The alkaloids canthin-6-one, 5-methoxy-canthin-6-one and canthin-6-one Noxide,as well as the alkylamide sanshool and three known coumarines were identified and quantified from stem bark, leaves (in this case an annual analysis was conducted), fruits and roots of Zanthoxylum chiloperone var. angustifolium (Rutaceae) collected in South America. Some canthin-6-one derivates were prepared by hemisynthesis by exploring the N-3 reactivity of the pyridine nitrogen. Other new derivates were prepared from different tryptamines and some functionalized anhydrides by an efficient new synthetic route (3 or 4 steps) in good overall yields. The biosynthetic pathway of the canthin-6-one was also chemically explored.Furthermore, this work has prompted us to explore the reactivity of some prenylated derivates of canthin-6-one and serotonin. The antitubercular activity, the antiproliferative activity on cancer stem cells and several antiparasitic activities (Chagas disease, malaria, nematicidal activity) were studied and various mechanisms of action proposed. Finally, an original study of the electrochemical behaviour of canthinones has been investigated and a pharmaceutical formulation was achieved.
Phytochemistry of Zanthoxylum chiloperone var. angustifolium (Rutaceae). Chemistry and pharmacochemistry of canthin-6-one