Studies on Anticancer Agents and Other Bioactive Compounds of Dietary Origin

Abstract

The work in this dissertation describes the bioassay-guided isolation, and structure elucidation of sixteen compounds isolated from the fruit part of Aristolochia indica Linn. The dichloromethane, and butanolic fractions of the plant material exhibited activities against prostrate (PC-3), and cervical (HeLa) cancer cell lines. The dichloromethane fraction afforded three new compounds, including aristoloquinone (1), aristolocenone (2), and aristoloanoide (3), while the known compounds were identified as dshamirone (4), chrysophanol (5), 4,8-dihydroxy-6-methoxy-2-methylanthraquinone (6),  -sitosterol (7), oleanolic acid (8), ursolic acid (9), 2-(hydroxymethyl)-3 O furaldehyde (10), hydroquinone (11), and 4 -(acetoxy) phenyl acetate (12). The butanolic fraction of the plant yielded three new constituents, aristoloside A (13), aristoloside B (14), and aristoloside C (15), along with a known compound which was identified as butyl 3-O-β- D-glucopyranosyl-(3R), 4-dihydroxy-butanoate (16). The structures of these constituents were elucidated by using modern spectroscopic techniques, including UV, IR, MS, 1D, and 2D-NMR. HO The isolated compounds were tested for their in vitro cytotoxicity against cancer cell lines. Compounds 8, 9, and 11 showed high sensitivity towards the cervical and prostrate cancer cell lines, as compared to the standard drug, doxorubicin. The other natural/ synthetic compounds were also evaluated for their antitumor activity. Among the natural compounds, physalin derivatives showed a potent activity, whereas among synthetic compounds, organotin (IV) carboxylate, and imidazole derivatives exhibited an excellent activity against the cancer cell lines.