Quinazolinocarboline alkaloids

The quinazolinocarboline alkaloids, as the name indicates, contain both carboline and quinazoline nuclei. The first known representatives were rutaecarpine and evodiamine, and two more representatives have been encountered more recently. Rhetsinine, which was at one time regarded as belonging here, is included in this chapter because of its affinity with rhetsine, though it does not contain the quinazoline ring system. This chapter is a summary and an extension of that dealing with these alkaloids in Volume II, p. 402. 

These alkaloids occur in the genera Evodia, Hortia, and Zanthoxylum, all members of the Rutaceae, and are restricted to only a few species. Most of the other species in these genera that have been examined yield furoquinoline and acridine alkaloids. Table I is a record of the occurrences, along with empirical formulas and melting points, of the quinazolinocarboline alkaloids. They are all optically inactive except evodiamine, [a]i> +352° (acetone), which is easily racemized. Wuchuyine, C10H13O2N, mp 237°, [a]D — 18°, occurring in E. rutaecarpa (1), evidently... 

Canonica, L., B. Danieli, P. Manitto, and G. Russo New Quinazolinocarboline Alkaloids from Euxylophora paraensis Hub. Tetrahedron Lett. 1968, 4865. Chakravarti, D., and R. N. Chakravarti Quinazolone Alkaloids. J. Proc. Inst. Chemists (India) 39 (Part III), 131 (1967). 

Distribution of Pyrroloquinazoline Alkaloids Biological Activity Quinazolinocarboline Alkaloids Quinoline, Furoquinoline, Acridone, and 4-Quinoline Alkaloids... 

Fig. 31.5. Typical quinazolinocarboline alkaloids (modified from Bergman, 1983 used with permission of the copyright owner, Academic Press, Orlando, FL).

The quinazolinocarboline alkaloids, rutaecarpine and evodiamine, were isolated from the fruit of Evodia rutaecarpa, which has been used in China as a drug for the treatment of headache, abdominal pain, etc. This type of alkaloid (11) occurs... 

Bergman J, Bergman S (1985) Studies of rutaecarpine and related quinazolinocarboline alkaloids. J Org Chem 50 1246-1255... 

In addition to the relatively simple anthranilic-derived metabolites mentioned above, several distinctive types of alkaloids are derived from this amino acid. Most of these are associated with the Rutaceae and related families of the Rutales. Among these groups of alkaloids are the quinazoline, pyrroloquinazoline, quinazolinocarboline, quinoline, furoquinoline, and acridone types. 

---