Diterpenoid alkaloids

Abstract

The lasting attention that researchers have devoted to diterpenoid alkaloids is due to their various bioactivities and toxicities, structural complexity, and intriguing chemistry. From 1998 to the end of 2008, more than 300 new diterpenoid alkaloids were isolated from Nature. This review focuses on their structural relationships, and investigations into their chemical reactions, synthesis, and biological activities. A table that lists the names, plant sources, and structural types is given along with 363 references.

Cardioactive C₁₉-Diterpenoid Alkaloids from the Lateral Roots of <i>Aconitum carmichaeli</i> “Fu Zi”

“…Consequently, fraction B was subjected to repeated column chromatography over silica gel H (CHCl 3 -MeOH), leading to the isolation of N-deethylaconine (1), beiwutinine (2), hypaconine (3), mesaconine (4), and 15α-hydroxyneoline (5 47) On the other hand, a doublet signal at δ H 3.89 (J = 4.1 Hz) was attributed to H-14β. 47) A one-proton doublet signal at δ H 4.18 (J = 3.9 Hz) was assigned to H-3β based on the correlations between this signal and C-1 (δ 79.9 d) as well as C-18 (δ 76.8 t) in the heteronuclear multiple bond connectivity (HMBC) spectrum. The assignment of H-15 (δ H 4.51, d, J = 6.0 Hz) was based on the correlations of H-15 and C-8 (δ 77.9 s) and C-16 (δ 91.6 d) in the HMBC spectrum.…”

“…1). Its Dreiding molecular modeling shows that the dihedral angles between H-16α and H-15β, and between H-16α and H-15α are around 45° and 75°, respectively (ring D possesses boat conformation 47) ). Theoretically, J 16α-15β and J 16α-15α should be ca.…”

Diterpenoid Alkaloids from the Chinese Traditional Herbal “Fuzi” and Their Cytotoxic Activity

“…In order to find more anti-tumor active substances, the secondary roots of Aconitum carmichaeli were phytochemically and pharmacologically investigated to obtain eight aconitine-type C 19 -diterpenoid alkaloids: aconitine (1), chasmanine (2), crassicauline A (3), oxonitine (4), deoxyaconitine (5), hypaconitine (6), mesaconitine (7), senbusine A (8), and two atisine-type C 20 -diterpenoid alkaloids, songoramine (9), 15-cetylsongoramine (10). The structures of isolated alkaloids were confirmed by the spectral analysis utilizing UV, IR, MS, and NMR, and comparison with the published data.…”

“…The structures of isolated alkaloids were confirmed by the spectral analysis utilizing UV, IR, MS, and NMR, and comparison with the published data. Among them chasmanine (2), oxonitine (4) and 15-acetylsongoramine (10) were isolated for the first time from this medicinal plant. The cytotoxicity of isolated compounds was tested against several human cancer cell lines.…”

“…(Ranunculaceae), a famous Chinese traditional herbal known as "Fuzi", found mainly distributed in Jiangyou City of Sichuan Province in China, have long been used as an analgesic, anti-inflammatory and anti-tumor agent [1]. Diterpenoid alkaloids classed as belonging to the C 18 -, C 19 -and C 20 -subtypes have been reported to be the main bioactive constituents of plants from the Aconitum genus [2]. Recently, the anti-tumor activity of these diterpenoid alkaloids with complex structures have attracted increasing interest [3,4].…”