Abstract
For a long time, the ability to produce alkaloids was thought to be restricted to the plant kingdom. It is now clear that at least some animals are able to biosynthesize these compounds, even if the remarkable variety of structures found in plants has no parallel in the animal kingdom. Generally, alkaloids are defined as being basic, nitrogen-containing natural compounds. However some compounds, such as colchicine, which contain a nonbasic nitrogen atom, are nevertheless considered as alkaloids. In this chapter, we will use the term alkaloid in a broad sense, but we will not consider nitrogen-containing derivatives such as amino acids, purine and pyrimidine bases, pigments, common poly-amines (e.g., spermine, putrescine), nitro compounds, or cyanogenic glycosides. Similarly, biogenic amines which are widespread in mammals (see Brossi, 1993; Collins, 1983) and alkaloids sequestered or derived from plants by insect herbivores and their natural enemies which are covered elsewhere (see Wink, Chapter 11, this volume) will not be included in this chapter. Even so, it will not be possible to present an exhaustive list of species producing alkaloids, nor an exhaustive list of the alkaloids identified in animals. All major taxa in which alkaloids were described will be considered, however, as well as all major classes of alkaloids in terrestrial animals. Because of the huge number of alkaloids from marine animals, this overview is restricted to a few examples illustrating the diversity of compounds isolated from this source. When possible, review papers in which more detailed information can be found will be quoted.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
General Reviews
Alvarez, M., Salas, M., and Joule, J. A., 1991a, Marine, nitrogen-containing heterocyclic natural products. Structures and syntheses of compounds containing quinoline and/or isoquinoline units, Heterocycles 32:759–795.
Alvarez, M., Salas, M., and Joule, J. A., 1991b, Marine, nitrogen-containing heterocyclic natural products. Structures and syntheses of compounds containing indole units, Heterocycles 32:1391–1429.
Arai, T., and Kubo, A., 1983, Isoquinolinequinones from Actinomycetes and sponges, in: The Alkaloids, Vol. 21 (A. Brossi, ed.), Academic Press, San Diego, pp. 56–100.
Attygalle, A. B., and Morgan, E. D., 1984, Chemicals from the glands of ants, Chem. Soc. Rev. 13:245–278.
Bettini, S., (ed.), 1978, Arthropod Venoms, Springer-Verlag, Berlin, Chapters 6–11.
Blum, M. S., 1981, Sex pheromones in social insects: Chemotaxonomic potential, in: Biosystematics of Social Insects (P. E. House and J.-L. Clément, eds.), Academic Press, San Diego, pp. 163–174.
Blum, M. S., and Hermann, H. R., 1978, Venoms and venom apparatuses of the Formicidae: Myrmeciinae, Ponerinae, Dorylinae, Pseudomyrmecinae, Myrmicinae and Formicinae, in: Arthropod Venoms (S. Bettini, ed.), Springer-Verlag, Berlin, pp. 801–869.
Braekman, J. C., and Daloze, D., 1990, Chemical defense in ants, in: Studies in Natural Products Chemistry, Vol. 6, Part D (Attaur Rahman, ed.), Elsevier, Amsterdam, pp. 421–466.
Brossi, A., 1993, Mammalian alkaloids II, in: The Alkaloids, Vol. 43 (G. A. Cordell, ed.), Academic Press, San Diego, pp. 119–183.
Brown, K. S., and Trigo, J. R., 1995, The ecological activity of alkaloids, in: The Alkaloids, Vol. 47 (G. A. Cordell, ed.), Academic Press, San Diego, pp. 227–354.
Chevolot, L., 1981, Guanidine derivatives, in: Marine Natural Products, Chemical and Biological Perspectives, Vol. 4 (P. J. Scheuer, ed.), Academic Press, New York, pp. 54–91.
Christophersen, C., 1983, Marine indoles, in: Marine Natural Products, Chemical and Biological Perspectives, Vol. 5 (P. J. Scheuer, ed.), Academic Press, New York, pp. 259–285.
Christophersen, C., 1985a, Bioactive metabolites from marine bryozoans. A review, Acta Chem. Scand. 39:517–529.
Christophersen, C., 1985b, Marine alkaloids, in: The Alkaloids, Vol. 24 (A. Brossi, ed.), Academic Press, San Diego, pp. 25–112.
Collins, M. A., 1983, Mammalian alkaloids I, in: The Alkaloids, Vol. 21 (A. Brossi, ed.), Academic Press, San Diego, pp. 329–358.
Daloze, D., Braekman, J. C., and Pasteels, J. M., 1995, Ladybird defence alkaloids: structural, chemotaxonomic and biosynthetic aspects, Chemoecology 5/6:173–183.
Daly, J. W., 1982, Alkaloids of neotropical poison frogs (Dendrobatidae), in: Progress in the Chemistry of Organic Natural Products, Vol. 41 (W. Hertz, H. Grisebach, and G. W. Kirby, eds.), Springer-Verlag, Berlin, pp. 205–340.
Daly, J. W., and Spande, T. F., 1986, Amphibian alkaloids: chemistry, Pharmacology, and biology, in: Alkaloids: Chemical and Biological Perspectives, Vol. 4 (S. W. Pelletier, ed.), Wiley, New York, pp. 1–274.
Daly, J. W., Garraffo, H. M., and Spande, T. F., 1993, Amphibian alkaloids, in: The Alkaloids, Vol. 43 (G. A. Cordell, ed.), Academic Press, New York, pp. 185–288.
Davidson, B. S., 1993, Ascidians: Producers of amino acid derived metabolites, Chem. Rev. 93:1771–1791.
Eisner, T., 1970, Chemical defense against predation in arthropods, in: Chemical Ecology (E. Sondheimer and J. B. Simeone, eds.), Academic Press, San Diego, pp. 157–217.
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 3:1–34
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 4:539–576
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 5:613–663
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 7:269–310
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 8:97–148
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 9:323–364
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 10:497–539
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 11:355–394
Faulkner, D. J., 1986–1995, Marine natural products, Nat. Prod. Rep. 12:223–270.
Garson, M. J., 1993, The biosynthesis of marine natural products, Chem. Rev. 93:1699–1734.
Habermehl, G. G., 1967, The steroid alkaloids: The Salamandra group, in: The Alkaloids, Vol. 9 (R. H. F. Manske and H. L. Holmes, eds.), Academic Press, San Diego, pp. 427–439.
Habermehl, G., 1971, Toxicology, pharmacology, chemistry and biochemistry of salamander venom, in: Venomous Animals and Their Venoms, Vol. 2 (W. Bucherl and E. E. Buckley, eds.), Academic Press, San Diego, pp. 569–584.
Habermehl, G. G., 1981, Venomous Animals and Their Toxins, Springer-Verlag, Berlin.
Hölldobler, B., and Wilson, E. O., 1990, The Ants, Springer-Verlag, Berlin.
Jones, T. H., and Blum, M. S., 1983, Arthropod alkaloids: Distribution, functions, and chemistry, in: Alkaloids: Chemical and Biological Perspectives, Vol. 1 (S. W. Pelletier, ed.), Wiley, New York, pp. 33–84.
King, A. G., and Meinwald, J., 1996, Review of the defensive chemistry of coccinellids, Chem. Rev. 96:1105–1122.
McCormick, K. D., and Meinwald, J., 1993, Neurotoxic acylpolyamines from spider venoms, J. Chem. Ecol. 19:2411–2451.
Molinski, T. F., 1993, Marine pyridoacridine alkaloids: Structure, synthesis and biological activity, Chem. Rev. 93:1825–1834.
Numata, A., and Ibuka, T., 1987, Alkaloids of ants and other insects, in: The Alkaloids, Vol. 31 (A. Brossi, ed.), Academic Press, San Diego, pp. 193–315.
Pasteels, J. M., Braekman, J. C., and Daloze, D., 1988, Chemical defense in the Chrysomelidae, in: The Biology of Chrysomelidae (P. Jolivet, E. Petitpierre, and T. H. Hsiao, eds.), Kluwer, Dordrecht, pp. 233–252.
Pasteels, J. M., Braekman, J. C., and Daloze, D., 1994, Chemical defense in adult leaf beetles updated, in: Novel Aspects of the Biology of Chrysomelidae (P. H. Jolivet, M. L. Cox, and E. Petitpierre, eds.), Kluwer, Dordrecht, pp. 289–301.
Schmidt, J. O., 1986, Chemistry, pharmacology, and ecology of ant venoms, in: Venoms of the Hymenoptera: Biochemical, Pharmacological, and Behavioural Aspects (T. Piek, ed.), Academic Press, San Diego, pp. 425–508.
Tu, T., (ed.), 1984, Handbook of Natural Toxins, Vol. 2, Dekker, New York, Chapters 12–14.
Tursch, B., Braekman, J. C., and Daloze, D., 1976, Arthopod alkaloids, Experientia 32:401–407.
Witkop, B., and Gossinger, E., 1983, Amphibian alkaloids, in: The Alkaloids, Vol. 21 (A. Brossi, ed.), Academic Press, San Diego, pp. 139–253.
Specialist References
Attygalle, A. B., Cammaerts, M.-C., Cammaerts, R., Morgan, E. D., and Ollett, D. G., 1986, Chemical and ethological studies of the trail pheromone of the ant Manica rubida (Hymenoptera: Formicidae), Phys. Entomol. 11:125–132.
Attygalle, A. B., Xu, S. C., McCormick, K. D., Meinwald, J., Blankespoor, C. L., and Eisner, T., 1993a, Alkaloids of the Mexican bean beetle, Epilachna varivestis (Coccinellidae), Tetrahedron 49:9333–9342.
Attygalle, A. B., McCormick, K. D., Blankespoor, C. L., Eisner, T., and Meinwald, J., 1993b, Azamacrolides: A family of alkaloids from the pupal defensive secretion of a ladybird beetle (Epilachna varivestis), Proc. Natl. Acad. Sci. USA 90:5204–5208.
Attygalle, A. B., Blankespoor, C. L., Eisner, T., and Meinwald, J., 1994, Biosynthesis of a defensive insect alkaloid: Epilachnene from oleic acid and serine, Proc. Natl. Acad. Sci. USA 91:12790–12793.
Ayer, W., and Browne, L. M., 1977, The ladybug alkaloids including synthesis and biosynthesis, Heterocycles 7:685–707.
Blum, M. S., Jones, T. H., Hölldobler, B., Fales, H. M., and Jaouni, T., 1980, Alkaloidal venom mace: Offensive use by a thief ant, Naturwissenschaften 67:144–145.
Braconnier, M. F., Braekman, J. C., Daloze, D., and Pasteels, J. M., 1985, (Z)-1,17-diaminooctadec-9-ene, a novel aliphatic diamine from Coccinellidae, Experientia 41:519–520.
Braekman, J. C., Daloze, D., Pasteels, J. M., Vanhecke, P., Declercq, J. P., Sinnwell, V., and Francke, W., 1987, Tetraponerine-8, an alkaloidal contact poison in a Neoguinean pseudomyrmecine ant, Tetraponera sp., Z. Naturforsch. 42c:627–630.
Brand, J. M., and Mpuru, S. P., 1993, Dufour’s gland and poison gland chemistry of the myrmicine ant, Messor capensis (Mayr), J. Chem. Ecol. 19:1315–1321.
Brophy, J. J., Clezy, P. S., Leung, C. W. F., and Robertson, P. L., 1993, Secondary amines isolated from venom gland of dolichoderine ant, Technomyrmex albipes, J. Chem. Ecol. 19:2183–2192.
Brown, C. A., Watkins, J. F., II, and Eldridge, D. W., 1979, Repression of bacteria and fungi by the army ant secretion: Skatole, J. Kansas Entomol. Soc. 52:119–122.
Brown, W. V., Jones, A. J., Lacey, M. J., and Moore, B. P., 1985, The chemistry of buprestins A and B. Bitter principles of jewel beetles (Coleoptera: Buprestidae), Aust. J. Chem. 38:197–206.
Capelli, E., Attolini, C., Mazza, G., Pavan, M., and De Carli, L., 1982, Studies on the genotoxic effects of pederin, Publ. Istit. Entomol. Univ. Pavia 1982 (21): 1–16.
Cardani, C., Ghiringhelli, D., Mondelli, R., and Selva, A., 1973a, On the methanolysis products of pederin, Gazz. Chim. Ital. 103:247–253.
Cardani, C., Fuganti, C., Ghiringhelli, D., Grasselli, P., Pavan, M., and Valcurone, M. D., 1973b, The biosynthesis of pederin, Tetrahedron Lett. 14:2815–2818.
Daly, J. W., Myers, C. W., and Whittaker, N., 1987, Further classification of skin alkaloids from neotropical poison frogs (Dendrobatidae), with a general survey of toxic/ noxious substances in the Amphibia, Toxicon 25:1023–1095.
Daly, J. W., Secunda, S. I., Garraffo, H. M., Spande, T. F., Wisnieski, A., Nishihira, C., and Cover, J. F., Jr., 1992, Variability in alkaloid profiles in neotropical poison frogs (Dendrobatidae): Genetic versus environmental determinants, Toxicon 30:887–898.
Daly, J. W., Garraffo, H. M., Spande, T. F., Jaramillo, C., and Rand, A. S., 1994a, Dietary source for skin alkaloids of poison frogs (Dendrobatidae)? J. Chem. Ecol. 20:943–955.
Daly, J. W., Secunda, S. I., Garraffo, H. M., Spande, T. F., Wisnieski, A., and Cover, J. F., Jr., 1994b, An uptake system for dietary alkaloids in poison frogs (Dendrobatidae), Toxicon 32:657–663.
Dettner, K., 1983, Vergleichende Untersuchungen zur Wehrchemie und Drüsenmorphologie von Kurzflüglern aus dem Subtribus Philonthina (Coleoptera, Staphylinidae), Z. Naturforsch. 38c:319–328.
De Vijver, C., Macours, P., Braekman, J. C., Daloze, D., and Pasteels, J. M., 1995, Short syntheses of (±)-tetraponerines 5 and 6. The structures of tetraponerines 1 and 2, and a revision of the structures of tetraponerines 5 and 6, Tetrahedron 51:10913–10922.
Dumbacher, J. A., Beeler, B., Garraffo, H. M., Spande, T. F., and Daly, J. W., 1992, Homobatrachotoxin in the genus Pitohui: Chemical defense in birds, Science 258:799–801.
Eisner, T., Goetz, M., Aneshansley, D., Ferstandig-Arnold, G., and Meinwald, J., 1986, Defensive alkaloids in blood of Mexican bean beetle (Epilachua varivestis) Experientia, 42: 204–207.
Ekpa, O., Wheeler, J. W., Cokendelpher, J. C., and Duffield, R. M., 1984, N,N-dimethyl-β-phenylethylamine and bornyl esters from the harvestman Sclerobunus robustus (Arachnida: Opiliones), Tetrahedron Lett. 25:1315–1318.
Enders, D., and Bartzen, D., 1991, Enantioselective total synthesis of harmonine, a defence alkaloid of ladybugs (Coleoptera: Coccinellidae), Liebigs Ann. 569–574.
Enders, D., Tiebes, J., De Kimpe, N., Keppens, M., Stevens, C., Smagghe, G., and Betz, O., 1993, Enantioselective synthesis and determination of the configuration of stenusine, the spreading agent of the beetle Stenus comma, J. Org. Chem. 58:4881–4884.
Escoubas, P., and Blum, M. S., 1990, The biological activities of ant-derived alkaloids, in: Applied Myrmecology: A World Perspective (R. K. Vander Meer, K. Jaffe, and A. Cedeno, eds.), Westview Press, Boulder, pp. 482–489.
Escoubas, P., Le Maire, M., Clément, J.-L., Lhommet, G., and Celerier, J. P., 1987, European Monomorium alkaloids: Toxicity against preys and emitters, in: Chemistry and Biology of Social Insects (J. Eder and H. Rembold, eds.), Verlag J. Peperny, Munich, pp. 419–420.
Fales, H. M., Blum, M. S., Bian, Z., Jones, T. H., and Warwick Don, A., 1984, Volatile compounds from ponerine ants in the genus Mesoponera, J. Chem. Ecol. 10:651–665.
Furusaki, A., Watanabe, T., Matsumoto, T., and Yanagiya, M., 1968, The crystal and molecular structure of pederin di-p-bromobenzoate, Tetrahedron Lett. 9:6301–6304.
Habermehl, G. G., and Haaf, A., 1968, Samandarine and related alkaloids. XVIII. Cholesterol as precursor in the biosynthesis of salamander alkaloids, Chem. Ber. 101:198–200.
Ho, H. Y., and Chow, Y. S., 1993, Chemical identification of defensive secretion of stick insect, Megacrania tsudai Shiraki, J. Chem. Ecol. 19:39–46.
Huth, A., and Dettner, K., 1990, Defense chemicals from abdominal glands of 13 rove beetles species of subtribe Staphylina (Coleoptera: Staphylinidae, Staphylinae), J. Chem. Ecol. 16:2691–2711.
Jackson, B. D., Morgan, E. D., and Billen, J. P. J., 1990, Contents of the pygidial gland of the ant Myrmecia nigriceps, Naturwissenschaften 77:187–188.
Jasys, V. J., Kelbaugh, P. R., Nason, D. M., Phillips, D., Rosnack, K. J., Saccomano, N. A., Stroh, J. G., and Volkmann, R. A., 1990, Isolation, structure elucidation and synthesis of novel hydroxylamine-containing polyamines from the venom of the Agelenopsis aperta spider, J. Am. Chem. Soc. 112:6696–6704.
Jemiolo, B., and Novotny, M., 1994, Inhibition of sexual maturation in juvenile female and male mice by a chemosignal of female origin, Physiol. Behav. 55:519–522.
Jones, T. H., Blum, M. S., Fales, H. M., and Thompson, C. R., 1980, (5Z,8E)-3-heptyl-5-methylpyrrolizidine from a thief ant, J. Org. Chem. 45:4778–4780.
Jones, T. H., Highet, R. J., Blum, M. S., and Fales, H. M., 1984, (5Z,9Z)-3-alkyl-5-methylindolizidines from Solenopsis (Diplorhoptrum) species, J. Chem. Ecol. 10:1233–1249.
Jones, T. H., Stahly, S. M., Warwick Don, A., and Blum, M. S., 1988, Chemotaxonomic implications of the venom chemistry of some Monomorium “antarcticum” populations, J. Chem. Ecol. 14:2197–2212.
Jones, T. H., Blum, M. S., Fales, H. M., Brandao, C. R. F., and Lattke, J., 1991, Chemistry of venom alkaloids in the ant genus Megalomyrmex, J. Chem. Ecol 17:1897–1908.
Kalivretenos, A. G., and Nakanishi, K., 1993, Synthesis of philanthotoxin analogs with a branched polyamine moiety, J. Org. Chem. 58:6596–6608.
Leclercq, S., Thirionet, I., Broeders, F., Daloze, D., Vander Meer, R. K., and Braekman, J. C., 1994, Absolute configuration of the solenopsins, venom alkaloids of the fire ants, Tetrahedron 50:8465–8478.
McCormick, K. D., Kobayashi, K., Goldin, S. M., Reddy, N. L., and Meinwald, J., 1993, Characterization and synthesis of a new calcium antagonist from the venom of a fishing spider, Tetrahedron 49:11155–11168.
McCormick, K. D., Attygalle, A. B., Xu, S. C., Svatos, A., Meinwald, J., Houck, M. A., Blankespoor, C. L., and Eisner, T., 1994, Chilocorine: Heptacyclic alkaloid from a coccinellid beetle, Tetrahedron 50:2365–2372.
Macours, P., Braekman, J. C., and Daloze, D., 1995, Concise asymmetric syntheses of (+)- and (-)-tetraponerine-8, (-1-)- and (-)-tetraponerine-7, and their ethyl homologues. A correction of the structures of tetraponerine-3 and -7, Tetrahedron 51:1415–1428.
Marples, N. M., 1993, Toxicity assays of ladybirds using natural predators, Chemoecology 4:33–38.
Marples, N. M., Brakefield, P. M., and Cowie, R. J., 1989, Differences between the 7-spot and 2-spot ladybird beetles (Coccinellidae) in their toxic effects on a bird predator, Ecol. Entomol. 14:79–84.
Matsuda, F., Tomiyoshi, N., Yanagiya, M., and Matsumoto, T., 1988, Stereocontrolled total synthesis of (+)-pederine, Tetrahedron 44:7063–7080.
Meinwald, J., Smolanoff, J., McPhail, A. T., Miller, R. W., Eisner, T., and Hicks, K., 1975, Nitropolyzonamine: A spirocyclic nitro compound from the defensive glands of a millipede (Polyzonium rosalbum), Tetrahedron Lett. 2367–2370.
Meinwald, Y. C., Meinwald, J., and Eisner, T., 1966, 1,2-Dialkyl-4(3H)-quinazolinones in the defensive secretion of a millipede (Glomeris marginata), Science 154:390–391.
Merlin, P., Braekman, J. C., Daloze, D., and Pasteels, J. M., 1988, Tetraponerines, toxic alkaloids in the venom of the Neoguinean pseudomyrmecine ant, Tetraponera sp., J. Chem. Ecol. 14:517–527.
Miller, R. W., and McPhail, A. T., 1978, Structure and revised absolute stereochemistry for nitropolyzonamine, 2′,2′-dimethyl-6-nitrospiro{1-azabicyclo[3.3.0]octane-4,1′-cyclopentane}, a novel spirocyclic nitro compound from the defensive glands of the millipede Polyzonium rosalbum: X-ray analysis of nitropolyzonam-monium Perchlorate, J. Chem. Res. (S) 76.
Moore, B. P., and Brown, W. V., 1978, Precoccinelline and related alkaloids in the Australian soldier beetle, Chauliognathus pulchellus (Coleoptera: Cantharidae), Insect Biochem. 8:393–395.
Moore, B. P., and Brown, W. V., 1981, Identification of warning odour components, bitter principles and antifeedants in an aposematic beetle: Metriorrhynchus rhipidius (Coleoptera: Lycidae), Insect Biochem. 11:493–499.
Moore, B. P., Brown, W. V., and Rothschild, M., 1990, Methylalkylpyrazines in aposematic insects, their hostplants and mimics, Chemoecology 1:43–51.
Mueller, R. H., Thompson, M. E., and Di Pardo, R. M., 1984, Stereo- and regioselective total synthesis of the hydropyrido[2,1,6-de]quinolizine ladybug defensive alkaloids, J. Org. Chem. 49:2217–2231.
Obin, M. S., and Vander Meer, R. K., 1985, Gaster flagging by fire ants (Solenopsis spp.): Functional significance of venom dispersal behavior, J. Chem. Ecol. 11:1757–1768.
Pasteels, J. M., Deroe, C., Tursch, B., Braekman, J. C., Daloze, D., and Hootele, C., 1973, Distribution et activités des alcaloïdes défensifs des Coccinellidae, J. Insect Physiol. 19:1771–1784.
Pasteels, J. M., Braekman, J. C., Daloze, D., and Ottinger, R., 1982, Chemical defence in chrysomelid larvae and adults, Tetrahedron 38:1891–1897.
Perry, N. B., Blunt, J. W., Munro, M. H. G., and Pannell, L. K., 1988, Mycalamide A, an antiviral compound from a New Zealand sponge of the genus Mycale, J. Am. Chem. Soc. 110:4851–4853.
Proksch, P., Witte, L., Wray, V., and Hartmann, T., 1993, Ontogenic variation of defensive alkaloids in the Mexican bean beetle, Epilachna varivestis (Coleoptera: Coccinellidae), Entomol. Gener. 18:1–7.
Randoux, T., Braekman, J. C., Daloze, D., and Pasteels, J. M., 1991, De novo biosynthesis of Δ3-soxazolin-5-one and 3-nitropropanoic acid derivatives in Chrysomela tremulae, Naturwissenschaften 78:313–314.
Reder, E., Veith, H. J., and Buschinger, A., 1995, Neuartige Alkaloide aus dem Giftdrüsensekret sozialparasitischer Ameisen (Myrmicinae: Leptothoracini), Helv. Chim. Acta 78:73–79.
Renson, B., Merlin, P., Daloze, D., Braekman, J. C., Roisin, Y., and Pasteels, J. M., 1994, Biosynthesis of tetraponerine 8, a defence alkaloid of the ant Tetraponera sp., Can. J. Chem. 72:105–109.
Schildknecht, H., 1970, The defensive chemistry of land and water beetles, Angew. Chem. Int. Ed. Engl. 9:1–9.
Schildknecht, H., and Wenneis, W. F., 1967, Anthranilsaure als Precursor der Arthropodenalkaloide Glomerin und Homoglomerin, Tetrahedron Lett. 1815–1818.
Schildknecht, H., Maschwitz, U., and Wenneis, W. F., 1967, Neue Stoffe aus dem Wehrsekret der Diplopodengattung Glomeris, Naturwissenschaften 54:196–197.
Schildknecht, H., Berger, D., Krauss, D., Connert, J., Gelhaus, J., and Essenbreis, H., 1976, Defense chemistry of Stenus comma (Coleoptera: Staphylinidae). LXI, J. Chem. Ecol. 2:1–11.
Smolanoff, J., Kluge, A. F., Meinwald, J., McPhail, A., Miller, R. W., Hicks, K., and Eisner, T., 1975, Polyzonimine: A novel terpenoid insect repellent produced by a millipede, Science 188:734–736.
Teshima, T., Matsumoto, T., Wakamiya, T., Shiba, T., Aramaki, Y., Nakajima, T., and Kawai, N., 1991, Total synthesis of NSTX-3, spider toxin of Nephila maculata, Tetrahedron 47:3305–3312.
Timmermans, M., Braekman, J. C., Daloze, D., Pasteels, J. M., Merlin, J., and Declercq, J. P., 1992, Exochomine, a dimeric ladybird alkaloid, isolated from Exochomus quadripustulatus (Coleoptera: Coccinellidae), Tetrahedron Lett. 33:1281–1284.
Toki, T., Yasuhara, T., Aramaki, Y., Osawa, K., Miwa, A., Kawai, N., and Nakajima, T., 1988, Isolation and chemical characterization of a series of new spider toxin (nephilatoxins) in the venom of Joro spider, Nephila clavata, Biomed. Res. 9:421–428.
Tumlinson, J. H., Silverstein, R. M., Moser, J. C., Brownlee, R. G., and Ruth, J. M., 1971, Identification of the trail pheromone of a leaf-cutting ant, Atta texana, Nature 234:348–349.
Tursch, B., Daloze, D., Braekman, J. C., Hootele, C., and Pasteels, J. M., 1975, The structure of myrrhine and the biosynthesis of coccinelline, Tetrahedron 31:1541–1543.
Vander Meer, R. K., and Morel, L., 1994, Ant queens deposit pheromones and antimicrobial agents on eggs, Naturwissenschaften 82:93–95.
Veith, M., Lorenz, M., Boland, W., Simon, H., and Dettner, K., 1994, Biosynthesis of iridoid monoterpenes in insects: Defensive secretions from larvae of leaf beetles (Coleoptera: Chrysomelidae), Tetrahedron 50:6859–6874.
Witkop, B., 1971, New directions in the chemistry of natural products: The organic chemist as a pathfinder for biochemistry and medicine, Experientia 27:1121–1138.
Yue, C., Nicolay, J. F., Royer, J., and Husson, H. P., 1994, A new stereoselective synthesis of ladybug defence alkaloid precoccinelline, Tetrahedron 50:3139–3148.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1998 Springer Science+Business Media New York
About this chapter
Cite this chapter
Braekman, J.C., Daloze, D., Pasteels, J.M. (1998). Alkaloids in Animals. In: Roberts, M.F., Wink, M. (eds) Alkaloids. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-2905-4_15
Download citation
DOI: https://doi.org/10.1007/978-1-4757-2905-4_15
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4419-3263-1
Online ISBN: 978-1-4757-2905-4
eBook Packages: Springer Book Archive