VILLALSTONINE

Description

An A lstonia alkaloid, the base occurs in A. rnacrophylla Wall, A. sornersetensis F. M. Bailey and A. villosa Blum. It forms a whitish, granular powder which sinters at 218-230°C before melting. The ultraviolet spectrum has absorption maxima at 231, 286 mJ.1 with a shoulder at 250 and an inflexion at 293 mJ.1. The salts are well crystallized: the hydrochloride forms crystals of the tetrahydrate, m.p. 270°C (dec.); [α]_D + 56.3° (H2O); the hydrobromide tetrahydrate yields needles, m.p. 293°C; the sulphate hexahydrate crystallizes with difficulty in prismatic rods, m.p. > 310°C; [α]_D + 52.94° (H2O); oxalate, colourless leaflets from EtOH, m.p. 235°C (dec.); [α]_D + 55.6° (H2O); dimethiodide, m.p. 287°C (dec.) and the O-acetate, m.p. 228-9°C (dec.). The N-benzyl derivative yields a crystalline hydrochloride, m.p. 246°C (dec.). On alkaline hydrolysis, one methoxyl group present as a methyl ester is eliminated with the formation of an amphoteric substance, isolated as the hydrochloride, m.p. 291-3°C (dec.). Reduction with LiAIH4 gives villalstoninol, C39H49O3N4, colourless needles from Me2CO, m.p. 274-6°C (dec.). When fused with KOH, the alkaloid yields a-methylindole and indole-2-carboxylic acid together with the β3-carboline base.

References

Sharp.,J. Chern. Soc., 1227 (1934) Chatterjee, Talapatra, Adityachaudhury., Chern. & Ind., 667 (1961) VILMORRIANINE