Skip to main content

Venoms of Coleoptera

  • Chapter
Arthropod Venoms

Abstract

The order Coleoptera contains more than a quarter of a million species divided amongst about 200 families. The members of this order undergo a complete metamorphosis. Species are known that live on the ground, on plants, in wood, on flowers, in carrion, etc., and in and on water. As will be seen below only 12 families have been studied regarding toxins.

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 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight 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

  • Abou-Donia, S.A., Fish, L.J., Pattenden, G.: Iridodial from the odoriferous glands of Staphylinus olens (Col. Staphylinidae). Tetra. Lett. No. 43, 4037–4038 (1971).

    Article  Google Scholar 

  • Alexander, P., Barton, D.H.P.: The excretion of ethylquinone from a flour beetle. Biochem. J. 37, 463–465 (1943).

    PubMed  CAS  Google Scholar 

  • Aneshansley, D.J., Eisner, T., Widom, T.A., Widom, B.: Biochemistry at 100° C: Explosive secretory discharge of bombardier beetles (Brachinus). Science 165, 61–63 (1969).

    Article  PubMed  CAS  Google Scholar 

  • Arara, G.L., Rai, D.: Pygidial glands in Pherosophus sp. (Carabidae: Coleoptera). Curr. Sci. 28, 379–380 (1959).

    Google Scholar 

  • Araujo, J.: Morphologie et histologie de la glande pygidiale défensive de Bledius spectablis Kr. (Staphylinidae-Oxytelinae). C.R. Acad. Sci. (Paris) D276, 2713–2716 (1973).

    Google Scholar 

  • Ayer, W., Dawes, R.: —Canad. J. Chem. impress. Barth, R.: Ueber die Pygidialdruese von Enhydrus sulcatus (Wied. 1821) (Coleoptera, Grynidae). Mem. Inst. Osw. Cruz. 58, 135–147 (1960).

    Google Scholar 

  • Beams, H.W., Anderson, E.: Fine structure of “intracellular ductules” in certain glands of the carabid beetle. J. Morph. 109, 159–171 (1961).

    Article  Google Scholar 

  • Bellas, T.E., Brown, W.V., Moore, B.P.: The alkaloid actinidine and plausible precrusors in defensive secretions of rove beetles. J. Insect Physiol. 20, 277–280 (1974).

    Article  CAS  Google Scholar 

  • Benn, M.H., Lencucha, A., Maxie, S., Telang, S.A.: The pygidial defence secretion of Carabus taedatus (Col. Carabidae). J. Insect Physiol. 19, 2173–2176 (1973).

    Article  Google Scholar 

  • Bierl, B.A., Beroza, M., Ashton, W.T.: Reaction Loops for Reaction Gas Chromatography. Subtraction of Alcohols, Aldehydes, Ketones, Epoxides, and Acids and Carbon-Skeleton, Chromatography of Polar Compounds. Mikrochim. Acta 3, 637–653 (1969).

    Google Scholar 

  • Blum, M.S., Brand, J.M., Wallace, J.B., Foles, H.M.: Chemical characterization of the defensive secretion of a chrysomelid larva Chrysomela interrupta). Life Sci. 11, 525–531 (1972).

    Article  CAS  Google Scholar 

  • Blum, M.S., Crain, R.D.: The occurrence of p-quinones in the abdominal secretion of Eleodes hispilabris. Ann. entomol. Soc. Amer. 54, 474 (1961).

    CAS  Google Scholar 

  • Blum, M.S., Crewe, R.M., Pasteeis, J.M.: Defensive secretion of Lomechusa strumosa, a mynnecophilous beetle (Coleoptera: Staphylinidae). Ann. entomol. Soc. Amer. 64, 975–976 (1971).

    Google Scholar 

  • Blumberg, D.: The repugnatorial glands of the tenebrionid beetle (Coleoptera) Eleodes obsoleta (Say.). Trans. Amer, entomol. Soc. 88, 45–55 (1961).

    Google Scholar 

  • Brand, J.M., Blum, M.S., Foles, H.M., Pasteels, J.M.: The chemistry of the defensive secretion of the beetle Drusilla canaliculata (Col. Staphylinidae). J. Insect Physiol. 19, 369–382 (1973).

    Article  CAS  Google Scholar 

  • Brega, A., Falaschi, A., de Carli, L., Pavan, M.: Studies on the mechanism of action of pederin. J. Cell Biol. 36, 485–496 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Cardani, C., Fuganti, C., Ghiringhelli, D., Grassell, P., Pavan, M., Valcurone, M.D.: The biosynthesis of pederin. Tetra. Lett. No. 30, 2815–2818 (1973).

    Article  Google Scholar 

  • Cardani, C., Ghiringhelli, D., Mondelli, R., Pavan, M., Quilico, A.: Propriétés biologiques et composition chimique de la Pédérine. Ann. Soc. entomol. Fr. 1, 813–816 (1965b).

    CAS  Google Scholar 

  • Cardani, C., Ghiringhelli, D., Mondelli, R., Quilico, A.: The structure of pederin. Tetra. Lett. No. 29, 2537–2545 (1965a).

    Article  Google Scholar 

  • Cardani, C., Ghiringhelli, D., Mondelli, R., Quilico, A.: Strutta delia pederina. Gazz. chim. Ital. 96, 3–38 (1966).

    Google Scholar 

  • Cardani, C., Ghiringhelli, D., Quilico, A., Selva, A.: The structure of pederone, a novel substance from Paederus spp. (Coleoptera: Staphylinidae). Tetra. Lett. No. 41, 4023–4025 (1967).

    Article  Google Scholar 

  • Carrel, J.E., Eisner, T.: Cantharidin: potent feeding deterrent to insects. Science, 183, 755-757 Casnati, G., Pavan, M., Ricca, A.: Sulla costituzione del veleno dell’ insetto Calosoma sychophanta L. [Coleoptera Carabidae]. Ann. Soc. entomol. Fr. 1, 705–710 (1965).

    Google Scholar 

  • Cavill, G.W.K.: The cyclopentanoid monoterpenes. Rev. pure appl. Chem. 10, 169–183 (1960).

    CAS  Google Scholar 

  • Cavill, G.W.K., Zeitlin, A.: Synthesis of D-(4)-tecostidine and related actinidine derivatives. Aust. J. Chem. 20, 349–357 (1967).

    CAS  Google Scholar 

  • Chadha, M.S., Eisner, T., Meinwald, J.: Defense mechanisms of arthropods. IV. p-Benzoquinones in the secretion of Eleodes longicollis Lec. (Coleoptera: Tenebrionidae). J. Insect Physiol. 7, 46–50 (1961).

    Google Scholar 

  • Chadha, M.S., Joshi, N.K., Mamdapur, V.R., Sipahimalani, A.T.: C-21 steroids in the defensive secretions of some Indian water beetles. Tetrahedron 26, 2061–2064 (1970).

    Article  CAS  Google Scholar 

  • Colombini, N.: Osservazioni sulla struttura delle ghiandole pigidiali di Cybister roeselii Fabr. Soc. toscana Sci. Nat. Pisa 45, 153–162 (1935b).

    Google Scholar 

  • Colombini, N.: Osservazioni sulla morfologia delle ghiandole pigidiali dei Carabidi. Soc. toscana Sci. Nat. Pisa 45, 271–281 (1935a).

    Google Scholar 

  • Edwards, J.S.: Spitting as a defensive mechanism in a predatory reduviid. Eleventh Intern. Cong. Ent. Vienna, Verhandlungen 3, 259–263 (1960).

    Google Scholar 

  • Eisner, T., Hurst, J.J., Meinwald, J.: Defense mechanisms of arthropods. XL The structure, function, and phenolic secretions of the glands of a chordeumoid millipede and carabid beetle. Psyche 70, 94–116 (1963b).

    CAS  Google Scholar 

  • Eisner, T., McHenry, F., Salpeter, M. M.: Defense mechanisms of arthropods. XV. Morphology of the quinone-producing glands of a tenebrionid beetle (Eleodes longicollis Lec). J. Morph. 115, 335–400 (1964).

    Google Scholar 

  • Eisner, T., Meinwald, Y.C., Alsop, D.W., Carrel, J.E.: Defense mechanisms of arthropods. XXI. Formic acid and n-nonyl acetate in the defensive spray of two species of Helluomorphoides. Ann. entomol. Soc. Amer. 61, 610–613 (1968).

    CAS  Google Scholar 

  • Eisner, T., Swithenbank, C., Meinwald, J.: Defense mechanisms of arthropods. VIII. Secretion of salicylaldehyde by a carabid beetle. Ann. entomol. Soc. Amer. 56, 37–41 (1963a).

    CAS  Google Scholar 

  • Endt, D.W.V., Wheeler, J.W.: 1-Pentadecene production in Tribolium confusum. Sci. 172, 60–61 (1971).

    Article  Google Scholar 

  • Engelhardt, M., Rapaport, H., Sokoloff, A.: Odourous secretion from normal and mutant Tribolium confusum. Sci. 150, 632–633 (1965).

    Article  CAS  Google Scholar 

  • Fish, L.J., Pattenden, G.: Iridodial and a new alkanone, 4-methylhexan-3-one, in the defensive secretion of the beetle Staphylinus olens. J. Insect Physiol. 21, 741–744 (1975).

    Article  CAS  Google Scholar 

  • Forsyth, D.J.: The structure of the defence glands in the Dytiscidae, Noteridae, Haliplidae and Gyrinidae (Coleoptera). Trans, roy. entomol. Soc. (Lond.) 120, 159–182 (1968).

    Article  Google Scholar 

  • Forsyth, D.J.: The ultrastructure of the pygidial defence glands of the carabid Pterostichus madidus F. J. Morph. 131, 397–416 (1970a).

    Article  Google Scholar 

  • Forsyth, D.J.: The structure of the defence glands of the Cirindelidae, Amphizoidae and Hygrobiidae (Coleoptera). J. Zool. (Lond.) 160, 51–69 (1970b).

    Article  Google Scholar 

  • Forsyth, D.J.: The structure of the pygidial defence glands of Carabidae (Coleoptera). Trans. zool. Soc. Lond. 32, 249–309 (1972).

    Article  Google Scholar 

  • Furusaki, A., Watanabe, T.: The crystal and molecular structure of pederin di-p-bromobenzo-ate. Tetra. Lett. No. 60, 6301–6304 (1968).

    Article  Google Scholar 

  • Gadamer, J.: The constitution of cantharidin. Arch. Pharm. (Weinheim) 252, 609 (1914).

    Article  CAS  Google Scholar 

  • Garb, G.: The eversible glands of a chrysomelid larva, Melasoma lapponica. J. entomol. Zool. 7, 88–95 (1915).

    Google Scholar 

  • Hackmann, R.H., Pryor, M.G.M., Todd, A.R.: The occurrence of phenolic substances in arthropods. Biochem. J. 43, 474–477 (1948).

    Google Scholar 

  • Happ, G.M.: Benzoquinones in the defenisve secretion of Leichenum canaliculatum variegatum (Coleoptera: Tenebrionidae). Ann. entomol. Soc. Amer. 60, 279 (1967).

    CAS  Google Scholar 

  • Happ, G.M.: Quinone and hydrocarbon production in the defensive glands of Eleodes longicollis and Tribolium castaneum (Coleoptera: Tenebrionidae). J. Insect Physiol. 14, 1821–1837 (1968).

    Article  CAS  Google Scholar 

  • Happ, G.M., Eisner, T.: Haemorrhage in a coccinellid beetle and its repellant effect on ants. Science 134, 329–331 (1961).

    Article  PubMed  CAS  Google Scholar 

  • Happ, G.M., Happ, C.M.: Fine structure of the pygidial glands of Bledius mandibularis (Coleoptera: Staphylinidae). Tissue Cell 5, 215–231 (1973).

    Article  PubMed  CAS  Google Scholar 

  • Hayes, W.P., Chu, H.F.: An undescribed eversible gland in the larvae of Chlaenius (Coleoptera: Carabidae). J. Kans. entomol. Soc. 20, 142–145 (1947).

    Google Scholar 

  • Henson, R.D., Thompson, A.C., Hedin, P.A., Nichols, P.R., Neel, W.W.: Identification of precoccinellin in the ladybird beetle, Coleomegilla maculata. Experientia (Basel) 31, 145 (1975).

    Article  CAS  Google Scholar 

  • Hinton, H.E.: On a little known protective device of some chrysomelid pupae (Coleoptera). Proc. roy. entomol. Soc. (Lond.) (A). 26, 69–73 (1951).

    Google Scholar 

  • Hisada, Y., Emura, M.: Cytological effects of chemicals on tumors. XXVIII. Notes on the effects of extract from Paederus fuscipes on a transplantable rat ascites tumor. J. Fac. Sci., Haikkaido Univ. Ser. VI 15, 684–692 (1965).

    CAS  Google Scholar 

  • Hollande, M.A. Ch.: Sur la fonction d’excrétion chez les insectes salicioles et un particular sur l’existence des derivées salicyles. Ann. Univ. Grenoble Sect. Sci. med. 21, 459 (1909).

    Google Scholar 

  • Hsiao, T.H. and Fraenkel, G.: Properties of leptinotarsin, a toxic hemolymph protein from the Colorado potato beetle. Toxicon 7, 119–130 (1969).

    Article  PubMed  CAS  Google Scholar 

  • Hurst, J.J., Meinwald, J., Eisner, T.: Defense mechanisms of arthropods. II. Glucose and hydrocarbons in the quinone containing secretion of Eleodes longicollis. Ann. entomol. Soc. Amer. 57, 44–46 (1964).

    CAS  Google Scholar 

  • Ikan, R., Cohen, E., Shulov, A.: Benzo-and hydroquinones in the defensive secretions of Blaps sulcata and B. wiedertnanni. J. Insect Physiol. 16, 2201–2206 (1970).

    Article  CAS  Google Scholar 

  • Kendall, D.A.: The structure of the defence glands in Alleculidae and Lagriidae (Coleoptera). Trans, roy entomol. Soc. (Lond.) 120, 139–156 (1968).

    Article  Google Scholar 

  • Kendall, D.A.: The dermal glands of some adult beetles. J. Entomol. A46, 153–159 (1972).

    Google Scholar 

  • Kendall, D.A.: The structure of defence glands in some Tenebrionidae and Nilionidae (Coleoptera). Trans, roy. entomol. Soc. (Lond.) 125, 437–487 (1974).

    Article  Google Scholar 

  • Kolbe, W., Proske, M.G.: Iso-valeriansäure im Abwehrsekret von Zyras humeralis Grav. (Coleoptera, Staphylinidae). Entomol. Bl. Biol. Syst. Käfer 69, 57–60 (1973).

    Google Scholar 

  • Leete, E., Murvill, J.B.: Biosynthesis of the tiglic acid moiety of metaloidine in Datura meteloides. Tetra. Lett. No. 18, 1727–1730 (1967).

    Article  CAS  Google Scholar 

  • Loconti, J.D., Roth, L.M.: Composition of odorous secretion of Tribolium castaneum. Ann. entomol. Soc. Amer. 46, 281–289 (1953).

    CAS  Google Scholar 

  • Matsumoto, T., Yanagiya, M., Maeno, S., Yasuda, S.: A revised structure of pederin. Tetra. Lett. 60, 6297–6300 (1968).

    Article  Google Scholar 

  • McCullough, T.: Quantitative determination of salicylaldehyde in the scent fluid of Calosoma macrum, C. alternans sayi, C. affini and C. parvicollis. Ann. entomol. Soc. Amer. 59, 1018 (1966a).

    CAS  Google Scholar 

  • McCullough, T.: Compounds in the defensive scent glands of Harpalus caliginosus (Coleoptera: Carabidae). Ann. entomol. Soc. Amer. 59, 1020 (1966b).

    CAS  Google Scholar 

  • McCullough, T.: Compounds found in the defensive scent fluid of Dicaelus splendidus and D. dilatatus. Ann. entomol. Soc. Amer. 60, 861 (1967).

    Google Scholar 

  • McCullough, T.: Chemical analysis of the defensive scent fluid produced by the ground beetle Calosoma peregrinator (Coleoptera: Carabidae). Ann. entomol. Soc. Amer. 62, 1498–1499 (1969a).

    PubMed  CAS  Google Scholar 

  • McCullough, T.: Chemical analysis of the scent fluid of Dicaelus pupuratus. Ann. entomol. Soc. Amer. 62, 1493–1494 (1969b).

    PubMed  CAS  Google Scholar 

  • McCullough, T.: Chemical analysis of the scent fluid of Pasimachus californicus and P. duplicatus. Ann. entomol. Soc. Amer. 62, 1492 (1969c).

    PubMed  CAS  Google Scholar 

  • McCullough, T.: Chemical analysis of the defensive scent fluid from Progaleritina mexicana (Coleoptera: Carabidae). Ann. entomol. Soc. Amer. 64, 1191 (1971).

    Google Scholar 

  • McCullough, T.: Defensive chemistry of the ground beetle Callisthenes luxatus (Coleoptera: Carabidae). Ann. entomol. Soc. Amer. 65, 275 (1972a).

    Google Scholar 

  • McCullough, T.: Analysis of the defensive scent fluid of Pasimachus elongatus (Coleoptera: Carabidae). Ann. entomol. Soc. Amer. 65, 772 (1972b).

    Google Scholar 

  • McCullough, T., Weinheimer, A.J.: Compounds found in the defensive scent fluids of Calosoma marginalis, C. externum and C. scrutator. Ann. entomol. Soc. Amer. 59, 410 (1966).

    Google Scholar 

  • Meinwald, J., Koch, K.F., Rogers, J.E., Eisner, T.: Biosynthesis of Arthropod Secretions. III. Synthesis of simple p-benzoquinones in a beetle (Eleodes longicollis). J. Amer. chem. Soc. 88, 1590–1592 (1966).

    CAS  Google Scholar 

  • Meinwald, J., Meinwald, Y.C., Chalmers, A.M.: Dihydromatricaria acid: acetylenic acid secreted by a soldier beetle. Science 160, 890 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Meinwald, J., Opheim, K., Eisner, T.: Gyrinidal: a sesqeuterpenoid aldehyde from the defensive glands of gyrinid beetles (Coleoptera). Proc. nat. Acad. Sci. (Wash.) 69, 1208–1210 (1972).

    Article  CAS  Google Scholar 

  • Meinwald, Y.C., Eisner, T.: Defense mechanisms of arthropods. XIV. Caprylic acid: an accessory component of the secretion of Eleodes longicollis. Ann. entomol. Soc. Amer. 57, 513 (1964).

    CAS  Google Scholar 

  • Miller, J.R., Hendry, L.B., Mumma, R.O.: Norsesquic terpenes as defensive toxins of whirligig beetles (Coleoptera: Gyrinidae). J. Chem. Ecol. 1, 59–82 (1975).

    Article  CAS  Google Scholar 

  • Miller, J.R., Mumma, R.O.: Defensive agents of the American water beetles Agabus seriatus and Graphoderus liberus (Coleoptera: Dytiscidae). J. Insect Physiol 19, 917–925 (1973).

    Article  CAS  Google Scholar 

  • Miller, J.R., Mumma, R.O.: Seasonal quantification of the defensive steroid titer in Agabus seriatus (Coleoptera: Dytiscidae). Ann. entomol. Soc. Amer. 67, 850–852 (1974).

    CAS  Google Scholar 

  • Miller, J.R., Mumma, R.O.: Physiological activity of water beetle defensive agents, I. Toxicity and anesthetic of steroids and norsesquiterpenes administered in solution to the minnow Pimephales promelas Raf. J. Chem. Ecol. 2, 115–130 (1976a).

    CAS  Google Scholar 

  • Miller, J.R., Mumma, R.O.: Physiological activity of water beetle defensive agents. II. Absorption of selected anesthetic steroids and norsesquiterpenes across the gill membranes of the minnow Pimephales promelas Raf. J. Chem. Ecol. 2, 130–146 (1976b).

    Google Scholar 

  • Moore, B.P., Brown, W.V.: Chemical defence in longhorn beetles of the genera Stenocentrus and Syllitus (Coleoptera: Cerambycidae). J. Aust. entomol. Soc. 10, 230–232 (1971a).

    Article  Google Scholar 

  • Moore, B.P., Brown, W.V.: Benzaldehyde in the defensive secretion of a tiger beetle (Coleoptera: Carabidae). J. Aust. entomol. Soc. 10, 142–143 (1971b).

    Article  Google Scholar 

  • Moore, B.P., Brown, W.V.: The chemistry of the metasternal gland secretion of the common eucalyt longicorn Phoracantha semipunctata (Coleoptera: Cerambycidae). Aust. J. Chem. 25, 591–598 (1972).

    Article  CAS  Google Scholar 

  • Moore, B.P., Wallbank, B.E.: Chemical composition of the defensive secretion in carabid beetles and its importance as a taxonomic character. Proc. roy. entomol. Soc. (Lond.) B, 37, 62–72 (1968).

    Google Scholar 

  • Moreau, L.: La secrétion du Blaps gigas. Soc. Linnéene de Province, Marseille Bull. 5, 34–37 (1931).

    Google Scholar 

  • Palm, N.: Structure and physiology of the stink glands in Tribolium destructor Uytt (Coleoptera). Opusc. entomol. 11, 119–132 (1946).

    Google Scholar 

  • Parker, R.: A comparison of the toxic protein in two species of Leptinotarsa. Toxicon 10, 79–80 (1972).

    Article  PubMed  CAS  Google Scholar 

  • Pasteels, J.M., Deroe, C., Tursch, B., Braekman, J.C., Daloze, D., Hootele, C: Distribution et activités des alcolo’s défensifs des Coccinellidae. J. Insect Physiol. 19, 1771–1784 (1973).

    Article  CAS  Google Scholar 

  • Pavan, M.: Biochemical aspects of insect poisons. Int. Congr. Biochem., 4th Meeting, Vienna 12, 15–36 (1959).

    CAS  Google Scholar 

  • Pavan, M.: Sunto delie attuali conoscenze sulla pederina. Publ. Ist. Entomol. agr. Univ. Pavia, 1-35 (1975).

    Google Scholar 

  • Pavan, M., Dazzini, M.V.: Toxicology and Pharmacology—Arthropoda. Chem. Zool. 6, 365–409 (1971).

    CAS  Google Scholar 

  • Robiquet, M.: (1810) from Weatherston, J.: The Chemistry of Arthropod Defensive Substances. Quart. Rev. 21 (1967).

    Google Scholar 

  • Roth, L.M.: Studies on the gaseous secretion of Tribolium confusum. Ann. entomol. Soc. Amer. 36, 397–424 (1943).

    CAS  Google Scholar 

  • Roth, L.M.: Odoriferous glands in the Tenebrionidae. Ann. Entomol. Soc. Amer. 38, 77–87 (1945).

    CAS  Google Scholar 

  • Roth, L.M., Howland, R.B.: Studies on the gaseous secretion of Tribolium confusum (Duval). Ann. entomol. Soc. Amer. 34, 151–175 (1941).

    CAS  Google Scholar 

  • Roth, L.M., Stay, B.: The occurrence of paraquinones in some arthropods, with emphasis on the quinone-secreting tracheal glands of Diploptera punctata (Blattaria). J. Insect Physiol. 1, 305–318 (1958).

    Article  CAS  Google Scholar 

  • Rudolph, W.: Cantharidin. Arch. Pharm. (Weinheim) 254, 423 (1916).

    Article  CAS  Google Scholar 

  • Schildknecht, H.: Zur Chemie des Bombardierkäfers. Angew. Chemie 69, 62 (1957).

    Article  CAS  Google Scholar 

  • Schildknecht, H.: Über das flüchtige Sekret vom gemeinen Mehlkäfer. Angew. Chemie 71, 524 (1959).

    Google Scholar 

  • Schildknecht, H.: Defensive substances of the arthropods, their isolation and identification. Angew. Chemie (Int. Ed.) 3, 73–84 (1964).

    Article  Google Scholar 

  • Schildknecht, H.: Das Arsenal der Schwimmkäfer: Sexualhormon und Antibiotica. Chemie Technik 18, 311–312 (1968).

    Google Scholar 

  • Schildknecht, H.: The defensive chemistry of land and water beetles. Angew. Chemie (Int. Ed.) 9, 1–9 (1970).

    Article  CAS  Google Scholar 

  • Schildknecht, H., Berger, D., Krauss, D., Connert, J., Gehlhaus, J., Essenbreis, H.: Defense chemistry of Stennus comma (Coleoptera: Staphylinidae). LXI. J. Chem. Ecol. 2, 1–23 (1976).

    Article  CAS  Google Scholar 

  • Schildknecht, H., Birringer, H.: Die Steroide des Schlamm Schwimmers Ilybius fenestratus. Z. Naturforsch. 24b, 1529–1534 (1969).

    Google Scholar 

  • Schildknecht, H., Birringer, H., Krauss, D.: Über Arthropodenabwehrstoffe, XXXVI. Aufklärung des gelben Prothorakabwehrdrüsen-farbstoffes aus Ilybius fenestratus. Z. Naturforsch. 24b, 38-47 (1969b).

    Google Scholar 

  • Schildknecht, H., Birringer, H., Maschwitz, U.: Testosterone as a protective agent of the water beetle Ilybius. Angew. Chemie (Int. Ed.) 6, 558–559 (1967c).

    Article  CAS  Google Scholar 

  • Schildknecht, H., Buhner, R.: Über Arthropodenabwehrstoffe. XXXIII. Über ein Glykoproteid in der Pygidialwehrblasen des Gelbrandkäfers. Z. Naturforsch. 23b, 1209-1213 (1968).

    Google Scholar 

  • Schildknecht, H., Holubek, K.: Über einen Inhaltsstoff der Wehrdrüsen des Gelbrandkäfers. Angew. Chemie 71, 524 (1959).

    Google Scholar 

  • Schildknecht, H., Holoubek, K.: Die Bombardierkäfer und ihre Explosionschemie, V. Mitteilung über Insektenabwehrstoffe. Angew. Chemie 73, 1–7 (1961).

    Google Scholar 

  • Schildknecht, H., Hotz, D.: Identifizierung der Nebensteroide des Prothorakabwehrdrüsen Systems des Gelbrandkäfers Dytiscus marginalis. Angew. Chemie (Int. Ed.) 6, 881–882 (1967).

    Article  CAS  Google Scholar 

  • Schildknecht, H., Hotz, D., Maschwitz, U.: Über Arthropodenabwehrstoffe. XXVII. Die C21-Steroides der Prothorakabwehrdrüsen von Acilius sulcatus. Z. Naturforsch. 22b, 938-944 (1967a).

    Google Scholar 

  • Schildknecht, H., Koob, K.: Zur Explosionschemie der Bombardierkäfer. Naturwissenschaften 56, 328 (1969).

    Article  PubMed  CAS  Google Scholar 

  • Schildknecht, H., Kornig, E.: Protective material from the prothoracic gland of a Mexican Cybister species. Angew. Chemie (Int. Ed.) 7, 62 (1968a).

    Google Scholar 

  • Schildknecht, H., Krämer, H.: Zum Nachweis von Hydrochinonen neben Chinonen in den Abwehrblasen von Arthropoden—XV. Mitt. über Insektenabwehrstoffe. Z. Naturforsch. 17b, 701-702 (1962).

    Google Scholar 

  • Schildknecht, H., Krauss, D., Connert, J., Essenbreis, H., Orfanides, N.: Spreading alkaloid stenusin from the brachypterous insect Stennus comma (Coleoptera: Staphylinidae). Angew. Chemie 87, 421–422 (1975).

    Article  CAS  Google Scholar 

  • Schildknecht, H., Maschwitz, E., Maschwitz, U.: Die Explosionschemie der Bombardierkäfer (Coleoptera: Carabidae). III. Isolierung und Charakterisierung der Explosionskatalysatoren. Z. Naturforsch. 23b, 1213-1218 (1968d).

    Google Scholar 

  • Schildknecht, H., Maschwitz, E., Maschwitz, U.: Die Explosionschemie der Bombardierkäfer: Struktur und Eigenschaften der Brennkammerenzyme. J. Insect Physiol. 16, 749–789 (1970).

    Article  CAS  Google Scholar 

  • Schildknecht, H., Maschwitz, U.: A vertebrate hormone as the defensive substance of the water beetle Dytiscus marginalis. Angew. Chemie (Int. Ed.) 5, 421–422 (1966).

    Article  CAS  Google Scholar 

  • Schildknecht, H., Maschwitz, U., Winkler, H.: Zur Evolution der Carabiden-Wehrdrüsensekret. Naturwissenschaften 55, 112–117 (1968e).

    Article  PubMed  CAS  Google Scholar 

  • Schildknecht, H., Maschwitz, U., Krauss, D.: Blausäure im Wehrsekret des Erdläufers Pachymerium ferrugineum. Naturwissenschaften 55, 230 (1968f).

    Google Scholar 

  • Schildknecht, H., Siewerdt, R., Maschwitz, U.: Über Arthropoden Abwehrstoffe. XXIII. Cybisteron, ein neues Arthropoden Steroid. Justus Liebigs Ann. Chem. 703, 182–189 (1967b).

    Article  CAS  Google Scholar 

  • Schildknecht, H., Tacheci, H.: Colymbetin, a new defensive substance of the water beetle Colymbetes fuscus (Coleoptera: Dytiscidae) that lowers blood pressure. J. Insect Physiol. 17, 1889–1896 (1971).

    Article  PubMed  CAS  Google Scholar 

  • Schildknecht, H., Tacheci, H., Maschwitz, U.: 4-Pregnen-15α,20β-diol-3-on im Wehrsekret eines Schwimmkäfers. Naturwissenschaften 56, 37–38 (1969a).

    Article  PubMed  CAS  Google Scholar 

  • Schildknecht, H., Weis, K.H.: Über die Tenebrioniden-chinon bei lebendem und totem Untersuchungsmaterial. Z. Naturforsch. 15b, 757-758 (1960a).

    Google Scholar 

  • Schildknecht, H., Weis, K.H.: Über das flüchtige Sekret von Totenkäfer Blaps mortisaga. Z. Naturforsch. 15b, 200 (1960b).

    Google Scholar 

  • Schildknecht, H., Weis, K.H.: Die Abwehrstoffe einiger Carabiden, insbesondere von Abax ater. XII. Mitteilung über Insektenabwehrstoffe. Z. Naturforsch. 17b, 439-447 (1962).

    Google Scholar 

  • Schildknecht, H., Winkler, H., Krauss, D., Maschwitz, U.: Über Arthropodenabwehrstoffe. XXVIII. Über das Abwehrsekret von Idiochroma dorsalis. Z. Naturforsch. 23b, 46-49 (1968c).

    Google Scholar 

  • Schildknecht, H., Winkler, H., Maschwitz, U.: Über Arthropodenabwehrstoffe. XXXI. Vergleichend chemische Untersuchungen der Inhaltsstoffe der Pygidialwehrblasen von Carabiden. Z. Naturforsch. 23b, 637-644 (1968b).

    Google Scholar 

  • Schlatter, Ch., Waldner, E.E., Schmid, H.: Biosynthesis of cantharidin. I. Experientia (Basel) 24, 994–995 (1968).

    Article  CAS  Google Scholar 

  • Schnepf, E., Wenneis, W., Schildknecht, H.: Über Arthropoden-Abwehrstoffe. XLI. Zur Explosionschemie der Bombardierkäfer (Coleoptera: Carabidae). IV. Zur Feinstruktur der Pygidialabwehrdrüsen des Bombardierkäfers (Brachynus crepitans L.). Z. Zellforsch. 96, 582–599 (1969).

    CAS  Google Scholar 

  • Scott, P.D., Hepburn, H.R., Crewe, R.M.: Pygidial defensive secretions of some carabid beetles. Insect Biochem. 5, 805–811 (1975).

    Article  CAS  Google Scholar 

  • Sierra, J.R., Woggon, W.D., Schmid, H.: Transfer of cantharidin during copulation from adult male to the female Lytta vesicatoria (Spanish Flies). Experientia (Basel) 32, 142–144 (1976).

    Article  CAS  Google Scholar 

  • Sipahimalani, A.T., Mamdapur, V.R., Joshi, N.K., Chadha, M.S.: Steroids in the defensive secretion of the water beetle Cybister limbatus. Naturwissenschaften 57, 40 (1970).

    Article  PubMed  CAS  Google Scholar 

  • Stork, G., von Tamelin, E.E., Friedman, L.J., Burgstahler, A.W.: A stereospecific synthesis of cantharidin. J. Amer. chem. Soc. 75, 384–392 (1953).

    Article  CAS  Google Scholar 

  • Sulc, K.: On the repugnatorial stink glands in the beetles of the genus Cantharis, Coleoptera. Ceska Akad. ved. a umeni v Praze Bull. Int. 50, 79–100 (1949).

    Google Scholar 

  • Suzuki, T., Suzuki, T., Huynh, V., Moto, T.: Isolation of 2-hydroxy-4-methoxypropiophenone from Tribolium castaneum and T. confusum. Agric. biol. Chem. 39, 1687–1688 (1975).

    Article  CAS  Google Scholar 

  • Tschinkel, W.R.: Phenols and quinones from the defensive secretion of the tenebrionid beetle Zophobas rugipes. J. Insect Physiol. 15, 191–200 (1969).

    Article  CAS  Google Scholar 

  • Tursch, B., Braekman, J.C., Daloze, D.: Arthropod alkaloids. Experientia (Basel) 32, 401–407 (1976).

    Article  CAS  Google Scholar 

  • Tursch, B., Braekman, J.C., Daloze, D., Hootele, C., Losman, D., Karlsson, R., Pasteels, J.M.: Chemical ecology of arthropods. VI. Adaline, a novel alkaloid from Adalia bipunctata L. (Coleoptera: Coccinellidae). Tetra. Lett. No. 3, 201–202 (1973b).

    Google Scholar 

  • Tursch, B., Chome, C., Braekman, J.C., Daloze, D.: Chemical ecology of arthropods. VIII. Synthesis and absolute configuration of adaline. Bull. Soc. chim. Belg. 82, 699–703 (1973a).

    CAS  Google Scholar 

  • Tursch, B., Daloze, D., Braekman, J.C., Hootele, C., Cravador, A.: Chemical ecology of arthropods. IX. Structure and absolute configuration of hippodamine and convergine, two novel alkaloids from the American ladybug Hippodamia convergens (Coleoptera). Tetra. Lett. No. 5, 409–412 (1974).

    Google Scholar 

  • Tursch, B., Daloze, D., Brakman, J.C., Hootele, C., Pasteels, J.M.: Chemical ecology of arthropods. X. The structure of myrrhine and the biosynthesis of coccinelline. Tetrahedron 31, 1541–1543 (1975).

    CAS  Google Scholar 

  • Tursch, B., Daloze, D., Dupont, M., Hootele, C., Kaisin, M., Pasteels, J.M., Zimmermann, D.: Coccinellin, the defensive alkaloid of the beetle, Coccinella septempunctata. Chimia 25, 307 (1971b).

    CAS  Google Scholar 

  • Tursch, B., Daloze, D., Dupont, M., Pasteels, J.M. and Tricot, M.C.: A defensive alkaloid in a carnivorous beetle. Experientia (Basel) 27, 1380–1381 (1971a).

    Article  CAS  Google Scholar 

  • Tursch, B., Daloze, D., Hootele, C.: The alkaloid of Propylaea quatuordecimpunctata L. (Coleoptera, Coccinellidae). Chimia 26, 74 (1972b).

    CAS  Google Scholar 

  • Tursch, B., Daloze, D., Pasteels, J.M., Cravador, A., Braekman, J.C., Hootele, C., Zimmermann, D.: Two novel alkaloids from the American ladybug Hippodamia convergens (Coleoptera: Coccinellidae). Bull. Soc. chim. Belg. 81, 649–650 (1972a).

    CAS  Google Scholar 

  • Tschinkel, W.R.: 6-Alkyl-l,4-naphthoquinones from the defensive secretion of the tenebrionid beetle Argoporis alutacea (Coleoptera). J. Insect Physiol. 18, 711–722 (1972).

    Article  CAS  Google Scholar 

  • Tschinkel, W.R.: A comparative study of the chemical defense system of tenebrionid beetles: chemistry of the secretions. J. Insect Physiol. 21, 753–783 (1975a).

    Article  CAS  Google Scholar 

  • Tschinkel, W.R.: Unusual occurrence of aldehydes and ketones in the defensive secretion of the tenebrionid beetle Eleodes beamri. J. Insect Physiol. 21, 659–672 (1975b).

    Article  CAS  Google Scholar 

  • Tseng, Y.C.L., Davidson, J.A., Menzer, R.E.: Morphology and chemistry of the odoriferous gland of the lesser mealworm. Ann. entomol. Soc. Amer. 64, 425–430 (1971).

    CAS  Google Scholar 

  • Vidari, G., DeBernardi, M., Pavan, M., Ragozzino, L.: Rose oxide and iridodial from Aromia moschata L. (Coleoptera: Cerambycidae). Tetra. Lett. No. 41, 4065–4068 (1973).

    Article  Google Scholar 

  • Wain, R.L.: The secretion of salicylaldehyde by the larvae of the brassy willow beetle, Phylo-decta vittelinae. Ann. Rep. Agric. Hort. Station, Long Ashton, Bristol 108-110 (1943).

    Google Scholar 

  • Wallace, T.B., Blum, M.S.: Refined defensive mechanisms in Chrysomela scripta. Ann. entomol. Soc. Amer. 62, 503–506 (1969).

    CAS  Google Scholar 

  • Wallace, J.B., Blum, M.S.: Reflex bleeding: a highly defined mechanism in Diabrotica larvae (Coleoptera: Chrysomelidae). Ann. entomol. Soc. Amer. 64, 1021–1024 (1971).

    Google Scholar 

  • Walter, W.G., Cole, J.F.: Isolation of cantharidin in Epicauta pestifera. J. pharm. Sci. 56, 174–176 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Weatherston, J., Percy, J.E.: Arthropod defensive secretions in Chemicals Controlling Insect Behaviour (Ed. M. Beroza). Acad. Press, N.Y. pp. 95-144 (1970).

    Google Scholar 

  • Wheeler, J.W., Araujo, J., Happ, G.M., Pasteels, J.W.: γ-Dodecalactone from rove beetles. Tetra. Lett. No. 46, 4635–4638 (1972a).

    Article  Google Scholar 

  • Wheeler, J.W., Chung, R.H., Oh, S.K., Benfield, E.F., Neff, S.E.: Defensive secretions of cychrine beetles (Coleoptera: Carabidae). Ann. entomol. Soc. Amer. 63, 469–471 (1970).

    CAS  Google Scholar 

  • Wheeler, J.W., Oh, S.K., Benfield, E.F., Neff, S.E.: Cyclopentanoid norsesquiterpenes from gyrinid beetles (Coleoptera). J. Amer. chem. Soc. 94, 7589–7590 (1972b).

    Article  CAS  Google Scholar 

  • Woodward, R.B., Loftfield, R.B.: Structure of cantharidin and the synthesis of desoxycantharidin. J. Amer. chem. Soc. 63, 3167–3171 (1941).

    Article  CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1978 Springer-Verlag Berlin/Heidelberg

About this chapter

Cite this chapter

Weatherston, J., Percy, J.E. (1978). Venoms of Coleoptera. In: Bettini, S. (eds) Arthropod Venoms. Handbook of Experimental Pharmacology / Handbuch der experimentellen Pharmakologie, vol 48. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-45501-8_19

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-45501-8_19

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-45503-2

  • Online ISBN: 978-3-642-45501-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics