Alkaloids of Ammodendron karelinii

Chemistry of Natural Compounds
1977.0

Abstract

In its botanical characteristics the plant Ammodendron karelinii Fisch. et Mey is very close to the species Ammodendron conollyi. The presence of alkaloids in it has been reported, and we have previously studied the biosynthesis and interconversions of its alkaloids. In this communication, we report the results of a chemical investigation of the alkaloids of A. karelinii. From 2 kg of air-dried leaves (collected in Bukhara oblast during the flowering period on May 15, 1974) of A. karelinii (family Leguminosae), 37 g of combined alkaloids were isolated by methanol extraction. The combined bases were separated by successive extraction of an alkaline solution with petroleum ether, benzene, and chloroform. The main alkaloid pachycarpine was isolated as the hydriodide (25 g) from the petroleum ether fraction. From the benzene fraction (8 g), pachycarpine (0.9 g), l-lupanine (0.2 g), anagyrine (0.5 g), methylcytisine (1.5 g), and a new base C₁₅H₂₄ON₂ (M⁺ 248, oily) were obtained by alumina column chromatography and preparative thin-layer chromatography. From the chloroform fraction (6 g), cytisine (0.1 g) and ammondendrine (0.8 g) were isolated by alumina column chromatography, and a new alkaloid pachycarpine N¹⁶-oxide (mp 139-140°C) was obtained from the mother liquor by alumina chromatography, identified by its IR spectrum (absorption bands at 2800-2600 cm⁻¹ for trans-quinolizidine and 950 cm⁻¹ for N→O) and reduction to pachycarpine. All alkaloids were identified by mixed melting points and comparison of their IR spectra with known samples.

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