Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents

Abstract

Two series of apigenin [5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one] derivatives, 3a-3j and 4a-4j, were synthesized. The apigenin and alkyl amines moieties of these compounds were separated by C 2 or C 3 spacers, respectively. The chemical structures of the apigenin derivatives were confirmed using 1 H-NMR, 13 C-NMR, and electrospray ionization mass spectroscopy. The in vitro antibacterial and antiproliferative activities of all synthesized compounds were determined. Among the tested compounds, 4a-4j displayed significant antibacterial activity against the tested strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa). Additionally, 4i showed the best inhibitory activity with minimum inhibitory concentrations of 1.95, 3.91, 3.91, and 3.91 μg/mL against S. aureus, B. subtilis, E. coli, and P. aeruginosa, respectively. The antiproliferative activity of the apigenin derivatives was evaluated by an MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] assay. We determined that 4a-4j displayed better growth inhibition activity against four human cancer cell lines, namely, human lung (A549), human cervical (HeLa), human hepatocellular liver (HepG2), and human breast (MCF-7) cancer cells, than the parent apigenin. Compound 4j was found to be the most active antiproliferative compound against the selected cancer cells. Structure-activity relationships were also discussed based on the obtained experimental data.

Evaluating Antioxidant Capacity of Different Propolis Samples from Konya, Turkey and Their Inhibitory Effect on Head and Neck Cancer Cells

“…Similar results were observed for different origins of same countries including Portugal(Silva et al 2012;Moreira et al 2008;Miguel et al 2010), Turkey(Aliyazıcıoglu et al 2013), Algeria(Benhanifia et al 2013), China(Dong et al 2013), Poland(Socha et al 2015) and Brazilia(Righi et al 2013). The major components, namely quercetin, hesperidin and apigenin, have considerable biological activities such as antioxidant, anticancer, antibacterial(Wilmsen et al 2005; Kumar, Pandey 2005;Liu et al 2013). In fact, the propolis samples could be considered as a source of valuable components.…”

Acylated glucosylflavones as α-glucosidase inhibitors from Tinospora crispa leaf

“…They were elucidated as isoorientin (1), 16 orientin (2), 16 luteolin-7-O-β-glucoside (4), 17,18 5 7-O-β-glucosyl-6''-(E)-p-cinnamate (13), 19 and 4'-O-β-glucoside (16), 18 isoorientin 2''-(E)-p-coumarate (7), 20 3'-O-methylluteolin (14), 21 luteolin (17), 22 isovitexin (3), 23 apigenin 7-O-β-glucoside (cosmosiin) (5), 24 cosmosiin-6''-(E)-p-coumarate (10) 24 and 6''-(Z)-p-coumarate (11), 25 and apigenin (12), 26 respectively, by comparison of their 1 H NMR spectroscopic data (Supplementary data) and MS with those reported in the literatures.…”

Synthesis and Evaluation of Ester Derivatives of 10-Hydroxycanthin-6-one as Potential Antimicrobial Agents

“…The antibacterial activity of the compounds was investigated using a previously reported method [14,25]. First, compounds 4-6 and 7a-7x (10 µg) were screened for their antibacterial activity against two Gram-positive (Bacillus cereus and Bacillus subtilis) and two Gram-negative bacterial strains (Ralstonia solanacearum and Pseudomonas syringae) using the disk diffusion method.…”