Antimicrobial and anti-biofilm properties of novel synthetic lignan-like compounds.

Antibiotic resistance and biofilm tolerance are among the principal factors involved in the persistence of chronic infections. The need for new antimicrobials is an ever-increasing challenge in clinical environments and in the control of global health. Arylfurans form a set of structures that have been identified in many natural products, e.g. lignans. Lignans are a sub-group of non-flavonoid polyphenols that play an active role in plants' defense against bacteria and fungi infections. The aim of this study was to identify novel synthetic arylfurans and lignan-like arylbenzylfurans exhibiting antimicrobial properties. The molecules synthetized were tested against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus and S. epidermidis. We found that among tested compounds, arylbenzylfuran 11 was active against S. aureus and S. epidermidis with an MIC of 4 µg ml-1. Compound 11 was also active on methicillin-resistant S. aureus and S. epidermidis. By confocal laser scanning microscopy, we showed that 32 µg ml-1 of compound 11 was able to induce a significant reduction in S. aureus and S. epidermidis biofilms viability. Finally, we demonstrated that compound 11 was not cytotoxic on HaCat cells up to 128 µg ml-1. This work shows the antimicrobial and anti-biofilm potential of a synthetic lignan-like furan.

Lignans by photo-oxidation of propenyl phenols.

Dimeric cyclic or acyclic lignan derivatives have been obtained from isoeugenol under light induced oxidations (mainly by MB-sensitized photooxygenation in water/CH(3)CN or di-tert-butyl peroxide photo-oxidation). Coniferyl alcohol gives lignans only under peroxide-mediated photo-oxidation while ferulic acid was unreactive under both conditions.