New alkaloids from Peganum harmala

Chemistry of Natural Compounds
1974.0

Abstract

After the separation of the bases described previously [1, 2], we continued the separation of the mother liquors of Peganum harmala and obtained four individual substances. Base (I), named isopeganidine, has mp 169-170°C (ethanol), [α]D ±0°, picrate 177-178°C; its UV and mass spectra coincide with peganidine, IR spectra are similar with some differences, and NMR spectra comparison shows it is probably a racemic diastereoisomer of peganidine, and deoxypeganidine was obtained from it by a known method. Base (II), named dipegine, has mp 221-223°C (acetone); its UV spectrum shows maxima at 226, 277, 305 (inflection), 317 (inflection) nm (log ε 4.48, 4.14, 4.05, 3.89), IR spectrum has peaks at 1590, 1620, 1660 cm⁻¹ (double bonds, amide carbonyl); mass spectrum shows molecular ion peak at m/e 356, strong peak at m/e 171 (100%) and m/e 185 (3%), indicating it is a biomolecular base consisting of deoxypeganine and deoxyvasicinone fragments; NMR spectrum analysis (absence of 4.5 ppm two-proton singlet) and oxidation with potassium permanganate (yielding deoxyvasicinone) confirm the most probable bridge position is 4-11'. Bases (III) and (IV) were isolated by vacuum distillation (15 mm Hg) of the liquid part of combined bases, with bp 126-134°C and 144-150°C; their picrates (mp 201-202°C and 187°C) were identified as quinoline and quinaldine by direct comparison. Thus, from the mixture of bases of Peganum harmala, we obtained another four substances: isopeganidine and dipegine (new alkaloids) and quinoline and quinaldine (first found in the family Zygophyllaceae).

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