ChemInform Abstract: New Cardenolide Glycosides from the Defence Glands of Chrysolinina Beetles (Coleoptera : Chrysomelidae).

Oycke, S. Van; Randoux, Thierry; Braekman, Jean‐Claude; Daloze, Désiré; Pasteels, Jacques

doi:10.1002/chin.198835290

Cited by 2 publications

(3 citation statements)

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“…The two Chrysolina species used as outgroups in this study feed on Lamiaceae. Their defensive secretions contain cardenolides (Van Oycke et al 1988;F. Eggenberger, pers.…”

Section: Natural History Of Oreinamentioning

confidence: 99%

HOST-PLANT SWITCHES AND THE EVOLUTION OF CHEMICAL DEFENSE AND LIFE HISTORY IN THE LEAF BEETLE GENUSOREINA

et al. 1996

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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.

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“…The two Chrysolina species used as outgroups in this study feed on Lamiaceae. Their defensive secretions contain cardenolides (Van Oycke et al 1988;F. Eggenberger, pers.…”

Section: Natural History Of Oreinamentioning

confidence: 99%

HOST-PLANT SWITCHES AND THE EVOLUTION OF CHEMICAL DEFENSE AND LIFE HISTORY IN THE LEAF BEETLE GENUSOREINA

et al. 1996

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“…Comparative studies of chrysomelid beetles have demonstrated a good correlation between current classification and the chemical nature of the secretions (Pasteels et al, 1984. In most species of Oreina and Chrysomela (Chrysolinina, Chrysomelini, Chrysomelinae), the defensive secretion are characterized by complex mixtures of cardenolides accompanied by ethanolamine Van Oycke et al, 1988). Contrary to well known examples of the use of cardenolides for defence in other insects (e.g.…”

Section: Discussionmentioning

confidence: 96%

“…In this genus, the adults but not the larvae have defensive glands. Like many other leaf beetles of the closely related genus Chrysolina, they secrete cardenolides (Pasteels et al, 1984;Van Oycke et al, 1988), which they biosynthesise from cholesterol (Van Oycke et al, 1987). We have now found one species, Oreina cacaliae which stands out as an exception: the major component of the secretion is the pyrrolizidine alkaloid seneciphylline N-oxide.…”

Section: Introductionmentioning

confidence: 89%

Pyrrolizidine alkaloids of probable host‐plant origin in the pronotal and elytral secretion of the leaf beetle Oreina cacaliae

Pasteels¹,

Rowell‐Rahier²,

Randoux³

et al. 1988

Entomologia Exp Applicata

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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.

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ChemInform Abstract: New Cardenolide Glycosides from the Defence Glands of Chrysolinina Beetles (Coleoptera : Chrysomelidae).

Abstract: Besides the known cardenolide aglycones sarmentogenin and oleandrigenin 14 new cardiac glycosides such as (I) are isolated.

Cited by 2 publications

References 1 publication

HOST-PLANT SWITCHES AND THE EVOLUTION OF CHEMICAL DEFENSE AND LIFE HISTORY IN THE LEAF BEETLE GENUSOREINA

HOST-PLANT SWITCHES AND THE EVOLUTION OF CHEMICAL DEFENSE AND LIFE HISTORY IN THE LEAF BEETLE GENUSOREINA

Pyrrolizidine alkaloids of probable host‐plant origin in the pronotal and elytral secretion of the leaf beetle Oreina cacaliae

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