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).
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References
Anon., Neem. A Tree for Solving Global Problems, National Academy Press, Washington, DC, 1992.
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).
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).
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.
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.
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).
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.
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).
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.
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.
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.
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.
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.
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.
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).
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.
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.
Epe, B. and A. Mondon, Zur Kenntnis der Bitterstoffe aus Cneoraceen, XII, Tetrahedron Lett., 2015–2018 (1979).
Geissman, T. A. and D. H. G. Crout, Organic Chemistry of Secondary Plant Metabolism, Freeman Cooper, San Francisco, 1969.
Gershenzon, J. and T. J. Mabry, Secondary metabolites and the higher classification of Angiosperms, Nordic J. Bot., 3, 5–34 (1983).
Harborne, J. B., Recent advances in chemical ecology, Nat. Prod. Rep., 7, 85–109 (1989).
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.
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).
Hasegawa, S., R. D. Bennett, and V. P. Maier, Biosynthesis of limonoids in Citrus seedlings, Phytochemistry, 23, 1601–1603 (1984).
Hasegawa, S., V. P. Maier, Z. Herman, and P. Ou, Phytohormone bioregulation of nomilin biosynthesis in Citrus limon seedlings, Phytochemistry, 25, 1323–1325 (1986).
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.
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).
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.
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).
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.
Kraus, W., M. Bokel, A. Klenk, and H. Pöhnl, Structure of azadirachtin and 22,23-dihydro-23ß-methoxyazadirachtin, Tetrahedron Lett., 26, 6435–6446 (1985).
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).
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).
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.
Kubo, I. and J. A. Klocke, Limonoids as insect control agents, Les Médiateurs Chemiques, in Les Colloques de I’INRA 7, 206–219, 1981.
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.
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.
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).
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).
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).
Maclachlan, L. K. and D. A. H. Taylor, Limonoids from Nymania capensis, Phytochemistry, 21, 1701–1703 (1982).
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.
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).
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).
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).
Mondon, A. and B. Epe, Bitter principles of Cneoraceae, Fortschr. Chem. Org. Naturst., 44, 101–188 (1983).
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).
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).
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.
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.
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.
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.
Schroeder, D. R. and K. Nakanishi, A simplified isolation procedure for azadirachtin, J. Nat. Prod., 50, 241–244 (1987).
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.
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).
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).
Smutterer, H., K. R. S. Ascher, and H. Rembold, Natural resources from the neem tree, in Proceedings 1st International Neem Conference, 1980.
Stone, R., A biopesticidal tree begins to blossom, Science, 255, 1070–1071 (1992).
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.
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.
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.
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.
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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
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DOI: https://doi.org/10.1007/978-1-4615-4913-0_25
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