Ant Venoms: Chemical and Pharmacological Properties

References

• Hölldobler B., Wilson E.O. The Ants. Belknap Press of Harvard University Press, Cambridge, Mass. 1990; 1
   Google Scholar
• Micks D.W. Insects and other arthropods of medical importance in Texas. Tex. Rep. Biol. Med. 1960; 18: 624
   Google Scholar
• Lockey R.F. Systemic reactions to stinging ants J. Allergy Clin. Immunol. 1974; 54: 132
   PubMedGoogle Scholar
• Pinnas J.L., Strunk R.C., Thompson H.C. Harvester ant sensitivity: in vitro and in vivo studies using whole body extracts and venom J. Allergy Clin. Immunol. 1977; 59: 10
   PubMedGoogle Scholar
• Yeager W. Frequency of fire ant stinging iin Lowndes County, Georgia J. Med. Assoc. Georgia 1978; 1978: 101
   Google Scholar
• Rhoades R.B., Schafer W.L., Newman M., Lockey R., Dozier R.M., Wubbena P.F., Townes A.W., Schmid W.H., Neder G., Brill T., Wittig. Hypersensitivity to the imported fire ant in Florida, report of 104 cases J. Fla. Med. Assoc. 1977; 64: 247
   PubMedGoogle Scholar
• Adams C.T., Lofgren C.S. Incidence of stings or bites of the red imported fire ant (Hymenoptera: Formicidae) and other arthropods among patients at Ft. Stewart, Georgia, USA J. Med. Entomol. 1982; 19: 366
   PubMed Web of Science ®Google Scholar
• Helmly R.B. Anaphylactic reaction to fire ant Hawaii Med. J. 1970; 29: 368
   Google Scholar
• Stablein J.J., Lockey R.F. Monograph on Insect Allergy, M.I. Levine, R.F. Lockey. Am. Acad. Allergy and Parker Printing, Hartland, Wisconsin 1981; 61–67
   Google Scholar
• Allard H.A. Dinoponera gigantea (Perty), a vicious stinging ant. J. Wash. Acad. Sci. 1951; 41: 88
   Google Scholar
• Schmidt J.O. Venoms of the Hymenoptera, T. Piek. Academic Press, New York, 425–508
   Google Scholar
• Weiner J., Ford S.A., Baldo B.A., Weiner J., Sutherland S. Identification of jack-jumper ant (Myrmecia pilosula) venom allergens. Clinical Exptl. Allergy 1991; 21: 167
   Google Scholar
• Cavill G.K.W., Robertson P.L., Whitfield F.B. Venom and venom apparatus of the bull ant, Myrmecia gulosa (Fabr.) Science 1964; 146: 79
   Google Scholar
• De la Lande I.S., Thomas D.W., Tyler M.J. Recent Advances in the Pharmacology of Toxins. Proc. 2nd Int. Pharm. Meeting, Prague. Pergamon Press, Oxford 1965
   Google Scholar
• Lewis J.C., De la Lande I.S. Pharmacological and enzymic constituents of the venom of an Australian ‘bulldog' ant Myrmecia pyriformis. Toxicon 1967; 4: 225
   Google Scholar
• Lewis J.C., Day A.J., De la Lande I.S. Phospholipase A in the venom of the Australian bulldog ant Myrmecia pyriformis. Toxicon 1968; 6: 109
   Google Scholar
• Wanstall J.C., De la Lande I.S. Fractionation of bulldog ant venom Toxicon 1974; 12: 649
   Google Scholar
• Ford S.A., Baldo B.A., Weiner J., Sutherland S. Identification of jack-jumper ant (Myrmecia pilosula) venom allergens Clin. Exp. Allergy 1991; 21: 167
   Google Scholar
• Weber N.A. The sting of the ant, Paraponera clavata. Science 1938; 89: 127
   Google Scholar
• Blum M.S., Hermann H.R. Arthropod Venoms, S. Bettini. Springer-Verlag, Heidelberg, 801–869
   Google Scholar
• Schmidt J.O., Blum M.S., Overal W.L. Comparative lethality of venoms from stinging Hymenoplera Toxicon 1980; 18: 469
   Google Scholar
• Piek T., Schmidt J.O., De long J.M., Mantel P. Kinins in ant venoms–A comparison with venoms of related Hymenoptera Comp. Biochem. Physiol. 1989; 92C: 117
   Google Scholar
• Piek T., Duval A., Hue B., Karst H., Lapied B., Mantel P., Nakajima T., Pelhate M., Schmidt J.O. Poneratoxin, a novel peptide neurotoxin from the venom of the ant, Paraponera clavata Comp. Biochem. Physiol. 1991; 99C: 487
   Google Scholar
• Piek T., Hue B., Mantel P., Nakajima T., Schmidt J.O. Pharamacological characterization and chemical fractionation of the venom of the ponerine ant, Paraponera clavata (F.) Comp. Biochem. Physiol. 1991; 99C: 481
   Google Scholar
• Schmidt J.O., Blum M., Overal W.L. Comparative enzymology of venoms from stinging Hymenoptera Toxicon 1986; 24: 907
   PubMed Web of Science ®Google Scholar
• Pluzhnikov K.A., Arseniev A.S., Drishin E.V.G. Toxic components of the venom from South American ants Paraponera clavata. Ectatomma tuberculatum Toxicon 1991; 29: 294
   Google Scholar
• Schmidt J.O., Blum M.S., Overal W.L. Hemolytic activities of stinging insect venoms Arch. Insect Biochem. Physiol. 1984; 1: 155
   Google Scholar
• Lange A. The Lower Amazon. Putnam, New York 1914
   Google Scholar
• Maschwitz U., Hahn M., Schönegge P. Paralysis of prey in ponerine ants Naturwissenschaften 1979; 66: 213
   Google Scholar
• Altman R.D., Schultz D.R., Collins-Yudiskas B., Aldrich J., Arnold P.I., Brown H.E. Arthritis Rheum. 1984; 27: 277
   PubMedGoogle Scholar
• Braekman J.C., Daloze D., Pasteels J.M., van Hecke P., Declercq, Sinnwell V., Francke W. Tetraponerine-8, an alkaloidal contact poison in a Neoguinean pseudomyrmecine ant, Tetraponera sp Z. Naturforsch 1987; 42c: 627
   Google Scholar
• Merlin P., Braekman J.C., Daloze D., Pasteels J.M. Tetraponerines, toxic alkaloids in the venom of the Neo-guinean pseudomyrmecine ant Tetraponera sp J. Chem. Ecol. 1988; 14: 517
   Google Scholar
• Schultz D.R., Arnold P.I. Venom of the ant Pseudomyrmex sp.: further characterization of two factors that affect human complement proteins J. Immunol. 1977; 119: 1690
   PubMedGoogle Scholar
• Schultz D.R., Arnold P.I. Clinical Aspects of the Complement System, W. Opferkuch, K. Rother, D.R. Schultz. Georg Thieme Publ., Stuttgart 1978; 172–186
   Google Scholar
• Schultz D.R., Byrnes J.J., Brown H.E. Response of mixed cryoglobulinemia to treatment with ant venom. Clin. Res. 1978; 26: 58A
   Google Scholar
• Schultz D.R., Arnold P.I. Immunochemical and clinical studies of venom from the ant Pseudomyrmex sp, A. Tu. Marcel Dekker, Inc., New York 1984; 243–290
   Google Scholar
• Wray J. Some uncommon observations and experiments made with an acid juyce (sic) to be found in ants Phil. Trans. R. Soc. London 1670; 5: 2063
   Google Scholar
• Stumper R. Sur la sécrétion d'acide Formique par les fourmis C.R. Acad. Sci. 1951; 233: 1144
   Google Scholar
• Osman M.F.H., Brander J. Weitere Beiträge zur Kenntnis der chemischen Zusammensetzung des Giftes von Ameisen aus der Gattung Formica Z. Naturforsch. 1961; 16B: 749
   Google Scholar
• Hermann H.R., Blum M.S. The hymenopterous poison apparatus. VI. Camponotus pennsylvanicus (Hymenoptera: Formicidae) Psyche 1968; 75: 216
   Google Scholar
• Hefetz A., Blum M.S. Biosynthesis and accumulation of formic acid in the poison gland of the carpenter ant Camponotus pennsylvanicus Science 1978; 201: 454
   Google Scholar
• Schmidt J.O., Blum M.S. A harvester ant venom: chemistry and pharmacology Science 1978; 200: 1064
   Google Scholar
• Blum M.S. Insect Poisons, Allergens, and Other Invertebrate Venoms, T. Tu. Marcel Dekker, Inc., New York 1984; 225–242
   Google Scholar
• Baer H., Liu T.-Y., Anderson M.C., Blum M., Schmid W.H., James F.J. Protein components of fire ant venom (Solenopsis invicta) Toxicon 1979; 17: 397
   PubMed Web of Science ®Google Scholar
• Baer H., Liu D.T., Hooton M., Blum M., James F., Schmid W.H. Fire ant allergy: isolation of three allergenic proteins from whole venom Ann. Allergy 1977; 38: 378
   Google Scholar
• Schmidt J.O., Blum M.S. The biochemical constituents of the venom of the harvester ant, Poponomvrmex badius Comp. Biochem. Physiol. 1978; 61C: 239
   Google Scholar
• Schmidt J.O., Blum M.S. Pharmacological and toxicological properties of harvester ant, Pogonomyrmex badius, venom Toxicon 1978; 16: 645
   Google Scholar
• Leluk J., Schmidt J., Jones D. Comparative studies on the protein composition of hymenopteran venom reservoirs Toxicon 1989; 27: 105
   PubMed Web of Science ®Google Scholar
• Piek T. A toxinological argument in favour of the close relationship of the Vespidae and the Scoliidae (Hymenoptera) Ent. Ber. Amst. 1987; 47: 96
   Google Scholar
• Bernheimer A.W., Avigad L.S., Schmidt J.O. A hemolytic polypeptide from the venom of the red harvester ant, Pogonomyrmex barbatus Toxicon 1980; 18: 271
   Google Scholar
• Jentsch J. A procedure for purification of Myrmica venom: The isolation of the convulsive component Proc. Int. Congr. IUSSI, Bern 1969; 6: 69
   Google Scholar
• Howl J.D., von Sicard N.A.E., Publicover S.J., Anderson M. A method for the manufacture of single barrel liquid ion-selective microelectrodes: an in situ study of ant venom pH Pflugers Archiv. 1988; 411: 212
   Google Scholar
• von Sicard N.A.E., Candy D.J., Anderson M. The biochemical composition of venom from the pavement ant (Tetramorium caespitum L.) Toxicon 1989; 27: 1127
   Google Scholar
• Williams M.W., Williams C.S. Collection and toxicity studies of ant venoms. Proc. Soc. Exp. Biol. Med., 116: 161, 163
   Google Scholar
• Hermann H.R., Blum M.S. The morphology and histology of the hymenopterous poison apparatus. II. Pogonomyrmex badius Ann. Ent. Soc. Amer. 1967; 60: 661
   Google Scholar
• Williams M.W., Williams C.S. Toxicity of ant venom, further studies of the venom from Pogonomyrmex barbatus Proc. Soc. Exp. Biol. Med. 1965; 119: 344
   Google Scholar
• Schmidt P.J., Sherbrooke W.C., Schmidt J.O. The detoxication of ant (Pogonomyrmex) venom by a blood factor in horned lizards (Phrynosoma) Copeia 1989; 1989: 603
   Google Scholar
• von Sicard N.A.E., Anderson M., Candy D.J. The effect of venom from the ant Tetramorium caespitum on neuromuscular transmisssion in the locust Schistocerca greparia J. Insect Physiol. 1989; 35: 651
   Google Scholar
• Jones T.H., Blum M.S., Fales H.M. Ant venom alkaloids from Solenopsis and Monomorium species Tetrahedron 1982; 38: 1949
   Web of Science ®Google Scholar
• Jones T.H., Blum M.S., Fales H.M., Brandao C.R.F., Lattke J. Chemistry of venom alkaloids in the ant genus Megalomyrmex J. Chem. Ecol. 1991; 17: 1897
   Google Scholar
• Bolton B. A world review of the Solenopsis genus group and revision of afrotropical Monomorium Mayr Bull. Br. Mils. (Nat. Hist.) 1987; 54: 263
   Google Scholar
• MacConnell J.G., Blum M.S., Fales H.M. The chemistry of fire ant venom Tetrahedron 1971; 26: 1129
   Google Scholar
• Brand J.M., Blum M.S., Fales H.M., MacConnell J.G. Toxicon 1972; 10: 259
   PubMed Web of Science ®Google Scholar
• MacConnell J.G., Blum M.S., Buren W.F., Williams R.N., Fales H.M. Fire ant venoms: chemotaxonomic correlations with alkaloidal compositions Toxicon 1976; 14: 69
   PubMed Web of Science ®Google Scholar
• Blum M.S., Fales H.M., Leadbetter G., Leonhardt B., Duffield R.M. A new dialkylpiperidine in the venom of the fire ant Solenopsis invicta. J. Nat. Toxins 1992; 2, in press
   Google Scholar
• MacConnell J.G., Blum M.S., Fales H.M. Alkaloid from fire ant venom: Identification and synthesis Science 1970; 168: 840
   PubMed Web of Science ®Google Scholar
• Blum M.S., Jones T.H., Lloyd H.A., Fales H.M., Snelling R.R., Lubin Y., Torres J. Poison gland products of Solenopsis and Monomorium species J. Ent. Soc. 1985; 20: 254
   Google Scholar
• Jones T.H., Blum M.S., Robertson H. Novel dialkylpiperidines in the venom of the ant Monomorium delagoense J. Nat. Prod. 1990; 53: 429
   Google Scholar
• Brand J.M., Blum M.S., Ross H.H. Biochemical evolution in fire ant venoms Insect Biochem. 1973; 3: 45
   Google Scholar
• Jones T.H., Laddago A., Don A.W., Blum M.S. A novel (5E, 9Z)-dialkylindolizidine from the ant Monomorium smithii J. Nat. Prod. 1990; 53: 375
   PubMedGoogle Scholar
• Ritter F.J., Persoons C.J. Recent developments in insect pheromone research, in particular in the Netherlands Neth. J. Zool. 1975; 25: 261
   Google Scholar
• Jones T.H., Blum M.S., Howard R.W., McDaniel C.A., Fales H.M., DuBois M.B., Torres J. Venom chemistry of ants in the genus Monomorium. J. Chem. Ecol. 1982; 8: 285
   PubMedGoogle Scholar
• Jones T.H., Blum M.S., Fales H.M. Synthesis of unsymmetrical 2,5-di-n-alkylpyrrolidines: 2-Hexyl-5-pentylpyrrolidine from the thief ants Solenopsis molesta, S. texanus, and its homologues Tetrahedron Lett. 1979; 1979: 1031
   Google Scholar
• Blum M.S., Jones T.H., Hölldobler B., Fales H.M., Jaouni T. Alkaloidal venom mace: offensive use by a thief ant Naturwissenschaften 1980; 67: 144
   Google Scholar
• Pedder D.J., Fales H.M., Jaouni T., Blum M.S., MacConnell J., Crewe R.M. Constituents of the venom of a South African fire ant (Solenopsis punctaticeps), 2, 5-dialkylpyrrolidines and -pyrrolines, identification and synthesis Tetrahedron 1976; 32: 2275
   Web of Science ®Google Scholar
• Jones T.H., Blum M.S., Escoubas P., Muskthak Ali T.M. Novel pyrrolidines in the venom of the ant Monomorium indicum J. Nat. Prod. 1989; 52: 779
   Google Scholar
• Jones T.H., Highet R.J., Son A.W., Blum M.S. Alkaloids of the ant Chelaner antarcticus J. Org. Chem. 1986; 51: 2712
   Google Scholar
• Jones T.H., deVries P.J., Escoubas P. Chemistry of the venom alkaloids in the ant Megalomyrmex foreli (Myrmicinae) from Costa Rica J. Chem. Ecol. 1991; 17: 2507
   Google Scholar
• Jones T.H., Stahly S.M., Don A.W., Blum M.S. Chemotaxonomic implications of the venom chemistry of some Monomorium “antarcticum” populations J. Chem. Ecol. 1988; 14: 2197
   PubMed Web of Science ®Google Scholar
• Jones T.H., Blum M.S., Andersen A.N., Fales H.M., Escoubas P. Novel 2-ethyl-5-alkylpyrrolidines in the venom of an Australian ant in the genus Monomorium J. Chem. Ecol. 1988; 14: 35
   PubMedGoogle Scholar
• Andersen A.N., Blum M.S., Jones T.H. Venom alkaloids in Monomorium “rothsteini” Forel repel other ants: is this the secret to success by Monomorium in Australian ant communities? Oecologia 1991; 61: 157
   Google Scholar
• Jones T.H., Blum M.S., Fales H.M., Thompson C.R. (5Z,8E)-3-Heptyl-5-methylpyrrolizidine from a thief ant J. Org. Chem. 1980; 45: 4778
   Google Scholar
• Lemaire M., Lange C., Bazire M., Cassier P., Clément J.L., Escoubas P., Basselier J.J. Alkaloid venom of European ants in the genus Monomorium. Site of synthesis, identification and quantification Exp. Biol. 1988; 48: 27
   Google Scholar
• Jones T.H., Highet R.J., Blum M.S., Fales H.M. (5Z,9Z)-3-Alkyl-5-methylindolizidines from Solenopsis (Diplorhoptrum) species J. Chem. Ecol. 1984; 10: 1233
   Google Scholar
• Law J.H., Wilson E.O., McCloskey J.A. Biochemical polymorphism in ants Science 1965; 149: 544
   Google Scholar
• Wheeler J.W., Olubajo O., Storm C.B., Duffield R.M. Anabaseine: venom alkaloid of Aphaenogaster ants Science 1981; 211: 1051
   Google Scholar
• Caro M.R., Derbes V.J., Jung R. Skin responses to the sting of the imported fire ant (Solenopsis saevissima). Arch. Dermatol. 1957; 75: 475
   Web of Science ®Google Scholar
• Bufkin D.C., Russell F.E. A study of the venom of the imported fire ant: physiopharmacology, chemistry, and therapeutics Proc. West. Pharmacol. Soc. 1974; 17: 223
   Google Scholar
• Adrouny G.A., Derbes V.J., Jung R.C. Isolation of a hemolytic component of fire ant venom Science 1959; 130: 449
   PubMed Web of Science ®Google Scholar
• Blum M.S., Walker J.R., Callahan P.S., Novak A.F. Chemical, insecticidal and antibiotic properties of fire ant venom Science 1958; 128: 306
   PubMed Web of Science ®Google Scholar
• Escoubas P., Clément J.-L., Blum M.S., Jones T.H., Lhommet G., Celerier J.P. Toxicité des alcaloïdes de fourmis Actes Coll. Insectes Soc. 1988; 4: 51
   Google Scholar
• Blum M.S., Everett D.M., Jones T.H., Fales H.M. Naturally Occurring Pest Bioregulators, P.A. Hedin. ACS, Washington, D.C. 1991; 14–26
   Google Scholar
• Jouvanez D.P., Blum M.S., MacConnell J.G. Antibacterial activity of venom alkaloids from the imported fire ant, Solenopsis invicta Buren Antimicrob. Agents Chemother. 1972; 2: 291
   Google Scholar
• Blum M.S. Biologically Active Natural Products, H.G. Cutler. ACS, Washington, D.C. 1988; 438–449
   Google Scholar
• Read G.W., Lind N.K., Oda C.S. Histamine release by fire ant (Solenopsis) venom Toxicon 1978; 16: 361
   PubMed Web of Science ®Google Scholar
• Lind N.K. Mechanism of action of fire ant (Solenopsis) venoms. I. Lytic release of histamine from mast cells Toxicon 1982; 20: 831
   Google Scholar
• Cheng E.Y., Cutkomp L.K., Koch R.B. Effect of an imported fire ant component on respiration and oxidative phosphorylation of mitochondria Biochem. Pharmacol. 1977; 26: 1179
   Google Scholar
• Koch R.B., Desaiah D., Foster D., Ahmed K. Effect of piperidines and fire ant venom on ATPase activities from brain homogenate fractions and characterization of Na+-K ATPase inhibition Biochem. Pharmacol. 1977; 26: 983
   Google Scholar
• Yen J.Z., Narahashi T., Almon R.R. Characterization of neuromuscular blocking action of piperidine derivatives J. Pharmacol. Exp. Ther. 1975; 194: 373
   Google Scholar
• David J.A., Crowley P.J., Hall S.G., Battersby M., Sattelle D.B. Actions of synthetic piperidine derivatives on an insect acetylcholine receptor/ion channel complex J. Insect Physiol. 1984; 30: 191
   Google Scholar
• Escoubas P. Alcaloïdes de fourmis: identification, toxicity et mode d'action. Ph. D. Thesis, Université Pierre et Marie Curie, Paris, 145
   Google Scholar
• Grünanger P., Quilico A., Pavan M. Sul secreto del formicidae, Myrmicaria natalensis Fred Accad. Nazion. Lincei 1960; 28: 293
   Google Scholar
• Brand J.M., Blum M.S., Lloyd H.A., Fletcher D.J.C. Monoterpene hydrocarbons in the poison gland secretion of the ant Myrmicaria natalensis (Hymenoptera: Formicidae) Ann. Entomol. Soc. Am. 1974; 67: 525
   Google Scholar
• Howse P.E., Baker R., Evans D.A. Multifunctional secretions in ants Proc. Int. Congr. IUSSI, Wageningen 1977; 7: 44
   Google Scholar
• Kaib M., Dittebrand H. The poison gland of the ant Myrmicaria eumenoides and its role in recruitment communication Chemoecology 1990; 1: 3
   Google Scholar
• Blum M.S., Lloyd H.A., Musthak Ali T.M., Schmidt J.O., Starr C. 1992, Unpublished data
   Google Scholar
• Hölldobler B. Sex pheromone in the ant Xenomyrmex floridanus J. Insect Physiol. 1971; 17: 1497
   Web of Science ®Google Scholar
• Buschinger A. Pheromones and Defensive Secretions in Social Insects, C.H. Noirot, P.E. Howse, G. Le Masne. Proc. Symp. IUSSI, Dijon, France, 225–233
   Google Scholar
• Tumlinson J.H., Silverstein R.M., Moser J.C., Brownlee R.G., Ruth J.M. Identification of the trail pheromone of a leaf-cutting ant, Atta texana Nature (London) 1971; 234: 348
   Google Scholar
• Robinson S.W., Moser J.C., Blum M.S., Amante E. Laboratory investigations of the trail-following responses of four species of leaf-cutting ants with notes on the specificity of a trail pheromone of Atta texana (Buckley) Insectes Soc. 1974; 21: 87
   Web of Science ®Google Scholar
• Blum M.S. Myrmicine trail pheromones: specificity, source and significance J.N.Y. Entomol. Soc. 1974; 82: 141
   Google Scholar
• Fletcher D.J.C. The glandular source and social functions of trail pheromones in two species of ants (Leptogenys) J. Entomol., Ser. A 1971; 46: 27
   Google Scholar
• Cross J.H., Byler R.C., Ravid U., Silverstein R.M., Robinson S.W., Baker P.M., Sabino de Oliveira J., Jutsum A.R., Cherrett J.M. The major component of the trail pheromone of the leaf-cutting ant, Atta sexdens rubropilosa Forel:3-Ethyl-2,5-dimethylpyrazine J. Chem. Ecol. 1979; 5: 187
   Web of Science ®Google Scholar
• Evershed R.P., Morgan E.D., Cammaerts M.C. 3-Ethyl-2,5-dimethylpyrazine, the trail pheromone from the venom gland of eight species of Myrmica ants Insect Biochem. 1982; 12: 383
   Google Scholar
• Wheeler J.W., Blum M.S. Alkylpyrazine alarm pheromone in ponerine ants Science 1973; 182: 501
   PubMed Web of Science ®Google Scholar
• Morgan J.D., Ollet D.G. Methyl 6-methylsalicylate, trail pheromone of the ant Tetramorium impurum Naturwissenschaften 1987; 74: 596
   Google Scholar
• Brand J.M., Duffield R.M., MacConnell J.G., Blum M.S., Fales H.M. Caste-specific compounds in male carpenter ants Science 1973; 179: 388
   PubMedGoogle Scholar
• Attygalle A.B., Vostrowsky O., Bestmann H.J., Steghaus-Kovac S., Maschwitz U. (3R,4S)-4-Methyl-3-heptanol, the trail pheromone of the ant Leptogenys diminuta Naturwissenschaften 1988; 75: 315
   Google Scholar
• McGurk D.J., Frost J., Eisenbraun E.J., Vick K., Drew W., Young J. Volatile compounds in ants: identification of 4-methyl-3-heptanone from Pogonomyrmex ants J. Insect Physiol. 1966; 12: 1435
   Google Scholar