title: Antioxidant and cytotoxic activities of canadine: biological effects and structural aspects.
abstract: The cytotoxic effects of four alkaloids, berberine, canadine, anonaine, and antioquine were evaluated using three different cell cultures, a primary culture (rat hepatocytes) and two cell lines (HepG2 and HeLa). Our results indicate that berberine, anonaine, and antioquine possess a significant the cytotoxic effect. In contrast, canadine does not possess cytotoxic effect at concentrations tested here. A molecular modeling study indicates that the quaternary nitrogen, the aromatic polycyclic and planar structure of berberine could be the pharmacophoric patron to produce the cytotoxic effect. In parallel our results demonstrated that canadine possess a significant antioxidant activity. Stereoelectronic aspects of this alkaloid were found to be closely related to those displayed by alpha-tocopherol and its water-soluble analogue trolox. The antioxidant activities of canadine, combined with its low-toxic effect, indicated that the potential of this alkaloid as a novel class of antioxidant agent is very interesting and deserves further research.
authors.affiliation: Departamento de Química, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Chacabuco 917, 5700 San Luis, Argentina.
authors.forename: Estela R
authors.initials: ER
authors.lastname: Correché
authors.forename: Sebastian A
authors.initials: SA
authors.lastname: Andujar
authors.forename: Rita R
authors.initials: RR
authors.lastname: Kurdelas
authors.forename: María J
authors.initials: MJ
authors.lastname: Gómez Lechón
authors.forename: Mónica L
authors.initials: ML
authors.lastname: Freile
authors.forename: Ricardo D
authors.initials: RD
authors.lastname: Enriz
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000737:chemistry* / Q000633:toxicity*; D001599:Berberine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D005978:Glutathione / Q000378:metabolism; D022781:Hepatocytes / Q000187:drug effects / Q000378:metabolism; D008297:Male; D008958:Models, Molecular; D015394:Molecular Structure; D051381:Rats; D017207:Rats, Sprague-Dawley
chemical_list: D000975:Antioxidants; D001599:Berberine; D005978:Glutathione; C004645:canadine