Coping with toxic plant compounds – The insect’s perspective on iridoid glycosides and cardenolides

Dobler, Susanne; Petschenka, Georg; Pankoke, Helga

doi:10.1016/j.phytochem.2011.04.015

Cited by 170 publications

(151 citation statements)

References 140 publications

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“…As discussed above, we know for the latter two species that they actually possess cardenolide-sensitive Na,K-ATPase (39). Alternatively, toxic effects of ingested cardenolides may be avoided by other mechanisms than target site insensitivity (43). Uptake of cardenolides into the body cavity may be restricted by impermeable guts or highly efficient excretion, as earlier studies have shown (44) and as tracer uptake studies in the non-cardenolide-adapted C. asclepiadeus indicate (45).…”

Section: (Pygoctenuchamentioning

confidence: 99%

Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase

Dobler

Dalla

Wagschal

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

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The extent of convergent molecular evolution is largely unknown, yet is critical to understanding the genetics of adaptation. Target site insensitivity to cardenolides is a prime candidate for studying molecular convergence because herbivores in six orders of insects have specialized on these plant poisons, which gain their toxicity by blocking an essential transmembrane carrier, the sodium pump (Na,K-ATPase). We investigated gene sequences of the Na,KATPase α-subunit in 18 insects feeding on cardenolide-containing plants (spanning 15 genera and four orders) to screen for amino acid substitutions that might lower sensitivity to cardenolides. The replacement N122H that was previously shown to confer resistance in the monarch butterfly (Danaus plexippus) and Chrysochus leaf beetles was found in four additional species, Oncopeltus fasciatus and Lygaeus kalmii (Heteroptera, Lygaeidae), Labidomera clivicollis (Coleoptera, Chrysomelidae), and Liriomyza asclepiadis (Diptera, Agromyzidae). Thus, across 300 Myr of insect divergence, specialization on cardenolide-containing plants resulted in molecular convergence for an adaptation likely involved in coevolution. Our screen revealed a number of other substitutions connected to cardenolide binding in mammals. We confirmed that some of the particular substitutions provide resistance to cardenolides by introducing five distinct constructs of the Drosophila melanogaster gene into susceptible eucaryotic cells under an ouabain selection regime. These functional assays demonstrate that combined substitutions of Q 111 and N 122 are synergistic, with greater than twofold higher resistance than either substitution alone and >12-fold resistance over the wild type. Thus, even across deep phylogenetic branches, evolutionary degrees of freedom seem to be limited by physiological constraints, such that the same molecular substitutions confer adaptation.insect-plant interactions | specialist herbivores | target site insensitivity | toxin resistance | cardiac glycosides

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Section: (Pygoctenuchamentioning

confidence: 99%

Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase

Dobler

Dalla

Wagschal

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

266

288

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“…Pentacosanol (C25 alcohol) was a deterrent against Plutella xylostella larvae [11] and triacontanol (C30 alcohol) exhibited antifeedant activity against S. litura with an ED 50 of 5.42 µg/cm 2 [2,12]. Although many iridoid glycoside compounds have been isolated from D. cynanchoides [13,14] and iridoid glycosides have been reported as deterring consumption by generalist insect herbivores [15], we did not find iridoids to be among the most active antifeedant compounds. Compound 1 did show strong antifeedant activity, suggesting that D. cynanchoides mostly relies on 1 for its defense against herbivores.…”

Section: Choice Assay Against S Frugiperda and E Paenulatamentioning

confidence: 58%

Insecticidal Properties of a Highly Potent Wax Isolated from Dolichandra cynanchoides Cham

2016

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Bioassay-guided fractionation of an ethanolic extract of the aerial parts of Dolichandra cynanchoides Cham. (Bignoniaceae) led to the isolation of a natural wax with anti-insect activity against Spodoptera frugiperda (Noctuidae) and Epilachna paenulata (Coleptera). The compound was identified spectroscopically as an ester of a C27 fatty acid and a C25 alcohol, pentacosyl heptacosanoate (1). The effective doses of 1 for 50% feeding inhibition (ED 50 ) of S. frugiperda and E. paenulata were 0.82 and 8.53 µg/cm 2 , respectively, in a choice test, while azadirachtin showed ED 50 of 0.10 and 0.59 µg/cm 2 , respectively. In a no-choice test, both insects refused to feed on leaves treated with 1 at doses of 0.1 µg/cm 2 or greater inhibiting larval growth and dramatically reducing survival. The lethal doses 50 (LD 50 ) of 1 were 0.39 and 0.68 µg/cm 2 for S. frugiperda and E. paenulata, respectively. These results indicate that 1 has potential for development as botanical insecticides. Similar esters might be obtainable in large quantities as many edible crops produce wax esters that are discarded during food processing. Research on these materials could lead to the detection of similar waxes with insecticidal activity.

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“…Multiple genera of leaf beetles, grasshoppers, butterflies, and moths are able to detoxify and partly sequester the pyrrolizidine alkaloids of Boraginaceae and other plant families, whereas others can cope with the deterrent terpene derivatives of Lamiaceae, for example iridoid glycosides (Dobler et al. 2000, 2011; Sehlmeyer et al. 2010; Opitz et al.…”

Section: Discussionmentioning

confidence: 99%

Climate and host‐plant associations shaped the evolution of ceutorhynch weevils throughout the Cenozoic

et al. 2018

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Using molecular phylogenetic data and methods we inferred divergence times and diversification patterns for the weevil subfamily Ceutorhynchinae in the context of host‐plant associations and global climate over evolutionary time. We detected four major diversification shifts that correlate with both host shifts and major climate events. Ceutorhynchinae experienced an increase in diversification rate at ∼53 Ma, during the Early Eocene Climate Optimum, coincident with a host shift to Lamiaceae. A second major diversification phase occurred at the end of the Eocene (∼34 Ma). This contrasts with the overall deterioration in climate equability at the Eocene‐Oligocene boundary, but tracks the diversification of important host plant clades in temperate (higher) latitudes, leading to increased diversification rates in the weevil clades infesting temperate hosts. A third major phase of diversification is correlated with the rising temperatures of the Late Oligocene Warming Event (∼26.5 Ma); diversification rates then declined shortly after the Middle Miocene Climate Transition (∼14.9 Ma). Our results indicate that biotic and abiotic factors together explain the evolution of Ceutorhynchinae better than each of these drivers viewed in isolation.

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Coping with toxic plant compounds – The insect’s perspective on iridoid glycosides and cardenolides

Cited by 170 publications

References 140 publications

Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase

Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase

Insecticidal Properties of a Highly Potent Wax Isolated from Dolichandra cynanchoides Cham

Climate and host‐plant associations shaped the evolution of ceutorhynch weevils throughout the Cenozoic

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