Evodia xanthoxyloides

Evoxine (XXIII), originally isolated from Evodia xanthoxyloides F. Muell. (120), has also been found in Choisya ternata (74) and in the... 

C]Tryptophan gave inactive alkaloids but tritiated 2,4-dihydroxy-quinoline (34) and its N-methyl derivative were incorporated into (47) (0.009 % and 0.020% respectively) an early route had suggested the derivation of what was essentially (34) from tryptophan. Radioisotope dilution showed the presence of both these quinoline precursors together with iV-acetyl- and N-methyl-anthranilic acid in A. baueri. A satisfactory incorporation of N-methylanthranilic acid into (47) was found in Evodia xanthoxyloides, and this, together with its natural occurrence, indicates that early methylation may be important in the biosynthesis of acridone alkaloids. 

Evodine [7-(2-Hydroxy-3-methylbut-3-enyl)oxy-8-methoxydictamnine] Evodia xanthoxyloides (Volume IX) 166... 

Dreyer (172) reinvestigated the alkaloids of Evodia xanthoxyloides F. Muell and isolated a new furoquinoline alkaloid, C17H17NO4, with a UV... 

Dreyer (172) obtained another new alkaloid, the epoxide 174, from Evodia xanthoxyloides its structure was determined by NMR spectroscopy and by acid hydrolysis to evoxine (175). The isolation of epoxides 167 and 174 from E. xanthoxyloides and the failure to detect evoxine, previously obtained from this species, are of considerable interest because of the fact that acid was employed in the earlier isolation work, it was suggested that evoxine may be an artifact derived from the corresponding epoxide. 

Acridone alkaloids have been obtained from other species evoxanthine, melicopidine, evoxanthidine, and xantheodine from Evodia xanthoxyloides, noracronycine, de-A/-methylacronycine, and de-A-methylnoracronycine from Gly-cosmis pentaphylla. 

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