Alkaloids ofVeratrum lobelianum

Chemistry of Natural Compounds
1982.0

Abstract

Two studies on alkaloids from Veratrum lobelianum and Aconitum karakolicum are reported. For Veratrum lobelianum Bernh. (Liliaceae) distributed in Georgian territory, the dynamics of combined alkaloid accumulation during different vegetation phases were investigated: the epigeal part had alkaloid content decreasing from 1.50% at the beginning of vegetation to traces at the end, while the hypogeal part remained stable at ~2.3-2.48%. From the roots and rhizomes, jervine (as sulfate, mp 298-300°C; base C27H39NO3, mp 245-247°C, [α]D -150°), pseudojervine (C27H39NO5, mp 283-285°C, [α]D -145°), rubijervine (C27H43O2N, mp 237-239°C), and alkamine-x (mp 216-218°C) were isolated and identified by spectral data and literature comparison. Some alkaloids showed specific pharmacological activity. For Aconitum karakolicum Rapaics. collected in the budding period from Kirghiz SSR, the total alkaloids of the epigeal part were further separated. Besides known alkaloids (delsoline, monticoline, neoline, etc.), two new alkaloids, karasamine (I) and l-benzoylkarasamine (II), were isolated. Karasamine (I) (composition C24H39NO5, M+ 391, mp 110-112°C) was characterized by IR (hydroxy groups at 3180 and 3590 cm⁻¹, ether bonds at 1100 cm⁻¹), NMR (N-ethyl group, tertiary C-methyl group, two methoxy groups), and mass spectra (lycoctonine skeleton, similar to karakoline). It was confirmed as the C14-monomethyl ether of karakoline by selective methylation experiment.

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