Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold.

Scientific reports 2023 Sep 25

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Stilbene dimers are well-known for their diverse biological activities. In particular, previous studies have demonstrated the high antibacterial potential of a series of trans-δ-viniferin-related compounds against gram-positive bacteria such as Staphylococcus aureus. The trans-δ-viniferin scaffold has multiple chemical functions and can therefore be modified in various ways to generate derivatives. Here we report the synthesis of 40 derivatives obtained by light isomerization, O-methylation, halogenation and dimerization of other stilbene monomers. The antibacterial activities of all generated trans-δ-viniferin derivatives were evaluated against S. aureus and information on their structure-activity relationships (SAR) was obtained using a linear regression model. Our results show how several parameters, such as the O-methylation pattern and the presence of halogen atoms at specific positions, can determine the antibacterial activity. Taken together, these results can serve as a starting point for further SAR investigations. © 2023. Springer Nature Limited.

Citation

Robin Huber, Laurence Marcourt, Margaux Héritier, Alexandre Luscher, Laurie Guebey, Sylvain Schnee, Emilie Michellod, Stéphane Guerrier, Jean-Luc Wolfender, Leonardo Scapozza, Thilo Köhler, Katia Gindro, Emerson Ferreira Queiroz. Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold. Scientific reports. 2023 Sep 25;13(1):15986