Voici les éléments 1 - 7 sur 7
  • Publication
    Accès libre
    Selective sequestration and metabolism of plant derived pyrrolizidine alkaloids by chrysomelid leaf beetles
    (1997)
    Hartmann, Thomas
    ;
    Witte, Ludger
    ;
    Ehmke, Adelheid
    ;
    Theuring, Claudine
    ;
    ;
    Pasteels, Jacques M.
    Pyrrolizidine alkaloids (PAs) are assumed to function as plant defence compounds against herbivory. A number of adapted insects are known to sequester plant derived PAs for their own benefit. Here we summarize the chemical interactions between leaf beetles of the genus Oreina (Coleoptera, Chrysomelidae) and their host plants Adenostyles spp., Senecio nemorensis, and S. fuchsii (Asteraceae, tribe Senecioneae). Seneciphylline N-oxide and senecionine N-oxide, the main PAs of Adenostyles, are sequestered in the bodies and exocrine defensive glands of the leaf beetles. The comparison with the PA patterns of the Senecio host plant indicates a selective PA uptake. The uptake into the body (hemolymph) is less specific, whereas the translocation into the defensive glands is highly specific. Only the N-oxides of macrocyclic retronecine esters of the senecionine type are found in significant amounts in the defensive secretions. Many other PAs such as monoesters and open-chain diesters as well as PAs of other structural types (e.g. monocrotaline N-oxide and senkirkine) are not transferred into the defensive glands. Leaf beetles sequester PAs exclusively as N-oxides. A novel PA not found in the food plants was detected in the defensive secretions of Oreina elongata; it was identified as 13,19-expoxisenecionine N-oxide (oreine), the epoxidation product of seneciphylline N-oxide. Besides this transformation, leaf beetles are able to catalyse further transformations such as the O-dealkylation of heliotrine N-oxide to rinderine N-oxide and the O-deacetylation of acetylseneciphylline N-oxide to seneciphylline N-oxide. The plant-beetle interactions are discussed in the functional context of PAs as powerful plant defensive chemicals.
  • Publication
    Accès libre
    Host-Plant Switches and the Evolution of Chemical Defense and Life History in the Leaf Beetle Genus Oreina
    (1996)
    Dobler, Susanne
    ;
    Mardulyn, Patrick
    ;
    Pasteels, Jacques M.
    ;
    Insect-plant interactions have played a prominent role in investigating phylogenetic constraints in the evolution of ecological traits. The patterns of host association among specialized insects have often been described as highly conservative, yet not all specialized herbivorous insect lineages display the same degree of fidelity to their host plants. In this paper, we present an estimate of the evolutionary history of the leaf beetle genus Oreina. This genus displays an amazing flexibility in several aspects of its ecology and life history (1) host plant switches in Oreina occurred between plant families or distantly related tribes within families and thereby to more distantly related plants than in several model systems that have contributed to the idea of parallel cladogenesis; (2) all species of the genus are chemically defended, but within the genus a transition between autogenous production of defensive toxins and sequestration of secondary plant compounds has occurred; and (3) reproductive strategies in the genus range from oviparity to viviparity including all intermediates that could allow the gradual evolution of viviparity Cladistic analysis of 18 allozyme loci found two most parsimonious trees that differ only in the branching of one species. According to this phylogeny estimate, Oreina species were originally associated with Asteraceae, with an inclusion of Apiaceae in the diet of one oligophagous species and an independent switch to Apiaceae in a derived clade. The original mode of defense appears to be the autogenous production of cardenolides as previously postulated; the additional sequestration of pyrrolizidine alkaloids could have either originated at the base of the genus or have arisen three times independently in all species that switched to plants containing these compounds. Viviparity apparently evolved twice in the genus, once without matrotrophy, through a retention of the eggs inside the female's oviducts, and once in combination with matrotrophy. We hypothesize that the combination of autogenous defense and a life history that involves mobile externally feeding larvae allowed these beetles to switch host plants more readily than has been reported for highly conservative systems.
  • Publication
    Accès libre
    A comparison between allozyme data and phenotypic distances from defensive secretion in Oreina leaf-beetles (Chrysomelinae)
    (1994) ;
    Pasteels, Jacques M.
    The genetic relationships between five Oreina species (Chrysomelidae, Coleoptera) were studied. Of these species, four (O. bifrons, O. gloriosa, O. speciosa, O. variabilis) feed on Apiaceae and secrete mixtures of autogenous cardenolides from defensive glands, whilst the other (O. speciosissima) feeds on Asteraceae and is able both to produce cardenolides and to sequester pyrrolizidines N-oxides (PAs). A dendrogram based on the different mixtures of cardenolides produced by the different species agreed with these genetic relationships. In other words, cardenolide mixtures are good taxonomic markers, since the clustering method based on chemical defense produces a branching pattern similar to that based on genetic relationships.
  • Publication
    Accès libre
    Sequestration of ingested [14C]senecionine N-oxide in the exocrine defensive secretions of chrysomelid beetles
    (1991)
    Ehmke, Adelheid
    ;
    ;
    Pasteels, Jacques M.
    ;
    Hartmann, Thomas
    Oreina cacaliae (Chrysomelidae) sequesters in its elytral and pronotal defensive secretion the N-oxides of pyrrolizidine alkaloids (PA N-oxides) from its food plant Adenostyles alliariae (Asteraceae). [14C]Senecionine N-oxide was applied for detailed studies of PA N-oxide sequestration. An average of 11.4% of total radioactivity is taken up by individual beetles which had received [14C]senecionine N-oxide with their food leaves 8 days before. An average of 28.9% of the ingested radioactivity could be recovered from the defensive secretions collected twice, i.e., 5 and 8 days after tracer feeding. The tracer transfer into the secretion seems to be a slow but progressive process as indicated by the high percentage of tracer still recovered from the secretion sampled after 8 days. Chromatographic analysis revealed that [14C]senecionine N-oxide is the only labeled compound in the defensive secretion. Beetles that fed on tertiary [14C]senecionine sequestered only trace amounts of radioactivity (exclusively present as labeled IV-oxide) in their secretions. O. speciosissima, a species also adapted to PA containing food plants, was shown to sequester [14C]senecionine N-oxide with the same efficiency as O. cacaliae. O. bifrons, a specialist feeding on Chaerophyllum hirsutum (Apiaceae), rejected PA treated leaf samples already at very low PA concentrations (10 nmol/leaf piece). In both O. cacaliae and O. speciosissima, [14C]senecionine N-oxide applied by injection into the hemolymph is rapidly transferred into the glands. O. bifrons, not adapted to pyrrolizidine alkaloid containing plants was unable to sequester [14C]-senecionineN- oxide in the secretion but rapidly eliminated the tracer with the frass. Again, only traces of labeled [14C]senecionine N-oxide were found in the defensive secretions of the two PA adapted species if labeled senecionine was injected. It is suggested that the beetles are adapted to the N-oxide form of PAs, similarly as their food plants, and that they lack the ability to efficiently N-oxidize tertiary PAs. No indication forde novo PA synthesis by the beetles was found in tracer feeding experiments with the biogenetic PA precursor putrescine.
  • Publication
    Accès libre
    Sequestration of plant pyrrolizidine alkaloids by chrysomelid beetles and selective transfer into the defensive secretions
    (1991) ;
    Witte, Ludger
    ;
    Ehmke, Adelheid
    ;
    Hartmann, Thomas
    ;
    Pasteels, Jacques M.
    Oreina cacaliae and O. speciosissima (Coleoptera, Chrysomelidae) sequester in their elytral and pronotal defensive secretions pyrrolizidine alkaloids (PAs) as Noxides (PA N-oxides). The PA N-oxide patterns found in the beetles and their host plants were evaluated qualitatively and quantitatively by capillary gas chromatography/mass spectrometry (GC-MS). Of the three host plants Adenostyles alliariae (Asteraceae) is the exclusive source for PA N-oxide sequestration in the defensive secretions of the beetles. With the exception of O-acetylseneciphylline the N-oxides of all PAs of A. alliariae, i.e. senecionine, seneciphylline, spartioidine, integerrimine, platyphylline and neoplatyphylline were identified in the secretion. PA N-oxides typical of Senecio fuchsii (Asteraceae) were detected in the bodies of the beetles but not in their secretion. No PAs were found in the leaves of the third host plant, Petasites paradoxus (Asteraceae). The results suggest the existence of two distinctive storage compartments for PA N-oxides in the beetle: (1) the defensive secretion, containing specifically PA N-oxides acquired from A. alliariae; (2) the body of the beetle, sequestering additionally but less selectively PA N-oxides from other sources, e.g. S. fuchsii or monocrotaline N-oxide fed in the laboratory. The concentration of PA N-oxides in the defensive secretion is in the range of 0.1 to 0.3 mol/1, which is more than 2.5 orders of magnitude higher than that found in the body of the beetle. No significant differences exist in the ability of the two species of beetles to sequester PA N-oxides from A. alliariae, although O. speciosissima, but not O. cacaliae, produces autogenous cardenolides. A negative correlation seems to exist between the concentrations of plant-derived PA N-oxides andde novo synthesized cardenolides in the defensive secretion of O. speciosissima.
  • Publication
    Accès libre
    Pyrrolizidine alkaloids of probable host-plant origin in the pronotal and elytral secretion of the leaf beetle Oreina cacaliae
    (1988) ;
    Pasteels, Jacques M.
    ;
    Randoux, T.
    ;
    Braekman, J. C.
    ;
    Daloze, D.
    Oreina cacaliae (Coleoptera, Chrysomelidae) produces in its elytral and pronotal defensive secretion seneciphylline N-oxide together with small amounts of another pyrrolizidine alkaloid tentatively identified as senecionine N-oxide. This is a strong departure from the chemical composition of the defensive secretions in related species, characterized by complex mixtures of cardenolides, synthesized by the beetles from cholesterol. It is suggested that O. cacaliae sequesters the alkaloids from its host-plant, Adenostyles leucophylla. Other specimens of O. cacaliae from far distant populations feeding on Senecio nemorensis, Petasites paradoxus or P. album also produced pyrrolizidine alkaloids, but not O. speciosissima feeding on the same food plants and producing cardenolides. In addition to pyrrolizidine alkaloids, O. cacaliae secretes ethanolamine, which is also found in all the cardenolide-producing species.
  • Publication
    Accès libre
    The chemical ecology of defense in arthropods
    (1983)
    Pasteels, Jacques M.
    ;
    Grégoire, J. C.
    ;
    Oreina cacaliae (Coleoptera, Chrysomelidae) produces in its elytral and pronotal defensive secretion seneciphylline N-oxide together with small amounts of another pyrrolizidine alkaloid tentatively identified as senecionine N-oxide. This is a strong departure from the chemical composition of the defensive secretions in related species, characterized by complex mixtures of cardenolides, synthesized by the beetles from cholesterol. It is suggested that O. cacaliae sequesters the alkaloids from its host-plant, Adenostyles leucophylla. Other specimens of O. cacaliae from far distant populations feeding on Senecio nemorensis, Petasites paradoxus or P. album also produced pyrrolizidine alkaloids, but not O. speciosissima feeding on the same food plants and producing cardenolides. In addition to pyrrolizidine alkaloids, O. cacaliae secretes ethanolamine, which is also found in all the cardenolide-producing species.