Glycosmis arborea

Quinazoline alkaloids are found in at least six botanical families of which the Rutaceae are the most important in this respect. Thus, arborine was isolated from Glycosmis arborea in 1952 and in the following year appeared its structure (990) and synthesis by thermal cyclization of the phenylacetyl derivative (989) of (V-methylanthranilamide (53JCS3337>. The same plant material yields three related alkaloids, glycosmicine (991), glycorine (992) and glycosminine (993) (63T1011>. 

Euodia xanthoxybides, Fagara leprimrii, Glycosmis arborea,... 

Glycosmis arborea (Roxb.) DC. Leaves, root bark 39, 40... 

Arborine.—The biosynthesis of arborine in Glycosmis arborea plants has been studied by two groups. The results are to some extent in conflict so that it is not clear which of the two pathways, a or b, in Scheme 26 is correct. In view of this dichotomy the two sets of results will be presented separately. 

In the second investigation77 the specific incorporation of an anthranilate unit was confirmed by feeding [Me-14C]lV-methylanthranilic acid. In further work (115) and (113) labelled with 3H and 14C respectively were fed to Glycosmis arborea plants the latter was incorporated well, whereas the former was not. These results again argue for path a and against path b. 

Glycosminine (6) has been isolated from Glycosmis arborea (12,43) and Ruta species (48). The chemistry of this base and its syntheses have close parallels with the other simple substituted quinazolines. The structure was established by Pakrashi et al. (77). Physical data are as follows UV nm (log e)] 225... 

Glycosmidne (4) 2-Caiboxy-4-methyl- C9H8N2O2 C oHgN202 270-271 Glycosmis arborea (Roxb.) DC. (43,44) Pseudomonas sp. (58,59)... 

It has been conclusively established 34,35,38) that the alkaloid named glycosine 41) from Glycosmia pentaphylla (Retz) DC is identical with (2) 36) isolated from Glycosmis arborea (Roxb.) DC. (Rutaceae) 156), G. pentaphylla is believed to be more correctly named G. arborea (Roxb.) DC. 22, 157). 

Glycorine (3) (Chart 1) was isolated together with glycosminine and glycosmicine as minor alkaloids of the leaves of Glycosmis arborea (Roxb.) DC. (153, 156). The structure elucidation of these alkaloids was described by Pakrashi and Bhattacharyya (757), using physical data. 

Glycosmis arborea is a shrub found along roadsides throughout West... 

Alkaloids of Glycosmis arborea. Part I. Isolation of Arborine and Arborinine The Structure of Arborine. J. Chem. Soc. 1953, 3337. 

Chakravarti, R. N., and S. C. Chakravarti Chemical Investigation of Glycosmis arborea Correa. J. Proc. Inst. Chemists (India) 24, 96 (1952). 

Zur Biosynthese einiger Alkaloide von Glycosmis arborea (Rutaceae). Z. 

Pakrashi, S. C., J. Bhattacharyya, L. F. Johnson, and H. Budzikiewicz Studies of Indian Medicinal Plants — VI. Structures of Glycosmicine, Glycorine and Glycosminine, the Minor Alkaloids from Glycosmis arborea (Roxb.) DC. Tetrahedron 19, 1011 (1963). 

Pakrashi, S. C., A. De, and S. Chattopadhyay Studies on 4-Quinazolinones Part I — Convenient Synthesis of Glycosminine and Arborine, the Alkaloids from Glycosmis arborea and Related 4-Quinazolinones. Indian J. Chem. 6, All (1968). 

The biosynthesis of quinazoline alkaloids is not resolved, but anthranilic acid, probably as A -acetylanthranilic acid, is a precursor (Cordell, 1981, Groger, 1980). Both anthranilic acid and phenylalanine serve as precursors for arborine (5) in Glycosmis arborea (Cordell, 1981). 

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