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Milkweed Cardenolides and Their Comparative Processing by Monarch Butterflies (Danaus plexippus L.)

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Biochemical Interaction Between Plants and Insects

Part of the book series: Recent Advances in Phytochemistry ((RBIO,volume 10))

Abstract

The milkweed family (Asclepiadaceae) comprises some 200 genera and 2500 species of perennial shrubs, herbs and vines distributed throughout the tropics and extending to temperate areas of the world. They include some highly prized ornamentals and economically significant weeds, and are generally characterized to the layman by the milky latex they exude when a leaf or other organ is ruptured. Chemical interest in the milkweeds has been stimulated by the use of some plants in medicinal preparations to treat cancers, tumors, and warts (Refs. in 54), as emetics, to treat bronchitis (Refs. in 64), and as a source of digitalislike therapeutic agents (Refs. in 44). They are also known for their poisonous nature, which has found advantageous use in the preparation of arrow poisons, and also causes occasional but extensive poisoning episodes among grazing sheep and cattle in milkweed-infested rangelands52,58.

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References

  1. Abisch, E. and T. Reichstein. 1962. Chemical orientation investigation of some Asclepiadaceae and Periplocaceae. Helv. Chim. Acta, 45:2090.

    CAS  Google Scholar 

  2. Bauer, S., L. Masler, O. Bauerova and D. Sikl. 1961. Uzarigenin and desglucouzarin from Asclepias syriaca L. Experientia, 17:15.

    PubMed  CAS  Google Scholar 

  3. Borison, H.L. and S.C. Wang. 1953. Physiology and pharmacology of vomiting. Pharmac. Rev., 5:193.

    CAS  Google Scholar 

  4. Brower, L.P. 1969. Ecological chemistry. Scient. Amer., 220:22.

    CAS  Google Scholar 

  5. Brower, L.P. 1970. Plant poisons in a terrestrial food chain and implications for mimicry theory. In: Biochemical Coevolution, Proceedings of the Twenty-Ninth Annual Biology Colloquim, 1968. K.L. Chambers (ed), Oregon State University Press, Corvallis, Oregon, p. 69.

    Google Scholar 

  6. Brower, L.P., and J.V.Z. Brower. 1964. Birds, butterflies and plant poisons:a study in ecological chemistry. Zoologica, 49:137.

    CAS  Google Scholar 

  7. Brower, L.P., J.V.Z. Brower and J.M. Corvino. 1967. Plant poisons in a terrestrial food chain. Proc. Nat. Acad. Sci., 57:893.

    PubMed  CAS  Google Scholar 

  8. Brower, L.P., M. Edmunds and C.M. Moffitt. 1975. Cardenolide content and palatability of a population of Danaus chrysippus butterflies from West Africa. J. Ent. (A), 49:183.

    Google Scholar 

  9. Brower, L.P. and S.C. Glazier. 1975. Localization of heart poisons in the monarch butterfly. Science, 188:19.

    PubMed  CAS  Google Scholar 

  10. Brower, L.P., P.B. McEvoy, K.L. Williamson and M.A. Flannery. 1972. Variation in cardiac glycoside content of monarch butterflies from natural populations in eastern North America. Science, 177:426.

    PubMed  CAS  Google Scholar 

  11. Brower, L.P. and C.M. Moffitt. 1974. Palatability dynamics of cardenolides in the monarch butterfly. Nature, 249:280.

    PubMed  CAS  Google Scholar 

  12. Brower, L.P., W.N. Ryerson, L.L. Coppinger and S.C. Glazier. 1968. Ecological chemistry and the palatability spectrum. Science, 161:1349.

    PubMed  CAS  Google Scholar 

  13. Brüschweiler, F., K. Stockel and T. Reichstein. 1969a. Calotropis-glycosides, presumed partial structure. Helv. Chim. Acta, 52:2276.

    PubMed  Google Scholar 

  14. Brüschweiler, F., W. Stocklin, K. Stockel and T. Reichstein. 1969b. Glycosides of Calotropis procera R. Br. Helv. Chim. Acta, 52:2086.

    PubMed  Google Scholar 

  15. Carman, R.M., R.G. Coombe and T.R. Watson. 1964. The cardiac glycosides of Gomphocarpus fruticosus (R. Br.) IV. The nuclear magnetic resonance spectrum of gomphoside. Aust. J. Chem., 17:573.

    CAS  Google Scholar 

  16. Chen, K.K., E.B. Robbins and H. Worth. 1938. The significance of sugar component in the molecule of cardiac glycosides. J. Am. Pharm. Ass., 27:189.

    CAS  Google Scholar 

  17. Chernobai, V.T. 1957. Cardiac glycosides of Gomphocarpus fruticosus. I. Glycosides of the seed. Med. Prom. S.S.S.R., 11: 38. [Chem. Abstr., 52:8465a]

    Google Scholar 

  18. Chernobai, V.T. and N.F. Komissarenko. 1971. Cardenolides from Gomphocarpus fruticosus and partial synthesis of uzarigenin glycosides. Khim. Prir. Soedin., 7:445. [Chem. Abstr., 75:141103w]

    CAS  Google Scholar 

  19. Coombe, R.G. and T.R. Watson. 1962. Structure of β-anhydrogomphogenin. Chem. and Ind., 1962:1724.

    Google Scholar 

  20. Coombe, R.G. and T.R. Watson. 1964. The cardiac glycosides of Gomphocarpus fruticosus R. Br. III. Gomphoside. Aust. J. Chem., 17:92.

    CAS  Google Scholar 

  21. Crout, D.H.G., R.F. Curtis, C.H. Hassall and T.L. Jones. 1963. The cardiac glycosides of Calotropis procera. Tetrahedron Lett., 1963:63.

    Google Scholar 

  22. Crout, D.H.G., C.H. Hassall and T.L. Jones. 1964. Cardenolides. Part VI. Uscharidin, calotropin, and calotoxin. J. Chem. Soc., 1964:2187.

    Google Scholar 

  23. Dethier, V.G. 1970. Chemical interactions between plants and insects. In: Chemical Ecology, E. Sondheimer and J.B. Simeone (eds), Academic Press, New York, Chapter 5.

    Google Scholar 

  24. Dixon, W.J. and F.J. Massey, Jr., 1957. Introduction to Statistical Analysis, McGraw-Hill, New York.

    Google Scholar 

  25. Duffey, S.S. 1970. Cardiac glycosides and distaste-fulness: some observations on the palatability spectrum of butterflies. Science, 169: 78.

    PubMed  CAS  Google Scholar 

  26. Duffey, S.S. and G.G.E. Scudder. 1972. Cardiac glycosides in North American Asclepiadaceae, a basis for unpalatability in brightly coloured Hemiptera and Coleoptera. J. Insect Physiol., 18:63.

    CAS  Google Scholar 

  27. Duffey, S.S. and G.G.E. Scudder. 1974. Cardiac glycosides in Oncopeltus fasciatus (Dallas) (Hemiptera: Lygaeidae). I. The uptake and distribution of natural cardenolides in the body. Can. J. Zool., 52:283.

    Google Scholar 

  28. Eisner, T. 1970. Chemical defense against predation in arthropods. In: Chemical Ecology, E. Sondheimer and J. B. Simeone (eds), Academic Press, New York, Chapter 8.

    Google Scholar 

  29. Erickson, J.M. 1973. The utilization of various Asclepias species by larvae of the monarch butterfly, Danaus plexippus. Psyche, 80:230.

    Google Scholar 

  30. Evans, F.J. and P.S. Cowley. 1972. Cardenolides and spirostanols in Digitalis purpurea at various stages of development. Phytochem., 11: 2971.

    CAS  Google Scholar 

  31. Feeny, P. 1975. Biochemical coevolution between plants and their insect herbivores. In: Coevolution of Animals and Plants, L.E. Gilbert and P.H. Raven (eds), University of Texas Press, Austin, p. 3.

    Google Scholar 

  32. Feir, D. and J. Suen. 1971. Cardenolides in the milkweed plant and feeding by the milkweed bug. Ann. Entomol. Soc. Am., 64:1173.

    CAS  Google Scholar 

  33. Fieser, L.F. and M. Fieser. 1959. Steroids, Reinhold, New York, Chapter 20.

    Google Scholar 

  34. Fraenkel, G.S. 1959. The raison d’etre of secondary plant substances. Science, 129:1466.

    PubMed  CAS  Google Scholar 

  35. Gaitonde, B.B. and S.N. Joglekar. 1975. Role of catecholamines in the central mechanism of emetic response induced by peruvoside and ouabain in cats. Br. J. Pharmacol., 54:157.

    PubMed  CAS  Google Scholar 

  36. Hassall, C.H. and K. Reyle. 1959. Cardenolides. Part III. Constitution of calotropagenin. J. Chem. Soc., 1959:85.

    Google Scholar 

  37. Hendry, L.B., J.K. Wichmann, D.M. Hindenlang, R.O. Mumma and M.E. Anderson. 1975. Evidence for origin of insect sex pheromones: presence in food plants. Science, 188:59.

    PubMed  CAS  Google Scholar 

  38. Hesse, G., H. Fasold and W. Geiger. 1959. African arrow poisons. X. Calotropin from uscharidin. Liebigs Ann. Chem., 625:157.

    CAS  Google Scholar 

  39. Hesse, G. and H.W. Gampp. 1952. African arrow poisons. VI. The heterocyclic part of uscharin. Chem. Ber., 85: 933.

    CAS  Google Scholar 

  40. Hesse, G., L.J. Heuser, E. Hutz and F. Reicheneder. 1950. African arrow poisons. V. Relationships between the most important poisons of Catotropis procera. Liebigs Ann. Chem., 566:130.

    CAS  Google Scholar 

  41. Hesse, G. and G. Lettenbauer. 1957. A second sulfur-containing compound from the milky-juice of Catotropis procera. Angew. Chem., 69:392.

    CAS  Google Scholar 

  42. Hesse, G. and G. Ludwig. 1960. African arrow poisons. XIV. Voruscharin, a second sulfur-containing heart poison from Catotropis procera L. Liebigs Ann. Chem., 632: 158.

    CAS  Google Scholar 

  43. Hesse, G. and K. Mix. 1959. African arrow poisons. IX. Structure and partial synthesis of uscharin. Liebigs Ann. Chem., 625:146.

    CAS  Google Scholar 

  44. Hesse, G. and F. Reicheneder. 1936. African arrow poison calotropin. I. Liebigs Ann. Chem., 526: 252.

    CAS  Google Scholar 

  45. Hesse, G., F. Reicheneder and H. Eysenbach. 1939. African arrow poisons. II. Heart poisons in Catotropis latex. Liebigs Ann. Chem., 537:67.

    Google Scholar 

  46. Hoch, J.H. 1961. A Survey of Cardiac Glycosides and Genins, Univ. of South Carolina Press, Charleston, South Carolina.

    Google Scholar 

  47. Hunger, A. and T. Reichstein. 1952a. Frugoside, a second crystallized glycoside from the seeds of Gomphocarpus fructicosus. Helv. Chim. Acta, 35:429.

    CAS  Google Scholar 

  48. Hunger, A. and T. Reichstein. 1952b. The constitution of gofruside and frugoside. Helv. Chim. Acta, 35: 1073.

    CAS  Google Scholar 

  49. Keller, M. and T. Reichstein. 1949. Gofruside, a crystalline glycoside from the seeds of Gomphocarpus fructicosus (L) R. Br. Helv. Chim. Acta, 32:1607.

    CAS  Google Scholar 

  50. Kelly, R.B., E.G. Daniels and L.B. Spaulding. 1965. Cytotoxicity of cardiac principles. J. Med. Chem., 8:547.

    PubMed  CAS  Google Scholar 

  51. Jaggi, K., H. Kaufmann, W. Stocklin and T. Reichstein. 1967. Glycosides of Asclepias swynnertonii S. Moore, roots. Helv. Chem. Acta, 50: 2457.

    CAS  Google Scholar 

  52. Kingsbury, J.M. 1964. Poisonous Plants of the United States and Canada, Prentice-Hall, Englewood Cliffs, N.J., p. 269.

    Google Scholar 

  53. Krieger, R.I., P.P. Feeny and C.F. Wilkinson. 1971. Detoxication enzymes in the guts of caterpillars: an evolutionary answer to plant defenses? Science, 172:579.

    PubMed  CAS  Google Scholar 

  54. Kupchan, S.M., J.R. Knox, J.E. Kelsey and J.A.S. Renauld. 1964. Calotropin, a cytotoxic principle isolated from Asclepias curassavica L. Science, 146:1685.

    PubMed  CAS  Google Scholar 

  55. Lardon, A., K. Stockel and T. Reichstein. 1969. Gomphogenin—partial synthesis and structure of calotropagenin. Helv. Chem. Acta, 52:1940.

    CAS  Google Scholar 

  56. Lardon, A., K. Stockel and T. Reichstein. 1970. Partial synthesis of 2α, 3β, 19-triacetoxy-14β-hydroxy-5α-card-20(22)-enolide. Additional proof of calotropagenin structure. Helv. Chim. Acta, 53:167.

    CAS  Google Scholar 

  57. Mahran, G.H., M.M. Rizkallah and A.H. Saber. 1971. A phytochemical study of Calotropis procera (Ait) R. Br. growing in Egypt. Bull. Fac. Pharm. Cario Univ., 10:1.

    CAS  Google Scholar 

  58. Marsh, C.D. and A.B. Clawson. 1924. The woolly-pod milkweed (Asclepias eriocarpa) as a poisonous plant. United States Department of Agriculture Bulletin. No. 1212.

    Google Scholar 

  59. Masler, L., S. Bauer, O. Bauerova, and D. Sikl. 1962a. Cardiac glycosides from Asclepias syriaca. I. Isolation of cardiac active steroids. Collect. Czech. Chem. Commun., 27:872.

    CAS  Google Scholar 

  60. Masler, L., S. Bauer, O. Bauerova and D. Sikl. 1962b. Cardiac glycosides from Asclepias syriaca. II. Structure of syriogenin and its glycosides. Collect. Czech. Chem. Commun., 27:895.

    CAS  Google Scholar 

  61. Mathavan, S. and R. Bhaskaran. 1975. Food selection and utilization in a Danaid butterfly. Oecologia, 18:55.

    Google Scholar 

  62. Mitsuhashi, H., K. Hayashi and K. Tomimoto. 1970. Studies on the constituents of the Asclepiadaceae plants. XXVIII. Components of Asclepias syriaca L. Chem. Pharm. Bull., 18:828.

    CAS  Google Scholar 

  63. Mitsuhashi, H. and M. Kurumi. 1968. Constituents of Asclepiadaceae plants. XXIII. Components of Gomphocarpus fruticosus. Shoyakagaku Zasshi, 22: 86. [Chem. Abstr., 71:88459f]

    CAS  Google Scholar 

  64. Mittal, O.P., Ch. Tamm and T. Reichstein. 1962. Glycosides of Pergularia extensa (Jacq) N.E. Br. Helv. Chem. Acta, 45:907.

    CAS  Google Scholar 

  65. Moe, G.K. and A.E. Farah. 1970. Digitalis and allied cardiac glycosides. In: The Pharmacological Basis of Therapeutics, L. S. Goodman and A. Gilman (eds), Macmillan, New York. Chapter 31.

    Google Scholar 

  66. Muller, C. H. 1970. The role of allelopathy in the evolution of vegetation. In: Biochemical Co-evolution, Proceedings of the Twenty-Ninth Annual Biology Colloquium, 1968. K.L. Chambers (ed), Oregon State University Press, Corvallis, Oregon, p. 13.

    Google Scholar 

  67. Nascimento, J.M. 1964. Cardenolides in leaves of Asclepias glaucophylla. Rev. Port. Quim., 6: 97. [Chem. Abstr., 64:5549f]

    CAS  Google Scholar 

  68. Nascimento, Jr., J.M., Ch. Tamm, H. Jager and T. Reichstein. 1964. Glycosides of Asclepias glaucophylla Schlechter roots. Helv. Chem. Acta, 47:1775.

    Google Scholar 

  69. Neher, R. 1969. TLC of steroids and related compounds. In: Thin-Layer Chromatography, A Laboratory Handbook, E. Stahl (ed), Springer-Verlag, New York, p. 311.

    Google Scholar 

  70. Parsons, J.A. 1965. A digitalis-like toxin in the monarch butterfly, Danaus plexippus L. J. Physiol., 178:290.

    PubMed  CAS  Google Scholar 

  71. Parsons, J.A. and R.J. Summers. 1971. Cat assay for the emetic action of digitalis and related glycosides (digitoxin, digoxin, lanatoside C, ouabain, and calactin). Br. J. Pharmacol., 42:143.

    PubMed  CAS  Google Scholar 

  72. Petricic, J. 1967. Cardenolides of some species of the genus Asclepias. Farm. Glas., 23:3. [Chem. Abstr., 67:8686g]

    CAS  Google Scholar 

  73. Petricic, J. 1966a. Desglucouzarin, the principal cardenolide glycoside of Asclepias mellodora St.Hil. Naturwissenschaften, 53:332.

    PubMed  CAS  Google Scholar 

  74. Petricic, J. 1966b. Cardenolides from the roots of Ascelpias tuberosa. Arch. Pharm., 299:1007. [Chem. Abstr., 66:76274a]

    CAS  Google Scholar 

  75. Pliske, T.E. and T. Eisner. 1969. Sex pheromone of the queen butterfly: biology. Science, 164:1170.

    PubMed  CAS  Google Scholar 

  76. Rabitzsch, G. and U. Tambor. 1969. Method for the quantitative determination of cardiac glycosides and genins of the cardenolide type with 2,4,2′,4′-tetranitrodiphenyl. Pharmazie, 24:262.

    PubMed  CAS  Google Scholar 

  77. Rajagopalan, S., Ch. Tamm and T. Reichstein. 1955. The glycosides of seeds of Calotropis procera R. Br. Helv. Chem. Acta, 38:1809.

    CAS  Google Scholar 

  78. Reichstein, T. 1967a. Cardenolide-and pregnanglycosides. Naturwissenschaften, 54:53.

    CAS  Google Scholar 

  79. Reichstein, T. 1967b. Cardiac glycosides as defensive substances in insects. Naturwiss. Rundsch., 20: 499.

    CAS  Google Scholar 

  80. Reichstein, T., J. von Euw, J.A. Parsons, and M. Rothschild. 1968. Heart poisons in the monarch butterfly. Science, 161:861.

    PubMed  CAS  Google Scholar 

  81. Repke, K. 1963, Metabolism of cardiac glycosides. In: New aspects of cardiac glycosides, Proceedings of the first international pharmacological meeting, W. Wilbrandt and P. Lindgren (eds), Macmillan, New York, Volume 3, p. 47.

    Google Scholar 

  82. Rice, E.L. 1974. Allelopathy. Academic Press, New York.

    Google Scholar 

  83. Robbins, W.E., J.N. Kaplanis, J.A. Svoboda and M.J. Thompson. 1971. Steroid metabolism in insects. In: Annual Review of Entomology. R.F. Smith and T.E. Mittler (eds), Palo Alto, Calif., Volume 16, p. 53.

    Google Scholar 

  84. Robinson, T. 1974. Metabolism and function of alkaloids in plants. Science, 184:430.

    PubMed  CAS  Google Scholar 

  85. Rothschild, M. 1972a. Secondary plant substances and warning colouration in insects. In: Insect/Plant Relationships, Symposia of the Royal Entomological Society of London, H.F. van Emden (ed), Blackwell Scientific Publications, Oxford, p. 59.

    Google Scholar 

  86. Rothschild, M. 1972b. Some observations on the relationship between plants, toxic insects, and birds. In: Phytochemical Ecology, J.B. Harborne (ed), Academic Press, New York. Chapter 1.

    Google Scholar 

  87. Rothschild, M., J. von Euw and T. Reichstein. 1970. Cardiac glycosides in the oleander aphid, Aphis nerii. J. Insect Physiol., 16:1141.

    PubMed  CAS  Google Scholar 

  88. Rothschild, M., J. von Euw, T. Reichstein, D.A.S. Smith, and J. Pierre. 1975. Cardenolide storage in Danaus chrysippus (L.) with additional notes on D. plexippus. Proc. R. Soc. Lond. B., 190:1.

    CAS  Google Scholar 

  89. Sawlewicz, L., E. Weiss and T. Reichstein. 1967. Cardenolide and pregnanglycosides of Asclepias lilacina Weimarck roots. I. Isolation. Helv. Chim. Acta, 50:504.

    CAS  Google Scholar 

  90. Schildknecht, H. 1971. Evolutionary peaks in the defensive chemistry of insects. Endeavor, 30:136.

    CAS  Google Scholar 

  91. Schoonhoven, L.M. 1972. Secondary plant substances and insects. In: Structural and Functional Aspects of Phytochemistry, Recent Advances in Phytochemistry, V.C. Runeckles and T.C. Tso (eds), Academic Press, New York; Volume 5, p. 197.

    Google Scholar 

  92. Scudder, G.G.E. and S.S. Duffey. 1972. Cardiac glycosides in the Lygaeinae (Hemiptera:Lygaeidae). Can. J. Zool, 50:35.

    CAS  Google Scholar 

  93. Singh, B. and R.P. Rastogi. 1969. Chemical investigation of Asclepias curassavica Linn. Indian J. Chem., 7:1105.

    CAS  Google Scholar 

  94. Singh, B. and R.P. Rastogi. 1970. Cardenolides—glycosides and genins. Phytochem., 9:315.

    CAS  Google Scholar 

  95. Singh, B. and R.P. Rastogi. 1972. Structure of asclepin and some observations on the nmr spectra of Calotropis glycosides. Phytochem., 11:757.

    CAS  Google Scholar 

  96. Seiber, J.N., J.M. Benson, C.N. Roeske and L.P. Brower. 1975. Qualitative and quantitative aspects of milk weed cardenolide sequestering by monarch butterflies. Paper presented at 170th National Meeting of the American Chemical Society, Division of Pesticide Chemistry (Pest 103), Chicago, August.

    Google Scholar 

  97. Tamm, Ch. 1956. New developments in the field of glycosidal cardiac poisons—fundamentals and the aglycons. Fortschr. Chem. Org. Naturstoffe, 13: 137.

    CAS  Google Scholar 

  98. Tamm, Ch. 1957. New results from the field of glyco-sidic heart poisons; sugar and glycoside. Fortschr. Chem. Org. Naturstoffe, 14:71.

    CAS  Google Scholar 

  99. Tamm, Ch. 1963. The stereochemistry of the glycosides in relation to biological activity. In: New Aspects of Cardiac Glycosides, Proceedings of the first international pharmacological meeting, W. Wilbrandt and P. Lindgren (eds), Macmillan, New York, Volume 3, p. 11.

    Google Scholar 

  100. Tschesche, R., D. Forstmann and V.K.M. Rao. 1958. Cardenolide components of Asclepias curassavica L. Chem. Ber., 91: 1204.

    CAS  Google Scholar 

  101. Tschesche, R., G. Snatzke and G. Grimmer. 1959. Calotropagenin from Asclepias curassavica L. Naturwissenschaften, 46:263.

    CAS  Google Scholar 

  102. von Euw, J., L. Fishelson, J.A. Parsons, T. Reichstein, and M. Rothschild. 1967. Cardeno-lides (heart poisons) in a grasshopper feeding on milkweeds. Nature, 214:35.

    Google Scholar 

  103. Waldbauer, G.P. 1968. The consumption and utilization of food by insects. In: Advances in Insect Physiology, Volume 5, J.W.L. Beament, J.E. Treherne and V.B. Wigglesworth (eds), Academic Press, New York, p. 229.

    Google Scholar 

  104. Watson, T.R. 1966. The cardiac glycosides of Asclepias fruticosa. Colloq. Int. Centre Nat.Rech. Sci. No. 144:173.

    Google Scholar 

  105. Watson, T.R. and S.E. Wright. 1954. The Cardiac glycosides of Gomphocarpus fruticosus (R. Br.). Chem. and Ind., 1954: 1178.

    Google Scholar 

  106. Watson, T.R. and S.E. Wright. 1956. The cardiac glycosides of Gomphocarpus fruticosus R. Br. I. Afroside. Aust. J. Chem., 9, 497.

    CAS  Google Scholar 

  107. Watson, T.R. and S.E. Wright. 1957. The cardiac glycosides of Gomphocarpus fruticosus R. Br. II. Gomphoside. Aust. J. Chem., 10:79.

    CAS  Google Scholar 

  108. Whittaker, R.H. and P.P. Feeny. 1971. Allelochemics: chemical interactions between species. Science, 171:757.

    PubMed  CAS  Google Scholar 

  109. Wood, D.L. 1970. Pheromones of bark beetles. In: Control of Insect Behaviour by Natural Products, D.L. Wood, R.M. Silverstein, and M. Nakajima (eds), Academic Press, New York, p. 301.

    Google Scholar 

  110. Woodson, Jr., R.E. 1941. The North American Asclepiadaceae. I. Perspective of the genera. Ann. Mo. Bot. Gard., 28:193.

    Google Scholar 

  111. Woodson, Jr., R.E. 1954. The North American species of Asclepias L. Ann. Mo. Bot. Gard., 41:1.

    Google Scholar 

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Authors and Affiliations

  1. Department of Environmental Toxicology, University of California, Davis, California, USA

    C. N. Roeske & J. N. Seiber

  2. Department of Biology, Amherst College, Amherst, Massachusetts, USA

    L. P. Brower & C. M. Moffitt

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  1. Western Carolina University, Cullowhee, North Carolina, USA

    James W. Wallace

  2. University of South Florida, Tampa, Florida, USA

    Richard L. Mansell

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Roeske, C.N., Seiber, J.N., Brower, L.P., Moffitt, C.M. (1976). Milkweed Cardenolides and Their Comparative Processing by Monarch Butterflies (Danaus plexippus L.). In: Wallace, J.W., Mansell, R.L. (eds) Biochemical Interaction Between Plants and Insects. Recent Advances in Phytochemistry, vol 10. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-2646-5_3

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