Summary
By means of gas chromatography, gas chromatographic coupled mass spectrometry, trail-following experiments and electrophysiological recordings from worker antennae, the major trail pheromone components from the hindgut of the formicine speciesCamponotus atriceps andC. floridanus were identified as 3,5-dimethyl-6-(1′-methylpropyl)-tetrahydropyran-2-one and nerolic acid, respectively. The Dufour's gland contents of both species, investigated by gas chromatographic coupled mass spectrometry, show significant differences.
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Akre RD, Hansen KD (1990) Management of carpenter ants. Pp 693–700in Vander Meer RK, Jaffe K, Cedeno A (eds) Applied Myrmecology. Boulder/CO, San Francisco/CA, GB-Oxford: Westview Press
Ali MF, Billen JPJ, Jackson BD, Morgan ED (1988) Secretion of the Dufour gland of two African desert ants,Camponotus aegyptiacus andCataglyphis savignyi (Hymenoptera: Formicidae). Biochem Syst Ecol 16:647–654
Attygalle AB, Herrig M, Vostrowsky O, Bestmann HJ (1987) A technique for injecting intact glands for analysis of sex pheromones of Lepidoptera by capillary gas chromatography: reinvestigation of the pheromone complex ofMamestra brassicae. J Chem Ecol 13:1299–1311
Attygalle AB, Morgan ED (1988) Pheromones in nanogram quantities: structure determination by combined microchemical and gas chromatographic methods. Angew Chem Int Ed Eng 27:460–478
Bagnéres A-G, Morgan ED, Clement J-L (1991) Species-specific secretion of the Dufour glands of three species of formicine ants (Hymenoptera: Formicidae). Biochem Syst Ecol 19:25–33
Bergström G, Kullenberg B, Ställberg-Stenhagen S, Stenhagen E (1968) Studies on natural odoriferous compounds. II. Identification of a 2,3-dihydrofarnesol as the main component of the marking perfume of male bumble bees of the speciesBombus terrestris L. Arkiv för Kemi 28:453–469
Bestmann HJ, Haak U, Kern F, Hölldobler B (1995) 2,4-Dimethyl-5-hexanolide, a trail pheromone component of the carpenter antCamponotus herculeanus (Hymenoptera: Formicidae: Formicinae). Naturwissenschaften 82:142–144
Bolton B (1995a) A taxonomic and a zoogeographical census of extant ant taxa (Hymenoptera: Formicidae). J Nat Hist 29: 1039–1056
Bolton B (1995b) A New General Catalogue of the Ants of the World. Cambridge/MA: Harvard University Press
Brown WV, Moore BP (1979) Volatile secretory products of an Australian formicine ant of the genusCalomyrmex (Hymenoptera: Formicidae). Insect Biochem 9:451–460
Cantwell SG, Lau EP, Watt DS, Fall RR (1978) Biodegradation of acyclic isoprenoids byPseudomonas species. J Bacteriol 135:324–333
Carlin NF, Hölldobler B (1986) The kin recognition system of carpenter ants (Camponotus spp.). I. Hierachical uses in small colonies. Behav Ecol Sociobiol 19:123–134
Corey EJ, Gilman NW, Ganem BE (1968) New Methods for the oxidation of aldehydes to carboxylic acids and esters. JACS 90: 5616–5617
Décombe J (1936) Préparation de cétonesβ-chloréthylées et des cétonesβ-vinylées. C R hebd Seanc Acad Sci Paris 202:1685–1687
Dev S, Rai C (1957) Organic reactions with polyphosphoric acid. Part V. Intramolecular acylation with lactones: cyclo pentenones from ∂-lactones. J Ind Chem Soc 34:266–274
Deyrup MA, Carlin N, Trager J, Umphrey G (1988) A review of the ants of the Florida Keys. Fla Entomol 71:163–176
Francis GW, Veland K (1981) Alkylthiolation for the determination of double-bond position in linear alkenes. J Chromatrogr 219:379–384
Hashmi AA (1973) A revision of the Neotropical ant subgenusMyrmothrix of the genusCamponotus (Hymenoptera: Formicidae). Studia Entomol 16:1–140
Hoffman JM, Schlessinger RH (1971) Sodium metaperiodat: a milk oxidizing agent for the generation of di-imide from hydrazine. Chem Comm 00:1245–1246
Hölldobler B (1962) Über die forstliche Bedeutung der Roβameisen. Waldhygiene 4:228–250
Hölldobler B, Wilson EO (1990) The Ants. Cambridge/MA: Belknap-Press of Harvard University and D-Heidelberg: Springer Verlag
Honkanen E, Moisio T, Krvonen P (1969) Mass spectra of some branched-chain aliphatic lactones. Acta Chem Scand 23:531–536
Ikan R, Gottlieb R, Bergmann ED, Ishay J (1969) The pheromone of the queen of the oriental hornet,Vespa orientalis. J Insect Physiol 15:1708–1712
Kern F, Bestmann HJ (1993) Antennal electrophysiological responsiveness of the Ponerinae antLeptogenys diminuta to trail and recruitement pheromones and its structure analogs. Naturwissenschaften 80:424–427
Kern F, Janssen E, Bestmann HJ, Schäfer D, Klein RW, Maschwitz U, Attygalle AB Mellein, A trail pheromone component of the antLasius fuliginosus (Formicidae, Formicinae). J Chem Ecol: in press
Ledl F, Schleicher E (1990) New aspects of the Maillard reaction in foods and in the human body. Angew Chem Int Ed Engl 29:565–594
Lloyd HA, Schmuff NR, Hefetz A (1984) Chemistry of the male mandibular gland secretion of the carpenter ant,Camponotus thoracicus fellah Emery. Comp Biochem Physiol 78B:687–689
Morgan ED, Wadhams LJ (1972) Gas chromatography of volatile compounds in small samples of biological materials. J Chromatogr Sci 10:528–529
Pickett JA, Williams IH, Martin AP, Smith MC (1980) Nasonov pheromone of the honey bee,Apis mellifera L. (Hymenoptera: Apidae). Part I. Chemical characterization. J Chem Ecol 6:425–434
Pinyarat W, Mori K (1993) Synthesis of 2,4-dimethyl-5-hexanolide, 2,4-dimethyl-5-heptanolide and 2,4-dimethyl-5-octanolide, the lactones identified in volatiles from the heads of the male black garden ant,Lasius niger. Biosci Biotechnol Biochem 57:419–421
Rocca JR, Tumlinson JH, Glancey BM, Lofgren CS (1983) Synthesis and stereochemistry of tetrahydro-3,5-dimethyl-6-(1-methyl-butyl(-2H-pyran-2-one, a component of the queen recognition pheromone ofSolenopsis invicta. Tetrahedron Lett 24:1893–1896
Schildknecht H (1976) Chemical ecology — a chapter of modern natural products chemistry. Angew Chem Int Ed Engl 15:214–222
Steghaus-Kovacs S, Maschwitz U, Attygalle AB, Frighetto R, Frighetto N, Vostrowsky O, Bestmann HJ (1992) Trail-following responses ofLeptogenys diminuta to stereoisomers of 4-methyl-3-heptanol. Experientia 48:690
Swedenborg PD, Jones RL, Liu H-W, Krick TP (1993) (3R*, 5S*,6R*)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one, a third sex pheromone component forMacrocentrus grandii (Goidanich) (Hymenoptera: Brachonidae) and evidence for its utility at eclosion. J Chem Ecol 19:485–502
Übler E, Kern F, Bestmann HJ, Hölldobler B, Attygalle AB (1995) Trail pheromone of two formicine ants,Camponotus silvicola andC. rufipes (Hymenoptera: Formicidae). Naturwissenschaften 82:523–525
Wheeler JW, Evans SL, Blum MS, Velthuis HHV, de Carmago JMF (1976)Cis-2-methyl-5-hydroxyhexanoic acid lactone in the mandibular gland secretion of a carpenter bee. Tetrahedron Lett 45:4029–4032
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Pheromones 104: Janssen E, Übler E, Bauriegel L, Kern F, Bestmann H-J, Attygalle AB, Steghaus-Kovacs S, Maschwitz U: Trail pheromone of the Ponerinae antLeptogenys peuqueti (Hymenoptera: Formicidae): a multicomponent mixture of related compounds
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Haak, U., Hölldobler, B., Bestmann, H.J. et al. Species-specificity in trail pheromones and Dufour's gland contents ofCamponotus atriceps andC. floridanus (Hymenoptera: Formicidae). Chemoecology 7, 85–93 (1996). https://doi.org/10.1007/BF01239485
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DOI: https://doi.org/10.1007/BF01239485