Abstract
Sixteen diterpenoid alkaloids (DAs), including six aconitine-type alkaloids (5 and 9 − 13), seven 7,17-seco-aconitine-type alkaloids (1 − 4, 6 − 8), two napelline-type alkaloids (14 and 15) as well as one veatchine-type alkaloid (16), were isolated from the aerial parts of Aconitum flavum Hand.-Mazz. In which, flavumolines A − D (1 − 4) were four new ones, and flavumoline E (5) was reported as natural compound for the first time. Their chemical structures were elucidated by the analysis of extensive spectroscopic data. The inhibitory activities of these isolates on Cav3.1 low voltage-gated Ca2+ channel, NO production in LPS-activated RAW264.7cells, five human tumor cell lines, as well as acetylcholinesterase (AChE) were tested.
Highlights
Aconitum species represent a large genus in the Ranunclaceae family [1]
The MeOH extract was subjected to repeated column chromatography to yield four new ones, one new natural compound (5), together with 11 known analogues 13-hydroxylfranchetine (6) [9], vilmorisine (7) [10], franchetine (8) [11], 3-acetylaconitine (9) [12], 15-dehydroxyldecludine A (10) [13], pubescensine (11) [14], 3-O-acetyl-20-deethyl-20-formylaconitine (12) [15], 14α-benzoyloxy-N-ethyl-3α,13β,15α-trihydroxy1α,6α,8β,16β,18-pentamethoxyaconitane (13) [16], 15-acetylsongoramine (14) [17], dehydrolucidusculine (15) [18], and veatchine azomethine (16) [19]
The 1H NMR spectrum of 1 verified resonances assignable to two oxygenated methines at δH 4.62 (d, J = 4.6 Hz, H-17) and δH 4.71 (d, J = 6.1 Hz, H-6), and a singlet at δH 5.78 (d, J = 5.8 Hz, H-7). These evidences, conjugated with the fact that a number of diterpenoid alkaloids (DAs) have been reported as the major constituents of this genus, suggested that compound 1 was assigned to be a typical franchetine-type C19-DA [20]
Summary
Aconitum species represent a large genus in the Ranunclaceae family [1]. It is estimated that there are more than 350 species of Aconitum all over the world, which are widely distributed in the northern temperate zone, of which 173 species are endemic to mainland China [1]. Around 1300 natural DAs, categorized into C 20-, C19-, and C18- families depending on the number of contiguous carbon atoms, have been reported [3], [4], [5] They have been the targets of medicinal chemists for a broad range of confirmed pharmacological properties including analgesic, antiarrhythmic,. Sixteen DAs including four new 7,17-seco-aconitine-type DAs (flavumolines A − D, 1 − 4), one new natural compound (5), together with 11 known analogues (6 − 16) were identified These compounds could be divided into four different types: six aconitines (5 and 9 − 13), seven 7,17-seco-aconitines (1 − 4 and 6 − 8), two napellines (14 and 15) as well as one veatchine-type alkaloid (16). The isolation, structural determination, and biological activity of these compounds were thoroughly described
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