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PubMed1987

Toxic actions of senaetnine, a new pyrrolizidine-type alkaloid, in rats.

Senaetnine is a new type of Senecio alkaloid with a dihydropyrrolizinone structure. A limited amount of the crude alkaloid was available for preliminary toxicity tests in weanling male rats via i.p., oral and i.v. routes. Single i.p. or p.o. doses up to 280 mg/kg were not acutely toxic, and showed no evidence of hepatotoxicity. The compound or its metabolites appeared to be eliminated rapidly via the kidneys. However, senaetnine had a direct irritant action on tissues near to the site of i.p. administration, and caused damage to pulmonary vascular tissue when given i.v. Senaetnine is closely related to, but less reactive than, dehydrosenecionine, a putative short-lived metabolite of the alkaloid senecionine. It possesses mild alkylating reactivity, and the evidence indicates that it can cause moderate tissue injury without the need for metabolic activation. This suggests the need for testing of this and related compounds for chronic toxicity and carcinogenicity.

Administration, Oral↗
PubMed1992

Medicinal plants in a Middle Paleolithic grave Shanidar IV?

This paper deals with phytopharmacological evaluation of the therapeutic potential of the plants found in the Neanderthal grave of a Shanidar IV individual (Iraq), where the palynological analysis of some other authors discovered the following flowers: Achillea-type, Centaurea solstitialis, Senecio-type, Muscari-type, Ephedra altissima, Althea-type. The purpose of our theoretical analysis was to evaluate the objective healing activity of the flowers. The result of the research revealed that Shanidar IV flowers possess considerable therapeutic effects with marked medical activity, which could be an intentional reason for the selection of the flowers in Middle Paleolithic Shanidar Neanderthals.

Humans↗
PubMed1994

Hepatotoxic pyrrolizidine alkaloids in the Mexican medicinal plant Packera candidissima (Asteraceae: Senecioneae).

A study of the hepatotoxic pyrrolizidine alkaloids (PAs) contained in Packera candidissima (Greene) Weber & Löve (Senecio candidissimus Greene), a Mexican medicinal plant used for the treatment of kidney ailments and noted for its antiseptic properties, is reported. Analysis by TLC and GC-MS have shown the presence in high levels of both PAs and their N-oxides in the root (0.76% dry weight) and the aerial parts (0.36% dry weight) of the plant material. GC-MS analysis showed the presence of senecionine, integerrimine, retrorsine, and usaramine in the aerial parts. The root was found to contain senkirkine as the major component. These results indicate that users of this herb are at high risk of poisoning, especially members of certain cultural groups in Northern Mexico and the Hispanic population in the southwestern United States. In addition, two sesquiterpenes, neoadenostylone and epineoadenostylone were identified from the neutral extracts of this plant material. The 6 alpha-angeloyloxy-9-oxo-delta 10(1)-furanoeremophilane is reported for the first time as a natural product.

Antineoplastic Agents, Phytogenic↗
PubMed2005

A multi-biosensor based on immobilized Photosystem II on screen-printed electrodes for the detection of herbicides in river water.

A multi-biosensor for detection of herbicides and pollutants was constructed using various photosynthetic preparations as biosensing elements. The photosynthetic thylakoid from Spinacia oleracea L., Senecio vulgaris and its mutant resistant to atrazine were immobilized with (BSA-GA) on the surface of screen-printed sensors composed of a graphite-working electrode and Ag/AgCl reference electrode deposited on a polymeric substrate. The biosensor was composed of four flow cells with independent illumination of 650 nm to activate electron transfer in Photosystem II. The principle of the detection was based on the fact that herbicides selectively block electron transport activity in a concentration-dependent manner and that the four PSII biomediators show differential recognition activity toward herbicides. Changes of the activity were registered amperometrically as rate of photoreduction of the artificial electron acceptor DQ. The setup resulted in a reusable herbicide multibiosensor with a good stability (half-life of 16.7 h for spinach thylakoids) and limit of detection of about 10(-8) M for herbicides recovered in spring in river.

Adsorption↗
PubMed2004

Bioindicator plants for ambient ozone in Central and Eastern Europe.

Sixteen species of native detector plants for ambient ozone have been identified for use in Central and Eastern Europe. They include the forbs Alchemilla sp., Astrantia major, Centuarea nigra, Centauria scabiosa, Impatiens parviflora, Lapsana communis, Rumex acetosa and Senecio subalpinus; the shrubs Corylus avellana, Cornus sanguinea and Sambucus racemosa; the trees Alnus incana, Pinus cembra and Sorbus aucuparia; and the vines Humulus lupulus and Parthenocissus quinquefolia. Sensitivity to ozone and symptoms have been verified under controlled exposure conditions. Under these conditions, symptom incidence, intensity and appearance often changed with time after removal from exposure chambers. Ozone sensitivity for four species: Astrantia major, Centuarea nigra, C. scabiosa and Humulus lupulus are reported here for the first time. The other 12 species have also been confirmed by others in Western Europe. It is recommended that these detector bioindicator species be used in conjunction with ozone monitors and passive samplers so that injury symptoms incidence can be used to give biological significance to monitored ambient ozone data.

Air Pollution↗
PubMed2005

Biological activity of some Patagonian plants.

Citotoxicity (inhibition of cell division in fertilized eggs of Loxechinus albus) and general toxicity (using embryos of Artemia salina) of plants belonging to the genera Senecio, Deschampsia, Alstroemeria, Anarthrophyllum, Chloraea and Geranium were investigated.

Animals↗
PubMed2004

Traditional medicine in Sakarya province (Turkey) and antimicrobial activities of selected species.

Traditional medicine in North-West of Turkey (Sakarya province) were studied during a 2 months field study by interviewing local informants from several villages. Plant species used to treat infections were tested for antimicrobial activity. Information was collected for 46 plant species from 30 families and for 5 animal species. Twenty four of the plant species were cultivated. Most used families were Asteraceae, Cucurbitaceae, Lamiaceae and Rosaceae and the most used plants were Artemisia absinthium, Equisetum telmateia, Lavandula stoechas, Melissa officinalis, Tussilago farfara and Urtica dioica. A total of 139 medicinal uses were obtained. Plants are used mainly for infectious diseases (18%), for neurological and psychological disorders (13.7%), cardiovascular disorders (13%), skin disorders (12.2%) and respiratory disorders (10.1%). Extracts were tested in vitro for antimicrobial activity against Staphylococcus aureus ATCC 65538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumonia ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri, Proteus mirabilis and Candida albicans ATCC 10231, using microbroth dilution technique according to National Committee for Clinical Laboratory Standards (NCCLS). This research showed that Arum maculatum, Datura stramonium, Geranium asphodeloides and Equisetum telmateia petroleum ether extracts had MIC values of 39.1 microg/ml, 78.1 microg/ml, 78.1 microg/ml and 39.1 microg/ml, respectively against Staphylococcus epidermidis. Datura stramonium petroleum ether extract had a MIC value of 39.1 microg/ml against Escherichia coli and Trachystemon orientalis ethanol extract had a MIC value of 39.1 microg/ml against Escherichia coli. The antimicrobial activity of Arum maculatum, Equisetum telmateia, Geranium asphodeloides, Plantago intermedia, Senecio vulgaris and Trachystemon orientalis has been reported here for the first time.

Anti-Infective Agents↗
PubMed2006

In vitro shoot and root organogenesis, plant regeneration and production of tropane alkaloids in some species of Schizanthus.

A rapid in vitro propagation system leading to formation of shoots from callus, roots, and plantlets was developed for Schizanthus hookeri Gill. (Solanaceae), an endemic Chilean plant. The genus Schizanthus is of particular interest due to the presence of several tropane alkaloids. So far, in vitro propagation of species of this genus has not been reported. Propagation of S. hookeri consisted of two phases, the first one for callus initiation and shoot formation and the second for rhizogenesis and plantlet regeneration. From a single callus that rapidly increased in cell biomass (from approximately 50 mg to approximately 460 mg/culture tube [25 x 130 mm] in 60 days) in the presence of 2.69 microM NAA and 2.22 microM BA, more than 10 shoots/callus explant were formed. From the latter, approx. twenty plantlets formed after 90-110 days shoot subculture in medium devoid of growth regulators that favored root formation. Ten alkaloids ranging from simple pyrrolidine derivatives to tropane esters derived from angelic, tiglic, senecioic or methylmesaconic acids were obtained from in vitro regenerated plantlets. One of them, 3alpha-methylmesaconyloxytropane, was not previously described. The same growth conditions, as well as other growth regulator levels tested, were required to induce callus and root formation in S. grahamii Gill. Root organogenesis occurred despite a high level of BA vs. NAA used, (i.e., 4.44 microM BA and 0.54 microM NAA); however no shoot formation was achieved. In the case of S. tricolor Grau et Gronbach, only callus formation was obtained in the presence of various growth regulators.

Isomerism↗
PubMed1985

In vivo covalent binding of retronecine-labelled [3H]seneciphylline and [3H]senecionine to DNA of rat liver, lung and kidney.

Retronecine-labelled [3H]seneciphylline ([3H]SPH) and [3H]senecionine ([3H]SON) of high specific radioactivity (22 and 49 mCi/mmol, respectively) were prepared biosynthetically with seedlings of Senecio vulgaris L. using [2,3-3H]putrescine as precursor. [2,3-3H]Putrescine was synthesized by Gabriel synthesis of 1,4-diamino-2-butene from 1,4-dibromo-2-butene and catalytic hydrogenation of the product with tritium gas. Rats of both sexes were treated with the labelled pyrrolizidine alkaloids (PAs) (75-215 microCi SPH or 40-485 microCi SON/kg body wt.) and killed after 6 h or 4-5 days. SON-treated females excreted 83.4 +/- 0.2% of applied radioactivity in faeces and urine within 4 days whereas equally treated males excreted 90.9 +/- 3.2% in the same time. Excretion of 3H-activity from SPH-treated females was completed within 5 days (104.7 +/- 6.4%). Corresponding with these results, tissue levels were highest in SON-treated females. DNA and proteins were isolated from liver, lungs and kidneys and covalent binding of the alkaloids to DNA was determined. A Covalent Binding Index (CBI, mumol alkaloid bound per mol nucleotides/mmol alkaloid administered per kg body wt.) of 210 +/- 12 was found for the liver from SON-treated females whereas binding to liver DNA of males was lower by a factor of 4. The DNA damage determined six hours after treatment persisted during the following 4 days. Administration of [3H]SPH to female and male rats resulted in a CBI of 69 +/- 7 and 73/92, respectively, for the liver DNA. Furthermore we found binding of both alkaloids to DNA of lungs and kidneys in male and female rats. The in vivo formation of [3H]SON derived DNA adducts could be proved by HPLC analysis of hydrolyzed DNA.

Animals↗
PubMed1991

Cynoglossum officinale toxicity in calves.

Six calves were given dried, ground Cynoglossum officinale daily in a dose which provided 15 (two calves) or 60 (four calves) mg per kg per day of total pyrrolizidine alkaloids. Those calves given 60 mg per kg of total pyrrolizidine alkaloids per day died following a single dose of plant material. These calves had a marked elevation of serum gamma-glutamyltransferase (GGT) and aspartate transaminase (AST) activities and serum bile acid and total bilirubin (TBili) concentrations. These four calves all had massive hepatocellular necrosis and haemorrhage of the liver. Of the two calves that were given 15 mg per kg of total pyrrolizidine alkaloids per day, one died on day 34 and the other survived until day 35 when it was painlessly killed. There were significant elevations in serum AST and GGT activities in these calves. The histological lesions of the calf surviving until 35 days were compatible with pyrrolizidine alkaloid toxicity, that is megalocytosis, karyomegaly and necrosis of hepatocytes with karyomegaly of biliary epithelium. The pyrrolizidine base present in Cynoglossum officinale (heliotridine) and its esters have a similar type of toxicity to the highly toxic and more familiar macrocyclic diester pyrrolizidine alkaloids of the pyrrolizidine base (retronecine), present in Senecio or Crotolaria species.

Animals↗
PubMed2000

Antioxidative and free radical scavenging activities of selected medicinal herbs.

The antioxidative and superoxide- and hydroxyl radical-scavenging activities and pro-oxidant effect of twelve selected medicinal herbs were studied. The aqueous extracts of Coptis chinensis, Paeonia suffruticosa, Prunella vulgaris and Senecio scandens exhibited the highest potency in inhibiting rat erythrocyte hemolysis and lipid peroxidation in rat kidney and brain homogenates. The aforementioned four herbs also demonstrated strong superoxide- and hydroxyl radical-scavenging activity, but exerted only a slight pro-oxidant effect.

Animals↗
PubMed2003

Effects of elevated soil copper on phenology, growth and reproduction of five ruderal plant species.

The repeated use of copper (Cu) fungicides to control vine downy mildew, caused by Plasmopara viticola, has been responsible for the heavy increase of Cu concentration in the upper layers of vineyard soils. To determine the effects of elevated soil Cu on plant development, we created an artificial soil gradient with Cu enrichments ranging from 0 to 400 mg kg-1. On this gradient, and for five ruderal plant species commonly found in vineyards in southern France (Poa annua L., Dactylis glomerata L., Senecio vulgaris L., Hypochoeris radicata L., and Andryala integriflolia L.), we quantified survival, growth, and reproduction throughout one flowering season. High concentrations of Cu in the soil resulted in low survival, low total plant biomass, delay in flowering and fruiting, and low seed set. However, the effects differed among species. Furthermore, high soil Cu concentrations had contrasting effects on patterns of resource allocation depending on the plant species.

Copper↗
PubMed2003

The response of some common Egyptian plants to ozone and their use as biomonitors.

Relative sensitivity of five common Egyptian plant species namely, Senecio vulgaris, Malva parviflora, Sonchus oleraceus, Medicago sativa and Melilotus indicus to elevated levels of ozone has been studied. The plants were exposed to charcoal filtered air (CFA) and different levels of O3 (50 and 100 ppb) for 5 h per day. The studied parameters were recorded for five consecutive days after fumigation. The foliar injury varied significantly among species in a dose-dependent manner. Severe injury symptoms were recorded on the leaves of M. sativa. With the exception of M. parviflora, all species exhibited significant increases in the percentage reduction of the above-ground dry weight as a result of reductions in both leaf and stem dry weights. M. sativa showed a marked reduction in its relative growth rate at elevated levels of O3. The extent of chlorophyll a destruction was higher in both M. sativa and S. oleraceus than in the other species tested. No differences in the sensitivity of chlorophylls a+b and carotenoids to ozone levels were recorded in this work. Percentage reduction of ascorbic acid was higher in M. sativa and S. oleraceus, compared with the other species studied. With respect to relative percentages of proline, there was a significant difference in the responses of plants to ozone. According to the ozone resistance (R%), measured as relative growth rate, the test species were arranged in the descending order: M. parviflora>M. Indicus>S. Vulgaris>S. Oleraceus>M. sativa. In M. sativa, both determinant and correlation coefficients are well reflected in the relationship between its physiological response, its performance and ozone levels, supporting its recommendation as a candidate for biomonitoring in Egypt.

Air Pollutants↗
PubMed2002

Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid.

A mixed culture of ovine ruminal microbes metabolizes the macrocyclic pyrrolizidine alkaloids present in the plant Senecio jacobaea, including jacobine and seneciphylline. Previous attempts to identify metabolites of these alkaloids have not been successful. The objective of this study was to compare the metabolism of pyrrolizidine alkaloids by a mixed culture of ovine ruminal microbes to the metabolism of pyrrolizidine alkaloids by the known organism Peptostreptococcus heliotrinreducens. P. heliotrinreducens metabolizes the pyrrolizidine alkaloids heliotrine and lasiocarpine to 7alpha-hydroxy-1-methylene-8alpha-pyrrolizidine and 7alpha-angelyl-1-methylene-8alpha-pyrrolizidine, respectively. This organism does not metabolize the pyrrolizidine alkaloids jacobine or seneciphylline. A mixed culture of ovine ruminal microbes also metabolized heliotrine and lasiocarpine to identical methylene compounds. This mixed culture also metabolized jacobine and seneciphylline, with the production of very low levels of the corresponding 1-methylene compounds. Samples were analyzed by TLC and GC/MS.

Animals↗
PubMed2003

Phylogenetic analysis of Puccinia distincta and P. lagenophorae, two closely related rust fungi causing epidemics on Asteraceae in Europe.

Phylogenetic analyses of the ITS1-5.8S-ITS2 region of the ribosomal RNA gene cluster were carried out with two short-cycled (aecial/telial) European rusts on Asteraceae, Puccinia distincta causing the current pan-European epidemic on Bellis perennis, and P. lagenophorae causing a similar disease on Senecio spp., as well as the macrocyclic P. obscura which alternates between B. perennis (pycnial and aecial host) and Luzula spp. (main host). All three species formed a well-resolved cluster when compared with the ITS sequences of a range of other rust fungi, using both parsimony and distance methods. The sequences of P. distincta and P. lagenophorae differed from each other at three positions whereas P. obscura differed from P. distincta at 37 points. Together with consistent morphological and epidemiological differences across Europe, these data support the recognition of P. distincta as a separate species from P. lagenophorae. Both may be derived from P. obscura, although the precise evolutionary history remains obscure.

Asteraceae↗
PubMedDate not supplied

Enzyme-linked immunosorbent assay detection of pyrrolizidine alkaloids: immunogens based on quaternary pyrrolizidinium salts.

Polyclonal antibody-based enzyme-linked immunosorbent assays (ELISAs) were developed for the detection of retrorsine (1, 351 g/mol), monocrotaline (2, 325 g/mol), and retronecine (3, 155 g/mol) in the parts per billion (ppb) range. A set of three bifunctional linking arms (6-8) was synthesized. By N-alkylation of pyrrolizidine alkaloids (PAs) retrorsine, monocrotaline, and retronecine acetonide (9), six haptens (6.1, 6.2, 7.1, 7.2, 7.9, and 8.9) were synthesized and used to generate rabbit antisera. The resulting anti-retrorsine antiserum gave a 50% inhibition (I50) value of 0.9 +/- 0.2 ppb for retrorsine with detection limits of 0.5-10 ppb. The same ELISA system also detected isatidine (4, retrorsine N-oxide) dihydrate (403 g/mol) with an I50 of 1 ppb and senecionine (5,352 g/mol) with an I50 of 100 ppb. A second monocrotaline-based ELISA detected monocrotaline with an I50 of 36 +/- 9 ppb 2 with detection limits of 5-500 ppb and shows no cross-reactivity with 1 or 5; this ELISA demonstrates the potential for the substrate-specific detection method. A third retronecine-based ELISA detects 3 with an I50 of 3000 +/- 600 ppb (3 +/- 0.6 ppm) and detection limits of 600-10,000 ppb. None of these ELISAs cross-react with the structurally similar swainsonine (10) or lupinine (11) alkaloids. PAs were detected in extracts of Senecio vulgaris and Crotalaria retusa, but not in Lupinus spp., as a demonstration of the ELISA's usefulness.

Alkylation↗
PubMed2001

Photochemical deconjugation of chiral 3-methyl-2-butenoates derived from carbohydrate-based alcohols: the influence of the sugar backbone on the facial diastereoselectivity.

The photodeconjugation of the alpha-(4-trimethylsilyl-3-butynyl)-substituted senecio acid esters 7 was studied. Chiral alcohols ROH (9) were employed as auxiliaries to control the facial diastereoselectivity of the protonation step. The conversion of the four sugar alcohols diacetone-D-glucofuranose, diacetone-D-allofuranose, diacetone-D-gulofuranose, and diacetone-D-fructopyranose (9a-d) to the esters 7 was achieved in four steps employing 4-iodo-1-trimethylsilylbut-1-yne (3) as the alkylating agent (27-45% yield overall). Their photodeconjugation gave the corresponding beta,gamma-unsaturated (R)-esters 14a-d with moderate to excellent diastereomeric excess. The best results were achieved with diacetone-D-glucofuranose and diacetone-D-fructopyranose as the auxiliary (>95% de). To achieve the synthesis of the target compound 1 which has the (S)-configuration, the deconjugation was conducted with the diacetone-L-fructopyranose (ent-9d) derived ester ent-7d. L-Fructose (20) was prepared from L-sorbose (15) in a modified procedure that allowed for the isolation of intermediates. The 2-fold inversion of configuration worked nicely, and the fructofuranose 19 was obtained in 19% yield from L-sorbose. The conversion of L-fructose to the ester ent-7d was conducted in full analogy to the synthesis of its enantiomer 7d. Deconjugation of ester ent-7d yielded the product 2d (70% yield), which was reduced to the alcohol 1 (85% yield).

Journal Article↗