ALKALOIDS OFSOLANUM ECUADORENSE

Planta Medica
1973.0

Abstract

Solanum ecuadorense Bitter is a small tree growing in the high Andean plateaus of Ecuador, locally known by the Quechua name "Jurapanga". The berries of this plant were investigated. Extraction of the juice with chloroform yielded a crude alkaloid mixture, which upon crystallization from methanol afforded two pure alkaloids. Substance I, with a molecular ion peak at m/e 489 (C29H47NO5), was identified as solaphyllidine through mass spectrometry, IR, PMR, and direct comparison with an authentic sample. Substance II, showing a molecular ion peak at m/e 447 (C27H45NO4), was identified as desacetylsolaphyllidine by hydrolysis of I (yielding a deacetyl base identical to II) and spectral analysis. Acetylation of I and II produced the same tetra-acetylated compound III. Reduction of I with LiAlH4 gave tetraol IV, which was also obtained by catalytic hydrogenation of II using PtO2 in acetic acid. Pharmacological screening indicated solaphyllidine is an analeptic. Previously isolated only from Solanum hypomalacophyllum Bitter, solaphyllidine is produced by S. ecuadorense at eight to ten times the amount, suggesting S. ecuadorense could be a valuable source of this rather uncommon alkaloid.

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