Toward a General Theory of Plant Antiherbivore Chemistry

  • David F. Rhoades
  • Rex G. Cates
Part of the Recent Advances in Phytochemistry book series (RBIO, volume 10)


Much research has been conducted in an attempt to fit the so-called plant secondary substances into the general framework of plant metabolism. Though some success has been achieved in this area, e.g., chlorogenic acid as a regulator of plant metabolic systems under stress21, most such studies have met with a conspicuous lack of success. Possible metabolic roles for the plant alkaloids as intermediate metabolites have probably received the greatest such attention and it was concluded at an early stage44 that, since a definitive metabolic role could not be assigned to alkaloids, they best be considered as plant waste products. More recent workers in the field of alkaloid biochemistry have concurred with this evaluation44,83 and the “waste product hypothesis” has been expanded, principally by Muller (1969, 1970), to include plant secondary substances in general.


Mature Leaf Condensed Tannin Specialist Herbivore Generalist Herbivore Woody Perennial 
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.
    Akahori, A., F. Yasuda, M. Togami, K. Kagawa and T. Okahishi. 1969. Variation in isodiotigenin and diosgenin content in aerial parts of Dioscorea tokoro. Phytochem. 8:2213–2217.CrossRefGoogle Scholar
  2. 2.
    Anderson, A. B., R. Riffer and A. Wong. 1969. Mono-terpenes, fatty and resin acids of Pinus contorta and Pinus attenuata. Phytochem. 8:2401–2403.CrossRefGoogle Scholar
  3. 3.
    Anderson, J. D., P. Andrews and L. Hough. 1957. Occurrence of 2-0-methyl-L-fucose as a constituent of plum leaf polysaccharides. Chem. and Ind. 1453.Google Scholar
  4. 4.
    Andrews, P. and L. Hough. 1956. The isolation of 2-0-methyl-d-xylose from plum leaf hemicellulose. Chem. and Ind. 1278.Google Scholar
  5. 5.
    Aspinall, G. O. and A. Canas-Rodriguez. 1958. Sisal pectic acid. J. Chem. Soc. (London) 810:4020–4027.CrossRefGoogle Scholar
  6. 6.
    — and R. S. Fanshaw. 1961. Pectic substances from Lucerne (Medicago sativa). Part I. Pectic Acid. J. Chem. Soc. (London) 822:4215–4225.CrossRefGoogle Scholar
  7. 7.
    Bacon, J. S. D. and M. V. Cheshire. 1971. Apiose and mono-o-methyl sugars as minor constituents of the leaves of deciduous trees and various other species. Biochem J. 124:555–562.PubMedGoogle Scholar
  8. 8.
    Bate-Smith, E. C. and C. R. Metcalf. 1957. Leuco-anthocyanins 3. The nature and systematic distribution of tannins in dicotyledenous plants. J. Linn. Soc. Bot. 55:669–705.CrossRefGoogle Scholar
  9. 9.
    Bate-Smith, E. C. and T. Swain. 1967. New leuco-anthocyanins in grasses. Nature 213:1033–1034.CrossRefGoogle Scholar
  10. 10.
    Beck, S. D. 1965. Resistance of plants to insects. Ann. Rev. Ent. 10:201–232.CrossRefGoogle Scholar
  11. 11.
    Bell, E. A. 1972. Toxic amino acids in the leguminosae. In Harborne, 1972:163–174.Google Scholar
  12. 12.
    Blohm, H. 1962. Poisonous plants of Venezuela. Harvard University Press. Cambridge, Mass. 136pp.Google Scholar
  13. 13.
    Brodie, B. 1961. Comparative biochemistry of drug metabolism. Proc. Int. Pharmacol. meeting. First Int. Cong. on Pharmacol. 6:299 pp.Google Scholar
  14. 14.
    Bonner, J. and J. E. Varner. 1965. Plant biochemistry. Academic Press, New York. 1054 pp.Google Scholar
  15. 15.
    Bull, L. B., C. C. J. Culvenor and A. T. Dick. 1968. The pyrrolizidine alkaloids. Elsevier, N. Y. 293 pp.Google Scholar
  16. 16.
    Burnett, W. C., S. B. Jones, T. J. Mabry and W. G. Padolina. Sesquiterpene lactones — insect feeding deterrents in Vernonia, (in press)Google Scholar
  17. 17.
    Cates, R. G. and D. F. Rhoades. Prosopis as a leaf resource. In A tree in perspective; mesquite (Prosopis spp.) in desert scrub ecosystems. B. Simpson (ed.) (in press).Google Scholar
  18. 18.
    Chestnut, V. K. and E. V. Wilcox. 1901. Stock poisoning plants of Montana. U.S.D.A. Div. of Bot. Bull. 26.Google Scholar
  19. 19.
    Clark, B. 1962. Balanced polymorphism and the diversity of sympatric species. System. Assoc. Publ. 4, Taxonomy and Geography: 47–70.Google Scholar
  20. 20.
    Clayton, R. B. 1970. The chemistry of nonhormonal interactions. Terpenoid compounds in ecology. p. 235–275 In Sondheimer and Simeone. 1970.Google Scholar
  21. 21.
    del Moral, R. 1972. On the variability of chlorogenic acid concentration. Oeoologia 9:289–300.CrossRefGoogle Scholar
  22. 22.
    Dement, W. A. and H. A. Mooney. 1974. Seasonal changes in the production of tannins and cyanogenic glycosides in the chaparral shrub, Heteromeles arbutifolia. Oecologia 13:62–76.Google Scholar
  23. 23.
    Difeo, D. R., M. Sakakibara and T. J. Mabry. 1975. Flavonoid aglycones of two disjunct species of Larrea. Proc. 15th Annual Meeting of the Phytochem. Soc. of N.A.Google Scholar
  24. 24.
    Duffy, S. S. and G. G. E. Scudder. 1972. Cardiac glycosides in North American asclepiadaceae. A basis for unpalatability in brightly colored Hemiptera and Coleoptera. J. Insect Physiol. 18:63–70.CrossRefGoogle Scholar
  25. 25.
    Ehrlich, P. R. and P. H. Raven. 1965. Butterflies and Plants. A study in coevolution. Evolution 18: 586–608.CrossRefGoogle Scholar
  26. 26.
    Eidt, D. C. and C. H. A. Little. 1970. Insect control through induced host-insect asynchrony. A progress report. J. Econ. Entomol. 63:1966–1968.Google Scholar
  27. 27.
    Eloff, J. N. and R. N. Grobbelaa. 1969. Isolation and characterization of N-methyl-L-serine from Dichapetalum cymosum. Phytochem. 8:2201–2204.CrossRefGoogle Scholar
  28. 28.
    Erdtman, H. and T. Norin. 1966. The chemistry of the order Cupressales, In Progress in the chemistry of organic natural products. L. Zechmeister (ed.). Springer-Verlag, N.Y. 475 pp.Google Scholar
  29. 29.
    Erickson, J. M. and P. P. Feeny. 1974. Sinigrin: A chemical barrier to larvae of the black swallowtail butterfly, Papilio polyxenes. Ecol. 55:103–111.CrossRefGoogle Scholar
  30. 30.
    Esau, K. 1953. Plant anatomy. John Wiley and Sons. N.Y. 735 pp.Google Scholar
  31. 31.
    Ettlinger, M. G., and A. Kjaer. 1968. Sulphur compounds in plants. In Recent Advances in Phytochemistry, 1:59–144.Google Scholar
  32. 32.
    Feeny, P. P. 1968. Seasonal changes in the tannin content of oak leaves. Phytochem. 7:871–880.CrossRefGoogle Scholar
  33. 33.
    Feeny, P. P. 1970. Seasonal changes in oakleaf tannins and nutrients as a cause of spring feeding by winter-moth caterpillars. Ecol. 51:656–681.CrossRefGoogle Scholar
  34. 34.
    Feeny, P. P. 1975. Biochemical coevolution between plants and their insect herbivores. In Coevolution of Animals and Plants. L. E. Gilbert and P. H. Ravens (eds.). Univ. of Texas Press. Austin (in press).Google Scholar
  35. 35.
    Fraenkel, G. 1953. The nutritional value of green plants for insects. Symp. of the 9th Int. Congr. Ent. 90–100.Google Scholar
  36. 36.
    Hanover, J. W. 1975. Physiology of tree resistance to insects. Ann. Rev. Ent. 20:75–95.CrossRefGoogle Scholar
  37. 37.
    Harborne, J. B. (ed.). 1972. Phytochemical Ecology. Academic Press, N.Y. 272 pp.Google Scholar
  38. 38.
    Henderson, R. 1971. Catalytic Activity of α-chymotrypsin in which histidine-57 has been methylated. Biochem. J. 124:13–18.PubMedGoogle Scholar
  39. 39.
    Hill, R. and R. van Heyninger. 1951. Ranunculin: The precursor of the vesicant substance of the buttercup. Biochem. J. 49:332–335.PubMedGoogle Scholar
  40. 40.
    Hoch, J. H. 1961. A survey of cardiac glycosides and genins. Univ. of South Carolina Press, Charleston. 93 pp.Google Scholar
  41. 41.
    Horber, E. 1972. Alfalfa saponins significant in resistance to insects. In Rodriguez. 1972:611–627.Google Scholar
  42. 42.
    Ishaaya, I. and Y. Birk. 1965. Soybean saponins IV. The effect of proteins on the inhibitory activity of soybean saponins on certain enzymes. J. Food Sci. 30:118–120.CrossRefGoogle Scholar
  43. 43.
    Jacobson, J. and D. G. Crosby. 1971. (eds.). Naturally Occurring Insecticides. Dekker, N.Y. 585 pp.Google Scholar
  44. 44.
    James, W. D. 1950. In The alkaloids VI. R.H.F. Manske and H. L. Holms (eds.). Academic Press, N.Y. 525 pp.Google Scholar
  45. 45.
    Jones, D. A. 1962. Selective eating of the acyanogenic form of the plant Lotus corniculatus L. by various animals. Nature 193:1109–1110.CrossRefGoogle Scholar
  46. 46.
    Jones, D. A. 1972. Cyanogenic glycosides and their function. In Harborne, 1972. p. 103–122.Google Scholar
  47. 47.
    Joseffson, E. 1967. Distribution of thioglucosides in different parts of Brassica plants. Phytochem. 6: 1617–1627.CrossRefGoogle Scholar
  48. 48.
    Kingsbury, J. M. 1964. Poisonous plants of the United States and Canada. Prentice-Hall, N.Y. 626 pp.Google Scholar
  49. 49.
    Kircher, H. W., W. B. Heed, J. S. Russell and J. Grove. 1967. Senita cactus alkaloids and sonoran desert Drosophila. J. Insect Physiol. 13:1869–1871.CrossRefGoogle Scholar
  50. 50.
    Krieger, R., P. P. Feeny, and C. Wilkinson. 1971. Detoxification enzymes in the guts of caterpillars: an evolutionary answer to plant defenses? Science 172:579–580.PubMedCrossRefGoogle Scholar
  51. 51.
    La Du, B. N., H. G. Mandel, and E. L. Way. 1971. Fundamentals of drug metabolism and drug disposition. The Williams and Wilkins Co., Baltimore. 615 pp.Google Scholar
  52. 52.
    Langenheim, J. H. 1973. Leguminous resin-producing trees in Africa and South America. In Tropical forest ecosystems in Africa and South America. A comparative review: 89–104. Smithsonian, N.Y.Google Scholar
  53. 53.
    Laskowski, M. 1970. In Structure — Function relationships of proteolytic enzymes. P. Desnuelle, H. Neurath and M. Ottesen (eds.). Academic Press, N.Y. 309 pp.Google Scholar
  54. 54.
    Lawton, J. H. The structure of the arthropod community on bracken (Pteridium aquilinium) (L.) (Kuhn). (in press).Google Scholar
  55. 55.
    Loomis, W. D. and J. Battaile. 1966. Plant phenolics and the isolation of plant enzymes. Phytochem. 5: 423–438.CrossRefGoogle Scholar
  56. 56.
    Levin, D. A. 1971. Plant phenolics: an ecological perspective. Am. Nat. 105:157–181.CrossRefGoogle Scholar
  57. 57.
    —. 1973. The role of plant trichomes in plant defense. Quart. Rev. Biol. 48:3–15.CrossRefGoogle Scholar
  58. 58.
    —. 1975. Alkaloid-bearing plants: an ecographic perspective. Am. Nat. (in press).Google Scholar
  59. 59.
    McKey, D. 1974. Adaptive patterns in alkaloid physiology. Am. Nat. 108:305–320.CrossRefGoogle Scholar
  60. 60.
    Merck Index of Chemicals and Drugs VIIth Ed. 1960. Merck, Rathway, N.J. 1642 pp.Google Scholar
  61. 61.
    Metcalf, R. H. 1967. Mode of action of insecticide synergists. Ann. Rev. Entom. 12:229–256.PubMedCrossRefGoogle Scholar
  62. 62.
    Milner, M. 1975. (ed.) Nutritional improvement of food legumes by breeding. Proceedings of a Symposium, Rome, July 1972. Wiley Interscience, N.Y. 400 pp.Google Scholar
  63. 63.
    Muller, C. H. 1969. The “co” in coevolution. Science, 164:197–198.PubMedCrossRefGoogle Scholar
  64. 64.
    —. 1970. Phytotoxins as plant habitat variables. Rec. Adv. Phytochem. 3:106–121.Google Scholar
  65. 65.
    Munakata, K. 1970. Insect antifeedants in plants. In Wood. 1970:179–181.Google Scholar
  66. 66.
    Nash, J. Undated. Poisonous Plants. Etchells and Macdonald, London. 85 pp.Google Scholar
  67. 67.
    Nowacki, E. 1963. Inheritance and biosynthesis of alkaloids of Lupin. Genetica Polonica 4:161–202.Google Scholar
  68. 68.
    Oliver, B. F., F. G. Maxwell and J. N. Jenkins. 1971. Growth of the bollworm on glanded and glandless cotton. J. Econ. Entomol. 64:396–398.Google Scholar
  69. 69.
    Pammell, L. H. 1911. A manual of poisonous plants. The Torch Press, Cedar Rapids, Iowa. 977 pp.Google Scholar
  70. 70.
    Paulson, D. R. 1973. Predator polymorphism and apostatic selection. Evolution 27:269–277.CrossRefGoogle Scholar
  71. 71.
    Pridham, J. B. 1963. Enzyme Chemistry of Phenolic Compounds. Macmillan and Co., N.Y. 142 pp.Google Scholar
  72. 72.
    Rees, C. J. C. 1969. Chemoreceptor specificity associated with choice of feeding site by the beetle Chrysolina brunsvicensis on its food-plant Hypericum hirsutum. Ent. Exp. Appl. 12:565–583.CrossRefGoogle Scholar
  73. 73.
    Rehr, S. S., D. H. Janzen and P. P. Feeny. 1973(a). L-Dopa in legume seeds. A chemical barrier to insect attack. Science 181:81–82.PubMedCrossRefGoogle Scholar
  74. 74.
    Rehr, S. S., P. P. Feeny, and D. H. Janzen. 1973(b). Chemical defense in Central American non-ant-acacias. J. Anim. Ecol. 42:405–416.CrossRefGoogle Scholar
  75. 75.
    Rhoades, D. F. The anti-herbivore defenses of Larrea. In The biology and chemistry of the creosotebush (Larrea) in the new world deserts. T. J. Mabry, J. Hunziker and D. R. DiFeo, Jr. (eds.). (in press).Google Scholar
  76. 76.
    Rice, E. L. 1974. Allelopathy. Academic Press, N.Y. 354 pp.Google Scholar
  77. 77.
    Ribereau-Gayon, P. 1972. Plant phenolics. University Reviews in Botany, 3. V. H. Heywood (ed.). Oliver and Boyd, Edinburgh, 234 pp.Google Scholar
  78. 78.
    Rockwood, L. L. 1974. Seasonal changes in the susceptibility of Crescentia alata leaves to the flea beetle Oedionychus sp. Ecology 55:142–148.CrossRefGoogle Scholar
  79. 79.
    Rodriguez, J. G. 1972. Insect and mite nutrition. North-Holland, Amsterdam, 702 pp.Google Scholar
  80. 80.
    Rothschild, M. 1973. Secondary plant substances and warning coloration in insects. In H. F. van Emden (ed.). 1973.Google Scholar
  81. 81.
    Sakai, W. S., M. Hanson and R. C. Jones. 1972. Raphides with barbs and qrooves in Xanthasoma ragittifolium. Science 178:314–315.PubMedCrossRefGoogle Scholar
  82. 82.
    Sakakibara, M., D. DiFeo, Jr., N. Nakatani, B. Timmermann, and T. J. Mabry. Flavonoid methyl ethers on the external leaf surfaces of Larrea tridentata and L. divaricata (Zygophyllaceae). Phytochem., (in press).Google Scholar
  83. 83.
    Schmeltz, I. 1971. Nicotine and other tobacco alkaloids. In Jacobson and Crosby. 1971.Google Scholar
  84. 84.
    Schoonhoven, L. M. 1972. Secondary plant substances and insects. In Recent Advances in Phytochemistry, V. C. Runeckles and T. C. Tso (eds.). pp. 197–224. Vol. 5. Academic Press, N.Y. 350 pp.Google Scholar
  85. 85.
    Schultz, J. C., D. Otte and F. Enders. Larrea as a habitat component for desert arthropods. In The biology and chemistry of the creosotebush (Larrea) in the new world deserts. T. J. Mabry, J. Hunsiker and D. R. DiFeo (eds.). (in press).Google Scholar
  86. 86.
    Schwerdtfeger, F. 1956. Is the density of animal populations governed by chance? Tenth Int. Congr. Ent. 4:115–122. E. C. Becker, (ed.).Google Scholar
  87. 87.
    Self, L., F. Guthrie, and E. Hodgson. 1964. Adaptations of tobacco hornworms to the ingestion of nicotine. J. Insect Physiol. 10:907–909.CrossRefGoogle Scholar
  88. 88.
    Smith, B. D. 1966. Effect of the plant alkaloid sparteine on the distribution of the aphid Acrythosiphon spartii. Nature 212:213–214.CrossRefGoogle Scholar
  89. 89.
    Smith, J. N. 1962. Detoxification mechanisms. Ann. Rev. Ent. 7:465–480.CrossRefGoogle Scholar
  90. 90.
    Smith, R. H. 1961. The fumigant toxicity of three pine resins to Dendroctonus brevicomis and D. jeffreyi. J. Econ. Entomol. 54(2):359–365.Google Scholar
  91. 91.
    — and L. E. Green. 1972. Xylem resin in the resistance of the Pinaceae to bark beetles. U.S.D.A. For. Serv. Gen. Tech. Rep. PSW-1, 7 pp.Google Scholar
  92. 92.
    Sondheimer, E. J. and J. B. Simeone (eds.). 1970. Chemical Ecology. Academic Press, N.Y. 336 pp.Google Scholar
  93. 93.
    Stein, W. D. 1967. The Movement of Molecules Across Cell Membranes. Academic Press, N.Y. 369 pp.Google Scholar
  94. 94.
    Treub, M. 1896. Nouvelles Researches sur le role de l’acide cyanhyrique dans les plants vertes. Ann. Jard. Bot. Buitzenbor, Ser. II, 6:79–106.Google Scholar
  95. 95.
    van Emden, H. F. 1972. Aphids as phytochemists. In Harborne. 1972:25–43.Google Scholar
  96. 96.
    —. 1973. Insect/Plant Relationships. (ed.) John Wiley and Sons, N.Y. 215 pp.Google Scholar
  97. 97.
    — and M. A. Bashford. 1969. A comparison of the reproduction of Brevicoryne brassicae and Myzus persicae in relation to soluble nitrogen concentration and leaf age (leaf position) in the brussels sprout plant. Ent. Exp. Appl. 12:351–364.CrossRefGoogle Scholar
  98. 98.
    Vogel, R., I. Trautschold, and E. Werle. 1968. Natural Proteinase Inhibitors. Academic Press, N.Y. 159 pp.Google Scholar
  99. 99.
    Williams, C. M. 1970. Hormonal interactions between plants and insects. In Sondheimer and Simeone. 1970: 103–132.Google Scholar
  100. 100.
    Williams, R. J. and E. M. Lansford. 1967. The Encyclopedia of Biochemistry. Reinhold, N.Y. 876 pp.Google Scholar
  101. 101.
    Wood, D. L. 1973. Selection and colonization of Ponderosa Pine by Bark Beetles. In van Emden, 1973: 101–117.Google Scholar
  102. 102.
    —, R. M. Silverstein and M. Nakajima. 1970. Control of insect behavior by natural products. Academic Press, N. Y. 345 pp.Google Scholar

Copyright information

© Plenum Press, New York 1976

Authors and Affiliations

  • David F. Rhoades
    • 1
  • Rex G. Cates
    • 2
  1. 1.Department of ZoologyUniversity of WashingtonSeattleUSA
  2. 2.Department of BiologyUniversity of New MexicoAlbuquerqueUSA

Personalised recommendations