Active kill disk torrent6/7/2023 Prenylated flavonoids are a subclass of natural flavonoids characterized by the presence of a prenylated side chain (i.e., prenyl, geranyl and lavandulyl) attached to the flavonoid skeleton. According to docking results of S enantiomer of 11 with ATP-binding cassette transporter showed the most favorable binding energy however, more studies are needed to support this result. Compound 11 combined with ciprofloxacin was able to decrease the levels of ROS generated by ciprofloxacin. The combination of 11 or 12 with commercial antibiotics synergistically enhanced the antibacterial activity of vancomycin, ciprofloxacin, and methicillin in a factor of 10 to 100 times against drug-resistant bacteria. Compounds 11, 12 (flavanones) and 13 (isoflavone) were the most active against clinical isolated Staphylococcus aureus MRSA, showing that structural requirements as prenylation at position C-6 or C-8 and OH at positions C-5, 7, and 4′ are key to the antibacterial activity. Compounds 9, 11, and 12 showed inhibitory activity against human pathogenic fungi. Here, we showed the hemisynthesis and the determination of various biological activities of seven prenylated flavonoids, named 7–13, with an emphasis on antimicrobial ones. Prenylated flavonoids are an important class of naturally occurring flavonoids with important biological activity, but their low abundance in nature limits their application in medicines.
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