See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/328423406 Antibacterial activity of flavonoids and their structure–activity relationship: An update review Article in Phytotherapy Research · October 2018 DOI: 10.1002/ptr.6208 CITATIONS 24 READS 1,003 4 authors: Some of the authors of this publication are also working on these related projects: Study the effect of natural products on autoimmune diseases View project Antibacterial Activity of Silver Nanoparticle- Loaded Soft Contact Lens Materials: The Effect of Monomer Composition . View project Faegheh Farhadi Mashhad University of Medical Sciences 5 PUBLICATIONS 25 CITATIONS SEE PROFILE Bahman Khameneh Mashhad University of Medical Sciences 35 PUBLICATIONS 444 CITATIONS SEE PROFILE Mehrdad Iranshahi Mashhad University of Medical Sciences 234 PUBLICATIONS 5,009 CITATIONS SEE PROFILE Milad Iranshahi Mashhad University of Medical Sciences 35 PUBLICATIONS 582 CITATIONS SEE PROFILE All content following this page was uploaded by Faegheh Farhadi on 29 October 2018. The user has requested enhancement of the downloaded file.
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See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/328423406
Antibacterial activity of flavonoids and their structure–activity relationship:
An update review
Article in Phytotherapy Research · October 2018
DOI: 10.1002/ptr.6208
CITATIONS
24READS
1,003
4 authors:
Some of the authors of this publication are also working on these related projects:
Study the effect of natural products on autoimmune diseases View project
Antibacterial Activity of Silver Nanoparticle- Loaded Soft Contact Lens Materials: The Effect of Monomer Composition . View project
Faegheh Farhadi
Mashhad University of Medical Sciences
5 PUBLICATIONS 25 CITATIONS
SEE PROFILE
Bahman Khameneh
Mashhad University of Medical Sciences
35 PUBLICATIONS 444 CITATIONS
SEE PROFILE
Mehrdad Iranshahi
Mashhad University of Medical Sciences
234 PUBLICATIONS 5,009 CITATIONS
SEE PROFILE
Milad Iranshahi
Mashhad University of Medical Sciences
35 PUBLICATIONS 582 CITATIONS
SEE PROFILE
All content following this page was uploaded by Faegheh Farhadi on 29 October 2018.
The user has requested enhancement of the downloaded file.
Aderogba, M. A., Ndhlala, A. R., Rengasamy, K. R., & Van Staden, J. (2013).Antimicrobial and selected in vitro enzyme inhibitory effects of leafextracts, flavonols and indole alkaloids isolated from Crotonmenyharthii. Molecules, 18(10), 12633–12644.
Alam, M. S., Rahman, S. M., & Lee, D.‐U. (2015). Synthesis, biological eval-uation, quantitative‐SAR and docking studies of novel chalconederivatives as antibacterial and antioxidant agents. Chemical Papers,69(8), 1118–1129.
Allison, B. J., Allenby, M. C., Bryant, S. S., Min, J. E., Hieromnimon, M., &Joyner, P. M. (2017). Antibacterial activity of fractions from three Chu-mash medicinal plant extracts and in vitro inhibition of the enzymeenoyl reductase by the flavonoid jaceosidin. Natural Product Research,31(6), 707–712.
Almutairi, S., Edrada‐Ebel, R., Fearnley, J., Igoli, J. O., Alotaibi, W.,Clements, C. J., … Watson, D. G. (2014). Isolation of diterpenes and fla-vonoids from a new type of propolis from Saudi Arabia. PhytochemistryLetters, 10, 160–163.
Al‐Shabib, N. A., Husain, F. M., Ahmad, I., Khan, M. S., Khan, R. A., & Khan,J. M. (2017). Rutin inhibits mono and multi‐species biofilm formationby foodborne drug resistant Escherichia coli and Staphylococcus aureus.Food Control, 79, 325–332.
Alvarez, M., Debattista, N., & Pappano, N. (2008). Antimicrobial activityand synergism of some substituted flavonoids. Folia Microbiologica,53(1), 23–28.
Amin, M. U., Khurram, M., Khattak, B., & Khan, J. (2015). Antibiotic additiveand synergistic action of rutin, morin and quercetin against methicillinresistant Staphylococcus aureus. BMC Complementary and AlternativeMedicine, 15(1), 59.
An, J., Zuo, G., Hao, X., Wang, G., & Li, Z. (2011). Antibacterial and synergyof a flavanonol rhamnoside with antibiotics against clinical isolates ofmethicillin‐resistant Staphylococcus aureus (MRSA). Phytomedicine,18(11), 990–993.
Asiri, A. M., & Khan, S. A. (2012). Synthesis, characterization, and in vitroantibacterial activities of macromolecules derived from bis‐chalcone.Journal of Heterocyclic Chemistry, 49(6), 1434–1438.
Atta, E., Hashem, A., & Eman, R. E.‐S. (2013). A novel flavonoid compoundfrom Farsetia aegyptia and its antimicrobial activity. Chemistry of Natu-ral Compounds, 49(3), 432–436.
Babajide, O. J., Babajide, O. O., Daramola, A. O., & Mabusela, W. T. (2008).Flavonols and an oxychromonol from Piliostigma reticulatum. Phyto-chemistry, 69(11), 2245–2250.
Babii, C., Bahrin, L., Neagu, A. N., Gostin, I., Mihasan, M., Birsa, L., & Stefan,M. (2016). Antibacterial activity and proposed action mechanism of anew class of synthetic tricyclic flavonoids. Journal of Applied Microbiol-ogy, 120(3), 630–637.
Bahrin, L. G., Apostu, M. O., Birsa, L. M., & Stefan, M. (2014). The antibac-terial properties of sulfur containing flavonoids. Bioorganic & MedicinalChemistry Letters, 24(10), 2315–2318.
Bakar, N. S., Zin, N. M., & Basri, D. F. (2012). Synergy of flavone with van-comycin and oxacillin against vancomycin‐intermediate Staphyloccusaureus. Pakistan Journal of Pharmaceutical Sciences, 25, 633–638.
Barbieri, R., Coppo, E., Marchese, A., Daglia, M., Sobarzo‐Sánchez, E.,Nabavi, S. F., & Nabavi, S. M. (2017). Phytochemicals for human dis-ease: An update on plant‐derived compounds antibacterial activity.Microbiological Research, 196, 44–68.
Biloa Messi, B., Ho, R., Meli Lannang, A., Cressend, D., Perron, K.,Nkengfack, A. E., … Cuendet, M. (2014). Isolation and biological activityof compounds from Garcinia preussii. Pharmaceutical Biology, 52(6),706–711.
Bitchagno, G. T. M., Tankeo, S. B., Tsopmo, A., Mpetga, J. D. S., Tchinda, A.T., Fobofou, S. A. T., … Tane, P. (2016). Ericoside, a new antibacterialbiflavonoid from Erica mannii (Ericaceae). Fitoterapia, 109, 206–211.
Bitchagno, G. T. M., Tankeo, S. B., Tsopmo, A., Mpetga, J. D. S., Tchinda, A.T., Fobofou, S. A. T., … Tane, P. (2015). Lemairones A and B: Two newantibacterial tetraflavonoids from the leaves of Zanthoxylum lemairei(Rutaceae). Phytochemistry Letters, 14, 1–7. https://doi.org/10.1016/j.phytol.2015.08.012
Biva, I. J., Ndi, C. P., Griesser, H. J., & Semple, S. J. (2016). Antibacterial con-stituents of Eremophila alternifolia: An Australian aboriginal traditionalmedicinal plant. Journal of Ethnopharmacology, 182, 1–9.
Bozic, D. D., Milenkovic, M., Ivkovic, B., & Cirkovic, I. (2014). Newly‐syn-thesized chalcones‐inhibition of adherence and biofilm formation ofmethicillin‐resistant Staphylococcus aureus. Brazilian Journal of Microbi-ology, 45(1), 263–270.
Brahmachari, G., Mandal, N. C., Jash, S. K., Roy, R., Mandal, L. C.,Mukhopadhyay, A., … Gangopadhyay, A. (2011). Evaluation of the anti-microbial potential of two flavonoids isolated from Limnophila plants.Chemistry & Biodiversity, 8(6), 1139–1151.
Cai, W., Fu, Y., Zhang, W., Chen, X., Zhao, J., Song, W., … Zhang, F. (2016).Synergistic effects of baicalein with cefotaxime against Klebsiellapneumoniae through inhibiting CTX‐M‐1 gene expression. BMC Micro-biology, 16(1), 181. https://doi.org/10.1186/s12866‐016‐0797‐1
Carbonezi, C. A., Hamerski, L., Gunatilaka, A., Cavalheiro, A., Castro‐Gamboa, I., Silva, D. H. S., … Bolzani, V. S. (2007). Bioactive flavonedimers from Ouratea multiflora (Ochnaceae). Revista Brasileira deFarmacognosia, 17(3), 319–324.
Casero, C., Machín, F., Méndez‐Álvarez, S., Demo, M., Ravelo, A. G., Pérez‐Hernández, N., … Estévez‐Braun, A. (2014). Structure and antimicrobialactivity of phloroglucinol derivatives from Achyrocline satureioides.Journal of Natural Products, 78(1), 93–102.
Cha, J. D., Moon, S. E., Kim, J. Y., Jung, E. K., & Lee, Y. S. (2009). Antibac-terial activity of sophoraflavanone G Isolated from the roots of Sophoraflavescens against methicillin‐resistant Staphylococcus aureus.Phytotherapy Research, 23(9), 1326–1331.
Chan, B. C., Ip, M., Lau, C. B., Lui, S. L., Jolivalt, C., Ganem‐Elbaz, C., …Leung, P. C. (2011). Synergistic effects of baicalein with ciprofloxacinagainst NorA over‐expressed methicillin‐resistant Staphylococcusaureus (MRSA) and inhibition of MRSA pyruvate kinase. Journal ofEthnopharmacology, 137(1), 767–773.
Chan, E. W. L., Gray, A. I., Igoli, J. O., Lee, S. M., & Goh, J. K. (2014).Galloylated flavonol rhamnosides from the leaves of Calliandratergemina with antibacterial activity against methicillin‐resistant Staph-ylococcus aureus (MRSA). Phytochemistry, 107, 148–154.
Chen, J., Li, Y., Yang, L.‐Q., Li, Y.‐Z., Nan, Z.‐B., & Gao, K. (2012). Biologicalactivities of flavonoids from pathogenic‐infected Astragalus adsurgens.Food Chemistry, 131(2), 546–551.
Chen, Y., Liu, T., Wang, K., Hou, C., Cai, S., Huang, Y., … Chen, Y. (2016).Baicalein inhibits Staphylococcus aureus biofilm formation and the quo-rum sensing system in vitro. PLoS One, 11(4).
Chinnam, N., Dadi, P. K., Sabri, S. A., Ahmad, M., Kabir, M. A., & Ahmad, Z.(2010). Dietary bioflavonoids inhibit Escherichia coli ATP synthase in adifferential manner. International Journal of Biological Macromolecules,46(5), 478–486.
Chitsazian‐Yazdi, M., Agnolet, S., Lorenz, S., Schneider, B., Es'haghi, Z.,Kasaian, J., … Iranshahi, M. (2015). Foetithiophenes C‐F, thiophenederivatives from the roots of Ferula foetida. Pharmaceutical Biology,53(5), 710–714.
Chou, T. H., Chen, J. J., Peng, C. F., Cheng, M. J., & Chen, I. S. (2011). Newflavanones from the leaves of Cryptocarya chinensis and their antituber-culosis activity. Chemistry & Biodiversity, 8(11), 2015–2024.
Christopher, R., Nyandoro, S., Chacha, M., & de Koning, C. (2014). A newcinnamoylglycoflavonoid, antimycobacterial and antioxidant constitu-ents from Heritiera littoralis leaf extracts. Natural Product Research,28(6), 351–358.
Chukwujekwu, J., Van Heerden, F., & Van Staden, J. (2011). Antibacterialactivity of flavonoids from the stem bark of Erythrina caffra thunb.Phytotherapy Research, 25(1), 46–48.
Cui, Y., Taniguchi, S., Kuroda, T., & Hatano, T. (2015). Constituents ofPsoralea corylifolia fruits and their effects on methicillin‐resistantstaphylococcus aureus. Molecules, 20(7), 12500–12511.
Cushnie, T., Hamilton, V., Chapman, D., Taylor, P., & Lamb, A. (2007).Aggregation of Staphylococcus aureus following treatment with theantibacterial flavonol galangin. Journal of Applied Microbiology, 103(5),1562–1567.
Cushnie, T., & Lamb, A. (2006). Assessment of the antibacterial activity ofgalangin against 4‐quinolone resistant strains of Staphylococcus aureus.Phytomedicine, 13(3), 187–191.
Cushnie, T., Taylor, P., Nagaoka, Y., Uesato, S., Hara, Y., & Lamb, A. (2008).Investigation of the antibacterial activity of 3‐O‐octanoyl‐(−)‐epicate-chin. Journal of Applied Microbiology, 105(5), 1461–1469.
Cushnie, T. T., & Lamb, A. J. (2005a). Antimicrobial activity of flavonoids.International Journal of Antimicrobial Agents, 26(5), 343–356.
Cushnie, T. T., & Lamb, A. J. (2005b). Detection of galangin‐induced cyto-plasmic membrane damage in Staphylococcus aureus by measuringpotassium loss. Journal of Ethnopharmacology, 101(1), 243–248.
Cushnie, T. T., & Lamb, A. J. (2011). Recent advances in understanding theantibacterial properties of flavonoids. International Journal of Antimicro-bial Agents, 38(2), 99–107.
Drewes, S. E., & van Vuuren, S. F. (2008). Antimicrobial acylphloroglucinolsand dibenzyloxy flavonoids from flowers of Helichrysum gymnocomum.Phytochemistry, 69(8), 1745–1749.
Dzoyem, J. P., Hamamoto, H., Ngameni, B., Ngadjui, B. T., & Sekimizu, K.(2013). Antimicrobial action mechanism of flavonoids from Dorsteniaspecies. Drug Discoveries & Therapeutics, 7(2), 66–72.
Dzoyem, J. P., Melong, R., Tsamo, A. T., Tchinda, A. T., Kapche, D. G.,Ngadjui, B. T., … Eloff, J. N. (2017). Cytotoxicity, antimicrobial and anti-oxidant activity of eight compounds isolated from Entada abyssinica(Fabaceae). BMC Research Notes, 10(1), 118.
Echeverría, J., Opazo, J., Mendoza, L., Urzúa, A., & Wilkens, M. (2017).Structure‐activity and lipophilicity relationships of selected antibacte-rial natural flavones and flavanones of Chilean flora. Molecules, 22(4),608.
Edziri, H., Mastouri, M., Mahjoub, M. A., Mighri, Z., Mahjoub, A., &Verschaeve, L. (2012). Antibacterial, antifungal and cytotoxic activitiesof two flavonoids from Retama raetam flowers. Molecules, 17(6),7284–7293.
El‐Aasr, M., Kabbash, A., El‐Seoud, K. A. A., Al‐Madboly, A., & Ikeda, T.(2016). Antimicrobial and immunomodulatory activities of flavonol gly-cosides isolated from Atriplex halimus L. Herb. International Journal ofPharmaceutical Sciences and Research, 8, 1159–1168.
Eumkeb, G., & Chukrathok, S. (2013). Synergistic activity and mechanismof action of ceftazidime and apigenin combination against ceftazi-dime‐resistant Enterobacter cloacae. Phytomedicine, 20(3–4), 262–269.
Eumkeb, G., Sakdarat, S., & Siriwong, S. (2010). Reversing beta‐lactam anti-biotic resistance of Staphylococcus aureus with galangin from Alpiniaofficinarum Hance and synergism with ceftazidime. Phytomedicine,18(1), 40–45. https://doi.org/10.1016/j.phymed.2010.09.003
Evranos‐Aksöz, B., Onurdağ, F. K., & Özgacar, S. Ö. (2015). Antibacterial,antifungal and antimycobacterial activities of some pyrazoline,hydrazone and chalcone derivatives. Zeitschrift für Naturforschung,70(7–8), 183–189.
Fareza, M. S., Syah, Y. M., Mujahidin, D., Juliawaty, L. D., & Kurniasih, I.(2014). Antibacterial flavanones and dihydrochalcones from Macarangatrichocarpa. Zeitschrift für Naturforschung, 69(9–10), 375–380.
Farooq, S., Wahab, A. T., Fozing, C., Rahman, A. U., & Choudhary, M. I.(2014). Artonin I inhibits multidrug resistance in Staphylococcus aureusand potentiates the action of inactive antibiotics in vitro. Journal ofApplied Microbiology, 117(4), 996–1011.
Favela‐Hernández, J., García, A., Garza‐González, E., Rivas‐Galindo, V., &Camacho‐Corona, M. (2012). Antibacterial and antimycobacteriallignans and flavonoids from Larrea tridentata. Phytotherapy Research,26(12), 1957–1960.
Feldman, M., Santos, J., & Grenier, D. (2011). Comparative evaluation oftwo structurally related flavonoids, isoliquiritigenin and liquiritigenin,for their oral infection therapeutic potential. Journal of Natural Prod-ucts, 74(9), 1862–1867.
Feng, L., Maddox, M. M., Alam, M. Z., Tsutsumi, L. S., Narula, G., Bruhn, D.F., … Simmons, C. J. (2014). Synthesis, structure–activity relationshipstudies, and antibacterial evaluation of 4‐chromanones and chalcones,as well as olympicin A and derivatives. Journal of Medicinal Chemistry,57(20), 8398–8420.
Fowler, Z. L., Shah, K., Panepinto, J. C., Jacobs, A., & Koffas, M. A. (2011).Development of non‐natural flavanones as antimicrobial agents. PLoSOne, 6(10), e25681.
Frieri, M., Kumar, K., & Boutin, A. (2016). Antibiotic resistance. Journal ofInfection and Public Health. https://doi.org/10.1016/j.jiph.2016.08.007
Geoghegan, F., Wong, R., & Rabie, A. (2010). Inhibitory effect of quercetinon periodontal pathogens in vitro. Phytotherapy Research, 24(6),817–820.
Gopikrishnan, V., Radhakrishnanauthor, M., Shanmugasundaramauthor, T.,Pazhanimuruganauthor, R., & Balagurunathanauthor, R. (2015).Antibiofouling potential of quercetin compound from marine‐derivedactinobacterium, Streptomyces fradiae PE7and its characterization.Environmental Science and Pollution Research.
Gradišar, H., Pristovšek, P., Plaper, A., & Jerala, R. (2007). Green tea cate-chins inhibit bacterial DNA gyrase by interaction with its ATP bindingsite. Journal of Medicinal Chemistry, 50(2), 264–271.
Hassanzadeh, M., Rahimizadeh, M., Bazzaz, B. S. F., Emami, S. A., & Assili, J.(2001). Chemical and antimicrobial studies of Platycladus orientalisessential oils. Pharmaceutical Biology, 39(5), 388–390.
He, M., Wu, T., Pan, S., & Xu, X. (2014). Antimicrobial mechanism of flavo-noids against Escherichia coli ATCC 25922 by model membrane study.Applied Surface Science, 305, 515–521.
Hirai, I., Okuno, M., Katsuma, R., Arita, N., Tachibana, M., & Yamamoto, Y.(2010). Characterisation of anti‐Staphylococcus aureus activity ofquercetin. International Journal of Food Science and Technology, 45(6),1250–1254.
Hung, T. M., Na, M., Dat, N. T., Ngoc, T. M., Youn, U., Kim, H. J., … Bae, K.(2008). Cholinesterase inhibitory and anti‐amnesic activity of alkaloidsfrom Corydalis turtschaninovii. Journal of Ethnopharmacology, 119(1),74–80.
Iranshahi, M., Fata, A., Emami, B., Jalalzadeh Shahri, B. M., & Bazzaz, B. S. F.(2008). In vitro antifungal activity of polysulfides‐rich essential oil ofFerula latisecta fruits against human pathogenic dermatophytes. Natu-ral Product Communications, 3, 1543–1546.
Iranshahi, M., Hassanzadeh‐Khayat, M., Bazzaz, B. S. F., Sabeti, Z., &Enayati, F. (2008). High content of polysulphides in the volatile oil ofFerula latisecta Rech. F. et Aell. fruits and antimicrobial activity of theoil. Journal of Essential Oil Research, 20(2), 183–185.
Jamil, S. (2014). Antimicrobial Flavonoids from Artocarpus anisophyllus Miqand Artocarpus lowii King. J Teknol, 71(1), 95–99.
Jeong, K.‐W., Lee, J.‐Y., Kang, D.‐I., Lee, J.‐U., Shin, S. Y., & Kim, Y. (2009).Screening of flavonoids as candidate antibiotics against Enterococcusfaecalis. Journal of Natural Products, 72(4), 719–724.
Kanwal, Q., Hussain, I., Siddiqui, L. H., & Javaid, A. (2011). Antimicrobialactivity screening of isolated flavonoids from Azadirachta indica leaves.Journal of the Serbian Chemical Society, 76(3), 375–384.
Katerere, D. R., Gray, A. I., Nash, R. J., & Waigh, R. D. (2012). Phytochem-ical and antimicrobial investigations of stilbenoids and flavonoidsisolated from three species of Combretaceae. Fitoterapia, 83(5),932–940.
Kengap, R. T., Kapche, G. D., Dzoyem, J. P., Simo, I. K., Ambassa, P., Sandjo,L. P., … Ngadjui, B. T. (2011). Isoprenoids and flavonoids with antimi-crobial activity from Ficus conrauiWarburg (Moraceae). HelveticaChimica Acta, 94(12), 2231–2238.
Khameneh, B., Diab, R., Ghazvini, K., & Fazly Bazzaz, B. S. (2016). Break-throughs in bacterial resistance mechanisms and the potential waysto combat them. Microbial Pathogenesis, 95, 32–42.
Khan, S. A., Asiri, A. M., & Elroby, S. A. (2014). Green synthesis, character-ization, antibacterial activity of heterocyclic compounds from chalconeon basis of in vitro and quantum chemistry calculation. Asian Journal ofChemistry, 26(21), 7283.
Kohda, C., Yanagawa, Y., & Shimamura, T. (2008). Epigallocatechin gallateinhibits intracellular survival of Listeria monocytogenes in macrophages.Biochemical and Biophysical Research Communications, 365(2), 310–315.
Konduru, N. K., Dey, S., Sajid, M., Owais, M., & Ahmed, N. (2013). Synthe-sis and antibacterial and antifungal evaluation of some chalcone basedsulfones and bisulfones. European Journal of Medicinal Chemistry, 59,23–30.
Kong, N.‐N., Fang, S.‐T., Liu, Y., Wang, J.‐H., Yang, C.‐Y., & Xia, C.‐H.(2014). Flavonoids from the halophyte Apocynum venetum and theirantifouling activities against marine biofilm‐derived bacteria. NaturalProduct Research, 28(12), 928–931.
Kong, W., Zhao, Y., Xing, X., Ma, X., Sun, X., Yang, M., & Xiao, X. (2015).Antibacterial evaluation of flavonoid compounds against E. coli bymicrocalorimetry and chemometrics. Applied Microbiology and Biotech-nology, 99(14), 6049–6058.
Kowalski, K., Koceva‐Chyła, A., Szczupak, Ł., Hikisz, P., Bernasińska, J.,Rajnisz, A., … Therrien, B. (2013). Ferrocenylvinyl‐flavones: Synthesis,structure, anticancer and antibacterial activity studies. Journal of Organ-ometallic Chemistry, 741, 153–161.
Koysomboon, S., Van Altena, I., Kato, S., & Chantrapromma, K. (2006).Antimycobacterial flavonoids from Derris indica. Phytochemistry,67(10), 1034–1040.
Kuete, V., Fozing, D., Kapche, W., Mbaveng, A., Kuiate, J., Ngadjui, B., &Abegaz, B. (2009). Antimicrobial activity of the methanolic extractand compounds from Morus mesozygia stem bark. Journal ofEthnopharmacology, 124(3), 551–555.
Kuete, V., Simo, I. K., Ngameni, B., Bigoga, J. D., Watchueng, J., Kapguep, R.N., … Beng, V. P. (2007). Antimicrobial activity of the methanolicextract, fractions and four flavonoids from the twigs of Dorsteniaangusticornis Engl.(Moraceae). Journal of Ethnopharmacology, 112(2),271–277.
Kumar, S., & Pandey, A. K. (2013). Chemistry and biological activities offlavonoids: An overview. The Scientific World Journal, 2013, 16.
Kunthalert, D., Baothong, S., Khetkam, P., Chokchaisiri, S., & Suksamrarn, A.(2014). A chalcone with potent inhibiting activity against biofilm forma-tion by nontypeable Haemophilus influenzae. Microbiology andImmunology, 58(10), 581–589.
Lechner, D., Gibbons, S., & Bucar, F. (2008). Modulation of isoniazid sus-ceptibility by flavonoids in Mycobacterium. Phytochemistry Letters,1(2), 71–75.
Lee, G.‐S., Kim, E.‐S., Cho, S.‐I., Kim, J.‐H., Choi, G., Ju, Y.‐S., … Kim, H.‐J.(2010). Antibacterial and synergistic activity of prenylated chalconeisolated from the roots of Sophora flavescens. Journal of Korean Societyfor Applied Biological Chemistry, 53(3), 290–296.
Lee, J.‐H., Park, J.‐H., Cho, H. S., Joo, S. W., Cho, M. H., & Lee, J. (2013).Anti‐biofilm activities of quercetin and tannic acid against Staphylococ-cus aureus. Biofouling, 29(5), 491–499.
Lee, J.‐Y., Lee, E., Jeong, K.‐W., & Kim, Y. (2011). Antimicrobial flavonoid, 3,6‐dihydroxyflavone, have dual inhibitory activity against KAS III andKAS I. Bulletin of the Korean Chemical Society, 32(9), 3219.
Lee, K. A., Moon, S.‐H., Lee, J.‐Y., Kim, K.‐T., Park, Y.‐S., & Paik, H.‐D.(2013). Antibacterial activity of a novel flavonoid, 7‐O‐butyl naringenin,against methicillin‐resistant Staphylococcus aureus (MRSA). Food Sci-ence and Biotechnology, 22(6), 1725–1728.
Li, B.‐H., Zhang, R., Du, Y.‐T., Sun, Y.‐H., & Tian, W.‐X. (2006). Inactivationmechanism of the β‐ketoacyl‐[acyl carrier protein] reductase of bacte-rial type‐II fatty acid synthase by epigallocatechin gallate. Biochemistryand Cell Biology, 84(5), 755–762. https://doi.org/10.1139/o06‐047
Li, H. X., Wang, Z. C., Qian, Y. M., Yan, X. Q., Lu, Y. D., & Zhu, H. L. (2017).Design, synthesis, and biological evaluation of chrysin derivatives aspotential FabH inhibitors. Chemical Biology & Drug Design, 89(1),136–140.
Li, W., Cai, C.‐H., Dong, W.‐H., Guo, Z.‐K., Wang, H., Mei, W.‐L., & Dai, H.‐F.(2014). 2‐(2‐Phenylethyl) chromone derivatives from Chinese agarwoodinduced by artificial holing. Fitoterapia, 98, 117–123. https://doi.org/10.1016/j.fitote.2014.07.011
Lopes, L. A. A., dos Santos Rodrigues, J. B., Magnani, M., de Souza, E. L., &de Siqueira‐Júnior, J. P. (2017). Inhibitory effects of flavonoids on bio-film formation by Staphylococcus aureus that overexpresses effluxprotein genes. Microbial Pathogenesis, 107, 193–197.
Luo, J., Kong, J. L., Dong, B. Y., Huang, H., Wang, K., Wu, L. H., … Chen, Y.Q. (2016). Baicalein attenuates the quorum sensing‐controlled viru-lence factors of Pseudomonas aeruginosa and relieves theinflammatory response in p. Aeruginosa‐infected macrophages bydownregulating the MAPK and NFκB signal‐transduction pathways.Drug Design, Development and Therapy, 10, 183–203.
Makhafola, T. J., Samuel, B. B., Elgorashi, E. E., & Eloff, J. N. (2012).Ochnaflavone and ochnaflavone 7‐O‐methyl ether two antibacterialbiflavonoids from Ochna pretoriensis (Ochnaceae). Natural Product Com-munications, 7(12), 1601–1604.
Mallavadhani, U. V., Sahoo, L., Kumar, K. P., & Murty, U. S. (2014). Synthe-sis and antimicrobial screening of some novel chalcones and flavanonessubstituted with higher alkyl chains. Medicinal Chemistry Research,23(6), 2900–2908.
Manner, S., Skogman, M., Goeres, D., Vuorela, P., & Fallarero, A. (2013).Systematic exploration of natural and synthetic flavonoids for the inhi-bition of Staphylococcus aureus biofilms. International Journal ofMolecular Sciences, 14(10), 19434–19451.
Maresso, A. W., & Schneewind, O. (2008). Sortase as a target of anti‐infec-tive therapy. Pharmacological Reviews, 60(1), 128–141.
Mariani, R., Suganda, A., & Sukandar, E. (2016). Drug‐drug interactionsbetween griseofulvin and a new prenylated chalcone from elatostemaparasiticum and its antibacterial activity nortriptyline at binding sitesof bovine serum albumin. Pharmacology, 1, 1–6.
Martín‐Rodríguez, A. J., Ticona, J. C., Jiménez, I. A., Flores, N., Fernández, J.J., & Bazzocchi, I. L. (2015). Flavonoids from Piper delineatum modulatequorum‐sensing‐regulated phenotypes in Vibrio harveyi. Phytochemis-try, 117, 98–106.
Mazimba, O., Masesane, I. B., & Majinda, R. R. (2012). A flavanone andantimicrobial activities of the constituents of extracts from Munduleasericea. Natural Product Research, 26(19), 1817–1823.
Mbaveng, A. T., Ngameni, B., Kuete, V., Simo, I. K., Ambassa, P., Roy, R., …Abegaz, B. M. (2008). Antimicrobial activity of the crude extracts andfive flavonoids from the twigs of Dorstenia barteri (Moraceae). Journalof Ethnopharmacology, 116(3), 483–489.
Mbaveng, A. T., Sandjo, L. P., Tankeo, S. B., Ndifor, A. R., Pantaleon, A.,Nagdjui, B. T., & Kuete, V. (2015). Antibacterial activity of nineteenselected natural products against multi‐drug resistant Gram‐negativephenotypes. Springer Plus, 4(1), 823.
Moon, S. H., Lee, J. H., Kim, K.‐T., Park, Y.‐S., Nah, S.‐Y., Ahn, D. U., &Paik, H.‐D. (2013). Antimicrobial effect of 7‐O‐butylnaringenin, anovel flavonoid, and various natural flavonoids against Helicobacter
pylori strains. International Journal of Environmental Research and PublicHealth, 10(11), 5459–5469.
Mun, S.‐H., Joung, D.‐K., Kim, S.‐B., Park, S.‐J., Seo, Y.‐S., Gong, R., … Kang,O.‐H. (2014). The mechanism of antimicrobial activity ofsophoraflavanone B against methicillin‐resistant Staphylococcus aureus.Foodborne Pathogens and Disease, 11(3), 234–239.
Mun, S.‐H., Kang, O.‐H., Joung, D.‐K., Kim, S.‐B., Seo, Y.‐S., Choi, J.‐G., …Han, S.‐H. (2013). Combination therapy of sophoraflavanone B againstMRSA: In vitro synergy testing. Alternative Medicine, 2013, 7.
Mun, S. H., Lee, Y. S., Han, S. H., Lee, S. W., Cha, S. W., Kim, S. B., … Kwon,D. Y. (2015). In vitro potential effect of morin in the combination withβ‐lactam antibiotics against methicillin‐resistant Staphylococcus aureus.Foodborne Pathogens and Disease, 12(6), 545–550.
Musa, N., Musa, N., Ibrahim, W. N., Shariat, M. Z. A., Zamani, A. I., Abdullah,M. R., … Soh, A. S. A. (2011). Methanolic activities of selected weeds onbacteria isolated from Macrobrachium rosenbergii larvae. The Thai Jour-nal of Veterinary Medicine, 41(4), 535.
Navarro‐Martínez, M. D., Navarro‐Perán, E., Cabezas‐Herrera, J., Ruiz‐Gómez, J., García‐Cánovas, F., & Rodríguez‐López, J. N. (2005).Antifolate activity of epigallocatechin gallate against Stenotrophomonasmaltophilia. Antimicrobial Agents and Chemotherapy, 49(7), 2914–2920.
Navrátilová, A., Nešuta, O., Vančatová, I., Čížek, A., Varela‐M, R. E., Lopez‐Aban, J., … Žemličková, H. (2016). C‐Geranylated flavonoids from Pau-lownia tomentosa fruits with antimicrobial potential and synergisticactivity with antibiotics. Pharmaceutical Biology, 54(8), 1398–1407.
Nenaah, G. (2013). Antimicrobial activity of Calotropis procera Ait.(Asclepiadaceae) and isolation of four flavonoid glycosides as the activeconstituents. World Journal of Microbiology and Biotechnology, 29(7),1255–1262.
Novak, Z., Chlebek, J., Opletal, L., Jiros, P., Macakova, K., Kunes, J., &Cahlikova, L. (2012). Corylucinine, a new alkaloid from Corydalis cava(Fumariaceae), and its cholinesterase activity. Natural Product Commu-nications, 7(7), 859–860.
Oh, I., Yang, W.‐Y., Chung, S.‐C., Kim, T.‐Y., Oh, K.‐B., & Shin, J. (2011). Invitro sortase A inhibitory and antimicrobial activity of flavonoids iso-lated from the roots of Sophora flavescens. Archives of PharmacalResearch, 34(2), 217–222.
Okwu, D. E., & Nnamdi, F. U. (2011). Two novel flavonoids from Bryophyl-lum pinnatum and their antimicrobial Activity. Journal of Chemical andPharmaceutical Research, 3(2), 1–10.
Omosa, L. K., Amugune, B., Ndunda, B., Milugo, T. K., Heydenreich, M.,Yenesew, A., & Midiwo, J. O. (2014). Antimicrobial flavonoids andditerpenoids from Dodonaea angustifolia. South African Journal ofBotany, 91, 58–62.
Omosa, L. K., Midiwo, J. O., Mbaveng, A. T., Tankeo, S. B., Seukep, J. A.,Voukeng, I. K., … Omolle, R. A. (2016). Antibacterial activities and struc-ture–activity relationships of a panel of 48 compounds from Kenyanplants against multidrug resistant phenotypes. Springer Plus, 5(1), 1–15.
Orabi, M. A., Aoyama, H., Kuroda, T., & Hatano, T. (2014). Structures oftwo new flavonoids and effects of licorice phenolics on vancomycin‐resistant Enterococcus species. Molecules, 19(4), 3883–3897.
Orhan, D. D., Özçelik, B., Özgen, S., & Ergun, F. (2010). Antibacterial, anti-fungal, and antiviral activities of some flavonoids. MicrobiologicalResearch, 165(6), 496–504.
Patel, N. B., & Patel, M. D. (2017). Synthesis and evaluation of antibacterialand antifungal activities of 4‐thiazolidinones and 2‐azetidinones deriv-atives from chalcone. Medicinal Chemistry Research, 1–12.
Patra, A. K. (2012). An overview of antimicrobial properties of differentclasses of phytochemicals. In Dietary phytochemicals and microbes(pp. 1–32). Dordrecht: Springer.
Prabu, G., Gnanamani, A., & Sadulla, S. (2006). Guaijaverin—A plant flavo-noid as potential antiplaque agent against Streptococcus mutans.Journal of Applied Microbiology, 101(2), 487–495.
Qiu, F., Meng, L., Chen, J., Jin, H., & Jiang, L. (2016). In vitro activity of fiveflavones from Scutellaria baicalensisin combination with Cefazolin
against methicillin resistant Staphylococcus aureus (MRSA). MedicinalChemistry Research, 25(10), 2214–2219.
Rahman, M. M., Gibbons, S., & Gray, A. I. (2007). Isoflavanones fromUraria picta and their antimicrobial activity. Phytochemistry, 68(12),1692–1697.
Rajendran, N., Subramaniam, S., Christena, L. R., Muthuraman, M. S.,Subramanian, N. S., Pemiah, B., & Sivasubramanian, A. (2016). Antimi-crobial flavonoids isolated from Indian medicinal plant Scutellariaoblonga inhibit biofilms formed by common food pathogens. NaturalProduct Research, 30(17), 2002–2006.
Randhawa, H. K., Hundal, K. K., Ahirrao, P. N., Jachak, S. M., & Nandanwar,H. S. (2016). Efflux pump inhibitory activity of flavonoids isolated fromAlpinia calcarata against methicillin‐resistant Staphylococcus aureus.Biologia, 71(5), 484–493.
Rashed, K., Ćirić, A., Glamočlija, J., & Soković, M. (2014). Antibacterial andantifungal activities of methanol extract and phenolic compounds fromDiospyros virginiana L. Industrial Crops and Products, 59, 210–215.
Rattanachaikunsopon, P., & Phumkhachorn, P. (2007). Bacteriostatic effectof flavonoids isolated from leaves of Psidium guajava on fish pathogens.Fitoterapia, 78(6), 434–436.
Rigano, D., Formisano, C., Basile, A., Lavitola, A., Senatore, F., Rosselli, S., &Bruno, M. (2007). Antibacterial activity of flavonoids andphenylpropanoids from Marrubium globosum ssp. libanoticum.Phytotherapy Research, 21(4), 395–397.
Ruddock, P. S., Charland, M., Ramirez, S., Lopez, A., Neil Towers, G. H.,Arnason, J. T., … Dillon, J. A. (2011). Antimicrobial activity of flavonoidsfrom Piper lanceaefolium and other Colombian medicinal plants againstantibiotic susceptible and resistant strains of Neisseria gonorrhoeae.Sexually Transmitted Diseases, 38(2), 82–88.
Rukachaisirikul, T., Innok, P., Aroonrerk, N., Boonamnuaylap, W.,Limrangsun, S., Boonyon, C., … Suksamrarn, A. (2007). Antibacterialpterocarpans from Erythrina subumbrans. Journal of Ethnopharmacology,110(1), 171–175.
Salah, N. B., Casabianca, H., Jannet, H. B., Chenavas, S., Sanglar, C., Fildier,A., & Bouzouita, N. (2015). Phytochemical and biological investigationof two Diplotaxis species growing in Tunisia: D. virgata & D. erucoides.Molecules, 20(10), 18128–18143.
Salar Bashi, D., Bazzaz, B. S. F., Sahebkar, A., Karimkhani, M., & Ahmadi, A.(2012). Investigation of optimal extraction, antioxidant, and antimicro-bial activities of Achillea biebersteinii and A. wilhelmsii. Pharm. OBiologico, 52(9), 1168–1176.
Seleem, D., Pardi, V., & Murata, R. M. (2017). Review of flavonoids: Adiverse group of natural compounds with anti‐Candida albicans activityin vitro. Archives of Oral Biology, 76, 76–83.
Selvakumar, N., Kumar, G. S., Azhagan, A. M., Rajulu, G. G., Sharma, S.,Kumar, M. S., … Trehan, S. (2007). Synthesis, SAR and antibacterialstudies on novel chalcone oxazolidinone hybrids. Journal of MedicinalChemistry, 42(4), 538–543.
Shahzadi, I., & Shah, M. M. (2015). Acylated flavonol glycosides fromTagetes minuta with antibacterial activity. Microbial Pathogenesis, 6.
Shi, L. Z., & Czuprynski, C. J. (2009). Beta‐naphthoflavone causes an AhR‐independent inhibition of invasion and intracellular multiplication ofListeria monocytogenes in murine hepatocytes. Microbial Pathogenesis,47(5), 258–266.
Siriwong, S., Teethaisong, Y., Thumanu, K., Dunkhunthod, B., & Eumkeb, G.(2016). The synergy and mode of action of quercetin plus amoxicillinagainst amoxicillin‐resistant Staphylococcus epidermidis. BMC Pharma-cology and Toxicology, 17(1), 39.
Šmejkal, K., Chudík, S., Kloucek, P., Marek, R., Cvacka, J., Urbanová, M., …Holubová, P. (2008). Antibacterial C‐geranylflavonoids from Paulowniatomentosa fruits. Journal of Natural Products, 71(4), 706–709.
Stompor, M., & Żarowska, B. (2016). Antimicrobial activity of xanthohumoland its selected structural analogues. Molecules, 21(5), 608.
Taiwo, B. J., & Igbeneghu, O. A. (2014). Antioxidant and antibacterial activ-ities of flavonoid glycosides from Ficus exasperata Vahl‐Holl (moraceae)
FARHADI ET AL. 27
leaves. African Journal of Traditional, Complementary, and AlternativeMedicines, 11(3), 97–101.
Tajuddeen, N., Sallau, M. S., Musa, A. M., Yahaya, S. M., Habila, J. D., &Ismail, A. M. (2016). A novel antimicrobial flavonoid from the stem barkof Commiphora pedunculata (Kotschy & Peyr.) Engl. Natural ProductResearch, 30(10), 1109–1115.
Tajuddeen, N., Sani Sallau, M., Muhammad Musa, A., James Habila, D., &Yahaya, S. M. (2014). Flavonoids with antimicrobial activity from thestem bark of Commiphora pedunculata (Kotschy & Peyr.) Engl. NaturalProduct Research, 28(21), 1915–1918.
Tamba, Y., Ohba, S., Kubota, M., Yoshioka, H., Yoshioka, H., & Yamazaki, M.(2007). Single GUV method reveals interaction of tea catechin (−)‐epi-gallocatechin gallate with lipid membranes. Biophysical Journal, 92(9),3178–3194.
Tan, C. X., Schrader, K. K., Khan, I. A., & Rimando, A. M. (2015). Activities ofwogonin analogs and other flavones against Flavobacterium columnare.Chemistry & Biodiversity, 12(2), 259–272. https://doi.org/10.1002/cbdv.201400181
Tantry, M. A., Dar, J. A., Idris, A., Akbar, S., & Shawl, A. S. (2012). Acylatedflavonol glycosides from Epimedium elatum, a plant endemic to theWestern Himalayas. Fitoterapia, 83(4), 665–670.
Tebou, P., Tamokou, J.‐d.‐D., Ngnokam, D., Voutquenne‐Nazabadioko, L.,Kuiate, J.‐R., & Bag, P. (2017). Flavonoids from Maytenus buchananiias potential cholera chemotherapeutic agents. South African Journal ofBotany, 109, 58–65.
Tran, T.‐D., Do, T.‐H., Tran, N.‐C., Ngo, T.‐D., Tran, C.‐D., & Thai, K.‐M.(2012). Synthesis and anti Methicillin resistant Staphylococcus aureusactivity of substituted chalcones alone and in combination with non‐beta‐lactam antibiotics. Bioorganic & Medicinal Chemistry Letters,22(14), 4555–4560.
Tran, T.‐D., Nguyen, T.‐T.‐N., Do, T.‐H., Huynh, T.‐N.‐P., Tran, C.‐D., & Thai,K.‐M. (2012). Synthesis and antibacterial activity of some heterocyclicchalcone analogues alone and in combinationwith antibiotics.Molecules,17(6), 6684–6696.
Tsuchiya, H., & Iinuma, M. (2000). Reduction of membrane fluidity by anti-bacterial sophoraflavanone G isolated from Sophora exigua.Phytomedicine, 7(2), 161–165.
Ulanowska, K., Majchrzyk, A., Moskot, M., Jakóbkiewicz‐Banecka, J., &Węgrzyn, G. (2007). Assessment of antibacterial effects of flavonoidsby estimation of generation times in liquid bacterial cultures. Biologia,62(2), 132–135.
Ulanowska, K., Tkaczyk, A., Konopa, G., & Wȩgrzyn, G. (2006). Differentialantibacterial activity of genistein arising from global inhibition of DNA,RNA and protein synthesis in some bacterial strains. Archives of Micro-biology, 184(5), 271–278.
Ustün, O., Ozçelik, B., Akyön, Y., Abbasoglu, U., & Yesilada, E. (2006).Flavonoids with anti‐Helicobacter pylori activity from Cistus laurifoliusleaves. Journal of Ethnopharmacology, 108(3), 457–461.
Vasavi, H. S., Arun, A. B., & Rekha, P. D. (2014). Anti‐quorum sensing activ-ity of Psidium guajava L. flavonoids against Chromobacterium violaceumand Pseudomonas aeruginosa PAO1. Microbiology and Immunology,58(5), 286–293.
Venugopala, K. N., Rashmi, V., & Odhav, B. (2013). Review on natural cou-marin lead compounds for their pharmacological activity. BioMedResearch International, 2013, 963248.
Wan, C.‐X., Luo, J.‐G., Ren, X.‐P., & Kong, L.‐Y. (2015). Interconvertingflavonostilbenes with antibacterial activity from Sophora alopecuroides.Phytochemistry, 116, 290–297.
Wang, L., Yang, R., Yuan, B., Liu, Y., & Liu, C. (2015). The antiviral and anti-microbial activities of licorice, a widely‐used Chinese herb. ActaPharmaceutica Sinica B, 5(4), 310–315.
Wang, Q., Wang, H., & Xie, M. (2010). Antibacterial mechanism of soybeanisoflavone on Staphylococcus aureus. Archives of Microbiology, 192(11),893–898.
Wang, S., Wang, C., Gao, L., Cai, H., Zhou, Y., Yang, Y., … Muhammad, I.(2017). Rutin inhibits Streptococcus suis biofilm formation by affectingCPS biosynthesis. Frontiers in Pharmacology, 8, 379.
Wang, S. Y., Sun, Z. L., Liu, T., Gibbons, S., Zhang, W. J., & Qing, M. (2014).Flavonoids from Sophora moorcroftiana and their synergistic antibacte-rial effects on MRSA. Phytotherapy Research, 28(7), 1071–1076.
Wen, L., Wu, D., Jiang, Y., Prasad, K. N., Lin, S., Jiang, G., … Yang, B. (2014).Identification of flavonoids in litchi (Litchi chinensis Sonn.) leaf and eval-uation of anticancer activities. Journal of Functional Foods, 6, 555–563.
Woźnicka, E., Kuźniar, A., Nowak, D., Nykiel, E., Kopacz, M., Gruszecka, J.,& Golec, K. (2013). Comparative study on the antibacterial activity ofsome flavonoids and their sulfonic derivatives. Acta PoloniaePharmaceutica, 70(3), 567–571.
Wu, D., Kong, Y., Han, C., Chen, J., Hu, L., Jiang, H., & Shen, X. (2008).D‐Alanine: D‐alanine ligase as a new target for the flavonoidsquercetin and apigenin. International Journal of Antimicrobial Agents,32(5), 421–426.
Wu, T., He, M., Zang, X., Zhou, Y., Qiu, T., Pan, S., & Xu, X. (2013). A struc-ture–activity relationship study of flavonoids as inhibitors of E. coli bymembrane interaction effect. Biochimica et Biophysica Acta (BBA) ‐Biomembranes, 1828(11), 2751–2756.
Xie, Y., Yang, W., Tang, F., Chen, X., & Ren, L. (2015). Antibacterial activi-ties of flavonoids: Structure‐activity relationship and mechanism.Current Medicinal Chemistry, 22(1), 132–149.
Yang, W.‐Y., Won, T. H., Ahn, C.‐H., Lee, S.‐H., Yang, H.‐C., Shin, J., & Oh,K.‐B. (2015). Streptococcus mutans sortase A inhibitory metabolitesfrom the flowers of Sophora japonica. Bioorganic & Medicinal ChemistryLetters, 25(7), 1394–1397.
Zainuri, D. A., Arshad, S., Khalib, N. C., Razak, I. A., Pillai, R. R., Sulaiman, S.F., … Armaković, S. J. (2017). Synthesis, XRD crystal structure, spectro-scopic characterization (FT‐IR, 1 H and 13 C NMR), DFT studies,chemical reactivity and bond dissociation energy studies using molecu-lar dynamics simulations and evaluation of antimicrobial andantioxidant activities of a novel chalcone derivative,(E)‐1‐(4‐bromophenyl)‐3‐(4‐iodophenyl) prop‐2‐en‐1‐one. Journal of MolecularStructure, 1128, 520–533.
Zampini, I., Villena, J., Salva, S., Herrera, M., Isla, M., & Alvarez, S. (2012).Potentiality of standardized extract and isolated flavonoids fromZuccagnia punctata for the treatment of respiratory infections byStreptococcus pneumoniae: In vitro and in vivo studies. Journal ofEthnopharmacology, 140(2), 287–292. https://doi.org/10.1016/j.jep.2012.01.019
Zeng, Z., Qian, L., Cao, L., Tan, H., Huang, Y., Xue, X., … Zhou, S. (2008). Vir-tual screening for novel quorum sensing inhibitors to eradicate biofilmformation of Pseudomonas aeruginosa. Applied Microbiology and Biotech-nology, 79(1), 119.
Zhang, L., Kong, Y., Wu, D., Zhang, H., Wu, J., Chen, J., … Shen, X. (2008).Three flavonoids targeting the β‐hydroxyacyl‐acyl carrier protein