The Role of Cardenolides in a Crucifer-Insect Relationship

  • J. A. A. Renwick
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 405)


The cardenolides belong to a group of steroidal compounds, which, along with the bufadienolides, are referred to as cardiac glycosides because of their cardiotonic properties. As a result of this bioactivity, they are widely used to treat congestive heart failure. The bufadienolides are characteristic of toads in the family Bufonidae, which secrete the compounds from specialized glands when they are threatened by predators. Cardenolides, however, are produced almost exclusively by plants and serve to protect these plants from herbivory.1 The protective qualities of cardiac glycosides stem from their extreme toxicity to most higher animals and insects, due to inhibition of Na+K+-ATPase and the resulting effects on the sodium pump. However, at low concentrations, they are valuable medicinal drugs for humans and they have also been shown to have cytotoxic activity against cancer cell lines.2


Cardiac Glycoside Monarch Butterfly Plutella Xylostella Oviposition Deterrent Deterrent Activity 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    J.PJ. Joubert. Cardiac glycosides, in: Toxicants of Plant Origin; [Vol. II, Glycosides], P.R. Cheeke, ed., CRC Press, Inc., Boca Raton (1989).Google Scholar
  2. 2.
    N. Kaneda, H. Chai, J.M. Pezzuto, A.D. Kinghorn, N.R. Farnsworth, P. Tuchinda, J. Udchachon, T. Santisuk and V. Reutrakul, Cytotoxic activity of cardenolides from Beaumontia brevituba stems, Planta Medica 58:429–431(1992).PubMedCrossRefGoogle Scholar
  3. 3.
    W. Majak, Mammalian metabolism of toxic glycosides from plants, Journal of Toxicology — Toxin Reviews 11:1–40(1992).Google Scholar
  4. 4.
    J. von Euw, T. Reichstein and M. Rothschild, Heart poisons (cardiac glycosides) in the lygaid bugs Caeocoris nerii and Spilostethus pandurus, Insect Biochem. 1:373–384 (1971).CrossRefGoogle Scholar
  5. 5.
    J. von Euw, L. Fishelson, J.A. Parsons, T. Reichstein and M. Rothschild, Cardenolides (heart poisons) in a grasshopper feeding on milkweeds, Nature 214:35–39 (1967).CrossRefGoogle Scholar
  6. 6.
    M. Rothschild, J. von Euw and T. Reichstein, Cardiac glycosides in the oleander aphid, Aphis nerii, J. Insect Physiol. 16:1141–1145 (1970).PubMedCrossRefGoogle Scholar
  7. 7.
    G.G.E. Scudder and S.S. Duffey, Cardiac glycosides in the Lygaeinae (Hemiptera: Lygaeidae), Can. J. Zool. 50:35–42 (1972).CrossRefGoogle Scholar
  8. 8.
    S.S. Duffey and G.G.E. Scudder, Cardiac glycosides in North American Asclepiadaceae, a basis for unpalatability in brightly coloured Hemiptera and Coleoptera, J. Insect Physiol. 18:63–78 (1972).CrossRefGoogle Scholar
  9. 9.
    J.A. Cohen and L.P. Brower, Cardenolide sequestration by the dogbane tiger moth (Cycnia tenera; Arctiidae), J. Chem. Ecol. 9:521–532 (1983).CrossRefGoogle Scholar
  10. 10.
    G.G.E. Scudder and J. Meredith, The permeability of the midgut of three insects to cardiac glycosides, J. Insect Physiol. 23:689–694 (1982).CrossRefGoogle Scholar
  11. 11.
    L.V. Moore and G.G.E. Scudder, Selective sequestration of milkweed (Asclepias sp.) cardenolides in Oncopelus fasciatus (Dallas) (Hemiptera: Lygaeidae), J. Chem. Ecol. 11:667–687 (1985).CrossRefGoogle Scholar
  12. 12.
    M. Wink and D. Schneider, Fate of plant-derived secondary metabolites in three moth species (Syntomis mogadorensis, Syntomeida epilais, and Creatonotos transiens), J. Comp. Physiol. B 160:389–400 (1990).CrossRefGoogle Scholar
  13. 13.
    C.N. Roeske, J.N. Seiber, L.P. Brower and CM. Moffit, Milkweed cardenolides and their comparative processing by monarch butterflies, Recent Advances in Phytochemistry 10:93–167 (1976).Google Scholar
  14. 14.
    J.N. Seiber, P.M. Tuskes, L.P. Brower and C.J. Nelson, Pharmacodynamics of some individual milkweed cardenolides fed to larvae of the monarch butterfly (Danaus plexippus L.), J. Chem. Ecol. 6:321–339 (1980).CrossRefGoogle Scholar
  15. 15.
    L.P. Brower and P. B. McVoy, Variation of cardiac glycoside content of monarch butterflies from natural populations in eastern North America, Science 177:426–429 (1972).PubMedCrossRefGoogle Scholar
  16. 16.
    S.B. Malcolm, B.J. Cockrell and L.P. Brower, Cardenolide fingerprint of monarch butterflies reared on common milkweed, Asclepias syriaca L., J. Chem. Ecol. 15:819–853 (1989).CrossRefGoogle Scholar
  17. 17.
    M.P. Zalucki, L.P. Brower and S.B. Malcolm, Oviposition by Danaus plexippus in relation to cardenolide content of three Asclepias species in the southeastern U.S.A., Ecol. Entomol. 15:231–240 (1990).CrossRefGoogle Scholar
  18. 18.
    M. Haribal and J.A A. Renwick, Oviposition stimulants for the momarch butterfly: flavonol glycosides from Asclepias curassavica, Phytochemistry 41: 139–144 (1996).PubMedCrossRefGoogle Scholar
  19. 19.
    J.M. Pasteels and D. Daloze, Cardiac glycosides in the defensive secretion of Chrysomelid beetles: evidence for their production by the insects, Science 197:70–72 (1977).PubMedCrossRefGoogle Scholar
  20. 20.
    S. Dobler and M. Rowell-Rahier, Production of cardenolides versus sequestration of pyrrolizidine alkaloids in larvae of Oreina species (Coleoptera, Chrysomelidae), J. Chem. Ecol. 20:555–568 (1994).CrossRefGoogle Scholar
  21. 21.
    D. Daloze and J.M. Pasteels, Production of cardiac glycosides by chrysomelid beetles and larvae, J. Chem. Ecol 5:63–77 (1979).CrossRefGoogle Scholar
  22. 22.
    J.M. Pasteels, J.C. Braekman and D. Daloze, Chemical defense in the Chrysomelidae, in: Biology of Chrysomelidae, P. Jolivet, E. Petitpierre and T.H. Hsiao, eds., Kluwer Academic Publishers, The Netherlands (1988).Google Scholar
  23. 23.
    M. Hilker, D. Daloze and J.M. Pasteels, Cardenolide glycosides from the adults and eggs of Chrysolina fuliginosa (Coleoptera: Chrysomelidae), Experientia 48:1023–1027 (1992).CrossRefGoogle Scholar
  24. 24.
    S. van Oyke, J.C. Braekman, D. Daloze and J. M. Pasteels, Cardenolide biosynthesis in chrysomelid beetles, Experientia 43:460–462 (1987).CrossRefGoogle Scholar
  25. 25.
    L.P. Brower, J.V.Z. Brower and J.M. Corvino, Plant poisons in a terrestrial food chain, Proc. Nat. Acad. Sci. 57:893 (1967).PubMedCrossRefGoogle Scholar
  26. 26.
    D.L. Evans, N. Castoriades and H. Badruddine, Cardenolides in the defense of Caenocoris nerii (Hemiptera). Oikos 46:325–329 (1986).CrossRefGoogle Scholar
  27. 27.
    L.S. Fink, L.P. Brower, R.B. Waide and P.R. Spitzer, Overwintering monarch butterflies as food for insectiverous birds in Mexico, Biotropica 15:151–153 (1983).CrossRefGoogle Scholar
  28. 28.
    J: Glendinning and L.P. Brower, Feeding and breeding responses of five mice species to overwintering aggregations of the monarch butterfly, J. Anim. Ecol. 59:1091–1112 (1990).CrossRefGoogle Scholar
  29. 29.
    J.I. Glendinning, Responses of three mouse species to deterrent chemicals in the monarch butterfly. II. taste tests using intact monarchs, Chemoecology 1:124–130 (1990).CrossRefGoogle Scholar
  30. 30.
    J. Glendinning, L.P. Brower and C.A. Montgomery, Responses of three mouse species to deterrent chemicals in the monarch butterfly. I. Taste and toxicity tests using artificial diets laced with digitoxin or monocrotaline, Chemoecology 1:114–123 (1990).CrossRefGoogle Scholar
  31. 31.
    J. Glendinning, Effectiveness of cardenolides as feeding deterrents to Peromyscus mice, J. Chem. Ecol. 18:1559–1575 (1992).CrossRefGoogle Scholar
  32. 32.
    S. B. Malcolm, Disruption of web structure and predatory behavior of a spider by plant—derived chemical defenses of an aposematic aphid, J. Chem. Ecol. 15:1699–1716 (1989).CrossRefGoogle Scholar
  33. 33.
    P. Feeny, Defensive ecology of the Cruciferae, Annals of the Missouri Botanic Garden 64:221–234 (1977).CrossRefGoogle Scholar
  34. 34.
    J.K. Nielsen, Host plant discrimination within the Cruciferae: feeding responses of four leaf beetles (Coleoptera: Chrysomelidae) to glucosinolates, cucurbitacins and cardenolides, Entomol. exp. appl. 24:41–54 (1978).CrossRefGoogle Scholar
  35. 35.
    F. Chew, Coevolution of pierid butterflies and their cruciferous foodplants, Oecologia (Berl.) 20:117–127 (1975).CrossRefGoogle Scholar
  36. 36.
    J.E. Rodman and F S. Chew, Phytochemical correlates of herbivory in a community of native and naturalized Cruciferae, Biochem. Syst. and Ecol. 8:43–50 (1980).CrossRefGoogle Scholar
  37. 37.
    R. Hegnauer. Chemotaxonomie der Pflanzen [Vol. 3: Dicotyledoneae: Acanthaceae—Cyrillaceae] Birkhäuser Verlag, Basel, (1964).Google Scholar
  38. 38.
    J.A.A. Renwick and CD. Radke, Chemical stimulants and deterrents regulating acceptance or rejection of crucifers by cabbage butterflies, J. Chem. Ecol. 13:1771–1776 (1987).CrossRefGoogle Scholar
  39. 39.
    J.A.A. Renwick, CD. Radke and K. Sachdev-Gupta, Chemical constituents of Erysimum cheiranthoides deterring oviposition by the cabbage butterfly, Pieris rapae, J. Chem. Ecol. 15:2161–2169 (1989).CrossRefGoogle Scholar
  40. 40.
    K. Sachdev-Gupta, J.A.A. Renwick and CD. Radke, Isolation and identification of oviposition deterrents to cabbage butterfly, Pieris rapae, from Erysimum cheiranthoides, J. Chem. Ecol. 16:1059–1067(1990).CrossRefGoogle Scholar
  41. 41.
    M.B. Dimock, J.A.A. Renwick, CD. Radke and K. Sachdev-Gupta, Chemical constituents of an unacceptable crucifer, Erysimum cheiranthoides, deter feeding by Pieris rapae, J. Chem. Ecol. 17:525–533 (1991).CrossRefGoogle Scholar
  42. 42.
    K. Sachdev-Gupta, CD. Radke, J.A.A. Renwick and M.B. Dimock, Cardenolides from Erysimum cheiranthoides: feeding deterrents to Pieris rapae larvae, J. Chem. Ecol. 19:1355–1369 (1993).CrossRefGoogle Scholar
  43. 43.
    F.S. Chew and J.A.A. Renwick, Chemical ecology of hostplant choice in Pieris butterflies, in: Chemical Ecology of Insects II; R.T. Cardé and WJ. Bell, eds., Chapman and Hall, New York (1995).Google Scholar
  44. 44.
    X.P. Huang, J.A.A. Renwick and K. Sachdev-Gupta, A chemical basis for differential acceptance of Erysimum cheiranthoides by two Pieris species, J. Chem. Ecol. 19:195–210 (1993).CrossRefGoogle Scholar
  45. 45.
    X.P. Huang and J.A A. Renwick, Cardenolides as oviposition deterrents to two Pieris species: structure—activity relationships, J. Chem. Ecol. 20:1039–1051 (1994).CrossRefGoogle Scholar
  46. 46.
    J.A.A. Renwick, CD. Radke, K. Sachedev-Gupta and E. Städler, Leaf surface chemicals stimulating oviposition by Pieris rapae (Lepidoptera: Pieridae) on cabbage, Chemoecology 3:33–38 (1992).CrossRefGoogle Scholar
  47. 47.
    K. Sachdev-Gupta, CD. Radke and J A.A. Renwick, Chemical recognition of diverse hosts by Pieris rapae butterflies, in: Proc. of the 8th Int. Symposium on Insect—Plant Relationships; S.B J. Menken, J.H. Visser and P. Harrewijn, eds., Kluwer, Dordrecht (1992).Google Scholar
  48. 48.
    J.A.A. Renwick and X. Huang, Interacting chemical stimuli mediating oviposition by Lepidoptera, in: Functional Dynamics of Phytophagous Insects, T.N. Ananthakrishnan, ed., Oxford & IBH Publishing Co., New Delhi (1994).Google Scholar
  49. 49.
    U. Hugentobler and J.A.A. Renwick, Effects of plant nutrition on the balance of insect relevant cardenolides and glucosinolates in Erysimum cheiranthoides, Oecologia 102:95–105 (1995).Google Scholar
  50. 50.
    J.A.A. Renwick, CD. Radke and K. Sachdev-Gupta, Tolerance of cardenolides in Erysimum cheiranthoides by the diamondback moth, Plutella xylostella, in: Symp. Biol. Hung. [Vol.39], T. Jermy and A. Szentesi, eds., Akademiai Kiado, Budapest (1991).Google Scholar
  51. 51.
    J.A.A. Renwick and X.P. Huang, Rejection of host plant by larvae of cabbage butterfly: diet dependent sensitivity to an antifeedant, J. Chem. Ecol. 21:465–475 (1995).CrossRefGoogle Scholar
  52. 52.
    X. Huang and J.A.A. Renwick, Cross habituation to feeding deterrents and acceptance of a marginal host plant by Pieris rapae larvae, Entomol. exp. appl. 76: 295–302 (1995).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1996

Authors and Affiliations

  • J. A. A. Renwick
    • 1
  1. 1.Boyce Thompson InstituteIthacaUSA

Personalised recommendations