Abstract
The defensive osmeterial secretion of pre-final instar larvae of the citrus swallowtail,Papilio demodocus (Lepidoptera: Papilionidae) was found to contain methyl 3-hydroxybutanoate, 3-hydroxybutanoic acid, α-pinene, myrcene, limonene, β-phellandrene, (Z)-ocimene, (E)-ocimene, β-caryophyllene, (E)-β-farnesene, and germacrene-A, as well as a further number of unidentified sesquiterpenoid constituents. The presence of germacrene-A in the secretion was inferred from the formation of β-elemene under certain GC conditions. Larvae of the second, third, and fourth instars produce qualitatively similar secretions. Remarkable quantitative differences were found between the secretions of individual larvae. These variations could not be correlated with the diet on which the larvae were fed, their sex, instar, or color form. However, in a number of larvae the two prongs of the osmeterium were found to produce quantitatively different secretions.
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Bohlmann, F., andZdero, C. 1978. Neue Furanoeremophilane und andere Sesquiterpene aus Vertretern der GattungEurops.Phytochemistry 17:1135–1153.
Bremser, W., Francke, B., andWagner, H. 1982. Chemical Shift Ranges in Carbon-13 NMR Spectroscopy. Verlag Chemie, Weinheim.
Burger, B.V., Röth, M., Le Roux, M., Spies, H.S.C., Truter, V., andGeertsema, H. 1978. The chemical nature of the defensive larval secretion of the citrus swallowtail,Papilio demodocus.J. Insect Physiol. 24:803–805.
Clark, C.A., Dickson, C.G.C., andSheppard, P.M. 1963. Larval color pattern inPapilio demodocus.Evolution 17:130–137.
Crossley, A.C., andWaterhouse, D.F. 1969. The ultrastructure of the osmeterium and the nature of its secretion inPapilio larvae (Lepidoptera).Tissue Cell 1:525–554.
Eisner, T., andMeinwald, Y.C. 1965. Defensive secretion of the caterpillar (Papilio).Science 150:1733–1735.
Eisner, T., Pliske, T.E., Ikeda, M., Owen, D.F., Vázquez, L., Pérez, H., Franclemont, J.C., andMeinwald, J. 1970. Defense mechanisms of arthropods XXVII. Osmeterial secretion of papilionid caterpillars (Baronia, Papilio, Eurytides).Ann. Entomol. Soc. Am. 63:914–915.
Eisner, T., Kluge, A.F., Ikeda, M.I., Meinwald, Y.C., andMeinwald, J. 1971. Defense mechanisms of Arthropods XXIX. Sesquiterpenes in the osmeterial secretion of a papilionid butterfly,Battus polydamas.J. Insect Physiol. 17:245–250.
Formáček, V., andKubeczka, K.-H. 1982. Essential Oils Analysis. John Wiley & Sons, Chichester. pp. 93–117.
Grob, K., Grob, G., andGrob, K., Jr. 1977. The barium carbonate procedure for the preparation of glass capillary columns: Further information and developments.Chromatographia 10:181–187.
Grob, K. 1980. Deactivation of glass capillaries by persilylation.J. High Resolut. Chromatogr. Chromatogr. Commun. 3:493–496.
Honda, K. 1980a. Volatile constituents of larval osmeterial secretions inPapilio protenor demetrius.J. Insect Physiol. 26:39–45.
Honda, K. 1980b. Osmeterial secretions of papilionid larvae in the generaLuehdorfia, Graphium, andAtrophaneura (Lepidoptera).Insect Biochem. 10:583–588.
Honda, K. 1981. Larval osmeterial secretions of the swallowtails (Papilio).J. Chem. Ecol. 7:1089–1113.
Honda, K. 1983a. Defensive potential of components of the larval osmeterial secretion of papilionid butterflies against ants.Physiol. Entomol. 8:173–179.
Honda, K. 1983b. Evidence for de novo biosynthesis of osmeterial secretions in young larvae of the swallowtail butterflies (Papilio):Deuterium incorporated in vivo into sesquiterpene hydrocarbons as revealed by mass spectrometry.Insect Sci. Appl. 4:255–261.
López, A., andQuesnel, V.C. 1970. Defensive secretions of some papilionid caterpillars.Caribb. J. Sci. 10:5–7.
Patt, S.L., andShoolery, J.N. 1982. Attached proton test for carbon-13 NMR.J. Magn. Reson. 46:535–539.
Ramage, G.R., andWhitehead, R. 1954. The caryophyllenes. Part X. Oxides from the caryophyllenes.J. Chem. Soc. 1954:4336–4340.
Seligman, I.M., andDoy, F.A. 1972. β-Hydroxy-n-butyric acid in the defensive secretion ofPapilio aegeus.Comp. Biochem. Physiol. 42b:341–342.
Shirahama, H., Ōsawa, E., Chhabra, B.R., Shimokawa, T., Yokono, T., Kanaiwa, T., Amiya, T., andMatsumoto, T. 1981. Conformational aspects of caryophyllene. Population of stable conformers and ring inversion barrier oftrans-cyclononene ring portion.Tetrahedron Lett. 22:1527–1528.
Stenhagen, E., Abrahamsson, S., McLafferty, F.W. 1974. Registry of Mass Spectral Data. John Wiley & Sons, New York.
Sternhell, S. 1969. Correlation of interproton spin-spin coupling constants with structure.Chem. Soc. Q. Rev. 23:236–270.
Trenkle, K. 1972. Recent investigations on fennel (Foeniculum vulgare): 2. The essential oil of the fruit, herb, and root of the fruiting plants.Pharmazie 27:319–324.
Van Son, G. 1949. Butterflies of Southern Africa, Part 1: Papilionidae and Pieridae, Transvaal Museum, Pretoria.
Weinheimer, A.J., Youngblood, W.W., Washecheck, P.H., Karns, T.K.B., Weinheimer, A.J., Youngblood, W.W., Washecheck, P.H., Karns, T.K.B., andCiereszko, L.S. 1970. Isolation of the elusive (−)-germacrene-A from the gorgonian,Eunicea mammosa. Chemistry of coelenterates. XVIII.Tetrahedron Lett. 1970:497–500.
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Abstracted in part from the MSc thesis of Z. Munro, University of Stellenbosch, March 1981.
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Burger, B.V., Munro, Z., Röth, M. et al. Constituents of osmeterial secretion of pre-final instar larvae of citrus swallowtail,Papilio demodocus (Esper) (Lepidoptera: Papilionidae). J Chem Ecol 11, 1093–1113 (1985). https://doi.org/10.1007/BF01020678
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DOI: https://doi.org/10.1007/BF01020678