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 μµg/mL, minimal bactericidal concentration (MBC) >512 μµg/mL) led to the analogue 7 with increased activity (MIC 8 μµg/mL, MBC 64 μµg/mL).

Structural requirements of benzofuran derivatives dehydro-δ-and dehydro-ε-viniferin for antimicrobial activity against the foodborne pathogen listeria monocytogenes / G. Catinella, L.M. Mattio, L. Musso, S. Arioli, D. Mora, G.L. Beretta, N. Zaffaroni, A. Pinto, S. Dallavalle. - In: INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. - ISSN 1661-6596. - 21:6(2020 Mar), pp. 2168.1-2168.10. [10.3390/ijms21062168]

Structural requirements of benzofuran derivatives dehydro-δ-and dehydro-ε-viniferin for antimicrobial activity against the foodborne pathogen listeria monocytogenes

Catinella G.;Mattio L. M.;Musso L.;Arioli S.;Mora D.;Pinto A.;Dallavalle S.
2020-03

Abstract

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 μµg/mL, minimal bactericidal concentration (MBC) >512 μµg/mL) led to the analogue 7 with increased activity (MIC 8 μµg/mL, MBC 64 μµg/mL).
Antimicrobials; Benzofuran nucleus; Listeria monocytogenes; Viniferin derivatives
Settore CHIM/10 - Chimica degli Alimenti
Settore CHIM/08 - Chimica Farmaceutica
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/731620
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