Skip to main content

Limonoids, Quassinoids, and Related Compounds

  • Chapter
Plant Secondary Metabolism

Abstract

Two major groups of metabolically altered triterpenes, the limonoids (tetranortriterpenoids) and the quassinoids (decanortriterpenoids) are derived from euphol (1) (Fig. 25.1) or tirucallol (2) (Fig. 25.2). To date, these compounds are restricted in distribution to the Rutaceae, Meliaceae, Cneora-ceae, Simaroubaceae, and, perhaps, the Burseraceae (Connolly and Hill, 1991), and occur variously in seeds, fruits, and wood of plants of these families. In general, the limonoid and quassinoid content of leaves has not been examined (Taylor, 1983).

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 429.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 549.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 549.99
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

  • Anon., Neem. A Tree for Solving Global Problems, National Academy Press, Washington, DC, 1992.

    Google Scholar 

  • Ahmed, F. R., A. S. Ng, and A. G. Fallis, 7α-Acetoxydihydronom-ilin: Isolation, spectra, and crystal structure, Can. J. Chem., 56, 1020–1025 (1978).

    Article  CAS  Google Scholar 

  • Arigoni, D., D. H. R. Barton, E. J. Corey, O. Jeger, L. Caglioti, Sukh Dev, P. G. Ferrini, E. R. Glazier, A. Melera, S. K. Pradhan, K. Schaffner, S. Sternhell, J. F. Templeton, and S. Tobinga, Constitution of limonin, Experientia, 16, 41–49 (1960).

    Article  CAS  Google Scholar 

  • Blaskó, G. and G. A. Cordell, Recent developments in the chemistry of plant-derived anticancer agents, in Economic and Medicinal Plant Research, Vol. 2 (H. Wagner, H. Hikino, and N. R. Farnsworth, eds.), 119–191, Academic Press, London, 1988.

    Google Scholar 

  • Borris, R. P. and J. M. Schaeffer, Antiparasitic agents from plants, in Phytochemical Resources for Medicine and Agriculture (H. N. Nigg and D. S. Seigler, eds.), 117–158, Plenum Press, New York, 1992.

    Google Scholar 

  • Broughton, H. B., S. V. Ley, A. M. Z. Slawin, D. J. Williams, and E. D. Morgan, X-ray crystallographic structure determination of detigloyldihydroazdirachtin and reassignment of the structure of the limonoid insect antifeedant azadirachtin, J. Chem. Soc., Chem. Commun., 46–47 (1985).

    Google Scholar 

  • Champagne, D. E., M. B. Isman, and G. H. N. Towers, Insecticidal activity of phytochemicals and extracts of the Meliaceae, in Insecticides of Plant Origin (Arnason, J. T., B. J. R. Philogène, and P. Morand, eds.), ACS Symposium Series 387, 95–109, American Chemical Society, Washington, DC, 1989.

    Chapter  Google Scholar 

  • Champagne, D. E., O. Koul, M. B. Isman, G. G. E. Scudder, and G. H. N. Towers, Biological activity of limonoids from the Rutales, Phytochemistry, 31, 377–394 (1992).

    Article  CAS  Google Scholar 

  • Charlwood, B. V. and K. A. Charlwood, Terpenoid production in plant cell cultures, in Ecological Chemistry and Biochemistry of Plant Terpenoids (J. B. Harborne and F. A. Tomás-Barberán, eds.), Phytochemistry Society of Europe Vol. 31, 95–132, Clarendon, Oxford, 1991.

    Google Scholar 

  • Chitwood, Nematicidal compounds from plants, in Phytochemical Resources for Medicine and Agriculture (H. N. Nigg and D. S. Seigler, eds.), 185–204, Plenum Press, New York, 1992.

    Google Scholar 

  • Connolly, J. D., 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.), 175–213, Academic Press, London, 1983.

    Google Scholar 

  • Connolly, J. D. and R. A. Hill, Triterpenoids, in Terpenoids (B. V. Charlwood and D. V. Banthorpe, eds.), Vol. 7 of Methods in Plant Biochemistry (J. B. Harborne and P. M. Dey, eds.), 331–359, Academic Press, London, 1991.

    Google Scholar 

  • Connolly, J. D. and K. H. Overton, The triterpenoids, in Chemistry of Terpenes and Terpenoids (A. A. Newman ed.), 207–287, Academic Press, London, 1972.

    Google Scholar 

  • Cordell, G. A., Anticancer agents from plants, in Progress in Phytochemistry Vol. 5 (L. Reinhold, J. B. Harborne, and T. Swain, eds.), 273–316, Pergamon, London, 1978.

    Google Scholar 

  • Da Silva, M. F. D. G. F., O. R. Gottlieb, and D. E. Dreyer, Evolution of limonoids in the Meliaceae, Biochem. Syst. Ecol., 12, 299–310(1984).

    Article  Google Scholar 

  • Dreyer, D. L., Limonoids of the Rutaceae, in Chemistry and Chemical Taxonomy of the Rutales (P. G. Waterman and M. F. Grundon, eds.), 215–245, Academic Press, London, 1983.

    Google Scholar 

  • Dreyer, D. L., Biogenetic relationships of degraded triterpenes in the Rutales, in Isopentenoids in Plants (W. D. Nes, G. Fuller, and L. Tsai, eds.), 267–290, Marcel Dekker, Inc., New York, 1984.

    Google Scholar 

  • Epe, B. and A. Mondon, Zur Kenntnis der Bitterstoffe aus Cneoraceen, XII, Tetrahedron Lett., 2015–2018 (1979).

    Google Scholar 

  • Geissman, T. A. and D. H. G. Crout, Organic Chemistry of Secondary Plant Metabolism, Freeman Cooper, San Francisco, 1969.

    Google Scholar 

  • Gershenzon, J. and T. J. Mabry, Secondary metabolites and the higher classification of Angiosperms, Nordic J. Bot., 3, 5–34 (1983).

    Article  CAS  Google Scholar 

  • Harborne, J. B., Recent advances in chemical ecology, Nat. Prod. Rep., 7, 85–109 (1989).

    Article  Google Scholar 

  • Harborne, J. B., Recent advances in the ecological chemistry of plant terpenoids, in Ecological Chemistry and Biochemistry of Plant Terpenoids (J. B. Harborne and F. A. Tomás-Barberán, eds.), Phytochemistry Society of Europe Vol. 31, 399–426, Clarendon, Oxford, 1991.

    Google Scholar 

  • Hasegawa, S., M. N. Patel, and R. C. Snyder, Reduction of limonin bitterness in navel orange juice serum with bacterial cells immobilized in acrylamide gel, J. Agric. Food Chem., 30, 509–511 (1982).

    Article  CAS  Google Scholar 

  • Hasegawa, S., R. D. Bennett, and V. P. Maier, Biosynthesis of limonoids in Citrus seedlings, Phytochemistry, 23, 1601–1603 (1984).

    Article  CAS  Google Scholar 

  • Hasegawa, S., V. P. Maier, Z. Herman, and P. Ou, Phytohormone bioregulation of nomilin biosynthesis in Citrus limon seedlings, Phytochemistry, 25, 1323–1325 (1986).

    Article  CAS  Google Scholar 

  • Hegnauer, R., Chemical characters and the classification of the Rutales, in Chemistry and Chemical Taxonomy of the Rutales (P. G. Waterman and M. F. Grundon, eds.), Annual Proceedings Phytochemistry Society of Europe 22), 401–440, Academic Press, London, 1983.

    Google Scholar 

  • Kigodi, P. G. K., G. Blaskó, Y. Thebtaranonth, J. M. Pezzuto, and G. A. Cordell, Spectroscopic and biological investigation of nimbolide and 28-deoxonimbolide from Azadirachta indica, J. Nat. Prod., 52, 1246–1251 (1989).

    Article  PubMed  CAS  Google Scholar 

  • Klocke, A., Natural plant compounds useful in insect control, in Allelochemicals: Role in Agriculture and Forestry (G. R. Waller, ed.), ACS Symposium Series 330, 396–415, American Chemical Society, Washington, DC, 1987.

    Chapter  Google Scholar 

  • Klocke, J. A., M. Arisawa, S. S. Handa, A. D. Kinghorn, G. A. Cordell, and N. R. Farnsworth, Growth inhibitory, insecticidal and antifeedant effects of some antileukemic and cytotoxic quassinoids on two species of agricultural pests, Experientia, 41, 379–382 (1985).

    Article  PubMed  CAS  Google Scholar 

  • Klocke, J. A., Limonoids, phenolics and furanocoumarins as insect antifeedants, repellents, and growth inhibitory compounds, in Insecticides of Plant Origin (J. T. Arnason, B. J. R. Philogène, and P. Morand, eds.), ACS Symposium Series 387, 136–149, American Chemical Society, Washington, DC, 1989.

    Chapter  Google Scholar 

  • Kraus, W., M. Bokel, A. Klenk, and H. Pöhnl, Structure of azadirachtin and 22,23-dihydro-23ß-methoxyazadirachtin, Tetrahedron Lett., 26, 6435–6446 (1985).

    Article  CAS  Google Scholar 

  • Kraus, W., M. Bökel, A. Bruhn, R. Cramer, I. Klaiber, A. Klenk, G. Nagl, H. Pöhnl, H. Sadlo, and B. Vogler, Structure determination by NMR of Azadirachta indica A. Juss. (Meliaceae), Tetrahedron, 43, 2817–2830 (1987).

    Article  CAS  Google Scholar 

  • Kraus, W., W. Grimminger, and G. Sawitski, Toonacilin and 6-acetoxytoonacilin, two novel ß-seco-tetranortriterpenoids with antifeeding activity, Angew. Chem. Int. Ed., 17, 452–453 (1978).

    Article  Google Scholar 

  • Kraus, W., R. Kramer, M. Bokel, and G. Sawitzki, New insect antifeedants from Azadirachta indica and Melia azedarach, in Natural Pesticides from the Neem Tree (Azadirachta indica A. Juss.) (H. Schmutterer, K. R. S. Ascher, and H. Rembold, eds.), Proceedings 1st International Neem Conferences, 53–62, 1980.

    Google Scholar 

  • Kubo, I. and J. A. Klocke, Limonoids as insect control agents, Les Médiateurs Chemiques, in Les Colloques de I’INRA 7, 206–219, 1981.

    Google Scholar 

  • Kubo, I. and J. Klocke, Insect ecdysis inhibitors, in Natural Resistance of Plants to Pests (M. B. Green and P. A. Hedin, eds.), ACS Symposium Series 296, 206–219, American Chemical Society, Washington, DC, 1986.

    Chapter  Google Scholar 

  • Kubo, I. and K. Nakanishi, Insect antifeedants and repellents from African plants, in Host Plant Resistance to Pests (P. A. Hedin, ed.), ACS Symposium Series 62, 165–178, American Chemical Society, Washington, DC, 1977.

    Chapter  Google Scholar 

  • Lavie, D., M. K. Jain, and S. R. Shpan-Gabrielith, A locust phagorepellent from two Melia species, J Chem. Soc., Chem. Commun. 910–911 (1967).

    Google Scholar 

  • Ley, S. V., H. Lovell, and D. J. Williams, Chemistry of insect antifeedants from Azadirachta indica, Part 14. Absolute configuration of azadirachtin, J. Chem. Soc., Chem. Commun., 1304–1306 (1992).

    Google Scholar 

  • Ley, S. V., D. Santafianos, W. M. Blaney, and M. S. J. Simmonds, Synthesis of a hydroxy dihydrofuran acetal related to azadirachtin: A potent insect antifeedant, Tetrahedron Lett., 28, 221–224 (1987).

    Article  CAS  Google Scholar 

  • Maclachlan, L. K. and D. A. H. Taylor, Limonoids from Nymania capensis, Phytochemistry, 21, 1701–1703 (1982).

    CAS  Google Scholar 

  • Maier, V. P., Chemistry and significance of selected Citrus limonoids and flavonoids, in Chemistry and Chemical Taxonomy of the Rutales (P. G. Waterman and M. F. Grundon, eds.), 319–342, Academic Press, London, 1983.

    Google Scholar 

  • Mikolajczak, K. L. and D. K. Reed, Extractives of seeds of the Meliaceae: Effects on Spodopterafrugiperda (J. E. Smith), Acalymma vittatum (F.), andArtemia salina Leach, J. Chem. Ecol., 75, 99–111(1987).

    Article  Google Scholar 

  • Mikolajczak, K. L., D. Weisleder, L. Parkanyi, and J. Clardy, A limonoid antifeedant from seed of Carapa procera, J. Nat. Prod., 51, 606–610 (1988).

    Article  PubMed  CAS  Google Scholar 

  • Mikolajczak, K. L., B. W. Zilkowski, and R. J. Bartelt, Effect of meliaceous seed extracts on growth and survival of Spodoptera frugiperda (J. E. Smith), J. Chem. Ecol., 75, 121–128 (1989).

    Article  Google Scholar 

  • Mondon, A. and B. Epe, Bitter principles of Cneoraceae, Fortschr. Chem. Org. Naturst., 44, 101–188 (1983).

    Article  CAS  Google Scholar 

  • Nakatani, M., J. C. James, and K. Nakaniski, Isolation and structures of trichilins, antifeedants against the southern army worm, J. Am. Chem. Soc., 103, 1228–1230 (1981).

    Article  CAS  Google Scholar 

  • Oelrichs, P. B., M. W. Hill, P. J. Vallely, J. K. Macleod, and T. F. Molinski, Toxic tetranortriterpenes Melia azedarach, Phytochemistry, 22, 531–534 (1983).

    Article  CAS  Google Scholar 

  • Polonsky, J., Chemistry and biological activity of the quassinoids, in Chemistry and Chemical Taxonomy of the Rutales (P. G. Waterman and M. F. Grundon, eds.), 247–266, Academic Press, London, 1983.

    Google Scholar 

  • Polonsky, J., Recent advances in the quassinoid field, in Advances in Medical Phytochemistry (D. Barton and W. D. Ollis, eds.), 125–137, Libbey, London, 1986.

    Google Scholar 

  • Rembold, H., Azadirachtins: Their structure and mode of action, in Insecticides of Plant Origin (Arnason, J. T., B. J. R. Philogène, and P. Morand, eds.), ACS Symposium Series 387, 150–163, American Chemical Society, Washington, DC, 1989.

    Chapter  Google Scholar 

  • Saxena, R. C, Insecticides from neem, in Insecticides of Plant Origin (J. T. Arnason, B. J. R. Philogène, and P. Morand, eds.), ACS Symposium Series, 387, 110–135, American Chemical Society, Washington, DC, 1989.

    Chapter  Google Scholar 

  • Schroeder, D. R. and K. Nakanishi, A simplified isolation procedure for azadirachtin, J. Nat. Prod., 50, 241–244 (1987).

    Article  PubMed  CAS  Google Scholar 

  • Seigler, D. S., Terpenes and plant phylogeny, in Phytochemistry and Angiosperm Phylogeny (D. A. Young and D. S. Seigler, eds.), 117–148, Praeger, New York, 1981.

    Google Scholar 

  • Siddiqui, S., B. S. Siddiqui, S. Faizi, and T. Mahmood, Tetracyclic & riterpenoids and their derivatives from Azadirachta indica, J. Nat. Prod., 51, 30–43 (1988).

    Article  CAS  Google Scholar 

  • Simao, S. M., E. L. Barreiros, M. F. D. G. F. Da Silva, and O. R. Gottlieb, Chemogeographic evolution of quassinoids in Simaroubaceae, Phytochemistry, 30, 853–865 (1991).

    Article  CAS  Google Scholar 

  • Smutterer, H., K. R. S. Ascher, and H. Rembold, Natural resources from the neem tree, in Proceedings 1st International Neem Conference, 1980.

    Google Scholar 

  • Stone, R., A biopesticidal tree begins to blossom, Science, 255, 1070–1071 (1992).

    Article  PubMed  CAS  Google Scholar 

  • Taylor, D. A. H., Biogenesis, distribution, and systematic significance of limonoids in the Meliaceae, Cneoraceae, and allied taxa, in Chemistry and Chemical Taxonomy of the Rutales (P. G. Waterman and M. F. Grundon, eds.), 353–375, Academic Press, London, 1983.

    Google Scholar 

  • Thorne, R. F., A phylogenetic classification of the Angiospermae, in Evolutionary Biology, Vol. 9 (M. K. Hecht, W. C. Steere and B. Wallace, eds.), 35–106, Plenum Press, New York, 1976.

    Chapter  Google Scholar 

  • Towers, G. H. N., P. A. Spencer, and E. Rodriguez, Recent topics in phytochemical ecology research, in Phytochemical Ecology: Allelochemicals, Mycotoxins, and Insect Pheromones and Allomones (C. H. Chou and G. R. Waller, eds.), 1–17, Institute of Botany, Academia Sinica Monograph Series 9, Taipei, 1989.

    Google Scholar 

  • Waterman, P. G. Phylogenetic implications of the distribution of secondary metabolites within the Rutales Chemistry and Chemical Taxonomy of the Rutales; P. G. Waterman & M. F. Grundon, eds., 377–400 Academic Press, London, 1983.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1998 Springer Science+Business Media New York

About this chapter

Cite this chapter

Seigler, D.S. (1998). Limonoids, Quassinoids, and Related Compounds. In: Plant Secondary Metabolism. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4913-0_25

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-4913-0_25

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-7228-8

  • Online ISBN: 978-1-4615-4913-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics