Total Synthesis and Anti-Inflammatory Activity of Tectoridin and Related Isoflavone Glucosides.

The first total syntheses of four isoflavone glucosides, tectoridin (), tectoridin A (), tectorigenin 7--β-d-glucopyranosyl-12--β-d-glucopyranoside (), and isotectroigenin 7--β-d-glucopyranoside (), have been accomplished. Key steps in our synthetic approach include a regioselective halogenation reaction, followed by methanolysis to introduce the -OCH group into isoflavone frameworks and a PTC-promoted stereoselective glycosidation to establish glycosidic bonds. The synthesized isoflavone glucosides (-) and their corresponding aglycones ( and ) were evaluated for anti-inflammatory activity against nitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and interleukin-1 β (IL-1β) in lipopolysaccharide (LPS)-induced RAW264.

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.

Total Synthesis and Antibacterial Evaluation of Lupinifolin and Its Natural Analogues.

In this study, lupinifolin () and its natural analogues, mundulin (), minimiorin (), khonklonginol H (), flemichin D (), and eriosemaone A (), were obtained by chemical synthesis for the first time. Key steps involved an electrocyclization to build the linear pyran rings and a Claisen/Cope rearrangement to install the 8-prenyl substituents. All compounds were assessed for their antimicrobial activities against clinically relevant human pathogens, including one Gram-negative bacterial strain ( ATCC 25922) and four Gram-positive bacterial strains ( ATCC 29213, ATCC 29212, MRSA21-5, and VRE ATCC 51299).

Total syntheses and antibacterial evaluations of cudraflavones A-C and related Flavones.

The total syntheses of the natural prenylated flavones cudraflavones A-C (1-3), artoheterophyllin D (28) and artelasticin (29) are reported, along with the evaluations of their antibacterial activities. The key steps of the synthesis involved a Baker-Venkataraman rearrangement and an intramolecular cyclization for the construction of the flavone core and the regioselective formation of the pyran and isopentenyl scaffolds. The tested natural flavones 1-3 and 27-29 exhibited potent activity against S.