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  • Polymer and Materials Science  (15)
  • Lepidoptera  (5)
  • 2-phenylethanol  (2)
  • Danaidae  (2)
  • 2015-2019
  • 1995-1999  (12)
  • 1975-1979  (11)
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  • 1
    ISSN: 1420-9071
    Keywords: Oviposition stimulants ; Ideopsis similis ; Danaidae ; Tylophora tanakae ; Asclepiadaceae ; (+)-isotylocrebrine ; (−)-7-demethyltylophorine ; alkaloids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract Chemicals releasing oviposition by an Asclepiadaceae feeder,Ideopsis similis, were identified from a host plant,Tylophora tanakae. A strong positive response was evoked by a methanolic extract of the plant, which proved to contain multiple stimulants. A mixture of two phenanthroindolizidine alkaloids, (+)-isotylocrebrine and (−)-7-demethyltylophorine, isolated from organic fractions, elicited significant ovipositional responses from females.
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  • 2
    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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  • 3
    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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  • 4
    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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  • 5
    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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  • 6
    ISSN: 1573-1561
    Keywords: Flower-visiting ; floral scent ; Pieris rapae ; Pieridae ; Ligustrum japonicum ; Oleaceae ; proboscis extension ; EAG ; phenylacetaldehyde ; 2-phenylethanol ; 6-methylhept-5-en-2-one
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Floral scent compounds of Ligustrum japonicum that affect the foraging behavior of Pieris rapae adults were examined by means of chemical analyses, electroantennogram (EAG) responses, and behavioral bioassays; the behavioral biossays consisted of two tests: reflex extension of proboscis (REP) in response to odor, and attraction to scented and unscented artificial flowers. More than 30 compounds, including 2-phenylethanol, benzyl alcohol, and methyl phenylacetate as the major components were identified from L. japonicum flowers. Of these, 22 compounds were tested for their effect on foraging behavior. Phenylacetaldehyde (PA), 2-phenylethanol (PE), and 6-methylhept-5-en-2-one (MHO) elicited the highest REP responses, and benzaldehyde (BA) and methyl phenylacetate (MPA) evoked intermediate REP responses. EAG responses were not necessarily correlated with REP activities; the three high-REP compounds gave only moderate EAG responses, whereas two other compounds (ethyl phenylacetate and 2-phenylethyl acetate) that released high EAG responses showed low REP activities. In two-choice behavioral bioassays, flower models scented with any one of these high-REP compounds attracted significantly more adults, while compounds with low REP activities exhibited weak or no appreciable attractiveness. This suggests that the REP responsiveness closely reflects the attractiveness of a compound and could be an effective measure in elucidating which chemical attractants are involved in flower-visiting. A synthetic blend of five floral chemicals (PA, PE, MHO, BA, and MPA) displayed an attractiveness that was comparable to that of the floral extract and was more effective in attractiveness than the compounds tested singly. Consequently, it is highly likely that the flower-visiting by P. rapae to L. japonicum is mediated largely by floral scent chemicals and that a synergistic effect of the five floral components would be most responsible for attraction of the butterfly to this flower. The present results also strongly suggest that specific floral volatiles may facilitate close-range flower location by P. rapae, could serve in part as a cue for recognizing food sources, and also be profoundly implicated in flower preference.
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  • 7
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 179 (1978), S. 1643-1646 
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Additional Material: 1 Ill.
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  • 8
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 176 (1975), S. 2251-2261 
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Die reversible Oxygenierung des synthetischen polymeren Pyridin-Häm-Komplexes wurde bei Zimmertemperatur in wäßriger Lösung untersucht. Das polymere Hämochrom wurde durch die Koordination des partiell quartären Poly(4-vinylpyridin)s (QPVP) an der axialen Position des Protohäms in Wasser synthetisiert. Die Gleichgewichtskonstanten von Hämichrom und Hämochrom waren 2,60·102 und 2,77·104 dm3mol-1, und die Koordinationszahl der axialen Liganden (Pyridingruppen) war sowohl im Fall von Hämichrom als such im Fall von Hämochrom ca. 1,0.Die Kinetik der elementaren Prozesse der Oxygenierung, d. h. der “Adsorption von O2” bzw. der “irreversiblen Oxydation des resultierenden Sauerstoff-Komplexes” wurde als Funktion des lokalen Feldes um das Häm herum untersucht. Die Geschwindigkeit des irreversiblen Oxydationsprozesses des Häm-Sauerstoff-Komplexes wurde durch Hydrophobieren der Umgebung des Häm stark verringert. Diese Effekte wurden ausgelöst durch die stärkere Knäuelung von QPVP-Molekülen durch die Addition von Salzen {Natriumchlorid, Natriumdodecylsulfat und Poly[1-(natrium sulfonatophenyl)-äthylen]} oder durch die Komplexierung von QPVP mit Polymethacrylsäure. Das Redoxpotential des zentralen Metallions des Häms wurde infolge der Zunahme der Hydrophobie um das Häm verringert. Andererseits war die Geschwindigkeit des Adsorptionsprozesses an-nähernd konstant und unabhängig von der Veränderung der Mikroumwelt um das Ham.
    Notes: The reversible oxygenation of a synthetic polymeric pyridine-hemochrome was studied in aqueous solution at room temperature. The polymeric hemochrome was synthesized by coordination of partially quaternized poly(4-vinylpyridine), (QPVP), to the axial site of protoheme in water. The equilibrium constants of hemichrome and hemochrome were 2,60.102 and 2,77.104dm3 mol-1, respectively, and the coordination number of axial ligands (pyridine groups) both in the complexation of heme and hemin was approximately 1,0.The kinetics of the elementary processes of oxygenation, i.e. “adsorption of O2” and “irreversible oxidation of the resulting oxygen complex”, were studied as a function of the local field around heme. The rate of the irreversible oxidation process of the heme oxygen complex was greatly lowered as a result of situating the active site of heme inside the hydrophobic environment formed by shrinking QPVP with adding a salt {sodium chloride, sodium dodecylsulfate, and poly[1-(sodium sulfonatophenyl)-ethylene]} or by complexing QPVP with poly(methacrylic acid). The redox potential of the central metal ion of heme was lowered by increasing the hydrophobicity around heme. On the other hand, the rate of the adsorption process was approximately constant, regardless of the microenvironmental change around heme.
    Additional Material: 3 Ill.
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  • 9
    ISSN: 0887-624X
    Keywords: poly(aryleneethynylene) ; palladium-catalyzed ; copolymer ; optical properties ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Palladium-catalyzed polycondensation between 2,5-diiodo-3-hexylthiophene I-Th(Hex)-I with mixtures of p-diethynylbenzene HC≡C - Ph - C≡CH and α,ω-diethynylalkane HC≡C(CH2)lC≡CH (l = 3 or 8) gives poly(aryleneethynylene) PAE-type copolymers [C≡C(CH2)lC≡C - Th(Hex)]m[C≡C - Ph - C≡C - Th(Hex)]n containing the methylene unit. The copolymers have a molecular weight (Mn) of about 1.2 × 104 as determined by GPC (polystyrene standard) and are considered to possess essentially a random sequences in view of the  - C≡C(CH2)lC≡C -  and  - C≡C - Ph - C≡C -  units as judged from their UV-visible spectra. By the incorporation of the (CH2)l unit, the λmax position of the corresponding PAE homopolymer [C≡C - Ph - C≡C - Th(Hex)]n is shifted to a shorter wavelength. However, the copolymers give rise to a photoluminescence PL peak essentially agreeing with a PL peak of the homopolymer, suggesting occurrence of energy transfer in the copolymer. © 1998 John Wiley & Sons, Inc. J. Polym. Sci. A Polym. Chem. 36: 2201-2207, 1998
    Additional Material: 3 Ill.
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  • 10
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 25 (1999), S. 1895-1906 
    ISSN: 1573-1561
    Keywords: Flower-volatiles ; floral scent ; Pieris rapae ; Brassica rapa ; proboscis extension reflex ; EAG ; benzaldehyde ; phenylacetaldehyde ; 2-phenylethanol ; phenylacetonitrile ; UV nectar guide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Scent and coloration of corolla were examined as floral attributes responsible for preferential visiting by the cabbage butterfly, Pieris rapae, to rape flower, Brassica rapa. Floral volatile components that release the flower-visiting behavior of the butterfly were identified by chemical analyses, electroantennography (EAG), and two behavioral bioassays: proboscis extension reflex (PER) in response to odor and attraction to artificial flowers. GC and GC-MS analyses of the headspace volatiles from the flowers revealed the presence of six aromatic compounds, benzaldehyde, phenylacetaldehyde, benzyl alcohol, 2-phenylethanol, phenylacetonitrile, and indole in decreasing order of quantity. Of these, phenylacetaldehyde elicited the highest response in the PER assay. While benzyl alcohol, 2-phenylethanol, benzaldehyde, and phenylacetonitrile evoked moderate responses, the PER-eliciting activity of indole was very weak. In two-choice behavioral bioassays, artificial flowers scented with any one of these PER-active compounds attracted significantly more butterflies than control (unscented) flowers, whereas those treated with indole were almost inactive. The EAG activities of the six chemicals were not high and were about the same at a low dose (1 μg), but phenylacetaldehyde elicited a much stronger response from both sexes at higher doses (10 and 100 μg). An overall profile of EAG responses at a dose of 100 μg was analogous to that of PER performance, suggesting that floral volatiles may be involved in close-range location or recognition of flowers rather than long-range attraction. By spectroscopic and UV-photographic examinations of rape flower, the central part of the corolla was found to absorb UV rays in marked contrast to the other parts, which reflected near-UV rays (λmax = 350 nm). This indicates that the flower is endowed with a conspicuous nectar guide that is probably an important visual stimulus for attracting foraging adults of P. rapae. Consequently, the present findings strongly suggest that this elaborate pollination strategy of rape flower, characterized by its good combination of olfactory and visual attractiveness, accounts for preferential visiting by the cabbage butterfly to the flower.
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