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

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 ﬂavon...

Descripción completa

Detalles Bibliográficos
Autores principales:	Osorio, Mauricio E., Caravajal, Marcela A., Vergara, Alejandra P., Butassi, Estefanía, Zacchino, Susana, Mascayano, Carolina, Montoya, Margarita, Mejías, Sophia, Cortez-San Martín, Marcelo, Vásquez-Martínez, Yesseny A.
Formato:	article artículo
Lenguaje:	Inglés
Publicado:	MDPI 2022
Materias:	Prenylated Flavonoids Synthesis Antibacterial MRSA Synergism Antifungal
Acceso en línea:	http://hdl.handle.net/2133/23311 http://hdl.handle.net/2133/23311
Aporte de:	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario

id	I15-R121-2133-23311
record_format	dspace
institution	Universidad Nacional de Rosario
institution_str	I-15
repository_str	R-121
collection	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language	Inglés
orig_language_str_mv	eng
topic	Prenylated Flavonoids Synthesis Antibacterial MRSA Synergism Antifungal
spellingShingle	Prenylated Flavonoids Synthesis Antibacterial MRSA Synergism Antifungal Osorio, Mauricio E. Caravajal, Marcela A. Vergara, Alejandra P. Butassi, Estefanía Zacchino, Susana Mascayano, Carolina Montoya, Margarita Mejías, Sophia Cortez-San Martín, Marcelo Vásquez-Martínez, Yesseny A. Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study
topic_facet	Prenylated Flavonoids Synthesis Antibacterial MRSA Synergism Antifungal
description	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 40 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.
format	article artículo
author	Osorio, Mauricio E. Caravajal, Marcela A. Vergara, Alejandra P. Butassi, Estefanía Zacchino, Susana Mascayano, Carolina Montoya, Margarita Mejías, Sophia Cortez-San Martín, Marcelo Vásquez-Martínez, Yesseny A.
author_facet	Osorio, Mauricio E. Caravajal, Marcela A. Vergara, Alejandra P. Butassi, Estefanía Zacchino, Susana Mascayano, Carolina Montoya, Margarita Mejías, Sophia Cortez-San Martín, Marcelo Vásquez-Martínez, Yesseny A.
author_sort	Osorio, Mauricio E.
title	Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study
title_short	Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study
title_full	Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study
title_fullStr	Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study
title_full_unstemmed	Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study
title_sort	prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study
publisher	MDPI
publishDate	2022
url	http://hdl.handle.net/2133/23311 http://hdl.handle.net/2133/23311
work_keys_str_mv	AT osoriomauricioe prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT caravajalmarcelaa prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT vergaraalejandrap prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT butassiestefania prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT zacchinosusana prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT mascayanocarolina prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT montoyamargarita prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT mejiassophia prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT cortezsanmartinmarcelo prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy AT vasquezmartinezyessenya prenylatedflavonoidswithpotentialantimicrobialactivitysynthesisbiologicalactivityandinsilicostudy
bdutipo_str	Repositorios
_version_	1764820411952922624

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

Ejemplares similares