Structural diversity and defensive properties of diterpenoid alkaloids

Abstract

Diterpenoid alkaloids are compounds of pharmacological interest. Forty four C 19 norditerpenoid (NDAs) and 23 C 20 diterpenoid (DAs) alkaloids isolated from Aconitum, Delphinium and Consolida species were tested for their insecticidal effects (antifeedant and toxic) on Spodoptera littoralis and Leptinotarsa decemlineata, their cytotoxicity on tumoral cell lines with several multidrug resistance mechanisms, and their antiparasitic effects against Trypanososma cruzi and Leishmania infantum. Overall, C 19 norditerpene alkaloids (NDAs) resulted better insect antifeedants and post-ingestive toxicants than the related C 20 diterpene alkaloids (DAs). Their antifeedant or insecticidal potencies did not parallel their reported nAChR binding activity, but did correlate with the agonist/antagonist insecticidal/ antifeedant model proposed for nicotininc insecticides. Among the most potent antifeedants (EC 50 < 0.2 lg/cm 2 ) are the NDAs 1,14 diacetylcardiopetaline (10), 18-hydroxy-14-O-methylgadesine (34) and 14-O-acetyldelectinine (28) (to CPB) and the DA 19-oxodihydroatisine (55) (to S. littoralis). DAs had strong antiparasitic effects with molecular selectivity while NDAs were inactive. Delphigraciline (53), 15,22-O-Diacetyl-19-oxo-dihydroatisine (56), azitine (64) and isoazitine (65) were active against L. infantum promastigotes and had a moderate effect on T. cruzi epimastigotes, while atisinium chloride (59) and 13-oxocardiopetamine (48) had a potent effect on T. cruzi epimastigotes. These compounds were not toxic to the host cell, significantly reduced parasite infection capacity and severely affected the multiplication of their extracellular forms. Several NDAs exhibited selective cytotoxicity to cancerous cells and some of these had irreversible effects on SW480, HeLa and SkMel25 cell lines (neoline 5, pubescenine 16, 14-deacetylajadine 26, lycoctonine 27, dehydrotakaosamine 35, and ajadelphinine 38). These cytotoxic effects could be related to the inhibition of ATP production.

Bioefficacy of the triterpenoid friedelin againstHelicoverpa armigera(Hub.) andSpodoptera litura(Fab.) (Lepidoptera: Noctuidae)

“…litura respectively. The present work is consistent with the findings of Reina and Gonzalez‐Coloma, who observed that norditerpenoid and 23C 20 diterpenoid from Aconitum , Delphinium and Consolida species showed larvicidal activity against S. littoralis and Leptinotarsa decemlineata . Similarly, Senthil Nathan and Kalaivani reported that azadirachtin showed concentration‐dependent larval mortality against S. litura .…”

Cytotoxicity of Aconitum alkaloid and its interaction with calf thymus DNA by multi-spectroscopic techniques

“…Many studies have demonstrated that diterpenoid alkaloids often had damage to tumor cells and normal cells with their cytotoxicity that interfere the DNA synthesis during the cell divisions. Several C19-norditerpenoids like neoline, aconitine, pubescenine, 14-deacetylajadine, lycoctonine, dehydrotakaosamine and ajadelphinine had irreversible effects on SkMel25, SW480, HeLa and PC12 cell lines 26 , 27 . As it’s known to all, cardiomyocyte damage is one of the most important factors for DDAs’s cardiotoxity.…”

Fluorescence switching of sanguinarine in micellar environments

“…Fluorescence transients are shown in Fig. The above-mentioned lifetime results can be rationalized in terms of alternations in radiative and non-radiative decay pathways (eqn (2) and (3)) of SANG in the presence of confined micellar environments. Iminium and alkanolamine forms in water exhibit a single exponential decay (collected at 580 nm and 415 nm, respectively) with lifetimes of 2.37 ns and 3.16 ns, respectively.…”