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PubMedDate not supplied

Synthesis of [3,5-14C]trachelanthamidine and [5-3H]isoretronecanol and their incorporation into the retronecine moiety of riddelliine in Senecio riddellii.

(+/-)-[3,5-14C]Trachelanthamidine and (+/-)-[5-3H]isoretronecanol, which are diastereomers, were prepared from potassium [14C]cyanide and [5-3H]proline, respectively. These compounds and [1,4-14C]putrescine were administered to Senecio riddellii plants resulting in the formation of labeled riddelliine, in which almost all the radioactivity was located in its retronecine moiety. The activity of the beta-alanine obtained by degradation of the retronecine was consistent with specific labeling of this pyrrolizidine base at the expected positions. The extremely high absolute incorporation (15.1, 22.1%) of trachelanthamidine into riddelliine strongly favors this 1-hydroxymethylpyrrolizidine as the one on the main biosynthetic pathway to retronecine. The lower incorporation (0.75%) of isoretronecanol may represent a minor or aberrant pathway to retronecine.

Carbon Radioisotopes↗
PubMedDate not supplied

Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.

Ten 12-membered macrocyclic pyrrolizidine alkaloids, all of them esters of the necines, retronecine or otonecine, have been isolated from Senecio anonymus. The separation, carried out by droplet counter-current chromatography, afforded senecionine [1], integerrimine [2], retrorsine [3], senkirkine [5], neosenkirkine [6], otosenine [10], hydroxysenkirkine [7], and a new alkaloid given the trivial name anonamine [9]. Traces of usaramine [4] and another new alkaloid, hydroxyneosenkirkine [8], were detected by 1H nmr. In addition, the previously unreported 3a beta-hydroxy-4-ethoxy-2,6-perhydroindoledione [11] was isolated. X-ray structures were obtained for neosenkirkine [6], hydroxysenkirkine [7], anonamine [9], and [11]. 1H-13C heteronuclear shift correlated nmr (HETCOR) provided unambiguous chemical shift assignments for 13C-nmr data. Antitumor activity was assayed using the A204-rhabdomyosarcoma cell line in soft agarose.

Antineoplastic Agents, Phytogenic↗
PubMed2001

Phenotypic plasticity of Senecio vulgaris from contrasting habitat types: growth and pyrrolizidine alkaloid formation.

The growth-differentiation balance hypothesis (GDB), which postulates a physiological trade-off between growth and differentiation (morphological and chemical), has been tested almost exclusively for carbon-based secondary metabolites. Little attention has been paid to N-based compounds. In this study we aimed to test the predictions of the GDB hypothesis under field conditions for growth and pyrrolizidine alkaloid (PA) formation in Senecio vulgaris. We conducted a reciprocal transplant experiment at two sites differing widely in their nutrient supply. These included a conventionally managed vineyard (V) and a strip of local wild flowers between crop fields, which was established to promote species diversity in agroecosystems (C). No fertilizer or pesticides are allowed in such ecological compensation areas. In C, we expected lower growth but higher PA formation than in V. Due to differentiated selection regimes in the two habitat types with regard to nutrient (nitrogen) availability in the soil, we also expected different N-allocation patterns for the genotypes of the two collection sites. Plants of V produced more biomass and were taller than the plants of C. The relatively poor nitrogen conditions in C favored an earlier differentiation towards generative organs. In plants of C, higher concentrations of PAs were found than in plants of V. There exists a close negative correlation between growth and PA formation, indicating a trade-off. The origin of the plant material had only a little effect on PA formation. The observed phenotypic reaction of PA formation in S. vulgaris in the two habitats fits quite well the predictions of GDB theory. It is shown that this general response is overlaid by physiological factors leading to a pattern of PA accumulation, which is not readily predictable by nonmechanistic theories.

Analysis of Variance↗
PubMed2002

Pyrrolizidine alkaloids from Senecio jacobaea affect fungal growth.

We investigated the growth-reducing effects of pyrrolizidine alkaloids (PAs) from Senecio jacobaea on nine plant-associated fungi (five strains of Fusarium oxysporum, two of F. sambucinum, and two of Trichoderma sp). Fungal growth was monitored on water agar media containing different concentrations of monocrotaline, retrorsine, or a purified extract of PAs from S. jacobaea. The growth rate of six strains was inhibited by PAs at the highest test concentration (3.33 mM), with the magnitude of the inhibition (7-35%) being dependent upon the specific fungus-PA interaction. In general, the PA extract caused the largest inhibition. However, the fungi isolated from S. jacobaea were positively affected by the PA extract (7-9%). Retrorsine N oxide was as effective as retrorsine in its inhibition of mycelium growth.

Analysis of Variance↗
PubMed2002

Extinction of the Edinburgh lineage of the allopolyploid neospecies, Senecio cambrensis Rosser (Asteraceae).

Senecio cambrensis is a new allopolyploid species, which originated independently in North Wales and in Edinburgh, Scotland. Despite extensive searches, the species has not been found growing at any of its previously recorded sites in Edinburgh or at other potential sites in the area since 1993. We have concluded that the Edinburgh lineage of S. cambrensis is now extinct and discuss possible causes of its extinction. The lineage was present in Edinburgh from at least 1974 and therefore survived in the wild for a minimum of 19 years. The species remains well established in parts of North Wales.

Biological Evolution↗
PubMed2002

The population genetics of sporophytic self-incompatibility in Senecio squalidus L. (Asteraceae) I: S allele diversity in a natural population.

Twenty-six individuals of the sporophytic self-incompatible (SSI) weed, Senecio squalidus were crossed in a full diallel to determine the number and frequency of S alleles in an Oxford population. Incompatibility phenotypes were determined by fruit-set results and the mating patterns observed fitted a SSI model that allowed us to identify six S alleles. Standard population S allele number estimators were modified to deal with S allele data from a species with SSI. These modified estimators predicted a total number of approximately six S alleles for the entire Oxford population of S. squalidus. This estimate of S allele number is low compared to other estimates of S allele diversity in species with SSI. Low S allele diversity in S. squalidus is expected to have arisen as a consequence of a disturbed population history since its introduction and subsequent colonisation of the British Isles. Other features of the SSI system in S. squalidus were also investigated: (a) the strength of self-incompatibility response; (b) the nature of S allele dominance interactions; and (c) the relative frequencies of S phenotypes. These are discussed in view of the low S allele diversity estimates and the known population history of S. squalidus.

Crosses, Genetic↗
PubMed2003

Population genetics of sporophytic self-incompatibility in Senecio squalidus L. (Asteraceae) II: a spatial autocorrelation approach to determining mating behaviour in the presence of low S allele diversity.

We recently estimated that as few as six S alleles represent the extent of S locus diversity in a British population of the self-incompatible (SI) coloniser Senecio squalidus (Oxford Ragwort). Despite the predicted constraints to mating imposed by such a low number of S alleles, S. squalidus maintains a strong sporophytic self-incompatibility (SSI) system and there is no evidence for a breakdown of SSI or any obvious negative reproductive consequences for this highly successful coloniser. The present paper assesses mating behaviour in an Oxford S. squalidus population through observations of its effect on spatial patterns of genetic diversity and thus the extent to which it is responsible for ameliorating the potentially detrimental reproductive consequences of low S allele diversity in British S. squalidus. A spatial autocorrelation (SA) treatment of S locus and allozyme polymorphism data for four loci indicates that mating events regularly occur at all the distance classes examined from 60 to 480 m throughout the entire sample population. Less SA is observed for S locus data than for allozyme data in accordance with the hypothesis that SSI and low diversity at the S locus are driving these large-scale mating events. The limited population structure at small distances of 60 m and less observed for SA analysis of the Me-2 locus and by F-statistics for all the allozyme data, is evidence of some local relatedness due to limited seed and pollen dispersal in S. squalidus. However, the overall impression of mating dynamics in this S. squalidus population is that of ample potential mating opportunities with many individuals at large population scales, indicating that reproductive success is not seriously affected by few S alleles available for mating interactions.

Alleles↗
PubMed2004

Reproductive isolation of a new hybrid species, Senecio eboracensis Abbott & Lowe (Asteraceae).

The nature and extent of reproductive isolation was examined between a new self-compatible hybrid species Senecio eboracensis (2n=40) and its parents, self-incompatible S. squalidus (2n=20) and self-compatible S. vulgaris (2n=40). The triploid F(1) of S. eboracensis x S. squalidus exhibited very low seed set (x=0.63%), and F(2) and F(3) progeny were able to recover nominal levels of fertility (x=23.9 and 9.7%), while F(1) and F(2) offspring of S. eboracensis x S. vulgaris showed reduced seed set (x=63.8 and 58.8%). In both cases, evidence from previous work indicates that reduced fertility is associated with meiotic chromosome mispairing, and is a likely consequence of recombining both parental genomes within this new taxon. No hybrid offspring between S. eboracensis and S. squalidus were found in the wild, and only one such hybrid was recorded among 769 progeny produced by S. eboracensis surrounded by S. squalidus on an experimental plot. Natural crossing between S. eboracensis and S. vulgaris was recorded to be very low (between 0 and 1.46%) in the wild, but rose to 18.3% when individuals of S. eboracensis were surrounded by plants of S. vulgaris. It was concluded that strong breeding barriers exist between the new hybrid species and its two parents. Prezygotic isolation between S. eboracensis and S. vulgaris is likely to be largely due to both species reproducing by predominant self-fertilisation. However, differences recorded for germination, seedling survival, time of flowering and characters associated with pollinator attraction, plus significant clumping of juvenile and adult conspecifics in the wild, probably also contribute to reproductive isolation and ecological differentiation.

Chimera↗
PubMed2000

Genetic control of self-incompatibility in Senecio squalidus L. (Asteraceae): a successful colonizing species.

Senecio squalidus (Oxford ragwort) is a well-known introduction to the British flora that has proved to be an extremely successful colonist over the last 150 years. Unusually for a colonizing species, S. squalidus is self-incompatible (SI). Being a member of the Asteraceae, SI in S. squalidus is expected to be sporophytic. This paper presents genetic data showing that the SI system of S. squalidus is indeed sporophytic and is controlled by a single multiallelic S locus, alleles of which show the dominance/recessive relationships characteristic of sporophytic SI (SSI). Early indications are that the number of S alleles in populations is low because only four different S alleles were identified in a sample of four plants from two distinct populations; one S allele, S1, a pollen/stigma recessive allele, was present in all four plants. Forced inbreeding, using salt-treatment to overcome SI, was shown to generate 'pseudo-self-compatible' individuals with weakened SI and a loss/reduction in stigmatic S-specific discrimination. Relatively high frequencies of unpredictable compatible crossing 'anomalies' suggest that a 'gametophytic element' may influence the outcome of crosses in certain genetic backgrounds so as to increase levels of compatibility when S alleles are shared. Together, these findings indicate a genetic 'flexibility' in the SSI system of S. squalidus that could be crucial to its success as a colonizer.

Alleles↗
PubMed2000

Random amplified polymorphic DNA (RAPD) and quantitative trait analyses across a major phylogeographical break in the Mediterranean ragwort Senecio gallicus Vill. (Asteraceae).

Random amplified polymorphic DNA (RAPD) and quantitative trait variation of the widespread and ephemeral Senecio gallicus were surveyed in 11 populations sampled from the Iberian Peninsula and southern France. The aim of the study was to compare population relationships and levels of geographical differentiation with chloroplast (cp) DNA and allozyme variation assessed previously in the same populations. Employing multivariate statistics, a moderate level of intraspecific differentiation was observed among populations from Iberian coastal and inland regions for both RAPDs and quantitative traits. However, RAPDs provided greater resolution in identifying additional population structure within the hypothesized, Pleistocene refugial source area of the species in coastal Iberia. A major part of the geographical subdivision in RAPD and quantitative traits was concordant with the coastal vs. inland divergence as previously inferred from cpDNA haplotype frequencies, but strongly contrasted with the geographical uniformity of the species for allozymes. This concordance across various nuclear and cytoplasmic markers (RAPDs/quantitative traits, cpDNA) suggests that geographical uniformity for allozymes is more attributable to low rates of evolution and/or small genome sampling rather than high rates of pollen dispersal, slow rates of nuclear lineage sorting, or indirect balancing selection. The present study underscores the value of using additional classes of nuclear markers for narrowing the numbers of competing causal hypotheses about intraspecific cpDNA-allozyme discrepancies and their underlying evolutionary processes.

Alleles↗
PubMed2001

Genetic structure of the annual weed Senecio vulgaris in relation to habitat type and population size.

Throughout the world, the highly selfing annual common groundsel, Senecio vulgaris (Asteraceae) is a common weed. Recently, it has also colonized ecological compensation areas in agro-ecosystems. We investigated the genetic structure of S. vulgaris using random amplified polymorphic DNA (RAPD) profiles of 80 plants from nine populations representing three habitat types in two regions in Switzerland. RAPD variation among regions (19.8%), among populations within regions (19.2%) and within populations (61.1%) was highly significant (ANOVA; P < 0.001). Gene flow estimated from the observed differentiation among populations (PhiST = 0.382) was low (assuming Wright's island model, Nem = 0.404). Genetic distances between pairs of populations were significantly correlated with geographical distances (Mantel test; r = 0.37, P < 0.03). Molecular variance obtained with AMOVA was lowest in the small populations in compensation areas (1.13), intermediate in vineyard populations (2.49), all located in northern Switzerland and highest in the larger vegetable field populations from western Switzerland (3.41; P < 0.05). Overall, there was a positive correlation of molecular variance and population size (P < 0.05), as expected under genetic drift. However, molecular variance was negatively correlated with population size among populations in ecological compensation areas, suggesting that selection was also important. We also applied triazine herbicide to leaves of three offspring of each of the 80 plants. Plants from populations of compensation areas showed higher mean levels and reduced variation in the resistance to triazine herbicide than plants from vineyards and vegetable fields. This suggests that compensation areas were colonized from adjacent corn fields, in which there has been selection for herbicide resistance. We discuss the implications of our results for the biological control of S. vulgaris.

Drug Resistance↗
PubMed2003

Possible causes of morphological variation in an endemic Moroccan groundsel (Senecio leucanthemifolius var. casablancae): evidence from chloroplast DNA and random amplified polymorphic DNA markers.

Genetic variation was assessed in Senecio leucanthemifolius var. casablancae (Compositae), a Moroccan Atlantic coast endemic, in order to examine possible causes of atypical leaf morphology in three populations south of the known range. Evidence for introgression from S. glaucus ssp. coronopifolius and/or divergence was investigated with molecular markers. Both random amplified polymorphic DNA (RAPD) and chloroplast (cp) DNA restriction fragment length polymorphism (RFLP) differentiated the species well. Some evidence that hybridization may have occurred between the two species was provided by cpDNA markers. However, biparentally inherited RAPD markers failed to provide any support for the hypothesis that intermediate leaf morphologies in atypical populations arose through hybridization. Consequently, they are most likely to have arisen via divergence caused by drift and/or selection. Genetic distances among populations of S. leucanthemifolius were significant in all but one case. Isolation by distance was indicated by a significant positive correlation between genetic and geographical distances (r = 0.68, P = 0.01, Mantel test). These results suggest that long-distance achene dispersal is rare, despite the presence of a well-developed pappus. The observed loss of pappus at achene maturity may explain this unexpected result. Due to the morphological distinction of var. casablancae from other varieties of S. leucanthemifolius, we suggest elevation to species rank and treatment of the atypical material at infraspecific rank.

DNA, Chloroplast↗
PubMed2003

Low genetic differentiation among seasonal cohorts in Senecio vulgaris as revealed by amplified fragment length polymorphism analysis.

Common groundsel, Senecio vulgaris (Asteraceae), is a highly selfing semelparous ephemeral weed that belongs to the few plant species in central Europe capable of growing, flowering and fruiting all year round. In temperate climates, flowering S. vulgaris cohorts were found to appear up to three times per year. Using amplified fragment length polymorphism (AFLP) molecular markers we examined temporal genetic differentiation among spring, summer and autumn cohorts at each of seven sites located in two regions in Switzerland. Strong genetic differentiation among cohorts may indicate the existence of seasonal races of S. vulgaris, reproductively isolated by nonoverlapping flowering phenologies. Analysis of molecular variance (amova) revealed that < 2.5% of the AFLP variation resided among cohorts within sites, whereas there was significant genetic differentiation among plants from different sites (15.6%) and among individuals within cohorts (81.9%). Significant genetic differentiation was also observed between the two regions. Isolation-by-distance was found on a regional scale, but not on a local scale. Gene flow was estimated to be approximately 15-fold higher among cohorts within sites than among sites. We further found, on average, similar levels of genetic diversity within the three seasonal cohorts. The results of this study demonstrate that season of growth represents a weak barrier for genetic exchange among S. vulgaris populations and does not affect molecular variance. Therefore, there is no evidence for the existence of seasonally specialized races of S. vulgaris. We discuss some implications of the results for the biological control of S. vulgaris using a native rust fungus.

Analysis of Variance↗
PubMed1977

The effect of ragwort (Senecio jacobea) on the liver of the domestic fowl (Gallus domesticus) : a histopathological and enzyme histochemical study.

1. Twenty-five 1-week-old male chicks were fed for 6 weeks on a standard diet incorporating 7% dried and ground ragwort (Senecio jacobea). The chicks received the standard diet for a further 6 weeks whilst a control group of 25 similar birds received the standard diet throughout. 2. Two birds from each group were killed at intervals of about 1 week and their livers were examined histologically and histochemically. 3. Ragwort feeding caused megalocytosis, focal necrosis, focal hyperplasia and portal fibrosis. There were no veno-occlusive changes. 4. As the lesion progressed there was an overall loss of enzyme activity especially in the areas of necrosis. The groups of small hyperplastic cells showed normal or increased activity and there was increased enzyme activity in the megalocytes. 5. The development of groups of proliferating cells may be a prelude to the neoplastic changes described in earlier reports of longer term studies of the effects of pyrolizidine alkaloids on the liver of chicks.

Adenosine Triphosphatases↗
PubMed2002

A new lactone from Senecio cannabifolius Less.

A new lactone compound named cannabifolactone A was isolated from the water extract of the aerial parts of Senecio cannabifolius Less. Its structure was elucidated mainly by 1D- and 2D-NMR techniques.

Benzofurans↗
PubMed2004

Three new and two rare furanoeremophilanes from Senecio asirensis.

Three new furanoeremophilanes have been obtained from the aerial parts of Senecio asirensis (N. O. Asteraceae), and characterized as 6-hydroxylmethyl-9-methoxyl-4,11-dimethylnaphtho[2,3-b]furan, designated asirensane-a (1), 6-hydroxyl-1,2-dimethoxyl-4,6,11-trimethyl-6-hydronaphtho[2,3-a]furan-7-one, named asirensane-b (2), and (6,12-dihydroxyl-9-methoxyl-4-methyl-11-acetyl-3,4-dihydronaphtho[2,3-b]furan- 3-yl)methyl (2'Z)-2'-methyl-but-2'-enoate, designated asirensane-c (3). In addition, two rare furanoeremophilanes have also been isolated and characterized from this source, namely 9-methoxyl-4,11-dimethylnaphtho[2,3-b]furan, named 14-nordehydro-calohastine (4), and 4,11-dimethylnaphtho[2,3-b]furan-6,9-dione, designated as maturinone (5). Their structures have been elucidated on the basis of spectral analysis. The alcoholic extract was also tested for anti-inflammatory activity, which decreased edema by 22% at a dose of 500 mg kg-1 after 3 h with respect to the control group treated only with carrageenan, while the standard drug phenylbutazone showed a 50% decrease at a dose of 100 mg kg-1, indicating that the extract has moderate anti-inflammatory activity.

Animals↗
PubMedDate not supplied

Jacaranone glycosides from Senecio scandens.

Bioassay-guided fractionation of the ethanol extract of Senecio scandens led to the isolation of four new compounds 1-4. These compounds were obtained as tautomeric mixture of alpha/beta epimers, but their structures were confirmed unambiguously by 1D and 2D NMR spectra and LC NMR technology. 1H NMR spectra of pure 1alpha and 1beta were furnished by HPLC NMR technology. Compounds 1-4 exhibited moderate cytotoxicities against five tumor cell lines.

Benzoquinones↗
PubMed2006

Bioactive eremophilanolides from Senecio poepigii.

A new bioactive eremophilanolide, 1alpha-tigloyloxy-8betaH,10betaH-eremophil-7(11)-en-8alpha,12-olide, was isolated from Senecio poepigii and its structure was elucidated by spectral analysis. 1alpha-Angeloyloxy-8beta-methoxy-10betaH-eremophil-7(11)-en-8alpha,12-olide was also isolated. Antifungal and insect antifeedant properties were evaluated.

Animals↗