Abstract
The thoracic glands of males in two ant-lion speciesSynclysis baetica andAcanthaclisis occitanica, which occur sympatrically in Israel, were found to contain a volatile secretion with two-component blends of nerol oxide and (R,Z)-6-tridecen-2-ol (approx 1∶5) and nerol oxide and 10-homonerol oxide (approx. 1∶2), respectively. Chemical analyses were performed using gas chromatography-mass spectrometry, chiral gas chromatography, and ozonolysis, and the proposed structures were confirmed by synthesis. The species-specific, few-component volatile signals are thought to function as a reproductive isolation mechanism between the two sympatric species. Biochemical relationships between the nerol derivatives and between the unsaturated secondary alcohols are discussed.
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Ansell, M.F., Emmet, J.C., andCoombs, R.V. 1968. The intramolecular acylation of some hexhept and octenoic acids.J. Chem. Soc. C:217–225.
Baeckström, P., Bergström, G., Björkung, F., Hui-Zhu, H., Högberg, H.-E., Jacobsson, U., Guo-Qiang, L., Löfqvist, J., Norin, T., andWassgren, A.-B. 1989. Structures, absolute configurations, and syntheses of volatile signals from three sympatric ant-lion species,Euroleon nostras, Grocus bore, Myrmeleon formicarius (Neuroptera: Myrmeleontidae).J. Chem. Ecol. 10:61–80.
Beilstein, 1973. Handbuch der Organische Chemie. Band 1, Erg. Werk 4, p. 1566; Erg. Werk 3, p. 1663; Erg. Werk 4; p. 1770.
Beroza, M., andBierl, B.A. 1967, Rapid determination of olefin position in organic compounds in the microgram range by ozonolysis and gas chromatography.Anal. Chem. 39:1131–1135.
Boland, W., andGäbler, A. 1989. Biosynthesis of homoterpenes in higher plants.Helv. Chim. Acta. 72:247–253.
Elofson, R., andLöfqvist, J. 1974. The Eltringham organ and a new thoracic gland: Ultrastructure and presumed pheromone function (Insects, Myrmeleontidae).Zool. Scripta 3:31–40.
Gäbler A., Boland, W., Preiss, U., andSimon, H. 1991. Stereochemical studies on homoterpene biosynthesis in higher plants; Mechanistic, phylogenetic, and ecological aspects.Helv. Chim. Acta. 74:1773–1789.
Gerlach, D., Schneider, S., Göller, T., Kim, K.S., andSchreier, P. 1987. Screening of lipases for enantiomers resolution of secondary alcohols by esterification in organic medium, pp. 543–554,in S. Schneider (ed.). Bioflavour '87. Walter de Gruyter, Berlin.
Högberg, H.-E., Hedenström, E., Isaksson, R., andWassgren, A.-B. 1987. Preparation of the four stereoisomers of chalcogran, pheromone components ofPityogenes chalcographus and of both enantiomers of γ-caprolactone, pheromone component ofTragoderma granarium.Acta Chem. Scand. B 41:694–697.
König, W.A., Francke, W., andBenecke, I., 1982. Gas Chromatographic enantiomer separation of chiral alcohols.J. Chromatogr. 239:227–231.
Löfqvist, J., andBergström, G. 1980. Nerol-derived volatile signals as a biochemical basis for reproductive isolation between sympatric population of three species of ant-lions (Neuroptera: Myrmeleontidae).Insect Biochem. 10:1–10.
Pirkle, W.H., andAdams, P.E. 1979. Broad-spectrum synthesis of enantiomerically pure lactones 1. Synthesis of sex pheromones of the carpenter bee, rove beetle, Japanese beetle, black-tailed deer and oriental hornet.J. Org. Chem. 44:2169–2175.
Schurig, V., andWeber, R. 1981. Manganese(II)-bis[3-heptafluorobutyryl-l(R)-camphorate]: A versatile agent for the resolution of racemic cyclic ethers by complexation gas chromatography.J. Chromatogr. 217:51–70.
Simon, D. 1988. Ant-Lions (Neuroptera: Myrmeleontidae) of the Coastal Plain: Systematical, Ecological and Zoogeographical Aspects with Emphasis on the Coexistence of a Species Guild of the Unstable Dunes, p. 213,in Ph.D. thesis. Tel Aviv University, Tel Aviv (in Hebrew).
Stange, L.A., andMiller, R.B. 1985. A generic review of the Acanthaclisine ant-lions based on larvae (Neuroptera: Myrmeleontidae).Inseda Mundi 1:29–42.
Wassgren, A.-B., andBergström, G. 1984. Revolving fraction collector for preparative capillary gas chromatography in the 100-μg to 1-ng range.J. Chem. Ecol. 10:1543–1550.
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Bergström, G., Wassgren, A.B., Högberg, H.E. et al. Species-specific, two-component, volatile signals in two sympatric ant-lion species:Synclysis baetica andAcanthaclisis occitanica (Neuroptera, Myrmeleontidae). J Chem Ecol 18, 1177–1188 (1992). https://doi.org/10.1007/BF00980072
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DOI: https://doi.org/10.1007/BF00980072