Antibacterial and Antioxidant Activity of Synthetic Polyoxygenated Flavonoids

Author:

Osorio-Olivares Mauricio Enrique1ORCID,Vásquez-Martínez Yesseny2ORCID,Díaz Katy3ORCID,Canelo Javiera2,Taborga Lautaro4ORCID,Espinoza-Catalán Luis1ORCID

Affiliation:

1. Laboratorio de Síntesis Orgánica, Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2390123, Chile

2. Escuela de Medicina, Facultad de Ciencias Médicas, Laboratorio de Virología Molecular y Control de Patógenos, Facultad de Química y Biología, Universidad de Santiago de Chile, Santiago 9170022, Chile

3. Laboratorio de Pruebas Biológicas, Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2390123, Chile

4. Laboratorio de Productos Naturales, Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2390123, Chile

Abstract

Flavonoids are an abundant class of naturally occurring compounds with broad biological activities, but their limited abundance in nature restricts their use in medicines and food additives. Here we present the synthesis and determination of the antibacterial and antioxidant activities of twenty-two structurally related flavonoids (five of which are new) by scientifically validated methods. Flavanones (FV1–FV11) had low inhibitory activity against the bacterial growth of MRSA 97-7. However, FV2 (C5,7,3′,4′ = OH) and FV6 (C5,7 = OH; C4′ = SCH3) had excellent bacterial growth inhibitory activity against Gram-negative E. coli (MIC = 25 µg/mL for both), while Chloramphenicol (MIC = 25 µg/mL) and FV1 (C5,7,3′ = OCH3; 4′ = OH) showed inhibitory activity against Gram-positive L. monocytogenes (MIC = 25 µg/mL). From the flavone series (FO1–FO11), FO2 (C5,7,3′,4′ = OH), FO3 (C5,7,4′ = OH; 3′ = OCH3), and FO5 (C5,7,4′ = OH) showed good inhibitory activity against Gram-positive MRSA 97-7 (MIC = 50, 12, and 50 µg/mL, respectively), with FO3 being more active than the positive control Vancomycin (MIC = 25 µg/mL). FO10 (C5,7= OH; 4′ = OCH3) showed high inhibitory activity against E. coli and L. monocytogenes (MIC = 25 and 15 µg/mL, respectively). These data add significantly to our knowledge of the structural requirements to combat these human pathogens. The positions and number of hydroxyl groups were key to the antibacterial and antioxidant activities.

Funder

Dirección General de Investigación, Innovación y Emprendimiento (DGIIE) of the Universidad Técnica Federico Santa María

ANID

FONDEF IT21I003

Publisher

MDPI AG

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