Evodine and evoxoidine from Haplophyllum perforatum

Chemistry of Natural Compounds
1977.0

Abstract

We continued a study of the alkaloid composition of the epigeal part of the plant Haplophyllum perforatum growing in the Dzhungarian Ala-Tau, Kazakh SSR. The ether-soluble part of the main fraction after the separation of evoxine was chromatographed on a column of alumina, yielding two bases (I, mp 152-153°C from acetone, [α]D -60° (c 0.3; ethanol); II, mp 135-136°C from acetone), both with the composition C₁₉H₁₉NO₅ (mol. wt. 329, mass spectrometrically). Spectral (UV, IR, NMR, mass) analyses and literature comparisons identified base (I) as evodine and base (II) as evoxoidine, representing the first detection of these alkaloids in plants of the genus Haplophyllum. Additionally, the roots of the previously unstudied species Convolvulus krauseanus Rgl. et Schmalh., collected on August 31, 1976 in the region of Bakhmal village (Turkestan range), contained 0.62% total alkaloids. A phenolic base (I) with mp 214-215°C (methanol), composition C₁₅H₁₉NO₄ (mol. wt. 277), differing from known alkaloids, was isolated and named convolidine. Spectral (IR, mass, NMR) characteristics and chemical transformations (methylation to convolvine, alkaline hydrolysis to nortropine and vanillic acid) confirmed a tropane skeleton, leading to the proposal of the structure (+)-3α-vanilloyloxynortropane for convolidine.

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