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

被引：9
|
作者：
Dong, Hongbo [1 ,2 ]
Liao, Li [1 ,2 ]
Yu, Pei [1 ]
Long, Bin [1 ]
Che, Yufei [1 ]
Lu, Lan [2 ]
Xu, Bing [3 ]
机构：
[1] Chengdu Univ, Engn Res Ctr Pharmaceut & Equipment Sichuan Prov, Sch Pharm, Chengdu 610106, Peoples R China
[2] Chengdu Univ, Antiinfect Agent Creat Engn Res Ctr Sichuan Prov, Sch Pharm, Chengdu 610106, Peoples R China
[3] Univ Elect Sci & Technol China, Sichuan Prov Peoples Hosp, Dept Pediat Surg, Chengdu 610072, Peoples R China
来源：
BIOORGANIC CHEMISTRY | 2023年 / 140卷
基金：
中国国家自然科学基金;
关键词：
Natural product; Total synthesis; Prenylated flavone; Antibacterial activity; ISOPRENYLATED FLAVONES; CUDRANIA-TRICUSPIDATA; ROOT BARK; COMPONENTS; INHIBITORS;
D O I：
10.1016/j.bioorg.2023.106764
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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 & mu;g/mL to 16 & mu;g/mL. Compound 3 displayed the strongest potency, with MIC values in the range between 0.125 and 1 & mu;g/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.
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页数：8
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