The constitution of Actinodaphnine

Abstract

Greshoff2) discovered the wide distribution of the alkaloid laurotetanine in the N. 0. Lauraceae. He isolated it first from L i t s e a c h r y s o c o m a , but also mentions its presence in the genera T e t r a n t h e r a ( T . c i t r a t a N e e s ) , N o t a p h o e b e , A p e r p l a and A c t i n o d a p h n e (A. procera Nees). Although laurotetanine seems to be widely distributed in this order, Greshoff's work leaves some doubt as to whether it was always laurotetanine which he isolated.Chopru3) mentions that in British India alone about 50 species of Litsea are still uninvestigated so that the discovery of a new alkaloid actinodaphnine from Actinodaphne Hookeri (N. 0. Lauraceae) by ILrishnu and Ghose was of interest in this connexion4). laurotetanine = 2-hydroxy-3-5-6-trimethoxy-nor-aporphine. 5-6-methylenedioxy-aprphine. dicentrine = 2-3-dimethoxy-This base was certainly different from laurotetanine (I) and the authors discussed a similarity with bebeerine without adopting any final conclusions5). On the other hand it seemed to be more likely that actinodaphnine was closely related to laurotetanine, the latter having been isolated from another species of the same genus. With that view in mind we started again to work on the constitution of actinodaphnine and with a large supply of the base were able to determine its constitution apart from a slight doubt as to the respective positions of the methoxy and the phenolic hydroxy-group. l)