Alkaloids of Veratrum lobelianum isolation ofγ-solanine

Chemistry of Natural Compounds
1975.0

Abstract

The present communication gives the results of a further study of the alkaloids of Veratrum lobelianum growing in the Caucasus. An ethanolic extract of 16 kg of the epigeal part of the plant was fractionated by Salzberger's method. On concentration, an ether solution of the combined alkaloids deposited veralosine (I). The mother solution after the separation of the veralosine was separated by means of an acetate buffer with pH 4.0 into eight fractions. The fourth and fifth fractions were combined and chromatographed on a column of silica gel (KSK) with elution by benzene-acetone (10 : 1 and 4 : 1). At a ratio of 10 : 1, an alkaloid with mp 226-228°C (II), [α]D --70.46 °, was obtained, and at 4 : 1 a base with mp 220-222°C (III), [α]D - 65.46°. The alkaline hydrolysis of (II) gave the amino alcohol germine, α-methylbutyric acid, and acetic acid, and the saponification of (III) gave germine, α-methylbutyric acid, angelic acid, and acetic acid. It follows from the facts presented that compound (II) is identical with neogermitrine, and alkaloid (III) is germanitrine, which is confirmed by their NMR spectra. From the sparingly soluble metaphosphate fraction of the combined alkaloids by chromatography on a column of silica gel and elution with acetone-benzene (4 : 8) we isolated an alkaloid with mp 212-213°C, C27H43NO (IV), identified as solandine (IR and mass spectra, mp). The benzene-soluble fraction of the combined alkaloids was also separated by means of an acetate buffer at pH 4.0 into eight fractions. Treatment of the third and fourth fractions with chloroform led to the separation of a base with mp 237-239°C, [α]D --23.07, C33H53NO12 (V). The hydrolysis of (V) liberated an aglycone identical with an authentic sample of solanidine (IR spectrum, mp) and galactose (paper chromatography). Consequently, the alkaloid (V) is the known glycoalkaloid γ-solanine, and this is the first time it has been obtained from the genus Veratrum.

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