Cardiac Glycosides in the Defensive Secretion of Chrysomelid Beetles: Evidence for Their Production by the Insects

Pasteels, Jacques; Daloze, Désiré

doi:10.1126/science.867051

Cited by 78 publications

(26 citation statements)

References 22 publications

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“…The storage of plant-derived allelochemicals and of chemical defence compounds, synthesized by in sects themselves, in the integument has also been reported in other cases and might be a general phe nomenon. Examples are cardenolides in danaine butterflies [20], in a ctenuchid moth (Syntomeida epilais) [1,21], in the milkweed bug Oncopeltus [22] and a chrysomelid beetle [23]; cyanogenic gly cosides in zygaenid moths [24]; salicyl aldehydes in chrysomelid beetles [25]; flavonoids in a butterfly [26]; pyrrolizidine alkaloids in a chrysomelid beetle [27], quinolizidine alkaloids in a pyralid m oth (Uresiphita reversalis) [28,29] and gallic acid in a locust ( Anacridium melanorhodon) [39], Where and how pyrrolizidine alkaloids are stored in the integument of Creatonotos is an unsolved problem as yet. The storage of acquired or endogenous de fence com pounds in the integument may be eco logically im portant (it is the first tissue which a predator encounters) or physiologically advanta geous (because the allelochemicals are thus far away from internal organs and do not intoxicate the animals themselves).…”

Section: Pyrrolizidine Alkaloid Storage In the Integumentmentioning

confidence: 99%

Time-Course of Pyrrolizidine Alkaloid Processing in the Alkaloid Exploiting Arctiid Moth, Creatonotos transiens

Nickisch-Rosenegk

Schneider

Wink

1990

Zeitschrift Für Naturforschung C

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Creatonotos transiens, Pyrrolizidine Alkaloid, Pyrrolizidine Alkaloid-N-Oxide, 7 /?-Heliotrine Conversion, A lkaloid StorageThe processing o f dietary pyrrolizidine alkaloids by larvae and adults o f the arctiid moth Creatonotos transiens was studied in time-course experiments: In larvae, pyrrolizidine alkaloid uptake is quickly followed by the transformation o f the alkaloids into their N -oxides. Further more, if 7 S-heliotrine is applied, a stereochemical inversion o f the hydroxyl group at C 7 to 7 /?-heliotrine can be observed within 48 h o f feeding. The rate o f this biotransformation is substantially higher in males which use the 7 /?-form later as a precursor for the biosynthesis o f 7 /?-hydroxydanaidal, a pheromone. The resorbed pyrrolizidine alkaloids are deposited in the integument within 48 h, where they remain stored during the larval, pupal and partly also the imaginal stages. Virtually no alkaloids are lost during ecdysis. Some pyrrolizidine alkaloids can be recovered from the meconium which is released at eclosion by the imagines especially when disturbed. In the adults pyrrolizidine alkaloids are processed in different ways by the two sexes: In females, about 5 0 -8 0 % o f total alkaloids are transferred from the integument to the ovaries and the eggs within 2 -3 days after eclosion. If females mate with alkaloid-rich males they additionally receive with the spermatophore up to 290 |ig pyrrolizidine alkaloid, which are further translocated to the eggs. A biparental endowment o f eggs with acquired defence alkaloids is thus achieved. In males, 3 0 -5 0 % o f pyrrolizidine alkaloids remain in the integu ment; about 10-30% are transferred to the scent organ, the corema, where they are converted into 7 /?-hydroxydanaidal. A nother part (about 40% ) is passed to the spermatophore. In the laboratory experiments, the sizes o f the coremata and their respective 7 /?-hydroxydanaidal contents are strongly dependent on the availability o f dietary pyrrolizidine alkaloids during L 6 and especially L 7 stages. In the L7 stage even short-term feeding ( 4 -6 h) on Senecio jacobaea is sufficient to induce large coremata.

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Section: Pyrrolizidine Alkaloid Storage In the Integumentmentioning

confidence: 99%

Time-Course of Pyrrolizidine Alkaloid Processing in the Alkaloid Exploiting Arctiid Moth, Creatonotos transiens

Nickisch-Rosenegk

Schneider

Wink

1990

Zeitschrift Für Naturforschung C

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“…The coleopteran examples include Coccinellidae (Pasteels et al 1973), Pyrochroidae (Eisner et al 1996b;Holz et al 1994), Meloidae (McCormick andCarrel 1987), Oedemeridae (Holz et al 1994), and Chrysomelidae. Interestingly, some chrysomelids protect their eggs exclusively with compounds of seemingly endogenous origin (Daloze & Pasteels 1979, Hilker & Schulz 1991, Howard et al 1982, Pasteels & Daloze 1977, Pasteels et al 1986), while others do so with chemicals acquired from the diet (Ferguson et al 1985, Pasteels et al 1986). Moreover, several species of Chrysomela, and a species of Phratora (P. 6itellinae), protect their eggs with a combination of dietary salicin, and isoxazolinone glucosides that they themselves produce (Pasteels et al 1986).…”

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confidence: 99%

Chemical egg defense in Photuris firefly "femmes fatales"

1999

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“…There are, however, other defensive steroidal agents found in insects. Cardenolides have been isolated from certain danaid butterflies, grasshoppers, chrysomelid beetles, and other insects (17)(18)(19)(20)(21), and a diversity of steroids is secreted by dytiscid beetles (22). It is of interest that the vertebrate counterpart of the lucibufagins, the bufadienolides from toads, also serve as defensive agents.…”

Section: Discussionmentioning

confidence: 99%

Lucibufagins: Defensive steroids from the fireflies Photinus ignitus and P. marginellus (Coleoptera: Lampyridae)

Eisner

Wiemer

Haynes

et al. 1978

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

107

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Feeding tests with thrushes (Hylocichia spp.) led to the isolation of three novel steroid pyrones from fireflies (Photinus ignitus and P. marginellus) responsible, in part at least, for the unpalatability of these insects to the birds. The term lucibufagin is coined for these steroidal pyrones. The closest known relatives of lucibufagins are the familiar cardiotonic bufadienolides, found in certain toads and plants. It had previously been suspected that fireflies-the familiar luminescent beetles of the family Lampyridae-contain noxious substances that protect them against vertebrate predators. A diversity of lizards, birds, and mammals was said to reject these insects, but the defensive substances responsible, presumed to be present in the blood and tissues of the beetles, had not been characterized (2-4).Pursuant to our finding that fireflies of the genus Photinus are rejected by birds (thrushes of the genus Hylocichla), we developed a bioassay with these predators by which the feeding deterrency of extracts of Photinus, and that of fractions of the extracts, could be evaluated. The procedure led to the isolation of three novel steroidal pyrones, deterrent to the birds, and present in the beetles at defensively effective concentrations. We here describe the isolation and partial characterization of these compounds, for which we propose the term lucibufagins. Steroidal pyrones, or bufadienolides, are of restricted occurrence in nature. They have been found in some well-known toad venoms as well as in a small group of plants (ref. 5, pp. 469-476). However, no examples have been reported from invertebrates. MATERIALS AND METHODSThe two species of Photinus studied, P. ignitus and P. marginellus, are common in the northeastern United States. They were collected at night with nets in the environs of Ithaca, New York, and immediately brought to the laboratory for feeding tests or chemical extractions. Because the fireflies were taken in flight, they can be assumed to be virtually all males. Thrushes were chosen for the feeding tests because they adapted well to captivity and were known to be broadly insectivorous in their habits. A single Swainson's thrush (Hylocichla ustulata, male) and five hermit thrushes (H. guttata, three females and two males) were used. All had been taken months beforehand in mist nets during the migratory season. They were caged singly in the laboratory and were "experienced" at the time of experimentation, having previously been offered palatable and unpalatable insects in connection with other studies. They were sexed at autopsy.The initial tests with the single Swainson's thrush were in-The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U. S. C. §1734 solely to indicate this fact. 905tended to provide preliminary data on the food preferences of such a bird. These tests extended over a period of 23 days, during which the thrush was offered, in daily feedi...

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Cardiac Glycosides in the Defensive Secretion of Chrysomelid Beetles: Evidence for Their Production by the Insects

Cited by 78 publications

References 22 publications

Time-Course of Pyrrolizidine Alkaloid Processing in the Alkaloid Exploiting Arctiid Moth, Creatonotos transiens

Time-Course of Pyrrolizidine Alkaloid Processing in the Alkaloid Exploiting Arctiid Moth, Creatonotos transiens

Chemical egg defense in Photuris firefly "femmes fatales"

Lucibufagins: Defensive steroids from the fireflies Photinus ignitus and P. marginellus (Coleoptera: Lampyridae)

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