Engineering Research Center for Pharmaceuticals and Equipment of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China; Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China.
Engineering Research Center for Pharmaceuticals and Equipment of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China.
Bioorg Chem. 2023 Nov;140:106764. doi: 10.1016/j.bioorg.2023.106764. Epub 2023 Aug 9.
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. aureus ATCC 29213, S. epidermidis ATCC 14990, E. faecalis ATCC 29212 and B. subtilis ATCC 6633 with MIC values ranging from 0.125 μg/mL to 16 μg/mL. Compound 3 displayed the strongest potency, with MIC values in the range between 0.125 and 1 μg/mL, as a potential candidate to combat G bacterial infections. Preliminary mechanism of action studies suggested that this compound killed bacteria by disrupting bacterial membrane integrity.
天然异戊烯基黄酮类化合物 cudraflavones A-C（1-3）、artoheterophyllin D（28）和 artelasticin（29）的全合成及其抗菌活性评价报告。合成的关键步骤包括 Baker-Venkataraman 重排和分子内环化构建黄酮核以及区域选择性形成吡喃和异戊烯基骨架。测试的天然黄酮类化合物 1-3 和 27-29 对金黄色葡萄球菌 ATCC 29213、表皮葡萄球菌 ATCC 14990、粪肠球菌 ATCC 29212 和枯草芽孢杆菌 ATCC 6633 表现出很强的活性，MIC 值范围为 0.125μg/mL 至 16μg/mL。化合物 3 表现出最强的活性，MIC 值范围在 0.125 到 1μg/mL 之间，是一种有潜力的对抗 G 细菌感染的候选药物。初步作用机制研究表明，该化合物通过破坏细菌膜完整性杀死细菌。
