Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity

Molecules

Rui Liu¹  Bin Zhao¹  Dong-En Wang¹  Tianyu Yao¹  Long Pang¹  Qin Tu¹  Saeed Mahmoud Ahmed¹  Jian-Jun Liu¹ 

[1] ¹Colleges of Science and Forestry, Northwest A&F University, Yangling 712100, Shaanxi, China ²College of Agronomy and Life Sciences, Shanxi Datong University, Datong 037009, Shanxi, China

关键词: apigenin analogs;    antiproliferative activity;    antibacterial activity;    antioxidant activity;   

DOI  :  10.3390/molecules171214748

来源: mdpi

【 摘 要 】

A series of nitrogen-containing apigenin analogs 4a–j was synthesized via Mannich reactions to develop anticancer, antibacterial, and antioxidant agents from plant-derived flavonoids. The chemical structures of these compounds were confirmed using ¹H-NMR, ¹³C-NMR, and ESI-MS. The in vitro biological activities of the analogs were evaluated via assays of their antiproliferative, antibacterial, and antioxidant activities. The prepared apigenin analogs exhibited different antiproliferative activities against four human cancer cell lines, namely human cervical (HeLa), human hepatocellular liver (HepG2), human lung (A549), and human breast (MCF-7) cancer cells. Compound 4i showed the most favorable in vitro antiproliferative activity with IC₅₀ values of 40, 40, 223, and 166 μg/mL against HeLa, HepG2, A549, and MCF-7, respectively. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity assay also showed that 4i had the most potent antioxidant activity, with the smallest IC₅₀ value (334.8 μg/mL). The antibacterial activities of the analogs were determined using a two-fold serial dilution technique against four pathogenic bacteria, namely Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. All the prepared apigenin analogs exhibited more potent activities than the parent apigenin. Compounds 4h and 4j, in particular, exhibited the best inhibitory activities against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis with MIC values of 3.91 and 1.95 μg/mL, respectively.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.