title: Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
abstract: A series of gypsogenin (1) derivatives (1a-i) was synthesized in good yields, and the derivatives' structures were established using UV, IR, (1)H NMR, (13)C NMR, and LCMS spectroscopic data. Among the tested compounds, 1a, 1b, 1d, 1e, and gypsogenin (1) showed antimicrobial activities against Bacillus subtilis and Bacillus thrungiensis, with inhibition zones of 10-14 mm. In addition, compounds 1b, 1d, and 1e showed antimicrobial activities against Bacillus cereus, with inhibition zones of 9-14 mm. Using six human cancer cell lines in vitro, the cytotoxic activities of all tested compounds were determined by calculating the IC50 values. Doxorubicin and paclitaxel were used as controls. Among the tested compounds, 1a, 1c, and 1d had inhibitory effects with IC50 values of 3.9 μM (HL-60 cells), 5.15 μM (MCF-7 cells), and 5.978 μM (HL-60), respectively. To determine the type of cell death, Hoechst 33258 (HO) and propidium iodide (PI) double staining was used. Especially, gypsogenin (1) and compound 1a triggered the apoptotic mechanism at a concentration of 20 μM. Thus, gypsogenin (1) and compounds 1a, 1c, and 1d possess varying degrees of biological activities and can be considered as potential antitumor agents.
authors.affiliation: Chemistry Department, Faculty of Science, Ege University, Bornova, Izmir 35100, Turkey. Electronic address: safiyemirdag_ozturk@hotmail.com.
authors.forename: Safiye
authors.initials: S
authors.lastname: Emirdağ-Öztürk
authors.affiliation: Chemistry Department, Faculty of Science, Ege University, Bornova, Izmir 35100, Turkey.
authors.forename: Tamer
authors.initials: T
authors.lastname: Karayıldırım
authors.affiliation: Institute of Organic Chemistry I, University of Erlangen-Nuremberg, Henkestrasse 42, 91054 Erlangen, Germany.
authors.forename: Aysun
authors.initials: A
authors.lastname: Çapcı-Karagöz
authors.affiliation: Chemistry Department, Faculty of Science, Ege University, Bornova, Izmir 35100, Turkey.
authors.forename: Özgen
authors.initials: Ö
authors.lastname: Alankuş-Çalışkan
authors.affiliation: Biology Department, Adnan Menderes University, Aydin 09010, Turkey.
authors.forename: Ali
authors.initials: A
authors.lastname: Özmen
authors.affiliation: Biology Department, Adnan Menderes University, Aydin 09010, Turkey.
authors.forename: Esin
authors.initials: E
authors.lastname: Poyrazoğlu-Çoban
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001407:Bacillus / Q000187:drug effects*; D018938:Caco-2 Cells; D002175:Candida / Q000187:drug effects*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D019073:HT29 Cells; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D012503:Saponins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D012503:Saponins; C000595883:gypsogenin
keywords: Apoptosis; Cytotoxic; Gypsogenin; Gypsophila; Saponin