The Alkaloids of Hortia arborea Engl.1

Journal of the American Chemical Society
1960.0

Abstract

Seven bases were isolated from the bark of Hortia arborea Engl. Four of these are of the furoquinoline type; dictamine, γ-fagarine, nor-γ-fagarine and skimmianine. The remaining three are of the quinazoline group: rutecarpine and two new alkaloids, hortiamine and hortiacine. Hortiamine, a red alkaloid, C20H17N3O2, yields 6-methoxy-1-oxo-1,2,3,4-tetrahydropyrid [3,4-b]indole and N-methylanthranilic acid when heated with ethanolic potassium hydroxide. The alkaloid was resynthesized through condensation of these degradation products. It is 10-methoxy-14-methyl-5-oxo-5,7,8,14-tetrahydroindolo [2,3-c]quinazo [3,2-a]pyridine. Hortiamine undergoes hydration in aqueous solvents to form a crystalline yellow compound, C20H19N3O3, which is 2-(o-methylaminobenzoyl)-6-methoxy-1-oxo-1,2,3,4-tetrahydropyrid [3,4-b]indole (6-methoxyrhetsinine). The hydrochloride of the alkaloid evolves gas upon fusion to yield a base, C19H13N3O2 identical with the second new alkaloid, hortiacine, which is shown to be 10-methoxyrutecarpine.

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