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  • 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
    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.