Journal of Chemical Ecology

, Volume 27, Issue 12, pp 2517–2527

Ethyl m-Digallate from Red Maple, Acer rubrum L., as the Major Resistance Factor to Forest Tent Caterpillar, Malacosoma disstria Hbn.

  • Mamdouh M. Abou-Zaid
  • Blair V. Helson
  • Constance Nozzolillo
  • J. Thor Arnason


An ethanolic extract of red maple (Acer rubrum L.) leaves (RME) applied to trembling aspen (Populus tremuloides Michx.) leaves reduced feeding in choice test assays with forest tent caterpillar larvae (Malacosoma disstria Hbn.) (FTC), whereas a trembling aspen foliage extract, similarly applied, stimulated feeding. Compounds isolated from the RME were gallic acid, methyl gallate, ethyl gallate, m-digallate, ethyl m-digallate, 1-O-galloyl-β-D-glucose, 1-O-galloyl-α-L-rhamnose, kaempferol 3-O-β-D-glucoside, kaempferol 3-O-β-D-galactoside, kaempferol 3-O-β-L-rhamnoside, kaempferol-3-O-rhamnoglucoside, quercetin 3-O-β-D-glucoside, quercetin 3-O-β-L-rhamnoside and quercetin 3-O-rhamnoglucoside, (−)-epicatechin, (+)-catechin and ellagic acid. All of the gallates, (−)-epicatechin, and kaempferol 3-O-β-L-rhamnoside deterred feeding on trembling aspen leaf disks when applied at 0.28 mg/cm2. The two digallates deterred feeding by 90% and were the most effective. HPLC analysis indicated that ethyl m-digallate is present in amounts 10–100 × higher in RME (∼2.5–250 mg/g) than any other compound. Thus, ethyl m-digallate appears to be the major compound protecting red maple from feeding by FTC, with a minor contribution from other gallates.

Acer rubrum L., red maple A. saccharum L., sugar maple Aceraceae Populus tremuloides Michx., trembling aspen Salicaceae Malacosoma disstria Hubner forest tent caterpillar Lepidoptera Lasiocampidae feeding deterrence phenolics gallates flavonols 


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  1. ABOU-ZAID, M. M. and NOZZOLILLO, C. 1999. 1-O-Galloyl-α-L-rhamnose from Acer rubrum. Phytochemistry 52:1629–1631.Google Scholar
  2. ABOU-ZAID, M. M., NOZZOLILLO, C., HELSON, B. V., and LOMBARDO, D. A. 2000a. Phenolic composition of leaves of six maple species in the Great Lakes Forest region of Canada. Polyphenol Commun. 1:95–96.Google Scholar
  3. ABOU-ZAID, M. M., GRANT, G. G., HELSON, B. V., BENINGER, C. W., and DE GROOT, P. 2000b. Phenolics from deciduous leaves and coniferous needles as sources of novel control agents for lepidopteran forest pests, pp. 398–417, In Shahidi and Chi-Tang Ho (eds.). Phytochemicals and Phytopharmaceuticals. AOCS Press, Champaign, Illinois.Google Scholar
  4. ADDY, N. D. 1969. Rearing the forest tent caterpillar on an artificial diet. J. Econ. Entomol. 62:270.Google Scholar
  5. BAILEY, A. E., ASPLUND, R. O., and ALI, M. S. 1986. Isolation of methyl gallate as the antitumor principle of Acer saccharinum. J. Nat. Prod. 49:1149–1150.PubMedGoogle Scholar
  6. BATE-SMITH, E. C. 1978. Systematic aspects of the astringent tannins of Acer species. Phytochemistry 17:1945–1948.Google Scholar
  7. BLANEY, W. M., SIMMONDS, M. S. J., LEY, S. V., ANDERSON, J. C., SMITH, S. C., and Wood, A. 1994. Effect of azadirachtin-derived decalin (perhydronaphthalene) and dihydrofuranacetal (furo[2,3-b]pyran) fragments on the feeding behavior of Spodoptera littoralis. Pest. Sci. 40:169–173.Google Scholar
  8. DELENDICK, T. J. 1990. A survey of foliar flavonoids in the Aceraceae. Mem. NY Bot. Gard. 54:1–129.Google Scholar
  9. FARRAR, J. L. 1995. Trees in Canada. Canadian Forest Service & Fitzhenry and Whiteside Ltd., Markham, Ontario, Canada.Google Scholar
  10. HADDOCK, E. A., GUPTA, R. K., AL-SHAFI, S. M. K., LAYDEN, K., HASLAM., E., and MAGNOLATO, D. 1982. The metabolism of gallic acid and hexahydroxydiphenic acid in plants A: Biogenetic and molecular taxonomic considerations. Phytochemistry 21:1049–1062.Google Scholar
  11. HARBORNE, J. B. 1994. The Flavonoids: Advances in Research Since 1986. Chapman and Hall, London.Google Scholar
  12. HASLAM, E. 1965. Galloyl esters in the Aceraceae. Phytochemistry 4:495–498.Google Scholar
  13. HOWSE, G. M. 1995. Forest Insect Pests in the Ontario Region. In J. A. Armstrong and W. G. H. Ives (eds.). Forest Insect Pests in Canada. Natural Resources Canada, Ottawa, Ontario, Canada.Google Scholar
  14. MARKHAM, K. R. 1982. Techniques of Flavonoid Identification, Academic Press, London.Google Scholar
  15. MüLLER-SCHWARZE, D., SCHULTE, B. A., SUN, L., MüLLER-SCHWARZE, A., and MüLLER-SCHWARZE, C. 1994. Red maple (Acer rubrum) inhibits feeding by beaver (Castor canadensis). J. Chem. Ecol. 20:2021–2034.Google Scholar
  16. NICOL, R. W., ARNASON, J. T., HELSON, B. V., and ABOU-ZAID, M. M. 1997. Effect of host and non-host trees on the growth and development of the forest tent caterpillar, Malacosoma disstria Hubner (Lepidoptera: Lasiocampidae). Can. Entomol. 129:995–1003.Google Scholar
  17. RICKLEFS, R. E. and MATTHEWS, K. 1982. Chemical characteristics of the foliage of some deciduous trees in southeastern Ontario. Can. J. Bot. 60:2037–2045.Google Scholar
  18. SINGH, P. and MOORE, R. F. 1985. Handbook of Insect Rearing, Vol II. Elsevier Science Publishers, Amsterdam, The Netherlands, 369 pp.Google Scholar
  19. SLACANIN, I., MARSTON, A., HOSTETTMANN, K., DELABAYS, N., and DARABELLAY, C. 1991. Isolation and determination of flavonol glycosides from Epilobium species. J. Chromatogr. 557:391–394.Google Scholar
  20. VAN SUMERE, C., FACHE, P., CASTEELE, K. V., DE COOMAN, L., EVERAERT, E., DE LOOSE, R., and HUTSEBAUT, W. 1993. Improved extraction and reversed phase high performance liquid chromatographic separation of flavonoids and identification of Rosa cultivars. Phytochem. Anal. 4:279–292.Google Scholar

Copyright information

© Plenum Publishing Corporation 2001

Authors and Affiliations

  • Mamdouh M. Abou-Zaid
    • 1
  • Blair V. Helson
    • 1
  • Constance Nozzolillo
    • 2
  • J. Thor Arnason
    • 2
  1. 1.Natural Resources Canada, Canadian Forest ServiceGreat Lakes Forestry CentreSault Ste. MarieCanada
  2. 2.Ottawa-Carleton Institute of BiologyUniversity of OttawaOttawaCanada

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