Total Syntheses and Antibacterial Studies of Natural Isoflavones: Scandenone, Osajin, and 6,8-Diprenylgenistein.

Isoflavones are a class of natural products that exhibit a wide range of interesting biological properties, including antioxidant, hepatoprotective, antimicrobial, and anti-inflammatory activities. Scandenone (), osajin (), and 6,8-diprenylgenistein () are natural prenylated isoflavones that share the same polyphenol framework. In this research, the key intermediate was used for the synthesis of the natural isoflavones -, establishing a stereoselective synthetic method for both linear and angular pyran isoflavones. The antibacterial activities of - were also evaluated, and all of them displayed good antibacterial activity against Gram-positive bacteria. Among them, was the most potent one against MRSA, with a MIC value of 2 μg/mL, and the SEM assay indicated that the bacterial cell membranes of both MRSA and could be disrupted by . These findings suggest that this type of isoflavone could serve as a lead for the development of novel antibacterial agents for the treatment of Gram-positive bacterial infections.