LAUSR

The genus Aconitum (Ranunculaceae) comprises about 400 species that are distributed in the northern hemisphere in regions such as Asia, Europe, and North America. Many species of this genus are widely used in folk medicine as anesthetics, analgesics, anti-inflammatories, and sedatives and to treat rheumatism and toothache [1]. A. smirnovii Steinb. is endemic to Central Asia [2] although phytochemical studies of this plant have not been published. The aerial part of A. smirnovii collected in Xinjiang AR (Qinghe, Altay Prefecture, Xinjiang, China; August 2015) was studied. The air-dried aerial part (5 kg) was extracted at room temperature with EtOH (80%, 6 10 L). The extracts were evaporated. The residue (200 g) was dissolved in H2SO4 (2%, 1.5 L) and extracted with EtOAc (3 1.5 L). The aqueous layer was made basic to pH 10 using Na2CO3 and extracted with EtOAc (5 1.5 L) to produce total alkaloids (12.5 g). The mixture of alkaloids was separated by column chromatography over silica gel using CHCl3–MeOH (100:1, 60:1, 40:1, 20:1, 10:1, 5:1, and 1:1) to produce fractions A (0.6 g), B (0.4 g), C (1.5 g), D (2.0 g), E (2.8 g), F (2.8 g), G (1.7 g), and H (0.7 g). Fraction A was rechromatographed over a column of silica gel with gradient elution by petroleum ether–Me2CO– Et2N (from 10:1:0.1 to 2:1:0.1) to produce neoline (1) [3, 4], bullatine C (2) [5], vilmorisine (3) [6], and senbusine A (4) [7]. Fraction B was chromatographed over a column of silica gel with elution by petroleum ether–Me2CO–Et2N (5:1:0.1) to afford 12-epinapelline (5) [8]. Chromatography of fraction C over silica gel using petroleum ether–Me2CO–Et2N (from 10:1:0.1 to 1:2:0.1) produced 15-acetylsongorine (6) [9], songorine (7) [10], aconicarmichinium A (8) [11], benzoylaconine (9), 14-benzoyl-8-O-methylaconine (10), songoramine (11), and aconitine (12). Fraction D was chromatographed over a column of silica gel with elution by petroleum ether–Me2CO–Et2N (from 8:1:0.2 to 1:2:0.2) to afford 15 -hydroxyneoline (13) and 12-epi-19-dehydronapelline (14).