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And Dehydro-Ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria Monocytogenes

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And Dehydro-Ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria Monocytogenes International Journal of Molecular Sciences Article Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-"-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes Giorgia Catinella 1, Luce M. Mattio 1 , Loana Musso 1, Stefania Arioli 1 , Diego Mora 1 , Giovanni Luca Beretta 2 , Nadia Zaffaroni 2 , Andrea Pinto 1,* and Sabrina Dallavalle 1 1 Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Celoria 2, 20133 Milan, Italy; [email protected] (G.C.); [email protected] (L.M.M.); [email protected] (L.M.); [email protected] (S.A.); [email protected] (D.M.); [email protected] (S.D.) 2 Molecular Pharmacology Unit, Department of Applied Research and Technological Development, Fondazione IRCCS Istituto Nazionale Tumori, Via Amadeo 42, 20133 Milan, Italy; [email protected] (G.L.B.); nadia.zaff[email protected] (N.Z.) * Correspondence: [email protected] Received: 15 February 2020; Accepted: 19 March 2020; Published: 21 March 2020 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-"-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). Keywords: viniferin derivatives; benzofuran nucleus; antimicrobials; Listeria monocytogenes 1. Introduction Benzofuran derivatives are an important class of heterocyclic compounds, occupying a place in numerous bioactive natural products. Over time, they have attracted the attention of many researchers due to the broad scope of their activity, which includes anticancer, antimicrobial, immunomodulatory, antioxidant and anti-inflammatory properties [1,2]. In recent years, the benzofuran scaffold has emerged as a pharmacophore of choice for designing antimicrobial agents, and numerous achievements have revealed that benzofuran-based compounds have an extensive potential in this field [3]. As a part of our efforts in the search for new antimicrobial agents, we have recently evaluated the antimicrobial activity of a collection of resveratrol-derived monomers (e.g., resveratrol, pterostilbene) and dimers (e.g., trans-δ-viniferin, trans-"-viniferin, dehydro-δ-viniferin 1, viniferifuran 2), which were screened as single molecules against a panel of foodborne pathogens (Figure1)[4]. Int. J. Mol. Sci. 2020, 21, 2168; doi:10.3390/ijms21062168 www.mdpi.com/journal/ijms Int. J. Mol. Sci. 2020, 21, 2168 2 of 10 Int. J. Mol. Sci. 2020, 21, x FOR PEER REVIEW 2 of 10 FigureFigure 1. Structures 1. Structures of resveratrol of resveratrol an andd representative representative resveratrol- resveratrol-derivedderived monomers monomers and and dimers. dimers. The most promising dimeric compound, dehydro-δ-viniferin 1, was endowed with significant Theantibacterial most promising activity against dimeric Gram-positive compound, bacteria.dehydro- Itδ-viniferin was verified 1, was that theendowed activity with of 1 againstsignificant antibacterialL. monocytogenes activitywas against achieved Gram-positive by damaging bact theeria. cytoplasmic It was verified membrane that with the significant activity of membrane 1 against L. monocytogenesdepolarization, was aachieved loss of membrane by damaging integrity, the and cytoplas severe morphologicalmic membrane changes. with The si dimericgnificant compound membrane depolarization,2 showed significant a loss of antimicrobial membrane activity integrity, as well and [4]. severe morphological changes. The dimeric compoundThese 2 showed promising significant results antimicrobial prompted us to activity explore as1 welland 2[4].as platforms in the search for new Theseantimicrobial promising scaffolds. results To provideprompted a deeper us to insight explore into 1 the and activity 2 as ofplatforms these compounds, in the search we planned for new antimicrobialto perform scaffolds. preliminary To structure–activityprovide a deeper relationship insight into (SAR) the studies.activity Theof these unique compounds, structural features we planned of to performcompounds preliminary1 and 2, bothstructure–activity containing a versatile relationship benzofuran (SAR) core studies. structure, The make unique them amenablestructural for features the generation of differently substituted analogues. To shed light on the minimal structural features which of compounds 1 and 2, both containing a versatile benzofuran core structure, make them amenable retain antimicrobial activity, we designed a small collection of simplified derivatives of compounds for the generation of differently substituted analogues. To shed light on the minimal structural 1 and 2 by a systematic removal of the moieties linked to the benzofuran rings (groups A, B, C) features(Figure which2), and retain we testedantimicrobial all the derivatives activity, against we designedListeria monocytogenesa small collectionas a representative of simplified foodborne derivatives of compoundsGram-positive 1 and bacterium, 2 by a systematic which was removal found to of be the sensitive moieties to compounds linked to the1 and benzofuran2 [4]. rings (groups A, B, C) (FigureTherefore, 2), and we designed we tested the all three the possiblederivatives simplified against analogues Listeria ofmonocytogenes compound 1 (compounds as a representative3–5) foodborneand the Gram-positive three possible simplifiedbacterium, analogues which was of compound found to be2 (compounds sensitive to6 –compounds8) (Figure2). 1 In and addition, 2 [4]. we designed three representative analogues (9–11) containing the -OMe groups in place of the phenolic -OH on the aromatic rings. The evaluation of the antimicrobial activity of the compounds provided an integrated overview of the structural determinants for the activity against the foodborne pathogenic species L. monocytogenes Scott A. Int. J. Mol. Sci. 2020, 21, 2168 3 of 10 Int. J. Mol. Sci. 2020, 21, x FOR PEER REVIEW 3 of 10 Figure 2. Structures of compounds 1 and 2 and of the simplified analogues 3–8 and 9–11. Figure 2. Structures of compounds 1 and 2 and of the simplified analogues 3–8 and 9–11. 2. Results Therefore, we designed the three possible simplified analogues of compound 1 (compounds 3– In the present SAR study, different synthetic approaches were set up depending on the nature of 5) and the three possible simplified analogues of compound 2 (compounds 6–8) (Figure 2). In the benzofuran substitution pattern. addition, we designed three representative analogues (9–11) containing the -OMe groups in place of Initially, we focused on the synthesis of the simplified analogues of compound 1. Compound the phenolic -OH on the aromatic rings. 14 was obtained by a Cu-catalyzed tandem Sonogashira coupling–cyclization reaction starting with The evaluation of the antimicrobial activity of the compounds provided an integrated overview 12 13 14 of2-iodophenol the structuraland determinants 1-ethynyl-4-methoxybenzene for the activity against[5,6 ].the The foodborne iodination pathogenic of with species NIS gave L. 15 15 monocytogenescompound Scottin a 74%A. yield [7]. Suzuki coupling of with (3,5-dimethoxyphenyl)boronic acid gave the permethylated intermediate 16, which, after the deprotection of the phenolic -OH with BBr3, Int.2.aff Results ordedJ. Mol. Sci. 2,3-disubstituted 2020, 21, x FOR PEER benzofuran REVIEW 3 (Scheme1). 4 of 10 In the present SAR study, different synthetic approaches were set up depending on the nature of the benzofuran substitution pattern. Initially, we focused on the synthesis of the simplified analogues of compound 1. Compound 14 was obtained by a Cu-catalyzed tandem Sonogashira coupling–cyclization reaction starting with 2- iodophenol 12 and 1-ethynyl-4-methoxybenzene 13 [5,6]. The iodination of 14 with NIS gave compound 15 in a 74% yield [7]. Suzuki coupling of 15 with (3,5-dimethoxyphenyl)boronic acid gave the permethylated intermediate 16, which, after the deprotection of the phenolic -OH with BBr3, afforded 2,3-disubstituted benzofuran 3 (Scheme 1). Scheme 1. Reagents and conditions: (a) (i) PdCl2(PPh3)2 (5% mol), CuI (3% mol), TEA:THF 1:1, Scheme 1. Reagents and conditions: a) i) PdCl2(PPh3)2 (5% mol), CuI (3% mol), TEA:THF 1:1, N2, 40 N2, 40 ◦C, 40 min; (ii) ACN, 100 ◦C, 90 min, 50%; (b) NIS, p-TsOH, ACN, N2, overnight, 74%; (c) °C, 40 min; ii) ACN, 100 °C, 90 min, 50%; b) NIS, p-TsOH, ACN, N2, overnight, 74%; c) (3,5- (3,5-dimethoxyphenyl)boronic acid, K2CO3, PdCl2(dppf) CH2Cl2, THF:H2O 1:1, MW, 70 ◦C, 30 min, dimethoxyphenyl)boronic acid, K2CO3, PdCl2(dppf)·CH2Cl· 2, THF:H2O 1:1, MW, 70 °C, 30 min, 83%; 83%; (d) BBr3, DCM, 0 ◦C to rt, overnight, 61%. d) BBr3, DCM, 0 °C to rt, overnight, 61%. The synthesis of compound
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