Article

Antifeedant C20 diterpene alkaloids.

Centro de Ciencias Medioambientales, CSIC, Serrano 115-dpdo., ES-28006 Madrid.
Chemistry & Biodiversity (Impact Factor: 1.81). 10/2004; 1(9):1327-35. DOI: 10.1002/cbdv.200490095
Source: PubMed

ABSTRACT We have tested the insect antifeedant and toxic activity of 21 C20 diterpenoid alkaloids on Spodoptera littoralis and Leptinotarsa decemlineata. The antifeedant effects of the test compounds were structure- and species-dependent. The most active antifeedants to L. decemlineata and S. littoralis were the rearranged form of hetisine (20; EC50 = 1.7 microg/cm2) and 19-oxodihydroatisine (9; EC50 = 0.1 microg/cm2), resp. Glandulosine (8) moderately affected orally injected S. littoralis larvae. A few compounds (13-oxocardiopetamine (4), 9, and atisinium chloride (13)) had cytotoxic effects to insect-derived Sf9 cells with varying degrees of selectivity with respect to mammalian CHO cells. Compounds 4 and 15,22-O-diacetyl-19-oxodihydroatisine (10) increased Trypanosoma cruzi mortality. Our results support the plant protective role of C20 diterpenoid alkaloids and open a new field for parasite control strategies.

1 Bookmark
 · 
96 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: In the present study, 30 pure monoterpenes were tested for their toxicity against first, second and third instars larvae and adults of Colorado potato beetle (Leptinotarsa decemlineata Say). The majority of tested compounds were found to be toxic to the larvae and the adults, however variable degree of toxicity with a range of 20–100% mortality. In general, monoterpene hydrocarbons exhibited high toxicity as compared with oxygenated monoterpenes. Among the tested monoterpene hydrocarbons, β-pinene, γ-terpinene, 3-carene as well as myrcene showed strong toxicity against all instars larvae. On the other hand, 1,8-cineole, fenchone, linalool and terpinen-4-ol were more toxic against the larvae as compared with the toxicities of other oxygenated monoterpenes. Borneol, fenchol, geranyl acetate, menthol, nerol acetate and α-terpineol showed weak toxicity against the larvae, whereas no significant toxicity was observed for isomenthol against the larvae. Some tested compounds showed different toxicities against both adults and larvae. For instance, menthone was more toxic against the adults than the larvae. Likewise, monoterpene hydrocarbons showed the higher toxicity against the adults than oxygenated monoterpenes. Limonene, α-pinene and β-pinene caused 100% mortality against the adults at two doses after 24h of exposure. Among the tested oxygenated monoterpenes, 1,8-cineole, fenchone and menthone were much more effective against the adults. The present results indicated that 1,8-cineole, fenchone, β-pinene and γ-terpinene can be used as potential control agents against both the larvae and adults of Colorado potato beetle.
    Industrial Crops and Products 10/2007; 26(3):278-297. · 3.21 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Diterpenoid alkaloids are compounds of pharmacological interest. Forty four C19 norditerpenoid (NDAs) and 23 C20 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 Diterpenoid alkaloids are compounds of pharmacological interest. Forty four C19 norditerpenoid (NDAs) and 23 C20 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, C19 norditerpene alkaloids (NDAs) resulted better insect antifeedants and post-ingestive toxicants than the related C20 diterpene alkaloids (DAs). Their antifeedant or insecticidal potencies did not parallel their reported nAChR binding activity, Trypanososma cruzi and Leishmania infantum. Overall, C19 norditerpene alkaloids (NDAs) resulted better insect antifeedants and post-ingestive toxicants than the related C20 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 but did correlate␣with the␣agonist/antagonist insecticidal/ antifeedant model proposed for nicotininc insecticides.␣Among the most potent antifeedants (EC50<0.2µg/cm2) 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 the most potent antifeedants (EC50<0.2µg/cm2) 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 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. 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.
    Phytochemistry Reviews 03/2007; 6(1):81-95. · 2.89 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: ObjectivesA number of species belonging to herbal genus Aconitum are well-known and popular for their medicinal benefits in Indian, Vietnamese, Korean, Japanese, Tibetan and Chinese systems of medicine. It is a valuable drug as well as an unpredictable toxic material. It is therefore imperative to understand and control the toxic potential of herbs from this genus. In this review, the ethnomedicinal, phytochemistry, pharmacology, structure activity relationship and toxicology studies of Aconitum were presented to add to knowledge for their safe application.Key findingsA total of about 76 of all aconite species growing in China and surrounding far-east and Asian countries are used for various medical purposes. The main ingredients of aconite species are alkaloids, flavonoids, free fatty acids and polysaccharides. The tuberous roots of genus Aconitum are commonly applied for various diseases such as rheumatic fever, painful joints and some endocrinal disorders. It stimulates the tip of sensory nerve fibres. These tubers of Aconitum are used in the herbal medicines only after processing. There remain high toxicological risks of the improper medicinal applications of Aconitum. The cardio and neurotoxicities of this herb are potentially lethal. Many analytical methods have been reported for quantitatively and qualitatively characterization of Aconitum.SummaryAconitum is a plant of great importance both in traditional medicine in general and in TCM in particular. Much attention should be put on Aconitum because of its narrow therapeutic range. However, Aconitum's toxicity can be reduced using different techniques and then benefit from its pharmacological activities. New methods, approaches and techniques should be developed for chemical and toxicological analysis to improve its quality and safety.
    Journal of Pharmacy and Pharmacology. 10/2014;

Full-text

Download
5 Downloads
Available from
Oct 28, 2014