Abstract
Condensed tannins were isolated from bitterbnish (Purshia tridentata) and blackbrush (Coleogyne ramosissima). Structural analyses showed that both tannins were procyanidins of similar polymer length. The overall stereochemistries at C-3 and C-4, however, differed between the two tannins. These changes in stereochemistry resulted in blackbrush tannins being less preferred than bitterbrush tannins when offered to snowshoe hares (Lepus americanus). It is unlikely that differences in protein-precipitating abilities are the cause for the preference of the bitterbrush over the blackbrush tannins. Instead, we hypothesize that condensed tannins may be depolymerized and absorbed following ingestion. Differences in tannin structure can lead to different depolymerized products and rates of depolymerization, both of which may affect herbivore preferences.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Asquith, T.N., andButler, L.G. 1985. Use of dye-labeled proteins as spectrophotometric assay for protein precipitates such as tannins.J. Chem. Ecol. 11:1535–1544.
Asquith, T.N., andButler, L.G. 1986. Interactions of condensed tannins with selected proteins.Phytochemistry 25:1591–1593.
Blytt, H.J., Gusar, T.K., andButler, L.G. 1988. Antinutritional effects and ecological significance of dietary condensed tannins may not be due to binding and inhibition of digestive enzymes.J. Chem. Ecol. 14:1455–1466.
Butler, L.G., Rogler, J.C., Mehansho, H., andCarlson, D.M. 1986. Dietary effects of tannins, p. 141–157,in V. Cody, E. Middleton, Jr., and J.B. Harborne (eds.). Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure-activity Relationships. Alan R. Liss, New York.
Czochanska, Z.,Foo, L.Y.,Newman, R.H., andPorter, L.J. 1980. Polymeric proanthocyanidins. Stereochemistry, structural units, and molecular weight.J. Chem. Soc. Perkin I. 2278–2286.
Ellis, C.J., Foo, L.Y., andPorter, L.J. 1983. Enantiomerism: A characteristic of the proanthocyanidin chemistry of the monocotyledonae.Phytochemistry 22:483–487.
Feeny, P.R. 1969. Inhibitory effect of oak leaf tannins on the hydrolysis of proteins by trypsin.Phytochemistry 8:2119–2126.
Feeny, P.R. 1976. Plant apparency and chemical defense, pp. 1–40,in J.W. Wallace and R.L. Mansell (eds.). Recent Advances in Phytochemistry, Vol. 10, Biochemical Interaction between Plants and Insects. Plenum Press, New York.
Fletcher, A.C., Porter, L.J., Haslam, E., andGupta, R.K. 1977. Plant proanthocyanidins. Part 3. Conformational and configurational studies of natural procyanidins.J. Chem. Soc. Perkin I. 1628–1637.
Hagerman, A.E. 1987. Radial diffusion method for determining tannin in plant extracts.J. Chem. Ecol. 13:437–449.
Hagerman, A.E., andButler, L.G. 1980. Condensed tannin purification and characterization of tannin associated proteins.J. Agric. Food. Chem. 28:947–952.
Hagerman, A.E., andButler, L.G. 1981. The specificity of proanthocyanidin-protein interactions.J. Biol. Chem. 256:4494–4497.
Hagerman, A.E., andKlucher, K.M. 1986. Plant Flavanoids in Biology and Medicine: biochemical, Pharmacological and Structure-Activity relationships. Alan R. Liss, New York.
Hagerman, A.E., andRobbins, C.T. 1987. Implications of soluble tannin-protein complexes for tannin analysis and plant defense mechanisms.J. Chem. Ecol. 13:1243–1259.
Hemingway, R.W., andMcGraw, G.W. 1983. Kinetics of acid-catalyzed cleavage of procyanidins.J. Wood Chem. Technol. 3:421–435.
Hemingway, R.W., Foo, L.Y., andPorter, L.J. 1982. Linkage isomerism in trimeric and polymeric 2,3-cis-procyanidins.J. Chem. Soc. Perkin 1. 1209–1216.
Hemingway, R.W., McGraw, G.W., Karchesy, J.J., Foo, L.Y., andPorter, L.J. 1983. Recent advances in the chemistry of condensed tannins.J. Appl. Polym. Scl. Appl. Polym. Symp. 37:967–977.
Hsu, F., Nonaka, G., andNishioka. 1985. Acetylated flavanols and proanthocyanidins fromSalix sieboldiana.Phytochemistry 24:2089–2092.
Jacques, D., andHaslam, E. 1974. Plant proanthocyanidins. Part II. Proanthocyanidin-A2 and its derivatives.J. Chem. Soc. Perkin I. 2663–2671.
Jones, W.T., Broadhurst, B., andLyttleton, J.W. 1976. The condensed tannins of pasture legume species.Phytochemistry 15:1407–1409.
Karchesy, J.J., andHemingway, R.W. 1980. Loblolly pine bark polyflavanoids.J. Agric. Food Chem. 28:222–228.
Kufeld, R.C. 1973. Foods eaten by the rocky mountain elk.J. Range Manage. 26:106–113.
Kufeld, R.C., Wallmo, O.C., andFeddema, C. 1973. Foods of the rocky mountain mule deer. USDA Forest Service Resarch Report RM-111, Fort Collins, Colorado.
Lindroth, R.L., andBatzli, G.O. 1984. Plant phenolics as chemical defenses: effects of natural phenolics on survival and growth of prairie voles.J. Chem. Ecol. 10:229–244.
McManus, J.P., Davis, K.G., Lilley, T.H., andHaslam, E. 1981. The association of proteins with polyphenols.J. Chem. Soc. Chem. Commun. 7:309–311.
Mehansho, H., Butler, L.G., andCarlson, D.M. 1987. Dietary tannins and salivary prolinerich proteins: Interactions, induction and defense mechanisms.Annu. Rev. Nutr. 7:423–440.
Mole, S., andWaterman., D.G. 1987. A critical analyses of techniques for measuring tannins in ecological studies. I. Techniques for chemically defining tannins.Oecologia 72:137–147.
Mueller-Harvey, I., Reed, J.D., andHartley, R.D. 1987. Characterization of phenolic compounds, including flavanoids and tannins, of ten Ethiopian browse species of HPLC.J. Sci. Food Agric. 39:1–14.
Nonaka, G.,Hsu, F., andNishioka, I. 1981. Structures of dimeric, trimeric, and tetrameric procyanidins fromAreca catechu L.J. Chem. Soc. Chem. Commun. 781–783.
Porter, L.I. 1986. Number- and weight-average molecular weights for some proanthocyanidin polymers (condensed tannins).Aust. J. Chem. 39:557–562.
Porter, L.J., andWoodruffe, I. 1984. Haemanalysis: The relative astringency of proanthocyanidin polymers.Phytochemistry 23:1255–1256.
Porter, L.J., Newman, R.H., Foo, L.Y., andWong, H. 1982. Polymeric proanthocyanidins. [13C]NMR Studies of procyanidins.J. Chem. Soc. Perkin I. 1217–1221.
Porter, L.J., Foo, L.Y., andFurneaux, R.H. 1985. Isolation of three naturally occurringO-β-glucopyranosides of procyanidin polymers.Phytochemistry 24:567–569.
Provenza, F.D., andMalechek, J.C. 1984. Diet selection by domestic goats in relation to blackbrush twig chemistry.J. Appl. Ecol. 21:831–841.
Provenza, F.D.,Burritt, E.A.,Clausen, T.P.,Bryant, J.P.,Reichardt, P.B., andDistel, R.A. 1989. Conditioned taste aversions: A mechanism for goats to avoid condensed tannins in blackbrush.Am. Nat. In press.
Rhoades, D.F., andCates, R.G. 1976. Toward a general theory of plant antiherbivore chemistry, p. 168–213,in J.W. Wallace and R.L. Mansell (eds.). Recent Advances in Phytochemistry, Vol. 10, Biochemical Interaction between Plants and Insects. Plenum Press, New York.
Robbins, C.T., Hanley, T.A., Hagerman, A.E., Hjeljord, O., Baker, D.L., Schwartz, C.C., andMoutz, W.W. 1987. Role of tannins in defending plants against ruminants: Reduction in protein availability.Ecology 68:98–107.
Roux, D.G., Ferreira, D., andBotha, J.J. 1980. Structural considerations in predicting the utilization of tannins.J. Agric. Food Chem. 28:216–222.
Shen, Z., Haslam, E., Falshaw, C.P., andBegley, M.J. 1986. Procyanidins and polyphenols ofLarix gmelini bark.Phytochemistry 25:2629–2635.
Sheperd, H.R. 1971. Effects of clipping on key browse species in southwestern Colorado. Colorado Division of Game, Fish and Parks, Tech. Pub. 28, Denver, Colorado.
Swain, T. 1979. Tannins and lignins, p. 657–682,in G.A. Rosenthal and D.H. Janzen (eds.). Herbivores: Their Interaction with Plant Metabolites. Academic Press, New York.
Takechi, M., Tanaka, Y., Takehara, M., Nonaka, G., andNishioka, I. 1985. Structure and antiherpetic activity among the tannins.Phytochemistry 24:2245–2250.
Van Sumere, C.F., Albrecht, J., Dedonder, A., Depooter, H., andPé, I. 1975. Plant proteins and phenolics, p. 211–264,in J.B. Harborne and C.F. Van Sumere (eds.). The Chemistry and Biochemistry of Plant Proteins, Vol. 11. Academic Press, New York.
Williams, V.M., Porter, L.J., andHemingway, R.W. 1983. Molecular weight profiles of proanthocyanidin polymers.Phytochemistry 22:569–572.
Zucker, W.V. 1983. Tannins: Does structure determine function? An ecological perspective.Am. Nat. 121:335–365.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Clausen, T.P., Provenza, F.D., Burritt, E.A. et al. Ecological implications of condensed tannin structure: A case study. J Chem Ecol 16, 2381–2392 (1990). https://doi.org/10.1007/BF01017463
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01017463