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  • 1
    ISSN: 1570-7458
    Keywords: Cnaphalocrocis medinalis ; rice leaffolder ; Lepidoptera ; Pyralidae ; sex pheromone ; geographical variation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Sex pheromone components of the Japanese rice leaffolder moth, Cnaphalocrocis medinalis Guenée (Lepidoptera: Pyralidae) were identified from ovipositor extracts of virgin females as (Z)-11-octadecenal, (Z)-13-octadecenal, (Z)-11-octadecen-1-ol and (Z)-13-octadecen-1-ol at a ratio of 11:100:24:36 by GC-EAD, GC, GC-MS. The total amount was estimated to be ca.0.9 ng/female. Field bioassays in Kagoshima, Japan, showed that the two aldehydes are essential for male attraction and the alcohols may have a synergistic effect on the aldehydes. A rubber septum containing 0.9 mg of the four components at the natural ratio was shown to be an effective lure for monitoring this pest in Japan. The above four components are quite different from the sex pheromone components reported previously for the same species of either Philippine or Indian origin; components were shown to be (Z)-11-hexadecenyl acetate and (Z)-13-octadecenyl acetate at a ratio of 98:2 in the Philippine blend and 1:10 in the Indian blend. Furthermore, in the field tests in Japan, neither the Philippine blend nor the Indian blend showed any attractive activity, while the Japanese blend attracted significant numbers of male moths. These results suggest that there are remarkable geographical variations in the sex pheromone composition of this species or there are several distinct species using different sex pheromone blends.
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 21 (1995), S. 859-867 
    ISSN: 1573-1561
    Keywords: Osmeterial secretion ; Lepidoptera ; Papilionidae ; Parnassiinae ; Papilioninae ; Parnassius glacialis ; Sericinus montela ; Pachliopta aristolochiae ; aliphatic acid and ester ; monoterpene ; sesquiterpene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Volatile components of the larval osmeterial secretion ofParnassius glacialis (Parnassiinae, Parnassiini) consisted of isobutyric acid, 2-methylbutyric acid, and their methyl esters. In contrast, the osmeterial exudate ofSericinus montela (Parnassiinae, Zerynthiini) was characterized as monoterpene hydrocarbons comprisingβ-myrcene (Major),α-pinene, sabinene, limonene, andβ-phellandrene, whereas that ofPachliopta aristolochiae (Papilioninae, Troidini) was composed of numerous sesquiterpene hydrocarbons, includingα-himachalene,α-amorphene, and germacrene-A, and a few oxygenated sesquiterpenoids. In these three species, the chemical nature of the secretions of the last and the penultimate instars was essentially of similar quality, suggesting that the three genera,Parnassius, Sericinus, andPachliopta, are assigned to homogeneous types.
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  • 3
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 6 (1980), S. 867-873 
    ISSN: 1573-1561
    Keywords: Male scent ; Atrophaneura alcinous ; Lepidoptera ; Papilionidae ; benzaldehyde ; phenylacetaldehyde ; 2-phenylpropenal ; n-heptanal ; 6-methylhept-5-en-2-one ; linalool
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Benzaldehyde, phenylacetaldehyde (major component), 2-phenylpropenal,n-heptanal, 6-methylhept-5-en-2-one, and linalool were identified as compounds responsible for the male scent ofAtrophaneura alcinous alcinous. These substances were present predominantly in the wings, and the quantity of them was largest at the inner margin of the hind wing. Female wings also contained some of them in much smaller (except a few components) amounts. The relative proportion of each component exhibited manifests sexual differences.
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  • 4
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 22 (1996), S. 949-972 
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Danainae ; Idea leuconoe ; hairpencil ; pheromone ; Parsonsia laevigata ; pyrrolizidine alkaloid ; mellein ; defense
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Males of a giant danaine butterfly,Idea leuconoe, display hairpencils during courtship. The females were visually attracted to and olfactorily arrested by an artificial butterfly model to which male hairpencil extracts were added. The hairpencil extracts contained a complex mixture of volatiles, including pyrrolizidine alkaloid (PA) derivatives (danaidone, viridifloric β-lactone), aromatics (phenol,p-cresol, benzoic acid), terpenoids (geranyl methyl thioether, (E,E)-farnesol), a series of γ-lactones (6-hydroxy-4-undecanolides and its homologs), hydrocarbons [(Z)-9-tricosene, etc.], and several compounds with higher molecular weight. A mixture of the major volatiles applied to a butterfly dummy strongly elicited an abdomen-curling acceptance posture in females. Viridifloric β-lactone and danaidone induced significant electroantennogram responses on the female's antennae, suggesting their principal role together with other hairpencil components as a sex pheromone to seduce females.I. leuconoe males seem to acquire the precursor for both of the PA fragments from the host plant,Parsonsia laevigata (Apocynaceae), during the larval stage; thereby they do not show pharmacophagous behavior towards PA-containing plants during the adult stage. However, males are pharmacophagously attracted to and feed on a number of simple phenolic compounds in a manner similar to other danaine species towards PAs. Wild males sequester one of the phagostimulants, (−)-mellein, in the hairpencils in varying quantities. Phenolic compounds incorporated in the hairpencils may act primarily as warning odors linked with the defensive PAs present in the body tissues.
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  • 5
    ISSN: 1573-1561
    Keywords: Oviposition stimulants ; Idea leuconoe ; Lepidoptera ; Danaidae ; Parsonsia laevigata ; Apocynaceae ; pyrrolizidine alkaloids ; parsonsianine ; parsonsianidine ; 17-methylparsonsianidine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A giant danaid butterfly, Idea leuconoe, specializes on apocynaceous plants such as Parsonsia laevigata, which has been reported to contain pyrrolizidine alkaloids. Females of I. leuconoe deposited eggs in response to methanolic extract of P. laevigata, and subsequent bioassay-guided fractionation of the extract revealed that phytochemicals crucial for host recognition by ovipositing females are Parsonsia-specific macrocyclic pyrrolizidine alkaloids including parsonsianine, parsonsianidine, and 17-methylparsonsianidine. Parsonine, another P. laevigata pyrrolizidine component with a keto-dihydropyrrolizine moiety that is closely related in structure to male pheromones of the butterfly, and several nonhost pyrrolizidine alkaloids were entirely inactive. We interpret these data as strong evidence for an ancestral association through herbivory between danaid butterflies and pyrrolizidine alkaloids.
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  • 6
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 12 (1986), S. 1999-2010 
    ISSN: 1573-1561
    Keywords: Oviposition stimulant ; Papilio protenor ; Lepidoptera ; Papilionidae ; flavanone glycoside ; naringin ; hesperidin ; synergy ; Citrus natsudaidai
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Identification of chemical compounds responsible for the oviposition behavior in a Rutaceae feeder,Papilio protenor demetrius, was undertaken with the epicarp of sour orange (Citrus natsudaidai) which exhibited potent stimulatory activity as did its leaves for egg-laying by the females. The stimulants were present in the hydrosoluble fraction, and the kairomonal activity displayed by the peel was regarded as originating from the synergistic effect of the total chemical complex. One of the active compounds was identified as a flavanone glycoside, naringin (naringenin-7β-neohesperidoside), which, although showing no appreciable effectiveness when bioassayed alone, elicited positive response at the concentration of 0.2% either when admixed with other unidentified components or provided the females had been conditioned with them in advance. Another flavanone glycoside, hesperidin (hesperetin-7β-rutinoside) that was contained in a trace amount in the peel also had a positive effect comparable to that of naringin under similar conditions, while their corresponding aglycones were less active or inactive. In contrast, a flavone glycoside, rhoifolin, coexisting in the peel, and some other flavones and flavonols tested as possible candidates for oviposition stimulants were all found entirely ineffective.
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  • 7
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 16 (1990), S. 325-337 
    ISSN: 1573-1561
    Keywords: Oviposition stimulant ; Papilio protenor ; Lepidoptera ; Papilionidae ; d-(−)-quinic acid ; l-(−)-stachydrine ; (−)-synephrine ; l-(−)-proline ; chlorogenic acid ; Citrus natsudaidai ; C. unshiu ; Fagara ailanthoides
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The ovipositional response of a Rutaceae-feeding papilionid butterfly,Papilio protenor, toCitrus host plants was evoked by the synergistic action ofl-(−)-stachydrine,d-(−)-quinic acid, (−)-synephrine, andl-(−)-proline that characterize the chemical compositions of the leaves and epicarp ofCitrus plants (C. natsudaidai andC. unshiu). The stimulatory activity of their mixture was enhanced by the addition of flavanone glycosides, naringin and hesperidin, which coexist in these plants and have previously been demonstrated to serve as oviposition stimulants. However, sugars such as sucrose, glucose, and inositols, which abound in plant tissues, exerted no effect on egg-laying by the females. On the other hand, chlorogenic acid present in the leaves of another host plant,Fagara ailanthoides, was found to act as an excellent synergist. However, there existed significant qualitative dissimilarities between the chemical compositions of the leaves ofC. unshiu andF. ailanthoides. This strongly suggests thatP. protenor is likely to utilize different categories of compounds as chemical cues in recognizing each plant as a host.
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  • 8
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 7 (1981), S. 1089-1113 
    ISSN: 1573-1561
    Keywords: Osmeterial secretion ; Papilio larvae ; Lepidoptera ; monoterpene ; sesquiterpene ; aliphatic acid ; ester
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The larval osmeterial secretions of sixPapilio species examined displayed a remarkable qualitative change at the fourth larval ecdysis. The secretions of 4th (penultimate) instar larvae ofP. machaon, P. memnon, P. helenus, P. bianor, andP. maackii principally comprised mono- and/or sesquiterpenoids. The compounds identified from these species included α-pinene, sabinene, β-myrcene, limonene, β-phellandrene, (Z)-β-ocimene, (E)-β-ocimene, β-elemene, β-caryophyllene, (E)-β-farnesene, β-selinene, (E,E)-α-farnesene, germacrene-A, germacrene-B, caryophyllene oxide, methyl 3-hydroxy-n-butyrate, and acetic acid. In contrast, the secretion of 4th larval instar ofP. xuthus, although containing similar terpenic compounds, was accompanied by large amounts of aliphatic acids and their esters: isobutyric acid, 2-methylbutyric acid, methyl isobutyrate and methyl 2-methylbutyrate. On the other hand, the osmeterial secretions of 5th (last) instar larvae varied little in quality among the six species, and the identified compounds consisted of isobutyric acid, 2-methylbutyric acid, methyl isobutyrate, ethyl isobutyrate, methyl 2-methylbutyrate, ethyl 2-methylbutyrate, and isovaleric acid, the last of which was specific toP. bianor andP. maackii. The chemical alteration of osmeterial exudate synchronized at the final larval ecdysis with the larval morphological change (particularly in body coloration) that appears to be of defensive significance against predators.
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  • 9
    ISSN: 1573-1561
    Keywords: Oviposition stimulants ; Colias erate ; Lepidoptera ; Pieridae ; Trifolium repens ; Leguminosae ; cyanoglucosides ; linamarin ; lotaustralin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Host-plant chemicals stimulating oviposition by a Leguminosae-feeding pierid butterflyColias erate poliographyswere isolated and identified from one of its primary host plants, white clover (Trifolium repens). Females readily deposited eggs in response to methanolic extracts of the plant, and subsequent partition of the extracts with organic solvents revealed that chemical constituents critical for host recognition reside in the water-soluble fraction. Further fractionation of the hydrosoluble fraction by column chromatography led to the separation of an active fraction and two cyanoglucosides, linamarin and lotaustralin. Conspicuous oviposition response was evoked by unidentified polar compound(s), while these cyanoglucosides exerted no stimulatory activity by themselves. However, ovipositing females preferred samples containing either of the two cyanoglucosides. In dual-choice bioassays, significantly more eggs were laid on samples admixed with the cyanoglucosides, suggesting that the cyanoglucosides serve as synergistic oviposition stimulants and could play an important role in host selection.
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