| 1. |
- Bengtsson, M., et al.
(författare)
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Plant odor analysis of apple : Antennal response of codling moth females to apple volatiles during phenological development
- 2001
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Ingår i: Journal of Agricultural and Food Chemistry. - : American Chemical Society (ACS). - 0021-8561 .- 1520-5118. ; 49:8, s. 3736-3741
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Tidskriftsartikel (refereegranskat)abstract
- Volatile compounds were collected from apple branches (Malus domestica) at different developmental stages, and the antennal response of codling moth females (Cydia pomonella) to these compounds was recorded by electroantennography coupled to gas chromatography. Presence of a range of terpenoid compounds, many of which had antennal activity, was characteristic for volatile collections from branches with leaves, and from small green apples. Nine compounds from branches with leaves and green fruit consistently elicited an antennal response: methyl salicylate, (E)-beta -farnesene, fi-caryophyllene, 4,8-dimethyl-1,3(E),7-nonatriene, (Z)3-hexenol, (Z,E)-alpha -farnesene, linalool, germacrene D, and (EE)-alpha -farnesene. The bouquet emitted from flowering branches contained in addition several benzenoid compounds which were not found after bloom. Small green apples, which are the main target of codling moth oviposition during the first seasonal flight period, released very few esters. In comparison, fully grown apples released a large number of esters, but fewer terpenoids. The study of apple volatiles eliciting an antennal response, together with a survey of the seasonal change in the release of these compounds, is the first step toward the identification of volatiles mediating host-finding and oviposition in codling moth females.
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| 2. |
- Ashitani, Tatsuya, et al.
(författare)
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Activity studies of sesquiterpene oxides and sulfides from the plant Hyptis suaveolens (Lamiaceae) and its repellency on Ixodes ricinus (Acari:Ixodidae)
- 2015
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Ingår i: Experimental & applied acarology. - : Springer Science and Business Media LLC. - 0168-8162 .- 1572-9702. ; 67:4, s. 595-606
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Tidskriftsartikel (refereegranskat)abstract
- Hyptis suaveolens (Lamiaceae), a plant traditionally used as a mosquito repellent, has been investigated for repellent properties against nymphs of the tick Ixodes ricinus. Essential oils and volatile compounds of fresh and dried leaves, from plants originating from Laos and Guinea-Bissau, were identified by GC-MS and tested in a tick repellency bioassay. All the essential oils were strongly repellent against the ticks, even though the main volatile constituents differed in their proportions of potentially tick repellent chemicals. (+)/(-)-sabinene were present in high amounts in all preparations, and dominated the emission from dry and fresh leaves together with 1,8-cineol and alpha-phellandrene. 1,8-Cineol and sabinene were major compounds in the essential oils from H. suaveolens from Laos. Main compounds in H. suaveolens from Guinea-Bissau were (-)-sabinene, limonene and terpinolene. Among the sesquiterpene hydrocarbons identified, alpha-humulene exhibited strong tick repellency (96.8 %). Structure activity studies of oxidation or sulfidation products of germacrene D, alpha-humulene and beta-caryophyllene, showed increased tick repellent activity: of mint sulfide (59.4 %), humulene-6,7-oxide (94.5 %) and caryophyllene-6,7-oxide (96.9 %). The substitution of oxygen with sulfur slightly lowered the repellency. The effects of the constituents in the oils can then be regarded as a trade off between the subsequently lower volatility of the sesquiterpene derivatives compared to the monoterpenes and may thus increase their potential usefulness as tick repellents.
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| 3. |
- Backman, A. C., et al.
(författare)
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Volatiles from apple (Malus domestica) eliciting antennal responses in female codling moth Cydia pomonella (L.) (Lepidoptera : Tortricidae): Effect of plant injury and sampling technique
- 2001
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Ingår i: Zeitschrift für Naturforschung C - A Journal of Biosciences. - : Walter de Gruyter GmbH. - 0939-5075 .- 1865-7125. ; 56:04-mar, s. 262-268
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Tidskriftsartikel (refereegranskat)abstract
- The antennal responses of codling moth females, Cydia pomonella, to volatiles from apple branches with green fruits were recorded by electroantennography coupled to gas chromatography. The antennae strongly responded to 4,8-dimethyl-1,3(E),7-nonatriene, linalool, beta -caryophyllene, (E)-beta -farnesene, germacrene D, (Z,E)-alpha -farnesene, (E,E)-alpha -farnesene and methyl salicylate. These compounds were all present in volatile collections on Porapak Q from both living and cut branches. Analysis by the solid phase microextraction technique (SPME) showed that the emission of some electrophysiologically active compounds increased after branches had been cut, especially 4,8-dimethyl-1,3(E),7-nonatriene, linalool and (E,E)-alpha -farnesene. The identification of apple volatiles eliciting antennal responses is the first step towards the identification of compounds mediating host-finding and oviposition in codling moth females.
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| 4. |
- Eiras, A. E., et al.
(författare)
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Sex pheromone of the Brazilian apple leafroller, Bonagota cranaodes Meyrick (Lepidoptera, Tortricidae)
- 1999
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Ingår i: Zeitschrift für Naturforschung C - A Journal of Biosciences. - : Walter de Gruyter. - 0939-5075 .- 1865-7125. ; 54:7-8, s. 595-601
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Tidskriftsartikel (refereegranskat)abstract
- The female sex pheromone of Bonagota (=Phthteochroa) cranaodes (Meyrick) is a blend of (E,Z)-3,5-dodecadienyl acetate (E3,Z5-12:Ac) and (Z)-9-hexadecenyl acetate (Z9-16:Ac) according to analysis of pheromone - gland extracts and field trapping in apple orchards. This is the first time that E3,Z5-12:Ac has been identified as a lepidopteran sex pheromone. Traps baited with 100 mu g E3,Z5-12:Ac were attractive over 15 weeks in the field and were as effective as traps baited with virgin females. Addition of Z9-16:Ac to E3,Z5-12:Ac at ratio of 1:10 had a significantly increase of male moths. The addition of the Z,E and Z:Z isomers to rubber septa baited with E3,Z5-12:Ac did not modify B. cranaodes male attraction, but 10% of EE enhanced trap catch.
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| 5. |
- El-Sayed, A., et al.
(författare)
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Effect of codlemone isomers on codling moth (Lepidoptera : Tortricidae) male attraction
- 1998
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Ingår i: Environmental Entomology. - : Oxford University Press. - 0046-225X .- 1938-2936. ; 27:5, s. 1250-1254
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Tidskriftsartikel (refereegranskat)abstract
- We studied the effect of codlemone geometric isomers (E,Z)-, (Z,E)-, and (Z,Z)-8,10-dodecadienol on sex attraction of male codling moth, Cydia pomonella (L.), in the field and in a wind tunnel. The use of an ultrasound evaporator made it possible to apply known rates of compound at defined isomeric purity. In the wind tunnel, 5, 20, and 100% addition of Z,E isomer to (E,E) -8,10-dodecadienol (codlemone) slightly increased male night response. However, field captures with these blends were not significantly different from codlemone alone. A 20 and 100% addition of E,Z isomer decreased male landings on the odor source in the wind tunnel and trap captures in the field; Z,Z had an antagonistic effect at 100%. The equilibrium isomer blend (100% EB; 26% E,Z; 20% Z,E; 5% Z,Z) strongly reduced male attraction. The behavioral effect of isomerization of codlemone in dispenser materials used for mating disruption has to be taken into consideration.
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| 6. |
- Kalinova, B., et al.
(författare)
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Detection of sex pheromone components in Manduca sexta (L.)
- 2001
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Ingår i: Chemical Senses. - : Oxford University Press. - 0379-864X .- 1464-3553. ; 26:9, s. 1175-1186
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Tidskriftsartikel (refereegranskat)abstract
- The ability of olfactory receptor neurons to detect female-produced sex pheromone components and a limited sample of potential host plant odours was studied by single-sensillum recordings from olfactory sensilla present on male and female antennae in Manduca sexta, The majority of pheromone-sensitive receptor neurons examined in males was specialized for detection of the two major pheromone components, E10,Z12-hexadecadienal and E10,E12,Z14-hexadecatrienal or E10,E12,E14-hexadecatrienal. New olfactory receptor neurons tuned to the minor components E10,E12-hexadecadienal and Z11-hexadecenal were found. in females, olfactory receptor neurons specific to Z11-hexadecanal were discovered. Pheromone components and host volatiles were detected by separate sets of receptor neurons.
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| 7. |
- Larsdotter-Mellström, Helena, et al.
(författare)
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It's All in the Mix : Blend-Specific Behavioral Response to a Sexual Pheromone in a Butterfly
- 2016
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Ingår i: Frontiers in Physiology. - : Frontiers Media S.A.. - 1664-042X. ; 7
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Tidskriftsartikel (refereegranskat)abstract
- Among insects, sexual pheromones are typically mixtures of two to several components, all of which are generally required to elicit a behavioral response. Here we show for the first time that a complete blend of sexual pheromone components is needed to elicit a response also in a butterfly. Males of the Green-veined White, Pieris napi, emit an aphrodisiac pheromone, citral, from wing glands. This pheromone is requisite for females to accept mating with a courting male. Citral is a mixture of the two geometric isomers geranial (E-isomer) and neral (Z-isomer) in an approximate 1:1 ratio. We found that both these compounds are required to elicit acceptance behavior, which indicates synergistic interaction between processing of the isomers. Using functional Ca2+ imaging we found that geranial and neral evoke significantly different but overlapping glomerular activity patterns in the antennal lobe, which suggests receptors with different affinity for the two isomers. However, these glomeruli were intermingled with glomeruli responding to, for example, plant-related compounds, i.e., no distinct subpopulation of pheromone-responding glomeruli as in moths and other insects. In addition, these glomeruli showed lower specificity than pheromone-activated glomeruli in moths. We could, however, not detect any mixture interactions among four identified glomeruli, indicating that the synergistic effect may be generated at a higher processing level. Furthermore, correlations between glomerular activity patterns evoked by the single isomers and the blend did not change over time.
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| 8. |
- Mozuraitis, R., et al.
(författare)
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Parthenogenesis, calling behavior, and insect-released volatiles of leafminer moth Phyllonorycter emberizaepenella
- 2002
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Ingår i: Journal of Chemical Ecology. - : Springer. - 0098-0331 .- 1573-1561. ; 28:6, s. 1191-1208
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Tidskriftsartikel (refereegranskat)abstract
- We proved that the leafminer moth Phyllonorycter emberizaepenella (Lepidoptera: Gracillariidae) reproduces by parthenogenesis of the thelytoky type. Despite a complete absence of males, parthenogenetically reproducing females diurnally demonstrated the calling posture normally used for releasing signaling compounds. Two compounds, which we collected from a calling female, were identified as potential sex pheromone components: (8E,10E)-8,10-tetradecadienyl acetate and (8E,10E)-8,10-tetradecadienol, the latter occurring only in trace amounts. In field experiments, no males were attracted to traps baited with either the potential sex pheromone or with virgin females. Both the pattern of behavior and the chemical characteristics of the pheromone of Ph. emberizaepenella species were similar to those known for Lepidoptera with the usual amphimictic mode of reproduction. Theoretical speculations that in thelytoky, where there is no need to find a sexual partner, the individuals would obtain certain advantages due to reduction in their sexual behavior, were, thus, not confirmed for Ph. emberizaepenella.
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| 9. |
- Olsson, Christian, et al.
(författare)
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Electrophysiological and behavioral responses to chocolate volatiles in both sexes of the pyralid moths Ephestia cautella and Plodia interpunctella
- 2005
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 31:12, s. 2947-2961
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Tidskriftsartikel (refereegranskat)abstract
- Volatiles from chocolate mediate upwind flight behavior in Ephestia cautella and Plodia interpunctella. We used gas chromatography with electroantennographic detection and found 12 active compounds derived from three different chocolate types, i.e., plain, nut-containing, and rum-flavored. Eight of the compounds were identified with mass spectrometry, and the activity of three compounds, ethyl vanillin, nonanal, and phenylacetaldehyde (PAA), was subsequently confirmed in both electrophysiological and behavioral assays. In the electroantennogram experiment, PAA and nonanal were consistently eliciting responses in both species and sexes. Ethyl vanillin was active in males of both species, and also in P. interpunctella females. E. cautella females showed no antennal activity in response to ethyl vanillin. All three volatiles were attractive to E. cautella males and P. interpunctella females in a flight tunnel. E. cautella females were significantly attracted only to ethyl vanillin. P. interpunctella males were attracted to PAA. Ethyl vanillin is a novel insect attractant, whereas both nonanal and phenylacetaldehyde mediate behavior in many insect species. A final experiment revealed that a blend of the three volatiles was required to induce landing in the flight tunnel bioassay, and that the landing rate was dependent on dose. The three-component blend attracted both sexes of P. interpunctella and females of E. cautella, whereas E. cautella males were not attracted.
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| 10. |
- Santangelo, E. M., et al.
(författare)
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Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis
- 2001
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 66:16, s. 5384-5387
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Tidskriftsartikel (refereegranskat)abstract
- A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4 + 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio- and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid aglucones were discussed.
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| 11. |
- Stranden, M., et al.
(författare)
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(-)-germacrene D receptor neurones in three species of heliothine moths : structure-activity relationships
- 2003
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Ingår i: Journal of Comparative Physiology A. Sensory, neural, and behavioral physiology. - : Springer Science and Business Media LLC. - 0340-7594 .- 1432-1351. ; 189:7, s. 563-577
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Tidskriftsartikel (refereegranskat)abstract
- Specificity of olfactory receptor neurones plays an important role in food and host preferences of a species, and may have become conserved or changed in the evolution of polyphagy and oligophagy. We have identified a major type of plant odour receptor neurones responding to the sesquiterpene germacrene D in three species of heliothine moths, the polyphagous Heliothis virescens and Helicoverpa armigera and the oligophagous Helicoverpa assulta. The neurones respond with high sensitivity and selectivity to (-)-germacrene D, as demonstrated by screening via gas chromatography with numerous mixtures of plant volatiles. Germacrene D was present in both host and non-host plants, but only in half of the tested species. The specificity of the neurones was similar in the three species, as shown by the 'secondary' responses to a few other sesquiterpenes. The effect of (-)-germacrene D was about ten times stronger than that of the (+)-enantiomer, which again was about ten times stronger than that of (-)-alpha-ylangene. Weaker effects were obtained for (+)-beta-ylangene, (+)-alpha-copaene, beta-copaene and two unidentified sesquiterpenes. The structure-activity relationship shows that the important properties of (-)-germacrene D in activating the neurones are the ten-membered ring system and the three double bonds acting as electron-rich centres, in addition to the direction of the isopropyl-group responsible for the different effects of the germacrene D enantiomers.
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| 12. |
- Stranden, M., et al.
(författare)
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Receptor neurones in three heliothine moths responding to floral and inducible plant volatiles
- 2003
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Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 13:3, s. 143-154
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Tidskriftsartikel (refereegranskat)abstract
- Some plant volatiles are produced in response to herbivory of several insect species, including heliothine larvae. In the present study of female heliothine moths, four co-located receptor neurone types were identified, of which three types responded strongest to the inducible compounds E-beta-ocimene, E,E-alpha-farnesene and E,E-TMTT, respectively. The fourth type responded strongest to geraniol, which is a common floral volatile. The narrow tuning of each receptor neurone type was demonstrated by responses to a few structurally-related monoterpenes, sesquiterpenes, homo-terpenes and monoterpene alcohols, respectively, out of hundreds of plant constituents tested. The four neurone types showed the same relation of spike amplitudes and ranking of effective compounds in the three heliothine species; the polyphagous Heliothis virescens and Helicoverpa armigera and the oligophagous Helicoverpa assulta. The results indicate the presence of functionally similar types of plant odour-receptor neurones in the three related species, and suggest conservation or reappearance of functionally similar olfactory receptors in related species, independent of the evolution of polyphagy and oligophagy.
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| 13. |
- Unelius, C. Rikard, et al.
(författare)
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Synthesis and characterization of the four geometrical isomers of 3,5-dodecadienyl acetate
- 1998
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Ingår i: Acta Chemica Scandinavica. - : Danish Chemical Society. - 0904-213X .- 1902-3103. ; 52:7, s. 930-934
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Tidskriftsartikel (refereegranskat)abstract
- Practical convergent syntheses of the four geometrical isomers of 3,5-dodecadienyl acetate are presented. These substances have been characterized by NMR and mass spectroscopy. (3E,5Z)-3,5-Dodecadienyl acetate is the main female sex pheromone component of the leaf roller Bonagota cranaodes, which is an important insect pest in apples in South America. The isomeric 3,5-dodecadienyl acetates, as pure isomers and in defined mixtures, have been used as trap lures for Eying insects in field screening experiments in Lithuania. Although no insects were found in the control traps, the numbers of males caught in the baited traps were not high enough to be statistically significant.
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