Songorine N-oxide fromAconitum monticola

Chemistry of Natural Compounds
1977.0

Abstract

From the epigeal part of Aconitum monticola collected in the Dzhungarian Ala-Tau on the R. Kuyandysai, songorine, acomonine, norsongorine, and a base with mp 253-255°C (methanol), readily soluble in water and sparingly soluble in ethanol, acetone, chloroform, benzene, and ether were isolated. Its IR spectrum has absorption bands at 1710 cm⁻¹ (CO) and 1658 cm⁻¹ (double bond), UV spectrum shows maximum absorption at 292 nm (log ε 2.44) characteristic of 8,γ-unsaturated ketones, NMR spectrum has a three-proton singlet at 0.84 ppm (--C--CH₃) and a three-proton triplet at 1.36 ppm (N--C₂H₅), and mass spectrum displays peaks of ions with m/e 373 (M⁺), 357 (M -- 16), 356 (M -- 17), and 355 (M -- 18) characteristic of N-oxides. These facts suggested the base was songorine N-oxide, which was confirmed by reduction with Zn in 10% HCl at room temperature to give songorine. Thus, the isolated alkaloid is the previously undescribed songorine N-oxide.

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