Abstract
By means of a bioassay employing the minnowPimephales promelas, the anesthetic activities and toxicities of various defensive steroids and norsesquiterpenes produced by the Dytiscidae and Gyrinidae were compared with those of a wide selection of steroid standards. The most widely occurring major components of dytiscid secretions, 4-pregnen-3-ones and related derivatives, were among those compounds most active in minnow bioassays. The norsesquiterpenes gyrinidal and gyrinidione were among the most toxic compounds tested but they possessed little anesthetic action. The anesthetic activity of gyrinidone was comparable to that of testosterone. Steroid activity in the minnow bioassay was highly related to the degree of oxygenation; steroids oxygenated only at the termini of the molecule were most active. Less or additional oxygenation resulted in a loss of activity. When steroids were rapidly administered to minnows the activities of many of them were similar, suggesting they share a common mode of action.
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References
Benfield, E. 1972. A defensive secretion ofDineutus discolor (Coleoptera: Gyrinidae).Ann. Entomol. Soc. Am. 65:1324–1327.
Blunck, H. 1917. Die Schreckdrüsen des Dytiscus und ihr Secret. Zweiter und Letzter Teil.Z. Wiss. Zool. 117:205–256.
Chadha, M., Joshi, N., Mamdapur, V., andSipahimalani, A. 1970. C-21 steroids in the defensive secretions of some Indian water beetles. II.Tetrahedron 26:2061–2064.
Figdor, S., Kodet, M., Bloom, B., Agnello, E., Pán, S., andLaubach, G. 1957. Central activity and structure in a series of water-soluble steroids.J. Pharmacol. 119:299–309.
Kappas, A. andPalmer, R. 1963. Selected aspects of steroid pharmacology.Pharmacol. Rev. 15:123–167.
Meinwald, J., Opheim, K., andEisner, T. 1972. Gyrinidal: A sesquiterpene aldehyde from the defensive glands of gyrinid beetles.Proc. Nat. Acad. Sci. USA 69:1208–1210.
Miller, J.R., Hendry, L.B., andMumma, R.O. 1975. Norsesquiterpenes as defensive toxins of whirligig beetles (Coleoptera: Gyrinidae).J. Chem. Ecol. 1:59–82.
Miller, J.R. andMumma, R.O. 1973. Defensive agents of the American water beetlesAgabus seriatus andGraphoderus liberus.J. Insect Physiol. 19:917–925.
Rothblat, G., Hartzell, R., Mialhe, H., andKritchevsky, D. 1966. The uptake of cholesterol by L5178Y tissue-culture cells: Studies with free cholesterol.Biochim. Biophys. Acta 166:133–145.
Schildknecht, H. 1968. Das Arsenal der Schwimmkäfer sexual hormone und “Antibiotica.”Nach. Chem. Tech. 16:311–312.
Schildknecht, H. 1970. The defensive chemistry of land and water beetles.Angew. Chem. Int. Ed. 9:1–19.
Schildknecht, H. andHotz, D. 1967. Identification of the subsidiary steroids from the prothoracic protective gland system ofDytiscus marginalis.Angew. Chem. Int. Ed. 6:881–882.
Schildknecht, H. andKörnig, W. 1968. Prothoracic materials in the secretion from the prothoracic protective gland of a Mexican Cybister species.Angew. Chem. Int. Ed. 7:62–63.
Schildknecht, H. andBirringer, H. 1969. Die Steroide des SchlammschwimmersIlybius fenestratus. III.Z. Naturforsch. 24:1529–1534.
Schildknecht, H. andHotz, D. 1970. Das Prothorakalwehrsekret des SchwimmkäfersAgabus bipustulatus.Chemiker-Ztg. 94:130.
Schildknecht, H. andHotz, D. 1971. Naturally occurring steroid-isobutyrates, pp. 158–166,in James, V. and Martini, L. (eds.),Hormonal Steroids, Proceedings of the Third International Congress on Hormonal Steroids, Hamburg, 1970. Excerpta Medica, Amsterdam.
Schildknecht, H. andTacheci, H. 1971. Colymbetin, a new defensive substance of the water beetle,Colymbetes fuscus, that lowers blood pressure.J. Inspect. Physiol. 17:1889–1896.
Schildknecht, H., Siewerdt, R.S., andMaschwitz, V. 1966. A vertebrate hormone as defensive substance of the water beetle (Dytiscus marginalis).Angew. Chem. Int. Ed. 5:421–422.
Schildknecht, H., Birringer, H., andMaschwttz, V. 1967a. Testosterone as a protective agent of the water beetleIlybius.Angew. Chem. Int. Ed. 6:558–559.
Schildkneckt, H., Hotz, D., andMaschwitz, L. 1967b. Die C21-Steroide der Prothor-akalwehrdrusen vonAcilius sulcatus.Z. Naturforsch. 22:938–944.
Schildknecht, H., Siewerdt, R., andMaschwitz, V. 1967c. Cybisteron, ein neues Arthropoden-Steroid.Liebigs Ann. Chem. 703:182–189.
Schildknecht, H., Birringer, H., andKrauss, D. 1969a. Auf Klärung des gelben Protho-akalwehrdrüsen-Farbstoffes vonIlybius fenestratus.Z. Naturforsch. 24:38–47.
Schildknecht, H., Tacheci, H., andMaschwitz, V. 1969b. 4-Pregnen-15α, 20β-diol-3-one im Wehrseckret eines Schwimmkäfers.Naturwissenschaften 56:37.
Schildknecht, H., Neumaier, H., andTauscher, B. 1972. Gyrinal, die Pygidialdrüsensubstanz der Taumelkäfer (Coleoptera: Carabidae).Liebigs Ann. Chem. 756:155–161.
Seeman, P. 1969. Membrane expansion and stabilization by anesthetics and other drugs, pp. 40–56,in Bolis, L., Katchalsky, A., Keynes, R., Lowenstein, W., and Pethica, B. (eds.),Permeability and Function of Biological Membranes, Proceedings of the 1969 Meeting of the International Conference on Biological Membranes, 1969. North-Holland Publishing Company, Amsterdam.
Selye, H. 1941a. Anesthetic effect of steroid hormones.Proc. Soc. Exp. Biol. Med. 46:116–121.
Selye, H. 1941b. Studies concerning the anesthetic action of steroid hormones.J. Pharmacol. Exp. Therap. 73:127–141.
Selye, H. 1942. Correlations between the chemical structure and the pharmacological action of the steroids.Endocrinology 30:437–453.
Selye, H. andHeard, R. 1943. The fish assay for the anesthetic effect of the steroids.Anesthesiology 4:36–47.
Sipahimalani, A., Mamdapur, V., Joshi, N., andChadha, M. 1970. Steroids in the defensive secretion of the water beetle,Cybister limbratus. I.Naturwissenschaften 57:40.
Wheeler, J., Oh, S., Benfield, E., andNeff, S. 1972. Cyclopentanoid norsesquiterpenes from gyrinid beetles.J. Am. Chem. Soc. 94:7589–7590.
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Miller, J.R., Mumma, R.O. Physiological activity of water beetle defensive agents. I. Toxicity and anesthetic activity of steroids and norsesquiterpenes administered in solution to the minnowPimephales promelas Raf.. J Chem Ecol 2, 115–130 (1976). https://doi.org/10.1007/BF00987736
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DOI: https://doi.org/10.1007/BF00987736