Antioxidant and cytotoxic activities of canadine: Biological effects and structural aspects

ESTELA R. CORRECHE´, SEBASTIAN A. ANDUJAR, RITA R. KURDELAS, MARÝA J. GOMEZ LECHO N,D MONICA L. FREILEC AND RICARDO D. ENRIZ

BIOORGANIC & MEDICINAL CHEMISTRY.

Año: 2008 p. 3641 - 3651

0968-0896

The cytotoxic effects of four alkaloids, berberine, canadine, anonaine, and antioquine were evaluated using three differentcell 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 concentrationstested here. A molecular modeling study indicates that the quaternary nitrogen, the aromatic polycyclic and planar structure of berberinecould be the pharmacophoric patron to produce the cytotoxic effect. In parallel our results demonstrated that canadine possessa significant antioxidant activity. Stereoelectronic aspects of this alkaloid were found to be closely related to those displayed bya-tocopherol and its water-soluble analogue trolox. The antioxidant activities of canadine, combined with its low-toxic effect, indicatedthat the potential of this alkaloid as a novel class of antioxidant agent is very interesting and deserves further research.