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PubMed1984

Effects of dietary copper and molybdenum on tansy ragwort (Senecio jacobaea) toxicity in sheep.

Dried tansy ragwort (Senecio jacobaea), which contains pyrrolizidine alkaloids (PA), was fed to sheep to determine whether PA consumption influenced liver Cu concentrations. Nine Polypay wether lambs were allotted to 3 groups according to the diets: control diet + 50 micrograms of Cu/g of feed (control + Cu); tansy ragwort (TR) diet + 50 micrograms of Cu/g of feed (TR + Cu); and TR diet + 50 micrograms of Cu/g of feed and 10 micrograms of Mo/g of feed (TR + Cu + Mo). Liver Cu concentrations were sharply increased (13-fold) after 8 weeks of feeding the diets, and then decreased slightly. There were no significant differences in concentrations of liver Cu among treatment groups. All lambs in the group fed TR + Cu + Mo died by the end of 23 weeks, with the usual signs of PA poisoning, including liver necrosis, hepatic megalocytosis, and biliary hyperplasia. The TR intake was about 2.7 to 3.0 kg/kg of their initial body weight. All lambs in the group fed the control + Cu diet survived. The results indicated that sheep fed TR do not preferentially accumulate liver Cu. There was an indication that dietary Mo increased susceptibility to TR intoxication.

Animal Feed↗
PubMed1984

Toxicity of threadleaf groundsel (Senecio douglasii var longilobus) to cattle.

Threadleaf groundsel (Senecio douglasii var longilobus), a common plant on much of the rangeland of southwestern United States, was experimentally fed to 55 cattle by gastric gavage, mixed in alfalfa hay, or pelleted in feed. Since the pyrrolizidine alkaloid (PA) content of threadleaf groundsel fluctuates greatly, dosage was determined by the plant PA content. Animals that died survived up to 506 days. Whether they were acutely or chronically affected they had typical signs of seneciosis. Major gross and histopathologic changes are reported. The estimated minimum lethal plant dose by gavage was sufficient plant to provide 13 mg of PA/kg of calf body weight/day for 15 days or a total of approximately 200 mg of PA/kg in a 15-day period. Cattle that consumed up to 600 mg of PA/kg total in 20- to 100-day periods in hay or pellets were unaffected or minimally affected. These findings emphasize the importance of the time-dose relationship in PA toxicosis in cattle and indicate that there is a threshold level of PA that must be exceeded for the toxicosis to develop.

Animals↗
PubMed1984

Large scale extraction of pyrrolizidine alkaloids from tansy ragwort (Senecio jacobaea).

A new technique of large-scale pyrrolizidine alkaloid (PA) extraction was developed in response to toxicity studies on food animals. Results of toxicity experiments on cattle vary from those on rodents (2); therefore, dose/response studies need to be germaine to the appropriate species. This new technique for extraction utilizes protonation of the ring nitrogen and partition of solvent to preferentially extract the alkaloid. The primary equipment used in the system we developed includes a large stainless-steel extraction/separation tank, holding tanks, and a 100-liter vacuum distillation system. From 23 kg of plant material of Senecio jacobaea , our system was able to produce 8-10 g of alkaloid per run, compared to the 3 g which we achieved using other extraction methods (2,4). Additional advantages of our system include a lower labor cost and the ability to recycle the organic solvent.

Methods↗
PubMed1997

Recombinagenic activity of integerrimine, a pyrrolizidine alkaloid from Senecio brasiliensis, in somatic cells of Drosophila melanogaster.

Integerrimine (ITR), a pyrrolizidine alkaloid from Senecio brasiliensis, was tested for genotoxicity using the wing somatic mutation and recombination test (SMART) in Drosophila melanogaster. The compound was administered by chronic feeding (48 hours) of 3-day-old larvae. Two different crosses involving the markers flare (flr) and multiple wing hairs (mwh) were used, that is, the standard (ST) cross and the high bioactivation (HB) cross, which has a high cytochrome P450-dependent bioactivation capacity. In both crosses, the wings of two types of progeny were analyzed, that is, inversion-free marker heterozygotes and balancer heterozygotes carrying multiple inversions. ITR was found to be equally potent in inducing spots in a dose-related manner in the marker heterozygotes of both crosses. This indicates that the bioactivation capacity present in larvae of the ST cross is sufficient to reveal the genotoxic activity of ITR. In the balancer heterozygotes of both crosses, where all recombinational events are eliminated due to the inversions, the frequencies of induced spots were considerably reduced which documents the recombinagenic activity of ITR. Linear regression analysis of the dose response relationships for both genotypes shows that 85% to 90% of the wing spots are due to mitotic recombination.

Animals↗
PubMed1998

Pyrrolizidine alkaloids from Senecio nevadensis.

Two toxic pyrrolizidine alkaloids were isolated from Senecio nevadensis and their structures determined by spectroscopic methods. For the first time, a very complete structural assignment of all spectral data of alkaloid usaramine is given.

Magnetic Resonance Spectroscopy↗
PubMed1982

Modifications of chronic hepatotoxicity of pyrrolizidine (Senecio) alkaloids by butylated hydroxyanisole and cysteine.

The chronic hepatotoxic effects of mixed pyrrolizidine alkaloids (PAs) from the poisonous plant tansy ragwort (Senecio jacobaea) and the ability of butylated hydroxyanisole (BHA) and cysteine to alter these hepatic effects were studied in male rats. In control animals, the i.p. administration of a single dose of mixed PAs, 160 mg/kg, produced marked fibrosis, biliary hyperplasia, megalocytosis, necrosis and calcification in liver 8 weeks post injection. In contrast, consumption of 0.75% BHA diet 10 days before and 14 days after PA administration reduced the incidence and/or completely prevented the occurrence of these pathological changes. Similar treatment with 1% cysteine, however, only reduced the severity of the hepatic lesions.

Animals↗
PubMed1982

Consumption of poisonous plants (Senecio jacobaea, Symphytum officinale, Pteridium aquilinum, Hypericum perforatum) by rats: chronic toxicity, mineral metabolism, and hepatic drug-metabolizing enzymes.

Effect of dietary tancy ragwort (Senecio jacobaea), comfrey (Symphytum officinale), bracken (Pteridium aquilinum) and alfalfa (Medicago sativa) on hepatic drug-metabolizing enzymes in rats were measured. Tansy ragwort and bracken increased (P less than 0.05) the activity of glutathione transferase and epoxide hydrolase. Comfrey and alfalfa increased (P less than 0.05) the activity of aminopyrine N-demethylase. Feeding bracken or St. John's wort (Hypericum perforatum) in conjunction with tansy ragwort did not influence chronic toxicity of tansy ragwort as assessed by rat survival time. Dietary tansy ragwort resulted in increased (P less than 0.05) hepatic copper levels; the other plants did not affect copper levels. The results do not suggest any major interaction in the toxicity of tansy ragwort with bracken or St. John's wort.

Animals↗
PubMed1983

Toxicity of Senecio jacobaea and pyrrolizidine alkaloids in various laboratory animals and avian species.

The chronic toxicity of tansy ragwort (Senecio jacobaea) to several herbivorous laboratory animals and to chicks and turkey poults was examined by feeding the dried plant as a component of a mixed diet. Gerbils, hamsters and guinea pigs were resistant to chronic toxicity. Gerbils were highly resistant, consuming over 3500% of their body weight of the dried plant, whereas susceptible species succumb to a tansy ragwort intake of 5-20% of their body weight. Guinea pigs and gerbils were resistant to acute toxicity of injected monocrotaline, a pyrrolizidine alkaloid (PA). They were moderately resistant to acute toxicity of injected tansy ragwort alkaloids. Both chicks and turkey poults were susceptible to chronic toxicity of dietary tansy ragwort.

Animals↗
PubMed1998

Effects of rust infection with Puccinia lagenophorae on pyrrolizidine alkaloids in Senecio vulgaris.

The pyrrolizidine alkaloid pattern of Senecio vulgaris, infected with the obligate fungal pathogen Puccinia lagenophorae was analysed quantitatively in comparison to noninfected controls. The fungal infection did not significantly affect the plant's total PA contents and concentrations. In comparison to the controls the fungal-infected plants showed significantly lower PA concentrations in the capitula and roots but not the shoots which contain 90% of total PAs. There was little effect on the PA composition.

Journal Article↗
PubMed1999

The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests.

The chemical composition of the essential oil obtained from Senecio graveolens (Compositae) was analyzed by GLC-MS and the components identified were: isovaleraldehyde, alpha-pinene, alpha-phellandrene, alpha-terpinene, p-cymene, sabinene, gamma-terpinene, 1-methyl-4-isopropenylbenzene, terpinolene, terpinen-4-ol, piperitenone, alpha- and beta-eudesmol. The investigation by the agar-well diffusion method of the antimicrobial activity of the essential oil proved that it has antibacterial effects on Micrococcus luteus ATCC 9341, oxacillin-sensitive and oxacillin-resistant Staphylococcus aureus, as well as antifungal effects on clinically isolated Candida albicans. The minimal inhibitory concentration (MIC) values for M. luteus, oxacillin-sensitive S. aureus and C. albicans were 8.73, 10.91 and 2.13 x 10(-2) mg/ml, respectively. The antimicrobial activity related to known antibiotics was calculated. These results would be compatible with a potential concentration-dependent selectivity of antifungal effect of S. graveolens essential oil. Minimal bactericidal concentration (MBC) is above 87.3 mg/ml. Thus the MBC:MIC ratio would be clearly higher than 1 (above 8), indicating a bacteriostatic effect of the essential oil.

Anti-Bacterial Agents↗
PubMed2001

Cacalolides from Senecio madagascariensis.

14-Isovaleryloxy-O-methyl-1,2-dehydrocacalol (1) and cycloart-23-ene-3,25-diol, beta-sitosterol, and stigmasterol, along with five new cacalolides, 1-hydroxy-2-methoxy-1,2,3,4-dehydro-6-dehydroxycacalone (2), 1-hydroxy-2-methoxy-1,2,3,4-dehydrocacalone (3), 1,2-dimethoxy-1,2,3,4-dehydro-6-dehydroxycacalone (4), 1,2-dimethoxy-1,2,3,4-dehydrocacalone (5), and 2-methoxy-O-methyl-1-oxo-2,3-dehydrocacalol (6), were isolated from Senecio madagascariensis collected from Colombia. The structures of the new compounds were determined using one- and two-dimensional NMR techniques. In addition, the structure of 2 was corroborated by derivatizations and single-crystal X-ray diffraction studies.

Asteraceae↗
PubMed2002

C-5-substituted antifeedant silphinene sesquiterpenes from Senecio palmensis.

The new sesquiterpenes, 5alpha-senecioyloxysilphinen-3-one (5), 5alpha-tigloyloxysilphinen-3-one (7), and 3beta-hydroxy-5alpha-angeloyloxysilphinene (8), and the known compounds (6S)-2,10-bisaboladien-1-one (1), 6,7-epoxy-3(15)-caryophyllene (2), 6,7-epoxy-2,9-humuladiene (3), 5alpha-angeloyloxysilphinen-3-one (4), and 5alpha-acetoxysilphinen-3-one (6) were isolated from bioactive fractions of Senecio palmensis. The structures of these compounds were established by spectroscopic analysis and chemical evidence. The semisynthetic analogues silphinen-3,5-dione (9), 5alpha-hydroxysilphinen-3-one (10), 5beta-hydroxysilphinen-3-one (11), 5beta-acetoxysilphinen-3-one (12), and 5beta-isobutyryloxysilphinen-3-one (13) were generated to carry out a structure-activity study on the antifeedant action of these molecules against several divergent insect species.

Animals↗
PubMedDate not supplied

Acetylanonamine, a new secopyrrolizidine alkaloid from Senecio anonymus.

A new secopyrrolizidine alkaloid, acetylanonamine, was isolated from Senecio anonymus. The structure was established by high resolution nmr (1H-1H COSY and 1H-13C HETCOR), ms, comparison of these spectral data with those of anonamine, and synthesis of 1 from 2.

Magnetic Resonance Spectroscopy↗
PubMed1998

Callosine, a 3-alkyl-substituted pyrrolizidine alkaloid from senecio callosus

Two collections of Senecio callosus from different regions of Mexico contained a structural diversity of pyrrolizidine alkaloids (PAs), which may contribute to the easy adaptation of this species. In addition to some known compounds, two new PAs (1 and 2) were isolated, and their structures were established by chemical transformations and spectroscopic studies.

Journal Article↗
PubMedDate not supplied

Comparative effects of antioxidants on the toxicity of mixed pyrrolizidine alkaloids from Senecio jacobaea in mice.

The comparative effects of the antioxidants, butylated hydroxyanisole (BHA), ethoxyquin, and cysteine on pyrrolizidine-alkaloid-induced (PA-induced) lethality and acute hepatotoxicity were assessed in female mice. Diets containing 0.75% BHA, 0.25% ethoxyquin, or 1% cysteine were fed to mice for 10 d before the ip administration of mixed PAs from Senecio jacobaea (tansy ragwort), 280 mg/kg. Without the dietary antioxidants, the PAs produced 100% mortality in 24 h. The BHA and ethoxyquin diets were completely and partially protective, respectively, against the PA-induced lethality. The deaths were associated with severe hemorrhagic lesions in liver with or without hepatocytic necrosis. Both BHA and ethoxyquin significantly reduced the incidence of the hemorrhagic lesions but not the necrotic lesions in liver. Cysteine had no significant effect on either mortality or the liver lesions induced by the mixed PAs. These results suggest that dietary antioxidants have differential protective effects against lethality and acute hepatotoxicity induced by mixed PAs from tansy ragwort.

Animals↗