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Article

Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study

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Laboratorio de Productos Naturales, Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2390123, Chile
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Centro de Biotecnología CB-DAL, Universidad Técnica Federico Santa María, Valparaíso 2390136, Chile
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Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario 2000, Argentina
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Departamento de Ciencias del Ambiente, Facultad de Química y Biología, Universidad de Santiago de Chile, Santiago 9170022, Chile
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Laboratorio Bioquímica Celular, Departamento de Biología, Facultad de Química y Biología, Universidad de Santiago de Chile, Santiago 9170022, Chile
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Laboratorio de Virología Molecular y Control de Patógenos, Departamento de Biología, Facultad de Química y Biología, Universidad de Santiago de Chile, Santiago 9170022, Chile
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Programa Centro de Investigaciones Biomédicas Aplicadas, Escuela de Medicina, Facultad de Ciencias Médicas, Universidad de Santiago de Chile, Santiago 9170022, Chile
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Authors to whom correspondence should be addressed.
Academic Editor: Maurizio Battino
Int. J. Mol. Sci. 2021, 22(11), 5472; https://doi.org/10.3390/ijms22115472
Received: 27 April 2021 / Revised: 17 May 2021 / Accepted: 18 May 2021 / Published: 22 May 2021
(This article belongs to the Collection Feature Papers in Bioactives and Nutraceuticals)
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 7–13, 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′ 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. View Full-Text
Keywords: prenylated flavonoids; synthesis; antibacterial; MRSA; synergism; antifungal prenylated flavonoids; synthesis; antibacterial; MRSA; synergism; antifungal
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MDPI and ACS Style

Osorio, M.; Carvajal, M.; Vergara, A.; Butassi, E.; Zacchino, S.; Mascayano, C.; Montoya, M.; Mejías, S.; Martín, M.C.-S.; Vásquez-Martínez, Y. Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study. Int. J. Mol. Sci. 2021, 22, 5472. https://doi.org/10.3390/ijms22115472

AMA Style

Osorio M, Carvajal M, Vergara A, Butassi E, Zacchino S, Mascayano C, Montoya M, Mejías S, Martín MC-S, Vásquez-Martínez Y. Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study. International Journal of Molecular Sciences. 2021; 22(11):5472. https://doi.org/10.3390/ijms22115472

Chicago/Turabian Style

Osorio, Mauricio, Marcela Carvajal, Alejandra Vergara, Estefania Butassi, Susana Zacchino, Carolina Mascayano, Margarita Montoya, Sophia Mejías, Marcelo C.-S. Martín, and Yesseny Vásquez-Martínez. 2021. "Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study" International Journal of Molecular Sciences 22, no. 11: 5472. https://doi.org/10.3390/ijms22115472

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