Three New Simple Indole Alkaloids from Limonia acidissima

Journal of Natural Products
1986.0

Abstract

Dry woody stems of Limonia acidissima L. (Rutaceae) purchased from the market in Pagan, Burma, were powdered and extracted with cold EtOH. The extracts were partitioned between H₂O and petroleum ether, then between H₂O and CHCl₃. The combined petroleum ether and CHCl₃ extracts (nearly identical in composition by TLC) were separated using silica gel column and thin layer chromatography without acid treatment. A wide range of known natural products was obtained, including quinolones (4-methoxy-2-quinolone, edulitine, 4-methoxy-1-methyl-2-quinolone), the anthraquinone physcion, limonoids (limonin, methyl deacetylnominilate), amides (tembamide, N-(p-hydroxy-β-phenethyl)-p-hydroxycinnamide), the lignan (±)-syringaresinol, and indole derivatives (N,N-dimethyltryptamine, 3-formylindole, 2-methyltetrahydro-β-carboline). Additionally, three new simple indole alkaloids were isolated: N(b)-acetyl-N(b)-methyltryptamine (1), (+)-tanakine (2), and (+)-tanakamine (4). The structures of the new compounds were elucidated by UV, IR, MS, and NMR spectral data, as well as chemical reactions such as acetylation.

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