-444-64323-0.00003-5"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"162750","DOI":"10.1155\/2013\/162750","article-title":"Chemistry and Biological Activities of Flavonoids: An Overview","volume":"2013","author":"Kumar","year":"2013","journal-title":"Sci. World J."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3321","DOI":"10.1021\/jf405570u","article-title":"Substituent Effects on in Vitro Antioxidizing Properties, Stability, and Solubility in Flavonoids","volume":"62","author":"Plaza","year":"2014","journal-title":"J. Agric. Food Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1016\/j.bej.2017.09.018","article-title":"Highly Efficient Enzymatic Acetylation of Flavonoids: Development of Solvent-Free Process and Kinetic Evaluation","volume":"128","author":"Banjanac","year":"2017","journal-title":"Biochem. Eng. J."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2237","DOI":"10.1016\/j.procbio.2006.05.027","article-title":"Enzymatic Acylation of Flavonoids","volume":"41","author":"Chebil","year":"2006","journal-title":"Process Biochem."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Katsoura, M.H., Theodosiou, E., Stamatis, H., and Kolisis, F.N. (2008). Chapter 9- Strategies for the Biocatalytic Lipophilization of Phenolic Antioxidants. Modern Biocatalysis, Wiley.","DOI":"10.1002\/9783527623839.ch9"},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Viskupicova, J., Ondrejovic, M., and Maliar, T. (2012). Enzyme-Mediated Preparation of Flavonoid Esters and Their Applications. Biochemistry, InTech.","DOI":"10.5772\/34174"},{"key":"ref_10","first-page":"355","article-title":"The Potential and Practical Applications of Acylated Flavonoids","volume":"64","year":"2009","journal-title":"Pharmazie"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1793","DOI":"10.1016\/j.procbio.2015.07.014","article-title":"Enzyme Catalyzed Synthesis of Cosmetic Esters and Its Intensification: A Review","volume":"50","author":"Khan","year":"2015","journal-title":"Process Biochem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"6519","DOI":"10.1007\/s00253-016-7647-9","article-title":"Enzymatic Synthesis of Bioactive Compounds with High Potential for Cosmeceutical Application","volume":"100","author":"Antonopoulou","year":"2016","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Baldessari, A. (2012). Lipases as Catalysts in Synthesis of Fine Chemicals. Methods in Molecular Biology, Humana Press.","DOI":"10.1007\/978-1-61779-600-5_25"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"6475","DOI":"10.1039\/c3cs35484a","article-title":"Immobilised Lipases in the Cosmetics Industry","volume":"42","author":"Thum","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Contesini, F.J., Davan\u00e7o, M.G., Borin, G.P., Vanegas, K.G., Cirino, J.P.G., de Melo, R.R., Mortensen, U.H., Hild\u00e9n, K., Campos, D.R., and Carvalho, P.d.O. (2020). Advances in Recombinant Lipases: Production, Engineering, Immobilization and Application in the Pharmaceutical Industry. Catalysts, 10.","DOI":"10.3390\/catal10091032"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Faber, K. (2011). Biotransformations in Organic Chemistry, Springer.","DOI":"10.1007\/978-3-642-17393-6"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Kazlauskas Bornscheuer, U.T., and Kazlauskas, R.J. (2006). Hydrolases in Organic Synthesis: Regio-and Stereoselective Biotransformations, John Wiley & Sons.","DOI":"10.1002\/3527607544"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6082","DOI":"10.1002\/cctc.202001107","article-title":"Looking Back: A Short History of the Discovery of Enzymes and How They Became Powerful Chemical Tools","volume":"12","author":"Heckmann","year":"2020","journal-title":"ChemCatChem"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"24539","DOI":"10.1039\/C9RA02225B","article-title":"Metal Nanoparticles Fabricated by Green Chemistry Using Natural Extracts: Biosynthesis, Mechanisms, and Applications","volume":"9","author":"Khalifa","year":"2019","journal-title":"RSC Adv."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"7278","DOI":"10.3390\/ma8115377","article-title":"Green Synthesis of Metallic Nanoparticles via Biological Entities","volume":"8","author":"Shah","year":"2015","journal-title":"Materials"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Fotiadou, R., Chatzikonstantinou, A.V., Hammami, M.A., Chalmpes, N., Moschovas, D., Spyrou, K., Polydera, A.C., Avgeropoulos, A., Gournis, D., and Stamatis, H. (2021). Green Synthesized Magnetic Nanoparticles as Effective Nanosupport for the Immobilization of Lipase: Application for the Synthesis of Lipophenols. Nanomaterials, 11.","DOI":"10.3390\/nano11020458"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1739","DOI":"10.1039\/c2ob06784f","article-title":"Unexpected Enzyme-Catalyzed Regioselective Acylation of Flavonoid Aglycones and Rapid Product Screening","volume":"10","author":"Kyriakou","year":"2012","journal-title":"Org. Biomol. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"11684","DOI":"10.1021\/acs.jafc.9b04667","article-title":"Biocatalytic Synthesis of Lipophilic Baicalin Derivatives as Antimicrobial Agents","volume":"67","author":"Xin","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4355","DOI":"10.1021\/jf0483669","article-title":"Experimental Determination of Octanol\u2013Water Partition Coefficients of Quercetin and Related Flavonoids","volume":"53","author":"Rothwell","year":"2005","journal-title":"J. Agric. Food Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5136","DOI":"10.1038\/s41598-023-32361-6","article-title":"Synthesis and Physicochemical Characterization of Acyl Myricetins as Potential Anti-Neuroexocytotic Agents","volume":"13","author":"Cho","year":"2023","journal-title":"Sci. Rep."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1016\/j.jbiotec.2011.09.007","article-title":"Combined Docking and Molecular Dynamics Simulations to Enlighten the Capacity of Pseudomonas cepacia and Candida antarctica Lipases to Catalyze Quercetin Acetylation","volume":"156","author":"Christelle","year":"2011","journal-title":"J. Biotechnol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1016\/j.molcatb.2009.01.011","article-title":"A Molecular Modelling Study to Rationalize the Regioselectivity in Acylation of Flavonoid Glycosides Catalyzed by Candida antarctica Lipase B","volume":"59","author":"Humeau","year":"2009","journal-title":"J. Mol. Catal. B Enzym."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1002\/pca.970","article-title":"A Single HPLC-PAD-APCI\/MS Method for the Quantitative Comparison of Phenolic Compounds Found in Leaf, Stem, Root and Fruit Extracts of Vaccinium angustifolium","volume":"18","author":"Harris","year":"2007","journal-title":"Phytochem. Anal."},{"key":"ref_29","first-page":"997","article-title":"APCI(+)FT-ICR MS Analysis of Hydrocarbons Using Isooctane as Ionizing Reagent\u2014A Comparison with HTGC-FID, GC\u00d7GC-MS and NMR","volume":"30","author":"Tose","year":"2018","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"29624","DOI":"10.1007\/s11356-021-17081-6","article-title":"Production of Hydroxytyrosol Rich Extract from Olea europaea Leaf with Enhanced Biological Activity Using Immobilized Enzyme Reactors","volume":"29","author":"Chatzikonstantinou","year":"2022","journal-title":"Environ. Sci. Pollut. Res."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Krieger, E., Dunbrack, R.L., Hooft, R.W.W., and Krieger, B. (2012). Assignment of Protonation States in Proteins and Ligands: Combining PKa Prediction with Hydrogen Bonding Network Optimization. Computational Drug Discovery and Design, Springer.","DOI":"10.1007\/978-1-61779-465-0_25"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"114","DOI":"10.1002\/prot.22570","article-title":"Improving Physical Realism, Stereochemistry, and Side-Chain Accuracy in Homology Modeling: Four Approaches That Performed Well in CASP8","volume":"77","author":"Krieger","year":"2009","journal-title":"Proteins: Struct. Funct. Bioinform."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"8577","DOI":"10.1063\/1.470117","article-title":"A Smooth Particle Mesh Ewald Method","volume":"103","author":"Essmann","year":"1995","journal-title":"J. Chem. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Papanikolaou, A., Chatzikonstantinou, A.V., Zarafeta, D., Kourkoumelis, N., Skretas, G., Pavlidis, \u0399.V., and Stamatis, H. (2023). Substrate Specificity of the Highly Thermostable Esterase EstDZ3. ChemBioChem, 24.","DOI":"10.1002\/cbic.202200642"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.jbiotec.2015.02.012","article-title":"Highly Efficient and Regioselective Synthesis of Dihydromyricetin Esters by Immobilized Lipase","volume":"199","author":"Li","year":"2015","journal-title":"J. Biotechnol."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Lee, J., Kim, K., Son, J., Lee, H., Song, J.H., Lee, T., Jeon, H., Kim, H.S., Park, S.J., and Yoo, H.Y. (2022). Improved Productivity of Naringin Oleate with Flavonoid and Fatty Acid by Efficient Enzymatic Esterification. Antioxidants, 11.","DOI":"10.3390\/antiox11020242"},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Zappaterra, F., Presini, F., Venturi, V., Lerin, L.A., Giovannini, P.P., and Costa, S. (2023). Biocatalytic Insights for the Synthesis of New Potential Prodrugs: Design of Two Ibuprofen Derivatives. Appl. Sci., 13.","DOI":"10.3390\/app13179852"},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Zhu, S., Du, B., Huang, D., Xia, Y., Chen, S., and Li, Y. (2022). Highly Efficient Regioselective Acylation of Dihydromyricetin Catalyzed by Lipase in Nonaqueous Solvents. Processes, 10.","DOI":"10.3390\/pr10071368"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"9496","DOI":"10.1021\/jf071943j","article-title":"Enzymatic Acylation of Flavonoids: Effect of the Nature of the Substrate, Origin of Lipase, and Regioselectivity","volume":"55","author":"Chebil","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Baek, Y., Lee, J., Son, J., Lee, T., Sobhan, A., Lee, J., Koo, S.-M., Shin, W.H., Oh, J.-M., and Park, C. (2020). Enzymatic Synthesis of Formate Ester through Immobilized Lipase and Its Reuse. Polymers, 12.","DOI":"10.3390\/polym12081802"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"5604","DOI":"10.1021\/acs.iecr.5b00996","article-title":"Enzymatic Synthesis of Flavonoid Ester: Elucidation of Its Kinetic Mechanism and Equilibrium Thermodynamic Behavior","volume":"54","author":"Razak","year":"2015","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Zappaterra, F., Meola, D., Presini, F., Aprile, S., Venturi, V., Nosengo, C., De Luca, C., Catani, M., Lerin, L.A., and Giovannini, P.P. (2024). Differential Effect of Nine Cinnamic Acid Derivatives on the Biocatalytic Activity of Candida Antarctica Lipase Type B. Curr. Res. Biotechnol., 8.","DOI":"10.1016\/j.crbiot.2024.100231"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2424","DOI":"10.1111\/j.1742-4658.2007.05781.x","article-title":"Modeling Hydration Mechanisms of Enzymes in Nonpolar and Polar Organic Solvents","volume":"274","author":"Soares","year":"2007","journal-title":"FEBS J."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/s12575-016-0033-2","article-title":"Lipase Catalysis in Organic Solvents: Advantages and Applications","volume":"18","author":"Kumar","year":"2016","journal-title":"Biol. Proced. Online"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1016\/j.foodchem.2018.06.085","article-title":"Hydrophilization of Bixin by Lipase-Catalyzed Transesterification with Sorbitol","volume":"268","author":"Jahangiri","year":"2018","journal-title":"Food Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2400014","DOI":"10.1002\/ejlt.202400014","article-title":"Improvement of the Oxidative Stability of Edible Oils through Enzymatic Esterification with Hydroxytyrosol-rich Extract","volume":"126","author":"Fotiadou","year":"2024","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"8395","DOI":"10.1021\/jo015761e","article-title":"Improved Preparation and Use of Room-Temperature Ionic Liquids in Lipase-Catalyzed Enantio- and Regioselective Acylations","volume":"66","author":"Park","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"491","DOI":"10.1016\/j.jbiotec.2005.12.022","article-title":"Use of Ionic Liquids as Media for the Biocatalytic Preparation of Flavonoid Derivatives with Antioxidant Potency","volume":"123","author":"Katsoura","year":"2006","journal-title":"J. Biotechnol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"214","DOI":"10.1016\/j.lwt.2018.10.098","article-title":"Lipase Synthesis of Isoamyl Acetate Using Different Acyl Donors: Comparison of Novel Esterification Techniques","volume":"101","author":"Zare","year":"2019","journal-title":"LWT"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1396","DOI":"10.1002\/mnfr.201600025","article-title":"Dietary Flavonoid Fisetin for Cancer Prevention and Treatment","volume":"60","author":"Lall","year":"2016","journal-title":"Mol. Nutr. Food Res."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Mottaghi, S., and Abbaszadeh, H. (2021). The Anticarcinogenic and Anticancer Effects of the Dietary Flavonoid, Morin: Current Status, Challenges, and Future Perspectives. Phytother. Res.","DOI":"10.1002\/ptr.7270"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1397","DOI":"10.1007\/s12010-020-03330-w","article-title":"Mechanisms of Action of Luteolin Against Single- and Dual-Species of Escherichia Coli and Enterobacter Cloacae and Its Antibiofilm Activities","volume":"193","author":"Qian","year":"2021","journal-title":"Appl. Biochem. Biotechnol."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/S0009-3084(98)00030-9","article-title":"Anatomy of Lipase Binding Sites: The Scissile Fatty Acid Binding Site","volume":"93","author":"Pleiss","year":"1998","journal-title":"Chem. Phys. Lipids"},{"key":"ref_54","doi-asserted-by":"crossref","unstructured":"Ruiz-Cruz, S., Chaparro-Hern\u00e1ndez, S., Ruiz, K.L.H., Cira-Ch\u00e1vez, L.A., Estrada-Alvarado, M.I., Ortega, L.E.G., Ornelas-Paz, J.d.J., and Mata, M.A.L. (2017). Flavonoids: Important Biocompounds in Food. Flavonoids\u2014From Biosynthesis to Human Health, InTech.","DOI":"10.5772\/67864"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"8","DOI":"10.5530\/ijper.53.1.3","article-title":"Chemistry and Pharmacology of Flavonoids\u2014A Review","volume":"53","author":"Rana","year":"2019","journal-title":"Indian J. Pharm. Educ. Res."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1080\/10408398.2016.1196334","article-title":"Modifications of Dietary Flavonoids towards Improved Bioactivity: An Update on Structure\u2013Activity Relationship","volume":"58","author":"Chen","year":"2018","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1016\/j.foodres.2015.06.021","article-title":"Therapeutic Potential of Flavonoids and Their Mechanism of Action against Microbial and Viral Infections\u2014A Review","volume":"77","author":"Ahmad","year":"2015","journal-title":"Food Res. Int."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1007\/s11101-018-9591-z","article-title":"Comprehensive Review of Antimicrobial Activities of Plant Flavonoids","volume":"18","author":"Bartoszewski","year":"2019","journal-title":"Phytochem. Rev."},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"Babii, C., Mihalache, G., Bahrin, L.G., Neagu, A.-N., Gostin, I., Mihai, C.T., S\u00e2rbu, L.-G., Birsa, L.M., and Stefan, M. (2018). A Novel Synthetic Flavonoid with Potent Antibacterial Properties: In Vitro Activity and Proposed Mode of Action. PLoS ONE, 13.","DOI":"10.1371\/journal.pone.0194898"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1282","DOI":"10.1111\/jam.14271","article-title":"Synthetic Flavonoids with Antimicrobial Activity: A Review","volume":"127","author":"Sarbu","year":"2019","journal-title":"J. Appl. Microbiol."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1016\/j.jbiotec.2004.12.002","article-title":"Biocatalytic Preparation of Acylated Derivatives of Flavonoid Glycosides Enhances Their Antioxidant and Antimicrobial Activity","volume":"116","author":"Mellou","year":"2005","journal-title":"J. Biotechnol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"374","DOI":"10.1016\/j.ijantimicag.2004.03.024","article-title":"Anti-Staphylococcus Aureus Activity and Oxacillin Resistance Modulating Capacity of 3-O-Acyl-Catechins","volume":"24","author":"Stapleton","year":"2004","journal-title":"Int. J. Antimicrob. 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