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

被引：13

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.

引用

页数：8

共 38 条

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