Atropine fromPhysochlaina alaica

Chemistry of Natural Compounds
1985.0

Abstract

Continuing an investigation of the alkaloids of the plant Physochlaina alaica E. Korot., by extracting with chloroform the roots collected in the period of the withering of the epigeal part in the basin of the R. Shakhimardan (northern slope of Alai range) we isolated 1.45% of total alkaloids, which were separated into benzene, chloroform, and water-soluble fractions. By separating the mixture of bases according to their solubilities in various organic solvents and basicities with the aid of buffer solutions, and by chromatography on columns with alumina and silica gel, we isolated known alkaloids including hyoscyamine, 6-hydroxyhyoscyamine, hyoscine, α-belladonnine, β-belladonnine, physochlaine, 6-hydroxyatropine, apoatropine, apohyoscine, 6-hydroxyhyoscyamine N-oxide, tropine, 3,6-dihydroxytropane, and base A, as well as another alkaloid with the composition C₁₇H₂₃NO₃ (M⁺ 289, mp 116-117°C, optically inactive). The IR spectrum of this alkaloid showed absorption bands at 710 and 760 cm⁻¹ (monosubstituted benzene ring), 1722 cm⁻¹ (ester carbonyl group), and a broad band at 3380-3420 cm⁻¹ (hydroxy group). Its PMR spectrum (CDCl₃, δ scale) exhibited signals at 2.18 ppm (3H, singlet, N-CH₃), 5.00 ppm (1H, triplet, C3H), and 7.22 ppm (5H, singlet, monosubstituted benzene ring). The mass spectrum contained peaks at m/z 289 (M⁺), 124, 123, 113, 112, 97, 96, 95, 83, and 82, characteristic of tropane alkaloids. The absence of melting point depression in a mixture with an authentic sample confirmed the alkaloid as atropine, previously isolated from many plants of the family Solanaceae. Thus, 14 bases have been isolated from Ph. alaica, of which atropine has been detected in this plant for the first time.

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