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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Cellular and molecular life sciences 48 (1992), S. 1023-1027 
    ISSN: 1420-9071
    Keywords: Chrysolina fuliginosa ; Coleoptera ; Chrysomelidae ; beetles ; cardenolides ; eggs ; glands ; chemical defence
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract Besides the known sarmentogenin 3-O-β-D-allopyranoside (1) and digitoxigenin-3-O-[β-D-xylopyranosyl-(1→4)-2′, 3′-di-O-acetyl-β-D-allopyranoside] (4), four new cardiac glycosides (2, 3, 5 and6) have been isolated from the defensive glands of adults ofChrysolina fuliginosa. The structures of the new compounds were determined by1H NMR at 600 MHz and FABMS. Compounds1–6, present in the adults ofC. fuliginosa, have also been identified in the eggs.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 17 (1991), S. 2323-2332 
    ISSN: 1573-1561
    Keywords: Galeruca tanaceti ; Coleoptera ; Chrysomelidae ; anthraquinones ; eggs ; larvae ; hemolymph ; ovaries ; Tanacetum vulgäre ; Achillea millefolium ; feeding deterrence
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The overwintering eggs and the larvae of the leaf beetleGaleruca tanaceti (L.) contain hydroxylated anthraquinones. In both developmental stages, l,8-dihydroxy-3-methylanthraquinone (= chrysophanol) and 1,8-di-hydroxyanthraquinone (= chrysazin) were detected by GC-MS and GC-FTIR analyses. In the eggs, chrysazin was found only in traces. Anthraquinones were also present in ovaries and hemolymph of gravid females, which were investigated in order to examine the incorporation of these substances into the eggs. Neither in acidified nor in nonacidified extracts of the host plantsTanacetum vulgäre L. andAchillea millefolium L. were anthraquinones found. The activity of these anthraquinones as chemical defense substances was proved in bioassays with the antMyrmica ruginodis NYL. Further possible biological significances of anthraquinones are discussed.
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  • 3
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 20 (1994), S. 1075-1093 
    ISSN: 1573-1561
    Keywords: Coleoptera ; Chrysomelidae ; Chrysomela lapponica ; larval secretion ; defense
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The defensive secretion ofChrysomela lapponica larvae, which is produced by nine pairs of exocrine dorsal glands, has been chemically analyzed. TheC. lapponica larvae were kept in the laboratory on leaves of either birch (Betula pendula), alder (Alnus glutinosa), or willow (Salix fragilis). Larvae developed normally on birch and willow, whereas those on alder died within a few days. GC-MS analyses of the secretion of larvae on birch and willow revealed that the composition of this secretion differs distinctly from the known ones of several otherChrysomela species feeding exclusively on Salicaceae. In the exocrine secretion of larvae on birch, 69 compounds were identified, which included the main components isobutyric acid, 2-methylbutyric acid, and esters of the two. Several of the esters have not been reported previously from nature. The alcoholic components of the esters may be hydrolysis products ofBetula glycosides. Most components of the secretion of larvae feeding on birch were also found in the secretion of larvae feeding on willow. In addition, major amounts of benzoic acid and salicylalcohol were present in the secretion of the larvae feeding on willow.C. lapponica obviously acquires salicylalcohol by hydrolysis of salicin from willow leaves. However, in contrast to otherChrysomela species,C. lapponica larvae oxidize only traces of salicylalcohol to salicylaldehyde. The repellent activity of single authentic compounds of the secretion of larvae feeding on birch and willow, respectively, was tested in laboratory bioassays with ants (Myrmica sabuleti). Biosynthetic pathways to some identified compounds are suggested and discussed under evolutionary and functional aspects.
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