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Three new norditerpenoid alkaloids, nordhagenine A (1), nordhagenine B (2), and nordhagenine C (3), along with a known alkaloid, lycoctonine, were isolated from the aerial parts of Delphinium nordhagenii. The structures of the new compounds 1 and 2 were also deduced on the basis of single-crystal X-ray diffraction studies.
Tall larkspur (Delphinium barbeyi) is the principal mountain larkspur responsible for the majority of cattle deaths on mountain rangelands in western Colorado and central and southern Utah in the United States. Ten plants in each of two tall larkspur populations in the mountains near Ferron and Salina, Utah, were marked, and single stalks were harvested periodically through the growing season for 4 yr. Toxic alkaloid concentration [alkaloids containing the N-(methylsuccimimido)-anthranilik ester group] was determined by Fourier transform infrared (FTIR) spectroscopy. Individual larkspur plants varied in alkaloid concentrations, especially in early growth (14-38 mg/g). As the concentration declined over the growing season, variation among plants also declined. There were yearly differences in alkaloid concentration among individual plants (P < 0.01) and populations (P < 0.001), even after accounting for differences in phenological growth between years. Variables such as precipitation, temperature, days since snow melt, growing degree days (sum of mean temperature each day from snow melt), and plant height and weight were all considered in a Mallows Cp multiple regression selection procedure to predict alkaloid concentration. The mixed model procedure in SAS adjusted the regression equation for locations and years. Growing degree days was the best single predictor of alkaloid levels: In y = (3.581 - 0.00423 GDD), R2 = 0.85. Internal validation of this equation within individual years and locations from which the equation was developed, produced correlations between observed versus predicted values ranging from r = 0.73 to 0.93. External validations on nine other larkspur populations produced correlations ranging from r = 0.76 to 0.99. This predictive equation can provide a tool for ranchers and land managers to make management decisions of when to graze cattle in larkspur areas.
A new franchetine-type (leueandine 1) and two new lycoctonine-type [potanisines F (3) and G (5)] C19-diterpenoid alkaloids have been isolated from the roots of Aconitum hemsleyanum var. leueanthus and Delphinium potaninii, respectively, and their structures were established on the basis of spectral data.
From the roots of Delphinium potaninii var. jiufengshanense, two new lycoctonine-type C(19)-diterpenoid alkaloids called jiufengdine (1) and jiufengtine (4) have been isolated. The structures of the new alkaloids (1, 4) were established by 1D and 2D NMR spectra.
Three new norditerpenoid alkaloids, trifoliolasines A (1), B (3), and C (5), were isolated from the whole plant of Delphinium trifoliolatum FINET et GAGNEP, and their structures were established based on the spectral data.
Further investigation of the roots of Delphinium giraldii DIELS led to the isolation of three new C(19)-diterpenoid alkaloids, giraldines G (1), H (2), and I (3). The structures of 1-3 were established based on spectroscopic evidence.
The changes in flower color related to sepal pigmentation of cyanic Delphinium cultivars were investigated during anthesis. The sepal hues of the purple and blue flowered varieties observed on the initial day of unfurling had changed with a decrease in hue angle three days after anthesis. In both the purple and blue cultivars, violdelphin (3) was the major component on day one of anthesis, and the chromaticity improved with increasing sepal concentrations of violdelphin (3) and cyanodelphin (4) after three days of unfurling. The flower hue was dominated by the constitution of acylated anthocyanins, and the chromaticity was ordered by the sepal concentration. The biosynthesis of cyanodelphin (4) from violdelphin (3) was postulated since an increase in the sepal concentration of cyanodelphin (4) was accompanied by a decrease in violdelphin (3). Acylation of the anthocyanins was initiated by an increase in the respective possible precursors, tulipanin (2) and violdelphin (3), to subsequently synthesize violdelphin (3) and cyanodelphin (4) during flowering.
The Delphinium alkaloids methyllycaconitine (MLA), nudicauline, 14-deacetylnudicauline (14-DN), barbinine, and deltaline were investigated for their effects on neuromuscular transmission in lizards. The substituent at C14 provides the only structural difference among the alkaloids MLA, nudicauline, 14-DN, and barbinine. Deltaline lacks the N-(methylsuccinyl)anthranilic acid at C18 common to the other four alkaloids. Each alkaloid reversibly reduced extracellularly recorded compound muscle action potential (CMAP) amplitudes in a concentration-dependent manner. The IC(50) values for CMAP blockade were between 0.32 and 13.2 microM for the N-(methylsuccinimido)anthranoyllycacotonine-type alkaloids and varied with the C14 moiety; the IC(50) value for deltaline was 156 microM. The slopes of the concentration-response curves for CMAP blockade were similar for each alkaloid except barbinine, whose shallower curve suggested alternative or additional mechanisms of action. Each alkaloid reversibly reduced intracellularly recorded spontaneous, miniature end-plate potential (MEPP) amplitudes. Alkaloid concentrations producing similar reductions in MEPP amplitude were 0.05 microM for 14-DN, 0.10 microM for MLA, 0.50 microM for barbinine, and 20 microM for deltaline. Only barbinine altered the time constant for MEPP decay, further suggesting additional or alternative effects for this alkaloid. MLA and 14-DN blocked muscle contractions induced by exogenously added acetylcholine. All five alkaloids are likely nicotinic receptor antagonists that reduce synaptic efficacy and block neuromuscular transmission. The substituent at C14 determines the potency and possibly the mechanism of nicotinic acetylcholine receptor blockade for MLA, nudicauline, 14-DN, and barbinine at neuromuscular synapses. The lower potency of deltaline indicates that the N-(methylsuccinyl)anthranilic acid at C18 affects alkaloid interactions with nicotinic acetylcholine receptors at neuromuscular junctions.
Low larkspur (Delphinium nuttallianum) is a toxic plant found on many western US rangelands. Episodes of fatal poisoning are often related to the abundance and toxicity of the low larkspurs. This report documents the fatal intoxication of 53 cattle in a herd of 404 animals in south-central Idaho during Spring 2002. Low larkspur had a toxic alkaloid concentration of 8.26 mg/g. Several factors were involved in a loss of this magnitude, including climatic conditions ideal for low larkspur growth, poor grass growth during the spring, the high alkaloid concentration in larkspur, and the deaths of many cattle while being moved from the pasture. It is important for livestock owners and managers to recognize toxic plants growing in their area. If there is an unusual abundance of larkspur or other toxic plants, correct identification can provoke caution in grazing management.
Delphinium denudatum Wall. (Ranunculaceae) is a medicinal herb used for the treatment of epilepsy in the subcontinent. The present study reports the anticonvulsant activities in the maximal electroshock test (MEST) and subcutaneous pentylenetetrazole (PTZ), bicuculline (BIC), picrotoxin (PIC)-induced seizures of the FS-1 subfraction (FS-1) that was obtained by purification of an aqueous fraction isolated from the roots of D. denudatum. In CF 1 mice, FS-1 (600 mg/kg i.p.) exhibited very potent anticonvulsant activity that was comparable to the effects of the well-known antiepileptic drug phenytoin (20 mg/kg) in MEST and protected 100% animals from hind limb tonic extension phase of this model. FS-1 also suppressed PTZ-induced threshold seizure and the loss of the righting reflex with tonic fore and hind limb extension by 100%, similar to the antiepileptic drug valproic acid (350 mg/kg). BIC-induced seizures were suppressed in 80% of the animals. FS-1 exhibited weak anticonvulsant effect on PIC-induced seizures, however, it significantly reduced mortality and delayed the onset of seizures. FS-1 had no effect on strychnine (STN)-induced extensor seizures. The results demonstrate the broad and potent anticonvulsant activity of the compounds in FS-1 of D. denudatum.
We determined the complete nucleotide sequence of Aconitum latent virus (AcLV-D) isolated from Delphinium sp. The genomic RNA of AcLV-D is 8,657 nucleotides in length, excluding the poly (A) tail. Based on computer analysis, six open reading frames (ORFs) were identified as for other carlaviruses. Although each ORF differs from those of previously reported carlaviruses, the coat protein of AcLV and Potato virus M (PVM) shows a high level of identity. The results suggest that AcLV is a distinct carlavirus species but closely related to PVM.
Larkspur consumption is a major source of cattle losses on mountain and high plains rangelands of western North America. Our objective was to find a suitable laboratory animal model for measuring larkspur toxicity for subsequent use as an estimator of toxicity to cattle. The LD50 for subcutaneous injection and for oral gavage of extract from Delphinium barbeyi, a highly toxic and troublesome rangeland tall larkspur, was compared for mice, hamsters, rats and sheep. Similarity of primary clinical signs of poisoning and lack of significant difference in slope of the dose-response curves implied that the overall effect of the larkspur alkaloids was the same for all rodent species tested. Sheep were the most susceptible to poisoning by subcutaneous injection of larkspur extract with decreasing susceptibility in hamsters, mice and rats, but sheep had least susceptibility when comparing response to oral (by gavage) doses. Also, death occurred rapidly after gavage as compared with subcutaneous doses in mice, hamsters and rats, but was nearly the same for sheep. We conclude that, of the animals tested, mice would be the best choice for a bioassay of the toxicity of larkspur because of their high susceptibility, rapid response time, and small dose requirement.
The objective of this study was to determine whether differences in toxicity between Tall larkspur (Delphinium barbeyi) and Duncecap larkspur (D. occidentale) were genetically inherent within the species, or due to environmental influences unique to the different regions where they grow. There was no difference in the concentration of the toxic alkaloids between the two species when grown in common gardens. However, both species had higher concentration of toxic alkaloids when grown in the southern Rocky Mountain region which is characterized by summer monsoonal thunderstorms, compared to summer drought in the north. In a unique occurrence where Duncecap larkspur grew beside Tall larkspur, toxic alkaloids were very low in Duncecap larkspur, but total alkaloid concentration was often higher than in Tall larkspur.
Chronic treatment with Delphinium denudatum (Dd) (Jadwar) (family: Ranunculaceae, 200-1600 mg/kg) suppressed morphine withdrawal jumps in a dose-dependent manner, a sign of the development of dependence to opiate as assessed by naloxone (2 mg/kg) precipitation withdrawal on day 10 of testing in mice. Repeated administration of Dd (200-1600 mg/kg) for 9 days attenuated the development of tolerance to the analgesic effect of morphine (10 mg/kg), also produces significant change in tail-flick latency from the saline pretreated group in a dose-dependent manner.
Dried roots of Delphinium denudatum Wall. are a popular folk remedy for the treatment of epilepsy in the traditional Unani system of medicine in the sub-continent. We carried out anticonvulsant screening of the ethanolic extract (EE) and aqueous fraction (AF) of this plant utilising the maximal electroshock (MEST) and subcutaneous pentylenetetrazole (scPTZ), bicuculline (scBIC), picrotoxin (scPTX) and strychnine (scSTN) tests for anticonvulsant activity. EE had weak dose-dependent anticonvulsant effects on seizures induced by PTZ and BIC. AF exhibited dose-dependent activity against hind limb tonic extension phase (HLTE) of MEST and comparatively stronger anticonvulsant activity against seizures induced by PTZ and BIC. The results suggest the presence of potent anticonvulsant compounds in AF of D. denudatum and deserve further investigation for isolation of active compounds and elucidation of the mechanism of anticonvulsant action.
Larkspur (Delphinium spp.) poisons thousands of cattle on western rangelands each year. Because poisoning does not cause specific lesions, and poisoned animals are rarely found before they die, definitively identifying poisoned animals is difficult. Additionally, toxin concentrations in larkspur plants vary with environment, plant, and location. Rapid, sensitive, and specific diagnostic techniques are needed to identify poisoned animals and to determine when and what plants are likely to poison livestock. In this study, three competitive inhibition enzyme-linked immunosorbent assays (CI-ELISA) for toxic larkspur alkaloids were developed. One assay is class-specific toward the N-(methylsuccinimido)anthranoyllycoctonine (MSAL) alkaloids, and two assays are specific for individual alkaloids. The assay with the lowest limit of detection had an I(50) of 191 pg with a limit of detection of 30.5 pg for methyllycaconitine. Spike and recovery studies using bovine blood and brain tissue ranged from 52 to 89%. These findings suggest that with additional development these techniques are likely to be excellent tools for diagnosing poisoned animals and identifying highly toxic plants.
The insect antifeedant and toxic activity of the Delphinium diterpene alkaloids 15-acetylcardiopetamine, cardiopetamine along with its amino alcohol, the beta,gamma unsaturated ketone, and the acetylated ketone derivatives were studied in Spodoptera littoralis and Leptinotarsadecemlineata. Cardiopetamine and 15-acetylcardiopetamine strongly inhibited the feeding activity of S. littoralis and L. decemlineata, respectively. Structure-activity studies with S. littoralis showed that the C13 and C15 hydroxy substituents are essential features of the active molecule, while a C13 hydroxy and/or a C15 acetate determined their effect on L.decemlineata. The C11 benzoate group enhanced the biological effect on both insect species. These alkaloids were not toxic to S. littoralis, while their toxicity on L. decemlineata was inversely correlated with their antifeedant effects, the beta,gamma unsaturated ketone derivative being the most toxic. Cardiopetamine showed little antifungal action against several species of plant pathogens and did not have any mutagenic effects on Salmonella typhimurium by means of the Ames test.
Six volatile compounds, ethylmethylbenzene (1), 1-isopentyl-2,4, 5-trimethylbenzene (2), 2-(hex-3-ene-2-one)phenylmethyl ketone (3), E and Z isomers of 3-butylidene-3H-isobenzofuran-1-one (4 and 5), and 2-penten-1-ylbenzoic acid (6), were isolated from the mosquitocidal hexane extract of Delphinium x cultorum cv. Magic Fountains flowers. In addition, the ethyl acetate extract, which displayed corn earworm antifeedant activity, yielded 4-hydroxybenzoic acid (7) and bis(4-hydroxyphenyl)methanol (8). However, compounds 7 and 8 were not biologically active.