Alkaloids of pedicularis

Abstract

From the epigeal part of P. rhinanthoides Schrenk., collected on Iuly 2i, 1966, in the flowering period in the gorge of the R. Nura, KirgSSR, by chloroform extraction we have obtained 0.3% of total alkaloids. The ethereal fraction of the total alkaloids was treated with acetone, giving G. 04% of plantagonine [1]. By separating the mother liquor on a column of alumina [eluant: ether-chlorofor m (9 : 1)] we obtained a liquid base with Rf 0. 67 [in the butan-l-ol-water-aeetic acid (26 : 25: 1)system], [c~]~+5.9 (c 0.508; ethanol), C10H13NO, mol. wt. 163 (mass spectroscopy). The picrate has mp 151-152" C (water). IR spectrum: Xma x 263, 270 mp (log $ 2.74, 2.%). The IR spectrum of uhe base has absorption bands at 3450-3250 cm-I (OH), 2960 cm-I (C-CHs), 1595 em-1 (pyridine ring), and 895, 850, and 815 cm-1. Oxidation of the base with potassium permanganate in an alkaline medium added two oxygen atoms with the formation of an acid with mp 218-225" C (decomp.). A mixture of this acid with plantagonine, showed no depression of the melting point. Thus, the base that we have isolated is the dextrorotatory form of the knowr~ alkaloid 1-tecostidine [2J. From ~:he epigeal part of P~ olgae Rgl., collected on lune 15, 1968, in the flowering period in the village of Saed, TadzhSSR, we have obtained 0.65% of total alkaloids from which we have isolated 0.11% of plantagonine.

Encyclopedia of the Alkaloids

“…Nauk. Bolg., 22, 1019(1969 ALKALOID GI-A C ll H 13 NO One of two minor alkaloids found in Genista ispanica, this base occurs only in small quantities and insufficient has been isolated to permit of a full investigation of its chemical and physical characteristics. Skhilazhe, Tr.…”

“…J. Chem., 22, 2233(1969 ALKAMINE X This alkaloid has been isolated from Veratrum Iobelianum Bernh. It forms colourless crystals from MeOH.…”

“…Kapadia et al, J. Pharm. Sci., 58,1157(1969 4'DEMETHYLMESEMBRENONE C16H19N03 OH o A number of Scletium species yield this alkaloid which forms colourless oil that cannot be crystallized. The structure has been determined by chemical analysis and spectroscopy, particularly NMR and mass spectrometry.…”

“…225°C (dec.). Chibata et al, Experientia, 25,1237(1969) Kamiya et al, Tetrahedron Lett., 4729 (1969 Russian workers have recently given the ketonic structure for this alkaloid, rather than the original epoxy structure.…”

“…Danieli et aZ., Phytochem., 13, 1603 7 ( Dickinson, Jones, Tetrahedron, 25,1523(1969 16-HYDROXYSTRYCHNINE…”