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    Cytotoxic and Antimigratory Activity of Retrochalcones from Glycyrrhiza echinata L. on Human Cancer Cells
    (Wiley-V C H Verlag Gmbh, 2023) Cevik, Dicle; Erdogan, Suat; Serttas, Riza; Kan, Yuksel; Kirmizibekmez, Hasan
    Cytotoxic activity-guided fractionation studies on Glycyrrhiza echinata roots led to the isolation of eight compounds (1-8). Chemical structures of the isolates were identified by NMR and MS analysis. Among the tested molecules, retrochalcones namely echinatin (3) (IC50=23.45-41.83 mu M), licochalcone B (4) (IC50=36.04-39.53 mu M) and tetrahydroxylmethoxychalcone (5) (IC50=7.09-80.81 mu M) were the most active ones against PC3, MCF7 and HepG2 cells. Moreover, 5 exhibited selectivity on prostate cancer cells (SI: 5.19). Hoechst staining and Annexin V/PI binding assays as well as cell cycle analysis on the compounds 3 (23 mu M) and 5 (5 and 7 mu M) demonstrated that these retrochalcones induced apoptosis and significantly suppressed cell cycle in G(1) and G(2)/M phases. Furthermore, 3 and 5 showed antimigratory effects on PC3 cells by wound healing assay. The results indicated that tested retrochalcones most particularly 5 could be potential anticancer drug candidates that prevent proliferation and migration of cancer cells.
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    Isolation and characterisation of secondary metabolites from Trifolium vesiculosum Savi and their antiproliferative activities
    (Taylor & Francis Ltd, 2023) Cevik, Dicle; Aru, Basak; Karagoz, Sanem; Gurizi, Niyazi; Demirkiran, Ozlem
    One unreported flavonol namely morin-7-O-methyl ether (1) along with seven known compounds were isolated from the aerial parts of Trifolium vesiculosum Savi which were elucidated by using extensive spectroscopic methods such as 1D and 2D NMR and HR-MS. According to the cell viability assay (MTS) on the purified compounds (1-8), quercetin-3-O-(6''-trans-p-coumaroyl)-& beta;-galactoside (4) revealed remarkable antiproliferative activity most particularly against breast cancer cells (IC50 = 2.90 & PLUSMN; 0.25 & mu;M in HCC1937 and 7.98 & PLUSMN; 0.57 & mu;M in MCF7) while moderate inhibitory activity (IC50 = 17.96 & PLUSMN; 0.51-51.70 & PLUSMN; 2.69 & mu;M) on prostate, colorectal and liver cancer cell viability was observed. Further mechanistic examinations (Annexin V/PI staining, DNA content and detection of reactive oxygen species analyses) showed that compound 4 significantly induced apoptosis, enhanced mitochondrial reactive oxygen species (ROS) accumulation, and caused cell cycle arrest in cancer cells by increasing accumulation of cells at G(0)/G(1) and/or G(2)/M phases of the cell cycle.