Antioxidant and cytotoxic activities of canadine: biological effects and structural aspects.

Bioorg Med Chem

Departamento de Química, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Chacabuco 917, 5700 San Luis, Argentina.

Published: April 2008

AI Article Synopsis

  • The study evaluated the cytotoxic effects of four alkaloids (berberine, canadine, anonaine, and antioquine) on rat hepatocytes and two cell lines (HepG2 and HeLa) and found that berberine, anonaine, and antioquine were significantly cytotoxic, while canadine was not.
  • Molecular modeling suggested that the structure of berberine may be responsible for its cytotoxic effects, highlighting its pharmacophoric features.
  • Canadine showed significant antioxidant activity and low toxicity, indicating its potential as a novel antioxidant agent worth further research.

Article 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.

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http://dx.doi.org/10.1016/j.bmc.2008.02.015DOI Listing

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