Total syntheses and antibacterial evaluations of cudraflavones A-C and related Flavones.
Total syntheses and antibacterial evaluations of cudraflavones A-C and related Flavones.
复制标题
DOI：
10.1016/j.bioorg.2023.106764
复制
发表时间：
2023-08
影响因子：
5.1
通讯作者：
Hongbo Dong;Lihong Liao;P. Yu;Bin Long;Yufei Che;Lan Lu;Bing Xu
中科院分区：
文献类型：
--
作者：
Hongbo Dong;Lihong Liao;P. Yu;Bin Long;Yufei Che;Lan Lu;Bing Xu
报道了天然异戊烯化黄酮类化合物cudraflavone A-C（1-3），artoheterophyllin D（28）和artelasticin（29）的全合成，并对它们的抗菌活性进行了沿着评价。合成的关键步骤包括Baker-Venkataraman重排和分子内环化，用于黄酮核心的构建和吡喃和异戊烯基支架的区域选择性形成。天然黄酮1 - 3和27 - 29具有较强的抗S. aureusATCC29213、S. epidermidisATCC14990、E.粪菌ATCC 29212和B.枯草杆菌ATCC 6633，MIC值范围为0.125 μg/mL至16 μg/mL。化合物3显示出最强的效力，MIC值在0.125和1 μg/mL之间，作为对抗G+细菌感染的潜在候选物。初步的作用机制研究表明，这种化合物通过破坏细菌膜的完整性来杀死细菌。
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 flavones1–3and27–29exhibited potent activity againstS. aureusATCC 29213,S. epidermidisATCC 14990,E. faecalisATCC 29212 andB. subtilisATCC 6633 with MIC values ranging from 0.125 μg/mL to 16 μg/mL. Compound3displayed 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.