Alkaloids ofKorolkowia sewertzovii. Structure of sevkorine

Chemistry of Natural Compounds
1976.0

Abstract

The plant Korolkowia sewertzovii Rgl., growing in Katrantau, Kirghiz SSR, was first studied. From its epigeal part collected in the flowering stage, 1.68% of total alkaloids were isolated by chloroform extraction, and 1.55% from the hypogeal part. Korseveriline (I) and sevkorine (II, C35H57NO7, mp 236-238°C, [α]D-41.1°) were obtained by column chromatography. Hydrolysis of sevkorine with 10% hydrochloric acid in ethanol yielded D-glucose and bases including sevkoridinine (V, C20H37NO2, mp 241-243°C, [α]D-43.2°), the main alkaloid. Structural analysis using IR, mass spectrum, and NMR showed sevkorine is 3β-O-D-glucopyranosylsevkoridinine (II). For Reseda luteola (USSR, uninvestigated for alkaloids), 17 kg of comminuted raw material was extracted with 1% sulfuric acid, passed through KU-1/KU-2 cation-exchange resins, desorbed with 1% ethanolic ammonia, and solvent-extracted to obtain 55.64 g total alkaloids. Two new bases, resedine (5.5 g) and resedinine (3.5 g), were isolated by silica gel column chromatography of combined ether-soluble alkaloids.

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