Skip to main content
SpringerLink
Log in

Phytochemistry of the Meliaceae

So Many Terpenoids, So Few Insecticides

  • Chapter
Phytochemical Diversity and Redundancy in Ecological Interactions

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 30))

Abstract

Utilization of, and scientific interest in, botanical insecticides diminished precipitously following the introduction of Ddt, parathion, and numerous other synthetic insecticides in the late 1940’s and early 1950’s. However, concerns for human health and environmental impacts of synthetic insecticides (along with other pesticides) has provided the impetus for the search for alternative pest management products. Investigations into new botanical insecticides have increased substantially since the early 1980’s. In fact, one plant species is almost entirely responsible for reigniting interest and credibility in the discovery, development and use of botanical insecticides: the Indian neem tree, Azadirachta indica A. Juss.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.00
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. SCHMUTTERER, H. (ed.), 1995. The Neem Tree Azadirachta indica A. Juss. and Other Meliaceous Plants: Sources of Unique Natural Products for Integrated Pest Management, Medicine, Industry and Other Purposes. Vch, Weinheim, p. 696.

    Google Scholar 

  2. NAWROT, J., KOUL, O., ISMAN, M.B., HARMATHA, K., 1991. Naturally occurring an-tifeedants: effects on two polyphagous lepidopterans, J. Appl. Ent. 112: 194–201.

    Article  Google Scholar 

  3. MULLIN, C.A., MASON, C.H., CHOU, J.C., LINDERMAN, J.R., 1992. Phytochemical antagonism of y-aminobutyric acid based resistances in Diabrotica. In: Molecular Mechanisms of Insect Resistance (C.A. Mullin and S.G. Scott, eds.). American Chemical Society, Washington, D.C., pp. 288–308.

    Chapter  Google Scholar 

  4. GOULD, F., 1991. Evolutionary potential of crop pests, Amer. Sci. 79: 496–507.

    Google Scholar 

  5. TABASHNIK, B.E., CUSHING, N.L., FINSON, N., JOHNSON, M.W., 1990. Field development of resistance to Bacillus thuringiensis in diamondback moth (Lepidoptera: Plutellidae), J. Econ. Entomol. 83: 1671–1676.

    Google Scholar 

  6. FRAZIER, J.L., 1986. The perception of plant allelochemicals that inhibit feeding. In: Molecular Aspects of Insect-Plant Associations (L.B. Brattsten and S. Ahmad, eds.). Plenum Press, New York, pp. 1–42.

    Chapter  Google Scholar 

  7. JERMY, T., 1990. Prospects of antifeedant approaches to pest control — a critical review, J. Chem. Ecol. 16:3151–3166.

    Article  CAS  Google Scholar 

  8. SCHOONHOVEN, L.M., 1982. Biological aspects of antifeedants, Entomol. exp. appl. 31: 57–69.

    Article  CAS  Google Scholar 

  9. GRIFFITHS, D.C., MANIAR, S.P., MERRIT, L.A., MUDD, A., PICKETT, J.A., PYE, B.J., SMART, L.E., WADHAMS, L.J., 1991. Laboratory evaluation of pest management strategies combining antifeedants with insect growth regulator insecticides, Crop Protection 10: 145–151.

    Article  CAS  Google Scholar 

  10. MILLER, J.R., COWLES, R.S., 1990. Stimulo-deterrent diversion: a concept and its possible application to onion maggots, J. Chem. Ecol. 16: 3197–3212.

    Article  CAS  Google Scholar 

  11. MURRAY, K.D., ALFORD, A.R., GRODEN, E., DRUMMOND, F.A., STORCH, R.H., BENTLEY, M.D., SUGATHAPALA, P.M., 1993. Interactive effects of an antifeedant used with Bacillus thuringiensis var. san diego delta endotoxin on Colorado potato beetle (Coleoptera: Chrysomelidae), J. Econ. Entomol. 86: 1793–1801.

    CAS  Google Scholar 

  12. CHAMPAGNE, D.E., ISMAN, M.B., TOWERS, G.H.N., 1989. Insecticidal activity of phyto-chemicals and extracts of the Meliaceae. In: Insecticides of Plant Origin (J.T. Arnason, B.J.R. Philogene and P. Morand, eds.). American Chemical Society, Washington, D.C., pp. 95–109.

    Chapter  Google Scholar 

  13. ISMAN, M.B., 1993. Growth inhibitory and antifeedant effects of azadirachtin on six noctuids of regional economic importance, Pestic. Sci. 38: 57–63.

    Article  CAS  Google Scholar 

  14. JERMY, T., BERNAYS, E.A., SZENTESI, A., 1982. The effect of repeated exposure to feeding deterrents on their acceptability to phytophagous insects. In: Insect-Plant Relationships (J.H. Visser and A.K. Minks, eds.), Pudoc, Wageningen, pp. 25–32.

    Google Scholar 

  15. RAFFA, K.F., FRAZIER, J., 1988. A generalized model for quantifying behavioral de-sensiti-zation to antifeedants, Entomol. exp. appl. 46: 93–100.

    Article  Google Scholar 

  16. CONNOLLY, J.D., 1983. Chemistry of the limonoids of the Meliaceae and Cneoraceae. In: Chemistry and Chemical Taxonomy of the Rutales (P.G. Waterman and M.F. Grundon, eds.), Academic Press, London, pp. 175–213.

    Google Scholar 

  17. KRAUS, W., 1995. Azadirachtin and other triterpenoids. In: The Neem Tree, Azadirachta indica A. Juss. and Other Meliaceous Plants: Sources of Unique Natural Products for Integrated Pest Management, Medicine, Industry and Other Purposes (H. Schmutterer, ed.), Vch, Weinheim, pp. 35–88.

    Google Scholar 

  18. CHAMPAGNE, D.E., KOUL, O., ISMAN, M.B., SCUDDER, G.G.E., TOWERS, G.H.N., 1992. Biological activity of limonoids from the Rutales, Phytochem. 31: 377–394.

    Article  CAS  Google Scholar 

  19. BUTTERWORTH, J.H., MORGAN, E.D., 1968. Isolation of a substance that suppresses feeding in locusts, J. Chem. Soc, Chem. Commun., 23–24.

    Google Scholar 

  20. KRAUS, W., BOKEL, M., KLENK, A., PÖHNL, H., 1985. The structure of azadirachtin and 22,23-dihydro-23ß-methoxyazadirachtin, Tetrahedron Lett. 26: 6435–6438.

    Article  CAS  Google Scholar 

  21. LEY, S.V., DENHOLM, A.A., WOOD, A., 1993. The chemistry of azadirachtin, Nat. Prod. Rep., 100–157.

    Google Scholar 

  22. KRAUS, W., BOKEL, M., SCHWINGER, M., VOGLER, B., SOELLNER, R., WENDISCH, D., STEFFENS, R., WACHENDORFF, U., 1993. The chemistry of azadirachtin and other insecticidal constituents of Meliaceae. In: Phytochemistry and Agriculture (T.A. van Beek and H. Breteler, eds.), Clarendon Press, Oxford, pp. 18–39.

    Google Scholar 

  23. LEE, S.A., KLOCKE, J.A., BARNBY, M.A., YAMASAKI, R.B., BALANDRIN, M.F., 1991. Insecticidal constituents of Azadirachta indica and Melia azedarach (Meliaceae). In: Naturally Occurring Pest Bioregulators (P.A. Hedin, ed.), American Chemical Society, Washington, D.C., pp. 293–304.

    Chapter  Google Scholar 

  24. HANSEN, D.J., CUOMO, J., KHAN, M., GALLAGHER, R.T., ELLENBERGER, W.P., 1994. Advances in neem and azadirachtin chemistry and bioactivity. In: Natural and Engineered Pest Managment Agents (P.A. Hedin, J.J. Menn and R. M. Hollingworth, eds.), American Chemical Society, Washington, D.C., pp. 103–129

    Google Scholar 

  25. REMBOLD, H., PUHLMANN, I., 1993. Phytochemistry and biological activity of metabolites from tropical Meliaceae. In: Phytochemical Potential of Tropical Plants (K.R. Downum, J.T. Romeo and H.A. Stafford, eds.), Plenum Press, New York, pp. 153–165.

    Chapter  Google Scholar 

  26. REMBOLD, H., PUHLMANN, I., 1995. Azadirachtins: structure and activity relations in case of Epilachna varivestis. In: The Neem Tree Azadirachta indica A. Juss. and Other Meliaceous Plants: Sources of Unique Natural Products for Integrated Pest Management, Medicine, Industry and Other Purposes (H. Schmutterer, ed.), Vch, Weinheim, pp. 222–230.

    Google Scholar 

  27. BLANEY, W.M., SIMMONDS, M.S.J., LEY, S.V., ANDERSON, J.C., TOOGOOD, P.L., 1990. Antifeedant effects of azadirachtin and structurally related compounds on lepidopterous larvae, Entomol. exp. appl. 55: 149–160.

    Article  CAS  Google Scholar 

  28. SIMMONDS, M.S.J., BLANEY, W.M., LEY, S.V., ANDERSON, J.C., TOOGOOD, P.L., 1990. Azadirachtin: structural requirements for reducing growth and increasing mortality in lepidopterous larvae, Entomol. exp. appl. 55: 169–181.

    Article  CAS  Google Scholar 

  29. BLANEY, W.M., SIMMONDS, M.S.J., LEY, S.V., ANDERSON, J.C., SMITH, S.C., WOOD, A., 1994. Effect of azadirachtin-derived decalin (perhydronaphthalene) and dihydrofuranacetal (furo[2,3–6]pyran) fragments on the feeding behaviour of Spodoptera littoralis, Pestic. Sci. 40: 169–173.

    Article  CAS  Google Scholar 

  30. REMBOLD, H., 1989. Isomeric azadirachtins and their mode of action. In: Focus on Phytochemical Pesticides. Volume 1, The Neem Tree (M. Jacobson, ed.), CRC Press, Boca Raton, pp. 47–67.

    Google Scholar 

  31. KLOCKE, J.A., 1987. Natural plant compounds useful in insect control. In: Allelochemicals: Role in Agriculture and Forestry (G.R. Waller, ed.), American Chemical Society, Washington, D.C., pp. 396–415.

    Chapter  Google Scholar 

  32. YAMASAKI, R.B., KLOCKE, J.A., 1989. Structure-bioactivity relationships of salannin as an antifeedant against the Colorado potato beetle (Leptinotarsa decemlineata), J. Agric. Food Chem. 37: 1124–1130.

    Article  Google Scholar 

  33. MABBERLEY, D.J., 1984. A monograph of Melia in Asia and the Pacific. The history of white cedar and Persian lilac, Garden’s Bulletin 37: 49–64.

    Google Scholar 

  34. ISMAN, M.B., 1995. Leads and prospects for the development of new botanical insecticides, Rev. Pestic. Toxicol. 3: 1–20.

    CAS  Google Scholar 

  35. CHEN, W., ISMAN, M.B., CHIU, S.-F., 1995. Antifeedant and growth inhibitory effects of the limonoid toosendanin and Melia toosendan extractson the variegated cutworm, Peridroma saucia (Lep., Noctuidae), J. Appl. Ent. 119: 367–370.

    Article  Google Scholar 

  36. AHN, J.-W., CHOI, S.-U., LEE, C.-O., 1994. Cytotoxic limonoids from Melia azedarach var. japonica, Phytochem. 36: 1493–1496.

    Article  CAS  Google Scholar 

  37. ZHOU, J.-B., OKAMURA, H., IWAGAWA, T., NAKATANI, M., 1995. Limonoid antifeedants from Melia toosendan, Phytochem. 41:117–120.

    Article  Google Scholar 

  38. KHALID, S.A., FAROUK, A., GEARY, T.G., JENSEN, J.B., 1986. Potential antimalarial candidates from African plants: an in vitro approach using Plasmodium falciparum, J. Ethno-pharmacol. 15: 201–209.

    Article  CAS  Google Scholar 

  39. FRASER, L.A., MULHOLLAND, D.A., NAIR, J.J., 1994. Limonoids from the seed of Turraea floribunda, Phytochem. 35: 455–458.

    Article  CAS  Google Scholar 

  40. SEGURA, R., CALDERON, J., TOSCANO, R., GUTIERREZ, A., MATA, R., 1994. Cedre-lanolide I, a new limonoid from Cedrela salvadorensis, Phytochem. Soc. N. Amer. Newslett. 4(1): 29.

    Google Scholar 

  41. CHAMPAGNE, D.E., ISMAN, M.B., DOWNUM, K.R., TOWERS, G.H.N., 1993. Insecticidal and growth-reducing activity of foliar extracts from Meliaceae, Chemoecology 4: 165–173.

    Article  Google Scholar 

  42. GOVINDACHARI, T.R., KRISHNA KUMARI, G.N., SURESH, G., 1995. Triterpenoids from Walsura piscida, Phytochem. 39: 167–170.

    Article  CAS  Google Scholar 

  43. POWELL, R.G., MIKOLAJCZAK, K.L., ZILKOWSKI, B.W., 1991. Limonoid antifeedants from seed of Sandoricum koetjape, J. Nat. Prod. 54: 241–246.

    Article  PubMed  CAS  Google Scholar 

  44. AGOSTINHO, S.M.M., SILVA, M.F. DAS G.F. DA, FERNANDES, J.B., VIEIRA, P.C., PIN-HEIRO, A.L., VILELA, E.F., 1994. Limonoids from Toona ciliata and speculations on their chemosystematic and ecological significance, Biochem. Syst. Ecol. 22: 323–328.

    Article  CAS  Google Scholar 

  45. XIE, Y.S., ISMAN, M.B., GUNNING, P., MACKINNON, S., ARNASON, J.T., TAYLOR, D.R., SANCHEZ, P., HASBUN, C., TOWERS, G.H.N., 1994. Biological activity of extracts of Trichilia species and the limonoid hirtin against lepidopteran larvae, Biochem. Syst. Ecol. 22: 129–136.

    Article  CAS  Google Scholar 

  46. CHAN, W.R., TAYLOR, D.R., 1966. Hirtin and deacetylhirtin: new “limonoids”, from Trichilia hirta, J. Chem. Soc, Chem. Commun., 206–207.

    Google Scholar 

  47. KOUL, O., ISMAN, M.B., 1992. Toxicity of the limonoid allelochemical cedrelone to noctuid larvae, Entomol. exp. appl. 64: 281–287.

    Article  CAS  Google Scholar 

  48. GUNNING, P.J., JEFFS, L.B., ISMAN, M.B., TOWERS, G.H.N., 1994. Two limonoids from Chisocheton microcarpus, Phytochem. 36: 1245–1248.

    Article  CAS  Google Scholar 

  49. BORDOLOI, M., SAIKIA, B., MATHUR, R.K., GOSWAMI, B.N., 1993. A meliacin from Chisocheton paniculatus, Phytochem. 34: 583–584.

    Article  CAS  Google Scholar 

  50. SEGURA-CORREA, R., MATA, R., ANAYA, A.L., HERNANDEZ-BAUTISTA, B., VILLENA, R., SORIANO-GARCIA, M., BYE, R., LINARES, E., 1993. New tetranortriterpenoids from Swietenia humilis, J. Nat. Prod. 56: 1567–1574.

    Article  CAS  Google Scholar 

  51. ISHIBASHI, F., SATASOOK, C., ISMAN, M.B., TOWERS, G.H.N., 1993. Insecticidal 1 H-cyclopenta[6]benzofurans from Aglaia odorata (Lour.)(Meliaceae), Phytochem. 32: 307–310.

    Article  CAS  Google Scholar 

  52. KUBO, I., KLOCKE, J.A., 1982. An insect growth inhibitor from Trichilia roka (Meliaceae), Experientia 38: 63–640.

    Article  Google Scholar 

  53. BERENBAUM, M., 1985. Brementown revisited: interactions among allelochemicals in plants, Rec. Adv. Phytochem. 19: 139–169.

    CAS  Google Scholar 

  54. FENG, R., CHEN, W., ISMAN, M.B., 1995. Synergism of malathion and inhibition of midgut esterase activities by an extract from Melia toosendan (Meliaceae), Pestic. Biochem. Physiol. 53:34–41.

    Article  CAS  Google Scholar 

  55. ISMAN, M.B., KOUL, O., LUCZYNSKI, A., KAMINSKI, J., 1990. Insecticidal and an-tifeedant bioactivities of neem oils and their relationship to azadirachtin content, J. Agric. Food Chem. 38: 1406–1411.

    Article  CAS  Google Scholar 

  56. FENG, R., ISMAN, M.B., 1995. Selection for resistance to azadirachtin in the green peach aphid, Myzus persicae, Experientia 51: 831–833.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Plant Science, University of British Columbia, Vancouver, British Columbia, Canada, V6T 1Z4

    Murray B. Isman

  2. Department of Botany, University of British Columbia, Vancouver, British Columbia, Canada, V6T 1Z4

    Hideyuki Matsuura & G. H. Neil Towers

  3. Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada, K1N 6N5

    Shawna MacKinnon & Tony Durst

  4. Department of Biology, University of Ottawa, Ottawa, Ontario, Canada, K1N 6N5

    John T. Arnason

Authors
  1. Murray B. Isman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hideyuki Matsuura
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shawna MacKinnon
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tony Durst
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. H. Neil Towers
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. John T. Arnason
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

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

    John T. Romeo

  2. USDA, Beltsville, Maryland, USA

    James A. Saunders

  3. University of Maryland, College Park, Maryland, USA

    Pedro Barbosa

Rights and permissions

Reprints and permissions

Copyright information

© 1996 Springer Science+Business Media New York

About this chapter

Cite this chapter

Isman, M.B., Matsuura, H., MacKinnon, S., Durst, T., Towers, G.H.N., Arnason, J.T. (1996). Phytochemistry of the Meliaceae. In: Romeo, J.T., Saunders, J.A., Barbosa, P. (eds) Phytochemical Diversity and Redundancy in Ecological Interactions. Recent Advances in Phytochemistry, vol 30. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1754-6_6

Download citation

  • DOI: https://doi.org/10.1007/978-1-4899-1754-6_6

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-1756-0

  • Online ISBN: 978-1-4899-1754-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation