Alkaloids of Vinca erecta

Chemistry of Natural Compounds
1976.0

Abstract

Having continued an investigation of the alkaloids of Vinea erecta from the Surkhandar'ya oblast, three alkaloids were isolated: majdinine, 8-oxo-6,7-dehydrokopsinine N-oxide, and a new base (I) with composition C22H26N2O6, mp 246-247°C (methanol). Based on spectral data (UV, IR, NMR) and reduction to vinerine, (I) was identified as vinerine N-oxide. Heating vinerine with 10% acetic acid caused isomerization, yielding vinerine (II), vineridine (III), and two iso compounds (IV, V). Compound V, named isovineridine (C22H26N2O6, mp 184-185°C (acetone), [α]D-97°), was found to be a C3 isomer of vinerine with configuration (3S, 4R, 7R, 15S, 19S, 20S). It was also observed that the specific rotation sign of hydroxyindole alkaloids with cis D/E rings depends on the C3 proton orientation (C3αH for left rotation, C3βH for right rotation). For Paracynoglossum imeretinum roots (previously unstudied), chromatographic comparison showed identical qualitative alkaloid composition to the epigeal part. Four bases were isolated and identified as heliosupine, echinadine, and their N-oxides.

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