Aristoteline and aristotelone, unusual indole alkaloids from Aristotelia chilensis

Phytochemistry
1976.0

Abstract

In continuation of our general screening programme of Chilean flora, an examination of the alkaloids of Aristotelia chilensis (Eleocarpaceae) has been initiated. Extraction of the basic components of this plant with ethanol, followed by isolation of the acid soluble fraction, afforded a mixture containing alkaloids (< 0.01%). Separation by chromatography through silica gel afforded two alkaloids (aristoteline and aristotelone). The major compound aristoteline (1) (C₂₀H₂₆N₂) was identified as a conjugate between a tryptamine unit and an unrearranged terpene unit, with substitution at both positions 2 and 3 of the indole nucleus. The minor alkaloid aristotelone (2) (C₂₀H₂₆N₂O) was suggested to be a ψ-indoxyl derivative. Aristoteline and aristotelone are relatively rare indole alkaloids since most indole alkaloids arise from tryptophan and loganin-derived terpene skeletons, while these do not conform with the loganin type. Members of the genus Aristotelia thus appear to be the source of interesting indolic alkaloids.

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