Alkaloids from Delphinium staphisagria

Abstract

Three new diterpenoid alkaloids, isoazitine (1), 19-oxodihydroatisine (2), and 22-O-acetyl-19-oxodihydroatisine (3), and eight known alkaloids-azitine (4), dihydroatisine (5), delphinine, neoline, bullatine C (14-acetylneoline), chasmanine, 14-acetylchasmanine, and the quaternary base atisinium chloride (7)-were isolated from the aerial parts of Delphinium staphisagria. Structures of the new alkaloids were established mainly by 1D and 2D NMR spectroscopy, including (1)H COSY, HMQC, HMBC, and ROESY. The (1)H and (13)C NMR data for alkaloids 4 and 5 are also reported.

Structural characterization and identification of C19‐ and C20‐diterpenoid alkaloids in roots of Aconitum carmichaeli by rapid‐resolution liquid chromatography coupled with time‐of‐flight mass spectrometry

“…The signals at m/z 420.2619, 402.2470, 388.2433, 370.2301, and 360.2432, corresponding to losses of AcOH, AcOH+H 2 O, AcOH+CH 3 OH, AcOH+H 2 O+CH 3 OH, and AcOH+CH 3 OH+C 2 H 4 , indicated that F23 had an acetyl group instead of a hydroxyl linked on C 14 compared with F17. F23 could be identified as 14‐acetylneoline 21. F10 (C 26 H 42 NO 8 ) produced similar fragmentation pathways as F11.…”

“…Besides, F36 did not have the characteristic fragment ions of the C 15 hydroxyl and other ions corresponding to loss of one molecule of H 2 O were detected. Thus, F36 could be identified as delphinine,21 while F43 was identified as isodelphinine according to the literature 22. Diagnostic neutral losses of AcOH, CH 3 OH, H 2 O, BzOH or a combination of these were observed for F30 and F39, indicating they belong to the DDAs.…”

Acylated flavonol glycosides from Delphinium staphisagria

“…Several years ago one of us, with others, reported new diterpene alkaloids from the aerial parts of Delphinium staphisagria L. (Díaz et al, 2000). The present article deals with flavonols in the extracts of the aerial parts of this species.…”

Ongoing Pursuit of Diterpenoid Alkaloids: A Synthetic View

“…Elaborationo fk etone 36 to Pelletier's intermediate 15 was realizedi nf our more steps, involving hydrogenation of the D 13,14 double bond, introductiono f the exocyclic double bond, deketalization, andr eductiono f the resulting C15 ketone. On the other hand, the natural product isoazitine (3) [37] was synthesized from the same intermediate (15)b yd eprotection of acetamide and oxidation of the secondary amine to an imine.…”