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  • Papilionidae  (7)
  • 3-caffeoyl-muco-quinic acid  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Oviposition stimulants for the pipevine swallowtail butterfly,Battus philenor (Papilionidae), from anAristolochia host plant: Synergism between inositols, aristolochic acids and a monogalactosyl diglyceride (1993)
    Springer
    Chemoecology 4 (1993), S. 19-28 
    Details
    ISSN: 1423-0445
    Keywords: oviposition stimulant ; synergism ; aristolochic acids I and II ; 1,2-dilinolenyl-3-galactosyl-snglycerol ; D-( + )-pinitol ; sequoyitol ; Papilionidae ; Troidini ; Battus philenor ; Aristolochiaceae ; Aristolochia macrophylla
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Aristolochia macrophylla (Lam.) is a major host of the pipevine swallowtail butterfly,Battus philenor (L.), in the eastern United States. The female butterflies use a synergistic mixture of inositols, acids and a lipid as oviposition cues in recognizing this plant on contact. The acids and lipid, all isolated from the Et2O-CHCl3 fraction of an alcoholic extract of fresh foliage, were identified as aristolochic acid I (1), aristolochic acid II (2) and 1,2-[di(9Z,12Z,15Z)-octadeca-9, 12, 15-trienoyl]-3-galactosyl-sn-glycerol (3). Identifications were facilitated by UV, MS (EI and FAB) and NMR (1D and 2D) spectral techniques and by analysis of the hydrolysis products of 3. The active inositols were identified as D-(+)-pinitol, reported previously, and sequoyitol. Though this is apparently the first report of oviposition responses to a diacyl glycerol glycoside by a phytophagous insect, responses to aristolochic acids and sequoyitol have been reported previously for anAristolochia-feeding swallowtail of a different genus in Japan. This indicates substantial evolutionary conservatism in chemical oviposition cues within the tribe Troidini.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01245892
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  • 2
    Electronic Resource
    Electronic Resource
    Comparative electrophysiological analysis of plant odor perception in females of threePapilio species (1994)
    Springer
    Chemoecology 5-6 (1994), S. 26-36 
    Details
    ISSN: 1423-0445
    Keywords: chemoreception ; olfaction ; plant volatiles ; electroantennogram ; combined GC-EAG ; evolutionary adaptation ; Lepidoptera ; Papilionidae ; Papilio polyxenes ; Papilio machaon hippocrates ; Papilio troilus ; Apiaceae ; Daucus carota ; Pastinaca sativa ; Asteraceae ; Artemisia dracunculus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Antennae of femalePapilio butterflies perceive many volatile plant constituents with widely differing, constituent-specific sensitivities. We compared the responses of threePapilio species to volatiles from host and non-host plants to assess species-specificity and the degree of evolutionary conservatism in olfactory responses. Since previous studies had demonstrated that the polar constituents in odor fromDaucus carota stimulate oviposition behavior inPapilio polyxenes, we collected headspace volatiles fromD. carota, Pastinaca sativa (both Apiaceae) andArtemisia dracunculus (Asteraceae) and separated the polar fraction of these volatiles by gas chromatography. GC-coupled electroantennograms (GC-EAG) were recorded from the speciesPapilio polyxenes, P. machaon hippocrates andP. troilus. In addition, the responses of the three species to five compounds known as generally occurring constituents of plant odor were recorded. The relative sensitivities for these compounds were nearly identical in all threePapilio species. The response spectra to the separated plant volatiles also showed considerable similarities among the species. From the limited set of GC peaks evoking a response in one of the species, 64% (D. carota), 44% (P. sativa) and 29% (A. dracunculus) also evoked a response in both of the other species. The responses of the two closely related Apiaceae feeders (P. polyxenes, P. m. hippocrates) to volatiles fromD. carota were more similar to each other than was either to the response ofP. troilus, which feeds on Lauraceae. However, this was not true for the responses to volatiles fromP. sativa. The least congruence among the three species was found in the responses to volatiles fromA. dracunculus, a non-host for all of them. The differences and similarities found in the response profiles of the threePapilio species are discussed with respect to evolutionary adaptation to host odor versus evolutionary conservatism in adaptation of olfactory receptors.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01259970
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  • 3
    Electronic Resource
    Electronic Resource
    Oviposition stimulants for the black swallowtail butterfly: Identification of electrophysiologically active compounds in carrot volatiles (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 919-937 
    Details
    ISSN: 1573-1561
    Keywords: Papilio polyxenes ; Papilionidae ; Lepidoptera ; Daucus carota ; Apiaceae ; host-plant selection ; oviposition behavior ; electroantennogram ; combined GC-EAG ; plant volatiles ; sabinene hydrate ; 4-terpineol ; bomyl acetate ; (Z)-3-hexenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Headspace volatiles were collected from undamaged foliage of carrot,Daucus carota, a host-plant species of the black swallowtail butterfly,Papilio polyxenes. The volatiles were fractionated over silica on an open column, and the fractions were tested in behavioral assays withP. polyxenes females in laboratory experiments. The polar fractions, as well as the total mixture of volatiles, increased the landing frequency and the number of eggs laid on model plants with leaves bearing contact-oviposition stimulants. The nonpolar fraction, containing the most abundant compounds in carrot odor, was not stimulatory. Gas Chromatographic (GC) separation of the fractions was coupled with electroantennogram (EAG) recordings to identify the compounds perceived byP. polyxenes females. The EAG activity corresponded to the behavioral activity of the fractions. None of the nonpolar compounds, identified as various monoterpenes, evoked a major EAG response, but several constituents of the polar fractions elicited high EAG responses. Sabinene hydrate (both stereoisomers), 4-terpineol, bomyl acetate, and (Z)-3-hexenyl acetate were identified by GC-MS as active compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00992528
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  • 4
    Electronic Resource
    Electronic Resource
    An Oviposition Stimulant for Spicebush Swallowtail Butterfly, Papilio troilus, from Leaves of Sassafras albidum (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 1233-1245 
    Details
    ISSN: 1573-1561
    Keywords: Swallowtail butterfly ; Papilionidae ; Papilio troilus ; Lepidoptera ; Lauraceae ; Sassafras albidum ; oviposition stimulant ; 3-trans-caffeoyl-muco-quinic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Female butterflies of the spicebush swallowtail, Papilio troilus, are specialists, ovipositing on plants in the family Lauraceae. Column chromatography and HPLC were used to isolate an oviposition stimulant from the leaves of one of its hosts, Sassafras albidum. The stimulant was identified as 3-trans-caffeoyl-muco-quinic acid on the basis of FAB-MS and 1H NMR spectra as compared to a compound previously isolated from another plant. It was not active alone, but it increased the oviposition activity of butterflies when combined with other stimulant(s) at a concentration of 7 ng/mm2 leaf surface area. Other caffeoylquinic acid isomers tested did not have this effect. This is the first report of a swallowtail contact oviposition stimulant from a plant in the family Lauraceae.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1020962422712
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  • 5
    Electronic Resource
    Electronic Resource
    Host-Plant Chemistry Influences Oviposition Choice of the Spicebush Swallowtail Butterfly (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 1999-2009 
    Details
    ISSN: 1573-1561
    Keywords: Oviposition stimulants ; Lauraceae ; Sassafras albidum ; Lindera benzoin ; Persea borbonia ; Cinnamonum camphora ; Papilionidae ; Papilio troilus ; 3-caffeoyl-muco-quinic acid ; host-plant discrimination
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The spicebush swallowtail, Papilio troilus (L.), lays its eggs on plants in the family Lauraceae. Sassafras [Sassafras albidum (Nutt.) Nees], spicebush [Lindera benzoin (L.) Spreng.], redbay (Persea borbonia (L.)] and camphortree [Cinnamomum camphora (Nees) Eberm.] are four of its known host plants. In one-choice tests, free-flying spicebush swallowtail females laid eggs on chemical extracts of the leaves of each of these four hosts. In two-choice experiments, females always preferred to oviposit on an extract of sassafras compared to extracts of the other three hosts. It was shown for spicebush extract that this response was not due to oviposition experience. Previously we had identified one of the host plant chemicals acting as an oviposition stimulant in sassafras extract as 3-caffeoyl-muco-quinic acid (3-CmQA). Extracts of the other three hosts did not contain this compound. The addition of 3-CmQA alone to spicebush extract did not increase oviposition activity. It did, however, increase discrimination between hosts and nonhosts. When a fraction of sassafras extract containing 3-CmQA and other synergistic stimulants was added to spicebush extract, preference for sassafras extract was no longer recorded. These results show existing differences in oviposition chemistry among host plants of the spicebush swallowtail and how these differences can influence oviposition choice in bioassay experiments.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1021076404423
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  • 6
    Electronic Resource
    Electronic Resource
    d-(+)-Pinitol, an oviposition stimulant for the pipevine swallowtail butterfly,Battus philenor (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 799-815 
    Details
    ISSN: 1573-1561
    Keywords: Battus philenor ; Papilionidae ; Lepidoptera ; Aristolochia macrophylla ; Aristolochiaceae ; learning ; d-pinitol ; sequoyitol ; myo-inositol ; cyclitols ; oviposition stimulant
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Oviposition by females of the pipevine swallowtail butterfly,Battus philenor, was stimulated by contact with alcoholic extracts of host foliage.d-(+)-Pinitol was isolated and identified from leaf material of one host species,Aristolochia macrophylla (Aristolochiaceae). In combination with chloroform-soluble components of host leaf material, this compound was comparable to the parent extract in stimulating oviposition.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00994616
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  • 7
    Electronic Resource
    Electronic Resource
    Aristolochic acids fromThottea spp. (Aristolochiaceae) and the osmeterial secretions of Thottea-feeding troidine swallowtail larvae (Papilionidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1587-1594 
    Details
    ISSN: 1573-1561
    Keywords: Aristolochic acid ; Aristolochiaceae ; Thottea ; osmeteria ; swallowtail butterfly ; Papilionidae ; Troides ; Pachliopta ; Lepidoptera ; defense
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two aristolochiaceous plants in the genusThottea were shown to contain aristolochic acids. Larvae of two Malaysian troidine swallowtail butterflies,Troides (Troides) amphrysus andPachliopta (Losaria) neptunus, that fed onThottea leaves were found to sequester corresponding aristolochic acid analogs in the osmeterial glands.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984899
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