Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study

Autores
Osorio, Mauricio; Carvajal, Marcela; Vergara, Alejandra; Butassi, Estefanía; Zacchino, Susana Alicia Stella; Mascayano, Carolina; Montoya, Margarita; Mejías, Sophia; Cortés San Martín, Marcelo; Vásquez Martínez, Yesseny
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fil: Osorio, Mauricio. Universidad Técnica Federico Santa María; Chile
Fil: Carvajal, Marcela. Universidad Técnica Federico Santa María; Chile
Fil: Vergara, Alejandra. Universidad Técnica Federico Santa María; Chile
Fil: Butassi, Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Mascayano, Carolina. Universidad de Santiago de Chile; Chile
Fil: Montoya, Margarita. Universidad de Santiago de Chile; Chile
Fil: Mejías, Sophia. Universidad de Santiago de Chile; Chile
Fil: Cortés San Martín, Marcelo. Universidad de Santiago de Chile; Chile
Fil: Vásquez Martínez, Yesseny. Universidad de Santiago de Chile; Chile
Materia
ANTIBACTERIAL
ANTIFUNGAL
MRSA
PRENYLATED FLAVONOIDS
SYNERGISM
SYNTHESIS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/164040
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico studyOsorio, MauricioCarvajal, MarcelaVergara, AlejandraButassi, EstefaníaZacchino, Susana Alicia StellaMascayano, CarolinaMontoya, MargaritaMejías, SophiaCortés San Martín, MarceloVásquez Martínez, YessenyANTIBACTERIALANTIFUNGALMRSAPRENYLATED FLAVONOIDSSYNERGISMSYNTHESIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Prenylated 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.Fil: Osorio, Mauricio. Universidad Técnica Federico Santa María; ChileFil: Carvajal, Marcela. Universidad Técnica Federico Santa María; ChileFil: Vergara, Alejandra. Universidad Técnica Federico Santa María; ChileFil: Butassi, Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Mascayano, Carolina. Universidad de Santiago de Chile; ChileFil: Montoya, Margarita. Universidad de Santiago de Chile; ChileFil: Mejías, Sophia. Universidad de Santiago de Chile; ChileFil: Cortés San Martín, Marcelo. Universidad de Santiago de Chile; ChileFil: Vásquez Martínez, Yesseny. Universidad de Santiago de Chile; ChileMultidisciplinary Digital Publishing Institute2021-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/164040Osorio, Mauricio; Carvajal, Marcela; Vergara, Alejandra; Butassi, Estefanía; Zacchino, Susana Alicia Stella; et al.; Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study; Multidisciplinary Digital Publishing Institute; International Journal of Molecular Sciences; 22; 11; 5-2021; 1-221422-0067CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1422-0067/22/11/5472info:eu-repo/semantics/altIdentifier/doi/10.3390/ijms22115472info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:07:31Zoai:ri.conicet.gov.ar:11336/164040instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-10 13:07:31.412CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study
title Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study
spellingShingle Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study
Osorio, Mauricio
ANTIBACTERIAL
ANTIFUNGAL
MRSA
PRENYLATED FLAVONOIDS
SYNERGISM
SYNTHESIS
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
dc.creator.none.fl_str_mv Osorio, Mauricio
Carvajal, Marcela
Vergara, Alejandra
Butassi, Estefanía
Zacchino, Susana Alicia Stella
Mascayano, Carolina
Montoya, Margarita
Mejías, Sophia
Cortés San Martín, Marcelo
Vásquez Martínez, Yesseny
author Osorio, Mauricio
author_facet Osorio, Mauricio
Carvajal, Marcela
Vergara, Alejandra
Butassi, Estefanía
Zacchino, Susana Alicia Stella
Mascayano, Carolina
Montoya, Margarita
Mejías, Sophia
Cortés San Martín, Marcelo
Vásquez Martínez, Yesseny
author_role author
author2 Carvajal, Marcela
Vergara, Alejandra
Butassi, Estefanía
Zacchino, Susana Alicia Stella
Mascayano, Carolina
Montoya, Margarita
Mejías, Sophia
Cortés San Martín, Marcelo
Vásquez Martínez, Yesseny
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIBACTERIAL
ANTIFUNGAL
MRSA
PRENYLATED FLAVONOIDS
SYNERGISM
SYNTHESIS
topic ANTIBACTERIAL
ANTIFUNGAL
MRSA
PRENYLATED FLAVONOIDS
SYNERGISM
SYNTHESIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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.
Fil: Osorio, Mauricio. Universidad Técnica Federico Santa María; Chile
Fil: Carvajal, Marcela. Universidad Técnica Federico Santa María; Chile
Fil: Vergara, Alejandra. Universidad Técnica Federico Santa María; Chile
Fil: Butassi, Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Mascayano, Carolina. Universidad de Santiago de Chile; Chile
Fil: Montoya, Margarita. Universidad de Santiago de Chile; Chile
Fil: Mejías, Sophia. Universidad de Santiago de Chile; Chile
Fil: Cortés San Martín, Marcelo. Universidad de Santiago de Chile; Chile
Fil: Vásquez Martínez, Yesseny. Universidad de Santiago de Chile; Chile
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 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.
publishDate 2021
dc.date.none.fl_str_mv 2021-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/164040
Osorio, Mauricio; Carvajal, Marcela; Vergara, Alejandra; Butassi, Estefanía; Zacchino, Susana Alicia Stella; et al.; Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study; Multidisciplinary Digital Publishing Institute; International Journal of Molecular Sciences; 22; 11; 5-2021; 1-22
1422-0067
CONICET Digital
CONICET
url http://hdl.handle.net/11336/164040
identifier_str_mv Osorio, Mauricio; Carvajal, Marcela; Vergara, Alejandra; Butassi, Estefanía; Zacchino, Susana Alicia Stella; et al.; Prenylated flavonoids with potential antimicrobial activity: synthesis, biological activity, and in silico study; Multidisciplinary Digital Publishing Institute; International Journal of Molecular Sciences; 22; 11; 5-2021; 1-22
1422-0067
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1422-0067/22/11/5472
info:eu-repo/semantics/altIdentifier/doi/10.3390/ijms22115472
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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