(-)-annonaine

Anonaine is a bioactive noraporphine, present in members of the plant families Magnoliaceae and Annonaceae It is named after the plant it was first extracted from, Annona reticulata, which is commonly known as Anona.

==Extraction from Annonaceae== The alkaloid was first isolated from the bark of the Annona reticulata. It has since been found in Annona squamosa, the leaves of Michelia × alba, Fissistigma latifolium and Goniothalamus australis, among many others. The compound may be obtained by dry roasting the bark of Annona reticulata and extracting with methanol. The methanol is removed and the resulting syrup is then treated with hydrochloric acid and the insoluble salts filtered off. The filtrate can then made basic with NH4OH and extracted with diethyl ether. Shaking the extract with 5% sodium hydroxide and retaining the organic layer removes the phenolic content of the extract. The hydrogen chloride salt is then obtained by mixing with hydrochloric acid and recrystallized from diethyl ether. The free base can then be obtained. The anonaine content of Annona reticulata is approximately 0.12%, based on the weight of the starting dried bark.