Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms

Developing new types of effective antimicrobial compounds derived from natural products is of interest for the food industry. Some analogs to A-type proanthocyanidins have shown promising antimicrobial and antibiofilm activities against foodborne bacteria. We report herein the synthesis of seven add...

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Autores: Cobo Molinos, Antonio, Alejo Armijo, Alfonso, Cruz Sáez, Daniel, Altarejos Caballero, Joaquín, Salido Ruíz, Sofía, Ortega Morente, Elena
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Recursos:Universidad de Jaén
Repositorio:RUJA. Repositorio Institucional de la Producción Científica de la Universidad de Jaén
OAI Identifier:oai:ruja.ujaen.es:10953/7063
Acesso em linha:https://doi.org/10.3390/molecules28124844
https://hdl.handle.net/10953/7063
Access Level:acceso abierto
Palavra-chave:A-type proanthocyanidin analogs
flavylium chemistry
antimicrobial activity
antibiofilm activity
antioxidant activity
5
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spelling Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne MicroorganismsCobo Molinos, AntonioAlejo Armijo, AlfonsoCruz Sáez, DanielAltarejos Caballero, JoaquínSalido Ruíz, SofíaOrtega Morente, ElenaA-type proanthocyanidin analogsflavylium chemistryantimicrobial activityantibiofilm activityantioxidant activity5Developing new types of effective antimicrobial compounds derived from natural products is of interest for the food industry. Some analogs to A-type proanthocyanidins have shown promising antimicrobial and antibiofilm activities against foodborne bacteria. We report herein the synthesis of seven additional analogs with NO2 group at A-ring and their abilities for inhibiting the growth and the biofilm formation by twenty-one foodborne bacteria. Among them, analog 4 (one OH at B-ring; two OHs at D-ring) showed the highest antimicrobial activity. The best results with these new analogs were obtained in terms of their antibiofilm activities: analog 1 (two OHs at B-ring; one OH at D-ring) inhibited at least 75% of biofilm formation by six strains at all of the concentrations tested, analog 2 (two OHs at B-ring; two OHs at D-ring; one CH3 at C-ring) also showed antibiofilm activity on thirteen of the bacteria tested, and analog 5 (one OH at B-ring; one OH at D-ring) was able to disrupt preformed biofilms in eleven strains. The description of new and more active analogs of natural compounds and the elucidation of their structure-activity relationships may contribute to the active development of new food packaging for preventing biofilm formation and lengthening the food shelf life.This research was funded by the Andalusian Consejería de Economía y Conocimiento (FEDER program 2014–2020: grant number 1380669), Spain, and the Spanish Ministerio de Ciencia, Innovación y Universidades (grant RTI2018-098560-B-C22, co-financed by the FEDER funds of the European Union), and partially supported by the Centro de Instrumentación Científico-Técnica (CICT) of the University of Jaén, Spain.MDPI202620262023info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://doi.org/10.3390/molecules28124844https://hdl.handle.net/10953/7063reponame:RUJA. Repositorio Institucional de la Producción Científica de la Universidad de Jaéninstname:Universidad de JaénInglésMolecules 2023; 28(12): 4844info:eu-repo/semantics/openAccessoai:ruja.ujaen.es:10953/70632026-06-24T12:41:07Z
dc.title.none.fl_str_mv Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
title Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
spellingShingle Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
Cobo Molinos, Antonio
A-type proanthocyanidin analogs
flavylium chemistry
antimicrobial activity
antibiofilm activity
antioxidant activity
5
title_short Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
title_full Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
title_fullStr Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
title_full_unstemmed Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
title_sort Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
dc.creator.none.fl_str_mv Cobo Molinos, Antonio
Alejo Armijo, Alfonso
Cruz Sáez, Daniel
Altarejos Caballero, Joaquín
Salido Ruíz, Sofía
Ortega Morente, Elena
author Cobo Molinos, Antonio
author_facet Cobo Molinos, Antonio
Alejo Armijo, Alfonso
Cruz Sáez, Daniel
Altarejos Caballero, Joaquín
Salido Ruíz, Sofía
Ortega Morente, Elena
author_role author
author2 Alejo Armijo, Alfonso
Cruz Sáez, Daniel
Altarejos Caballero, Joaquín
Salido Ruíz, Sofía
Ortega Morente, Elena
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv A-type proanthocyanidin analogs
flavylium chemistry
antimicrobial activity
antibiofilm activity
antioxidant activity
5
topic A-type proanthocyanidin analogs
flavylium chemistry
antimicrobial activity
antibiofilm activity
antioxidant activity
5
description Developing new types of effective antimicrobial compounds derived from natural products is of interest for the food industry. Some analogs to A-type proanthocyanidins have shown promising antimicrobial and antibiofilm activities against foodborne bacteria. We report herein the synthesis of seven additional analogs with NO2 group at A-ring and their abilities for inhibiting the growth and the biofilm formation by twenty-one foodborne bacteria. Among them, analog 4 (one OH at B-ring; two OHs at D-ring) showed the highest antimicrobial activity. The best results with these new analogs were obtained in terms of their antibiofilm activities: analog 1 (two OHs at B-ring; one OH at D-ring) inhibited at least 75% of biofilm formation by six strains at all of the concentrations tested, analog 2 (two OHs at B-ring; two OHs at D-ring; one CH3 at C-ring) also showed antibiofilm activity on thirteen of the bacteria tested, and analog 5 (one OH at B-ring; one OH at D-ring) was able to disrupt preformed biofilms in eleven strains. The description of new and more active analogs of natural compounds and the elucidation of their structure-activity relationships may contribute to the active development of new food packaging for preventing biofilm formation and lengthening the food shelf life.
publishDate 2023
dc.date.none.fl_str_mv 2023
2026
2026
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://doi.org/10.3390/molecules28124844
https://hdl.handle.net/10953/7063
url https://doi.org/10.3390/molecules28124844
https://hdl.handle.net/10953/7063
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Molecules 2023; 28(12): 4844
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:RUJA. Repositorio Institucional de la Producción Científica de la Universidad de Jaén
instname:Universidad de Jaén
instname_str Universidad de Jaén
reponame_str RUJA. Repositorio Institucional de la Producción Científica de la Universidad de Jaén
collection RUJA. Repositorio Institucional de la Producción Científica de la Universidad de Jaén
repository.name.fl_str_mv
repository.mail.fl_str_mv
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