Tertiary Alkaloids of Alstonia spectabilis and Alstonia glabriflora (Apocynaceae)

Australian Journal of Chemistry
1972.0

Abstract

Examination of the tertiary base fraction from Alstonia spectabilis R.Br. has led to the isolation of villalstonine, macralstonidine, vincamajine, quebrachidine, pleiocarpamine, and N(,)-methylsarpagine. Pleiocarpamine, which is a constituent of Pleiocarpa mutica Benth. and Hunteria eburnea Pichon,l and N(,,-methylsarpagine have been obtained previously as hydrolysis products respectively of the bis-indoles villalstonine and macralstonidine. Drastic conditions are required for the hydrolysis of these bis-indoles, and it is unlikely that a significant amount of hydrolysis would have occurred during the isolation of the alkaloids. N(,)-3Ietliylsarpagine has not previously been isolated directly from natural sources but the quaternary N(b)-metho salt has been isolated from Pleiocarpa mutica.2 The occurrence of vincamajine and of esters of both vincamajine and quebrachidine in Alstonia constricts were recently reported.3From another Kew Guinea species, Alstonia glabriflora Mgf., the alkaloids villalstonine, macralstonine, pleiocarpamine, and alstophylline have been isolated. Alstophylline, which has been isolated previously as an hydrolysis product of macralstonine and as an alkaloid from Alstonia macrophylla Wall.,4 is one of the major constituents of the tertiary base fraction of A. glabriflora.

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