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Scientific Bibliography : Milkweed Biochemistry

Secondary Compounds

Adams, R. P., Tomb, A. S., Price, S. C. 1987. Investigation of hybridization between Asclepias speciosa and A. syriaca using alkanes, fatty acids, and triterpenoids. Biochemical Systematics and Ecology (Oxford) 15:395-399

Benson, J. M., Seiber, J. N. 1978. High-speed liquid chromatography of cardiac glycosides in milkweed plants and monarch butterflies. Journal of Chromatography (Amsterdam & London) 148:521-527

Bogner, F., Boppre, M. 1989. Single cell recordings reveal hydroxydanaidal as the volatile compound attracting insects to pyrrolizidine alkaloids. Entomologia Experimentalis et Applicata 50:171-184

Boppre, M. 1976. Pheromon-Transfer-Partikel auf einem Duftpinselhaar eines Monarchfalters (Danaus formosa). Naturwissenschaftliche Rundschau (Stuttgart) 29:[caption to frontispiece].

Boppre, M. 1979. Untersuchungen zur Pheromonbiologie bei Monarchfaltern (Danaidae). Dissertation der Fakultat fur Biologie der Ludwig-Maximilians-Universitat Munchen. :121

Boppre, M. 1984. Redefining "pharmacophagy.". Journal of Chemical Ecology 10:1151-1154

Brower, L. P. 1969. Ecological chemistry. Scientific American (New York) 220:22-29 [Keywords: ecology, defense, secondary compounds, cardenolides, Asclepias, see Slansky]

Brower, L. P. 1972. Ecological chemistry of the palatability-cardiac glycoside spectrum in Monarch butterflies, Danaus plexippus, and Asclepias milkweeds. American Zoologist 12:712-713

Brower, L. P., Brower, J. V. Z. 1964. Birds, butterflies and plant poisons: a study in ecological chemistry. Zool. (New York) 49:137-159

Brower, L. P., McEvoy, P. B., Williamson, K. L., Flannery, M. A. 1972. Variation in cardiac glycoside content of monarch butterflies from natural populations in eastern North America. Science (Washington) 177:426-429 [Keywords: chemical defense, cardiac glycosides, cardenolides, sex differences]

Brower, L. P., Ryerson, W. N., Coppinger, L. L., Glazier, S. C. 1968. Ecological chemistry and the palatability spectrum. Science (Washington) 161:1349-1350

Brower, L. P., Seiber, J. N., Nelson, C. J., Lynch, S. P., Hoggard, M. P., Cohen, J. A. 1984. Plant determined variation in cardenolide content and thin-layer chromatography profiles of monarch butterflies, Danaus plexippus reared on milkweed plants in California: 3. Asclepias californica. Journal of Chemical Ecology 10:1823-1857 [Keywords: physiology, chemical defense, cardiac glycosides, cardenolide fingerprint]

Brower, L. P., Seiber, J. N., Nelson, C. J., Lynch, S. P., Holland, M. M. 1984. Plant determined variation in the cardenolide content, thin-layer chromatography profiles, and emetic potency of monarch butterflies, Danaus plexippus L. reared on milkweed plants in California: 2. Asclepias speciosa. Journal of Chemical Ecology 10:601-639 [Keywords: physiology, chemical defense, cardiac glycosides, cardenolide fingerprint]

Brower, L. P., Seiber, J. N., Nelson, C. J., Lynch, S. P., Tuskes, P. M. 1982. Plant determined variation in the cardenolide content, thin layer chromatography profiles, and emetic potency of Monarch butterflies, Danaus plexippus, reared on the milkweed, Asclepias eriocarpa, in California. Journal of Chemical Ecology 8:579-633 [Keywords: physiology, chemical defense, cardiac glycosides, cardenolide fingerprint]

Brower, L. P., Williamson, K. L., Flannery, M. A., Uman, H. M. 1970. A quantitative assay for cardiac glycosides in the monarch butterfly and its milkweed foodplants. American Zoologist 10:540

Brown, P., Euw, J. V., Reichstein, T., Stockel, K., Watson, T. R. 1979. Cardenolides of Asclepias syriaca L., probable structure of syrioside and syrobioside. Helvetica Chimica Acta 62:412-441

Bull, L. B., Culvenor, C. C. J., Dick, A. T. 1968. The pyrrolizidine alkaloids, their chemistry, pathogenicity and other biological properties. Frontiers of Biology 9:xvi + 293

Cheeke, P. R. P.-G., M. L. 1983. Toxicity of Senecio jacobaea and pyrrolizidine alkaloids in various laboratory animals and avian species. Toxicology Letters (Amsterdam) 18:343-349

Cheung, H. T., Watson, T. R., Seiber, J. N., Nelson, C. J. 1980. 7b,8b-epoxycardenolide glycosides of Asclepias eriocarpa. Journal of the Chemical Society Perkin Transacts. I:2169-2173

Cheung, H. T. A., Chiu, F. C. K., Watson, T. R., Wells, R. J. 1983. Cardenolide glycosides of the Asclepiadaceae. New glycosides from Asclepias fruticosa and stereochemistry of uscharin, vonuscharin and calotoxin. Journal of the Chemical Society Perkin Transactions I:2827-2835

Cheung, H. T. A., Nelson, C. J., Watson, T. R. 1988. New glucoside conjugates and other cardenolide glycosides from the monarch butterfly reared on Asclepias fruticosa L. Journal of the Chemical Society Perkin Transactions I:1851-1857

Cheung, H. T. A., Watson, T. R., Lee, S. M., McChesney, M. M., Seiber, J. N. 1986. Structure of aspecioside from the monarch butterfly larvae food plants Asclepias speciosa and A. syriaca. Journal of the Chemical Society Perkin Transactions I:61-65

Cohen, J. A., Brower, L. P. 1982. Oviposition and larval success of wild monarch butterflies (Lepidoptera: Danaidae) in relation to host plant size and cardenolide concentration. Journal of the Kansas Entomological Society 55:343-348 [Keywords: behavior, reproduction, physiology, survivorship, cardenolides, cardiac glycosides]

Dannreuther, T. 1935. Note on the food-plant of Danaus plexippus L. Entomologist (London) 68:240-241

Deinzer, M. L., Thomson, P. A., Burgett, D. M., Isaacson, D. L. 1977. Pyrrolizidine alkaloids: Their occurrence in honey from Tansy Ragwort (Senecio jacobeae L.). Science (Washington) 195:497-499

Dixon, C. A., Erickson, J. M., Kellet, D. N., Rothschild, M. 1978. Some adaptations between Danaus plexippus and its food plant, with notes on Danaus chrysippus and Euploea core (Insecta: Lepidoptera). Journal of Zoology (London) 185:437-467 [Keywords: behavior, feeding, host plant use, chemical defence, cardiac glycosides, cardenolides, sequestration]

Dussourd, D. E., Denno, R. F. 1991. Deactivation of plant defense: Correspondence between insect behavior and secretory canal architecture. Ecology 72:1383-1396 [Keywords: feeding, foraging behavior, chemical defense, secondary compounds]

Erickson, J. M. 1973. The utilization of various Asclepias species by the larvae of the Monarch butterfly Danaus plexippus. Psyche (Cambridge) 80:230-244 [Keywords: behavior, feeding, Asclepias, cardiac glycosides, cardenolides, toxicity spectrum, fertility, fecundity]

Everist, S. L. 1981. Poisonous plants of Australia. Sydney: Angus and Robertson, 966 pp.

Fraenkel, G. 1959. The raison d'etre of secondary plant substances. Science (Washington) 129:1466-1470

Groeneveld, H. W., Steijl, H., van den Berg, B., Elings, J. C. 1990. Rapid, quantitative HPLC analysis of Asclepias fruticosa L. and Danaus plexippus L. cardenolides. Journal of chemical ecology 16:3373-3382 [Keywords: chemical defense, cardiac glycosides, cardenolides, milkweed, sequestration]

Guilford, T., Nicol, C., Rothschild, M., Moore, B. P. 1987. The biological roles of pyrazines: Evidence for a warning odour function. Biological Journal of the Linnean Society (London) 32:113-128

Harborne, J. B. 1982. Introduction to ecological biochemistry, 2nd. ed. London: Academic Press. xvi + 278 pp.

Harborne, J. B. e. 1972. Phytochemical ecology. N. Y. & Lond.: Acad. Press

Haribal, M., Renwick, J. A. A. 1996. Oviposition stimulants for the monarch butterfly: Flavonol glycosides from Asclepias curassavica. Phytochemistry 41:139-144 [Keywords: behavior, reproduction, oviposition, flavonoid glycosides]

Jolad, S. D., Bates, R. B., Cole, J. R., Hoffmann, J. J., Siahaan, T. J., Timmermann, B. N. 1986. Cardenolides and a lignan from Asclepias subulata. Phytochemistry 25:2581-2590

Keller, M., Reichstein, T. 1949. Gofrusid, ein krystallisiertes Gylkosid aus dem Samen von Gomphocarpus fruticosus (L.) R. Br. Helvetica Chimica Acta 32:1607-1612

Lynch, S. P., Martin, R. A. 1987. Cardenolide content and thin-layer chromatography profiles of monarch butterflies, Danaus plexippus L., and their larval host-plant milkweed, Asclepias viridis Walt., in northwestern Louisiana. Journal of Chemical Ecology 13:47-69 [Keywords: chemical defense, cardiac glycosides, cardenolides, cardenolide fingerprint]

Malcolm, S. B. 1987. The fourth chemical ecology meeting. Trends in Ecology and Evolution 2:292-293

Malcolm, S. B., Brower, L. P. 1986. Selective oviposition by monarch butterflies (Danaus plexippus L.) in a mixed stand of Asclepias curassavica L. and A. incarnata L. in south Florida. J. Lepid. Soc. 40:255-263 [Keywords: behavior, reproduction, oviposition, Asclepias, Florida, cardenolides]

Malcolm, S. B., Brower, L. P. 1989. Evolutionary and ecological implications of cardenolide sequestration in the monarch butterfly. Experientia (Basel) 45:284-295 [Keywords: behavior, migration, annual cycle, life history, overwintering, Asclepias, cardenolides, defense]

Malcolm, S. B., Cockrell, B. J., Brower, L. P. 1989. The cardenolide fingerprint of monarch butterflies reared on the common milkweed, Asclepias syriaca L. Journal of Chemical Ecology 15:819-853 [Keywords: chemical defense, cardiac glycosides, cardenolides, cardenolide fingerprint]

Martin, R. A., Lynch, S. P. 1988. Cardenolide content and thin-layer chromatography profiles of monarch butterflies, Danaus plexippus L., and their larval host-plant milkweed, Asclepias asperula subsp. capricornu (Woods.) Woods., in north central Texas. Journal of Chemical Ecology 14:295-318 [Keywords: chemical defense, cardiac glycosides, cardenolides, cardenolide fingerprint]

Martin, R. A., Lynch, S. P., Brower, L. P., Malcolm, S. B., Van Hook, T. 1992. Cardenolide content, emetic potency, and thin-layer chromatography profiles of monarch butterflies, Danaus plexippus, and their larval host-plant milk-weed, Asclepias humistrata, in Florida. Chemoecology (Stuttgart) 3:1-13 [Keywords: physiology, milkweed, Asclepias, chemical defense, cardiac glycoside, sequestration, cardenolide fingerprint]

Nelson, C. J. 1988. Milkweeds, monarchs and cardenolide glycosides, a study in three parts. . pp. 320. Sydney: University of Sydney

Nishio, S., Blum, M. S., Silverton, J. V., Highet, R. J. 1982. Structure of humistratin: A novel cardenolide from the sandhill milkweed Asclepias humistrata. Journal of Organic Chemistry 47:2154-2157

Nishio, S., Blum, M. S., Takahashi, S. 1983. Intraplant distribution of cardenolides in Asclepias humistrata (Asclepiadaceae), with additional notes on their fates in Tetraopes melanurus (Coleoptera: Cerambycidae) and Rhyssomatus lineaticollis (Coleoptera: Curculionidae). Memoirs of the College of Agriculture, Kyoto University 122:43-52

Oyeyele, S. O., Zalucki, M. P. 1990. Cardiac glycosides and oviposition by Danaus plexippus on Asclepias fruticosa in south-east Queensland (Australia), with notes on the effect of plant nitrogen content. Ecological Entomology 15:177-185 [Keywords: behavior, reproduction, oviposition, Asclepias, cardiac glycosides, cardenolides, Australia]

Punyarajun, S. 1965. Chemical investigations of Asclepias tuberosa. Ph.D. dissertation. West Lafayette, IN: Purdue University.

Robins, D. J. 1982. The pyrrolizidine alkaloids. In Progress In the Chemistry of Organic Natural Products , ed. W. Herz, H. Grisebach, G. W. Kirby. pp. 115-203. Vol. 41. Wien: Springer-Verlag

Roeske, C. M., Seiber, J. N., Brower, L. P., Moffitt, C. M. 1976. Milkweed cardenolides and their comparative processing by monarch butterflies (Danaus plexippus L.). Recent Advances in Phytochemistry 10:93-167

Rosenthal, G. A. 1986. The chemical defenses of higher plants. Scientific American (New York) 254:76-81 [Keywords: chemical defense, plant defense, chemical ecology, plant secondary compounds]

Rothschild, M. 1972. Some observations on the relationship between plants, toxic insects and birds. Ann. Proc. Phytochem. Soc. 8:1-12

Rothschild, M., Edgar, J. A. 1978. Pyrrolizidine alkaloids from Senecio vulgaris sequestered and stored by Danaus plexippus. J. Zool., Lond. 186:347-349

Sady, M., B., Seiber, J. N. 1991. Chemical differences between species of Asclepias from the intermountain region of North America. Phytochemistry 30:3001-3003 [Keywords: milkweed, cardenolides, cardiac glycosides, chemical differences]

Sady, M., B., Seiber, J. N. 1991. Field test for screening milkweed latex for cardenolides. Journal of Natural Products (Lloydia) 54:1105-1107 [Keywords: chemical defense, cardiac glycosides, cardenolides]

Seiber, J. N., Brower, L. P., Lee, S. M., McChesney, M. M., Cheung, H. T. A., et al. 1986. Cardenolide connection between overwintering monarch butterflies from Mexico and their larval food plant, Asclepias syriaca. Journal of Chemical Ecology 12:1157-1170 [Keywords: overwintering, chemical defense, cardenolides, cardiac glycosides]

Seiber, J. N., Lee, S. M., Benson, J. M. 1983. Cardiac glycosides (cardenolides) in species of Asclepias (Asclepiadaceae). In Handbook of natural toxins, Vol. 1: Plant and fungal toxins, eds. R. F. Keeler and A. T. Tu, 43-83. Amsterdam: Marcel Dekker.

Seiber, J. N., Lee, S. M., Benson, J. M. 1984. Chemical characteristics and ecological significance of cardenolides in Asclepias (milkweed) species. In Isopentenoids in plants: Biochemistry and function, eds. W. D. Nes, G. Fuller, and L. Tsai, 563-588. Amersterdam and New York: Marcel Dekker.

Seiber, J. N., Nelson, C. J., Lee, S. M. 1982. Cardenolides in the latex and leaves of seven Asclepias species and Calotropis procera. Phytochemistry 21:2343-2348

Seiber, J. N., Tuskes, P. M., Brower, L. P., Nelson, C. J. 1980. Pharmacodynamics of some individual milkweed cardenolides fed to the larvae of the monarch butterfly (Danaus plexippus L.). Journal of Chemical Ecology 6:321-339 [Keywords: physiology, cardenolide storage, metabolism]

Sieber, J. N., Lee, S. M., Benson, J. M. 1983. Cardiac glycosides (cadenolides) in species of Asclepias (Asclepiadaceae). In Handbook of natural toxins, Vol. 1. Plant and Fungal Toxins, eds. R. F. Keeler and A. T. Tu, 43-83. Amsterdam and New York: Marcel Dekker.

Slansky, F. 1972. Cardiac glycosides in Asclepias species. Journal of the lepidopterists' society 26:219 [Keywords: Asclepias, cardenolides]

Thomas, R. E. 1981. Cardiac drugs. In Burger's medicinal chemistry, Part III, ed. M. E. Wolff, 47-192. New York: John Wiley & Sons.

Tschesche, R., Snatzke, G., Grimmer, G. 1959. Calotropagenin aus Asclepias curassavica L. Naturwissenschaften (Berlin) 46:263-264

Zalucki, M. P., Brower, L. P. 1992. Survival of first instar larvae of Danaus plexippus (Lepidoptera: Danainae) in relation to cardiac glycoside and latex content of Asclepias humistrata (Asclepiadaceae). Chemoecology (Stuttgart) 3:81-93 [Keywords: chemical defense, milkweed, cardiac glycosides, neonate insect behavior]

Zalucki, M. P., Brower, L. P., Malcolm, S. B. 1990. Oviposition by Danaus plexippus in relation to cardenolide content of three Asclepias species in the southeastern USA. Ecological Entomology 15:231-240 [Keywords: behavior, reproduction, oviposition, physiology, cardiac glycosides, Asclepias, milkweeds]

Zalucki, M. P., Oyeyele, S., Vowles, P. 1989. Selective oviposition by Danaus plexippus L. (Lepidoptera: Nymphalidae) in a mixed stand of Asclepias fruticosa and A. curassavica in southeast Queensland. J. Aust. Ent. Soc. 28:141-146

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