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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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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). |
format | Online Article Text |
id | pubmed-7139904 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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