Abstract
Chemical analyses of three species in the Neotropical ant genusMegalomyrmex have identified this taxon as the third myrmicine genus to produce alkaloids as major venom products. Workers ofM. leoninus and workers and ergatoids ofM. goeldii produce one or more of fourtrans-2,5-dialkylpyrrolidines previously identified in other myrmicine genera.M. modestus, on the other hand, is distinctive in producing the novel alkaloid (5E,8E)-3-butyl-5-hexylpyrrolizidine (5d), whose structure was established using a micro-Hofmann degradation sequence. The relationship ofMegalomyrmex to other alkaloid-producing ant genera is discussed along with the possible chemotaxonomic significance of the analyzed species when viewed in terms of the recognized species groups in this genus.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bach, R.D., Andrzejewski, D., andBair, K.W. 1974. Nitrogen ylid intermediates in elimination reactions of quaternary ammonium salts.J. Chem. Soc. Chem. Commun. 1974:820–822.
Blum, M.S. 1985. Poisonous ants and their venoms, pp. 225–242,in A.T. Tu (ed.). Handbook of Natural Toxins 2, Insect Poisons, Allergens, and Other Invertebrate Venoms. Marcel Dekker, New York.
Blum, M.S., Jones, T.H., Holldobler, B., Fales, H.M., andJaouni, T. 1980. Alkaloidal venom mace: Offensive use by a thief ant.Naturwissenschaften 67:144–145.
Blum, M.S., Everett, D.M., Jones, T.H., andFales, H.M. 1991. Arthropod natural products as insect repellents, pp. 14–26,in P.A. Hedin (ed.). Naturally Occurring Pest Bioregulators. ACS Symposium Series 449. American Chemical Society, Washington, D.C.
Bolton, B., 1987. A world review of theSolenopsis genus group and revision of afrotropicalMonomorium Mayr.Bull. Br. Mus. (Nat. Hist.) (Entomol.) 54:263–452.
Borch, R.F., Bernstein, M.D., andDurst, H.D. 1971. The cyanohydrididoborate anion as a selective reducing agent.J. Am. Chem. Soc. 93:2897–2904.
Brand, J.M., Blum, M.S., andBarlin, M.R. 1973a. Fire ant venoms: Intraspecific and interspecific variation among castes and individuals.Toxicon 11:325–331.
Brand, J. M., Blum, M.S., andRoss, H.H. 1973b. Biochemical evolution in fire ant venoms.Insect Biochem. 3:45–51.
Brandão, C.R.F. 1990. Systematic revision of the neotropical ant genusMegalomyrmex Forel (Hymenoptera: Formicidae: Myrmicinae).Arq. Zool. 31:411–481.
Escoubas, P., andBlum, M.S. 1990. The biological activities of ant-derived alkaloids, pp. 482–489,in R.K. Vander Meer, K. Jaffe, and A. Cedeno (eds.). Applied Myrmecology. Westview Press, Boulder, Colorado.
Gessner, W., Takahashi, K., Brossi, A., Kowalski, M., andKaliner, M.A. 1987. Synthesis of (±)-trans-2,5-dialkylpyrrolidines from the Lukes-Sorm dilactam.Acta Chim. Helv. 70:2003–2010.
Jewers, K., andMcKenna, J. 1958. Stereochemical investigations of cyclic bases.J. Chem. Soc. 1958:2209–2217.
Jones, T.H., Blum, M.S., andFales, H.M. 1979. Synthesis of unsymmetrical 2,5-di-n-alkylpyrrolidines: 2-Hexyl-5-pentylpyrrolidine from the thief antsSolenopsis molesta, S. texanus, and its homologues.Tetrahedron Lett. 1979:1031–1034.
Jones, T.H., Blum, M.S., Fales, H.M., andThompson, C.R. 1980. (5Z,8E)-3-Heptyl-5-methylpyrrolizidine from a thief ant.J. Org. Chem. 45:4778–4780.
Jones, T.H., Blum, M.S., andFales, H.M. 1982. Ant venom alkaloids fromSolenopsis andMonomorium species.Tetrahedron 38:1949–1958.
Jones, T.H., Stahly, S.M., Don, A.W., andBlum, M.S. 1988. Chemotaxonomic implications of the venom chemistry of someMonomorium “antarcticum” populations.J. Chem. Ecol. 14:2197–2212.
Jones, T.H., Blum, M.S., Escoubas, P., andMusthak Ali, T.M. 1989. Novel pyrrolidines in the venom of the antMonomorium indicum.J. Nat. Prod. 52:779–784.
Jones, T.H., Laddago, A., Don, A.W., andBlum, M.S. 1990. A novel (5E,9Z)-dialkylindolizidine from the antMonomorium smithii.J. Nat. Prod. 53:375–381.
Kulinkovich, O.G., Tischenko, I.G., Sorokin, V.L. 1985. A new and convenient method of synthesis of γ-ketoaldehydes.Synthesis 1985:1058–1059.
Pedder, D.J., Fales, H.M., Jaouni, T., andBlum, M.S. 1976. Constituents of the venom of a South African fire ant (Solenopsis punctaticeps). Tetrahedron 32:2275–2279.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Jones, T.H., Blum, M.S., Fales, H.M. et al. Chemistry of venom alkaloids in the ant genusMegalomyrmex . J Chem Ecol 17, 1897–1908 (1991). https://doi.org/10.1007/BF00993736
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00993736