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Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes

In a recent study, we investigated the antimicrobial activity of a collection of resveratrol-derived monomers and dimers against a series of foodborne pathogens. Out of the tested molecules, dehydro-δ-viniferin and dehydro-ε-viniferin emerged as the most promising derivatives. To define the structur...

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Autores principales: Catinella, Giorgia, Mattio, Luce M., Musso, Loana, Arioli, Stefania, Mora, Diego, Beretta, Giovanni Luca, Zaffaroni, Nadia, Pinto, Andrea, Dallavalle, Sabrina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7139904/
https://www.ncbi.nlm.nih.gov/pubmed/32245220
http://dx.doi.org/10.3390/ijms21062168
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author Catinella, Giorgia
Mattio, Luce M.
Musso, Loana
Arioli, Stefania
Mora, Diego
Beretta, Giovanni Luca
Zaffaroni, Nadia
Pinto, Andrea
Dallavalle, Sabrina
author_facet Catinella, Giorgia
Mattio, Luce M.
Musso, Loana
Arioli, Stefania
Mora, Diego
Beretta, Giovanni Luca
Zaffaroni, Nadia
Pinto, Andrea
Dallavalle, Sabrina
author_sort Catinella, Giorgia
collection PubMed
description In a recent study, we investigated the antimicrobial activity of a collection of resveratrol-derived monomers and dimers against a series of foodborne pathogens. Out of the tested molecules, dehydro-δ-viniferin and dehydro-ε-viniferin emerged as the most promising derivatives. To define the structural elements essential to the antimicrobial activity against the foodborne pathogen L. monocytogenes Scott A as a model Gram-positive microorganism, the synthesis of a series of simplified benzofuran-containing derivatives was carried out. The systematic removal of the aromatic moieties of the parent molecules allowed a deeper insight into the most relevant structural features affecting the activity. While the overall structure of compound 1 could not be altered without a substantial loss of antimicrobial activity, the structural simplification of compound 2 (minimal inhibitory concentration (MIC) 16 µg/mL, minimal bactericidal concentration (MBC) >512 µg/mL) led to the analogue 7 with increased activity (MIC 8 µg/mL, MBC 64 µg/mL).
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spelling pubmed-71399042020-04-13 Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes Catinella, Giorgia Mattio, Luce M. Musso, Loana Arioli, Stefania Mora, Diego Beretta, Giovanni Luca Zaffaroni, Nadia Pinto, Andrea Dallavalle, Sabrina Int J Mol Sci Article In a recent study, we investigated the antimicrobial activity of a collection of resveratrol-derived monomers and dimers against a series of foodborne pathogens. Out of the tested molecules, dehydro-δ-viniferin and dehydro-ε-viniferin emerged as the most promising derivatives. To define the structural elements essential to the antimicrobial activity against the foodborne pathogen L. monocytogenes Scott A as a model Gram-positive microorganism, the synthesis of a series of simplified benzofuran-containing derivatives was carried out. The systematic removal of the aromatic moieties of the parent molecules allowed a deeper insight into the most relevant structural features affecting the activity. While the overall structure of compound 1 could not be altered without a substantial loss of antimicrobial activity, the structural simplification of compound 2 (minimal inhibitory concentration (MIC) 16 µg/mL, minimal bactericidal concentration (MBC) >512 µg/mL) led to the analogue 7 with increased activity (MIC 8 µg/mL, MBC 64 µg/mL). MDPI 2020-03-21 /pmc/articles/PMC7139904/ /pubmed/32245220 http://dx.doi.org/10.3390/ijms21062168 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Catinella, Giorgia
Mattio, Luce M.
Musso, Loana
Arioli, Stefania
Mora, Diego
Beretta, Giovanni Luca
Zaffaroni, Nadia
Pinto, Andrea
Dallavalle, Sabrina
Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes
title Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes
title_full Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes
title_fullStr Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes
title_full_unstemmed Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes
title_short Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes
title_sort structural requirements of benzofuran derivatives dehydro-δ- and dehydro-ε-viniferin for antimicrobial activity against the foodborne pathogen listeria monocytogenes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7139904/
https://www.ncbi.nlm.nih.gov/pubmed/32245220
http://dx.doi.org/10.3390/ijms21062168
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