| 1. |
- Ayasse, Manfred, et al.
(författare)
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Evolution of reproductive strategies in the sexually deceptive orchid Ophrys sphegodes: How does flower-specific variation of odor signals influence reproductive success?
- 2000
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Ingår i: Evolution. - 1558-5646. ; 54:6, s. 1995-2006
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Tidskriftsartikel (refereegranskat)abstract
- The orchid Ophrys sphegodes Miller is pollinated by sexually excited males of the solitary bee Andrena nigroaenea, which are lured to the flowers by visual cues and volatile semiochemicals. In O. sphegodes, visits by pollinators are rare. Because of this low frequency of pollination, one would expect the evolution of strategies that increase the chance that males will visit more than one flower on the same plant; this would increase the number of pollination events on a plant and therefore the number of seeds produced. Using gas chromatography-mass spectrometry (GC-MS) analyses, we identified more than 100 compounds in the odor bouquets of labellum extracts from O. sphegodes; 24 compounds were found to be biologically active in male olfactory receptors based on gas chromatography with electroantennographic detection (GC-EAD). Gas chromatography (GC) analyses of odors from individual flowers showed less intraspecific variation in the odor bouquets of the biologically active compounds as compared to nonactive compounds. This can be explained by a higher selective pressure on the pollinator-attracting communication signal. Furthermore, we found a characteristic variation in the GC-EAD active esters and aldehydes among flowers of different stem positions within an inflorescence and in the n-alkanes and n-alkenes among plants from different populations. In our behavioral field tests, we showed that male bees learn the odor bouquets of individual flowers during mating attempts and recognize them in later encounters. Bees thereby avoid trying to mate with flowers they have visited previously, but do not avoid other flowers either of a different or the same plant. By varying the relative proportions of saturated esters and aldehydes between flowers of different stem positions, we demonstrated that a plant may take advantage of the learning abilities of the pollinators and influence flower visitation behavior. Sixty-seven percent of the males that visited one flower in an inflorescence returned to visit a second flower of the same inflorescence. However, geitonogamy is prevented and the likelihood of cross-fertilization is enhanced by the time required for the pollinium deposited on the pollinator to complete its bending movement, which is necessary for pollination to occur. Cross-fertilization is furthermore enhanced by the high degree of odor variation between plants. This variation minimizes learned avoidance of the flowers and increases the likelihood that a given pollinator would visit several to many different plants within a population.
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| 2. |
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| 3. |
- Baker, T. C., et al.
(författare)
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Identification and bioassay of sex pheromone components of carob moth, Ectomyelois ceratoniae (Zeller)
- 1991
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 17:10, s. 1973-1988
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Tidskriftsartikel (refereegranskat)abstract
- Three sex pheromone components of the carob moth were isolated and identified from the extract of female pheromone glands, using a variety of techniques including coupled gas chromatographic-electroantennographic recordings, coupled gas chromatographic-mass spectrometric analysis, microozonolysis, electroantennographic assays of monounsaturated standards, wind-tunnel bioassays, and field trials. The major component was identified as (Z,E)-9,11,13-tetradecatrienal, a novel lepidopterous pheromone component structure. Two minor components, either one of which improves the upwind flight response of males when blended with the major component, were identified as (Z,E)-9,11-tetradecadienal, and (Z)-9-tetra-decenal.
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| 4. |
- Baker, T. C., et al.
(författare)
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Isolation, identification and synthesis of sex pheromone components of the carob moth, Ectomyelois ceratoniae
- 1989
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Ingår i: Tetrahedron Letters. - 0040-4039. ; 30:22, s. 2901-2902
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Tidskriftsartikel (refereegranskat)abstract
- The sex pheromone of females of the carob moth, Ectomyelois ceratoniae, was identified to be a mixture of (Z,E)-9,11,13-tetradecatrienal, (Z,E)-9,11-tetradecadienal and (Z)-9-tetradecenal in the ratio of 10:1:1. A synthetic blend proved to be attractive. GC/EAD + GC/MS investigations showed (Z,E)-9,11,13-tetradecatrienal, (Z,E)-9,11-tetradecadienal and (Z)-9-tetradecenal to be the sex pheromone of the carob moth. Blends of synthetic compounds are active.
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| 5. |
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| 6. |
- Bergmann, Jan, et al.
(författare)
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Identification and synthesis of new bicyclic acetals from caddisflies (Trichoptera)
- 2004
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Ingår i: Tetrahedron Letters. - : Elsevier BV. - 0040-4039. ; 45:18, s. 3669-3672
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Tidskriftsartikel (refereegranskat)abstract
- As shown by synthesis and enantioselective gas chromatography, males and females of the caddisfly species Potamophylax latipennis and Potamophylax cingulatus produce (1R,3S,5S,7S)-1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo[3.2.1]octane, while Glyphotaelius pellucidus produces 1,3-diethyl-4,6-dimethyl-2,7-dioxabicyclo[2.2.1]heptane, having either the (1S,3S,4R,6S) or (1R,3R,4S,6S)-configuration. As shown by electrophysiological investigations, the compounds are perceived by the antennae of both sexes. (C) 2004 Published by Elsevier Ltd.
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| 7. |
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| 8. |
- Hansson, Bill S., et al.
(författare)
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Electrophysiological and chemical analysis of sex pheromone communication system of the mottled umber, Erannis defoliaria (Lepidoptera : Geometridae)
- 1990
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 16:6, s. 1887-1897
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Tidskriftsartikel (refereegranskat)abstract
- (Z,Z,Z)-3,6,9-nonadecatriene (Z3, Z6, Z9-19Hy) and (Z,Z)-3,9-cis-6,7-epoxy-nonadecadiene (Z3, Z9-cis-6,7-epo-19Hy) were identified in pheromone gland extracts from female Erannis defoliaria. The two components were found in a 1:3 ratio, with the main component, Z3, Z9-cis-6,7-epo-19Hy present at an amount of about 1.5 ng per female. The components were identified by means of gas chromatography-mass spectrometry, gas chromatography-electroantennography and gas chromatography-single sensillum recordings. Single sensillum measurements on the male antenna showed two physiological types of sensilla. One type was characterized by a large spike amplitude cell responding to Z3, Z9-cis-6,7-epoxy-19Hy and a small spike amplitude cell responding to Z3, Z6, Z9-19Hy. A second type responded only with a large spike amplitude cell to the epoxide, and this cell was inhibited by the triene. Of the two pheromone components, the epoxide gave the higher response in the EAG tests. Preliminary field tests support the identification of the pheromone components. The epoxide was also found to be present in the extract of the pheromone gland of Colotois pennaria, and males of C. pennaria and Agriopis marginaria were trapped by the mixture of the identified compounds.
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| 9. |
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| 10. |
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| 11. |
- Larsson, Mattias C, et al.
(författare)
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Characteristic odor of Osmoderma eremita identified as a male-released pheromone
- 2003
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Ingår i: Journal of Chemical Ecology. - 1573-1561. ; 29:3, s. 575-587
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Tidskriftsartikel (refereegranskat)abstract
- Osmoderma eremita (Scopoli) is an endangered scarab beetle living in hollow trees. It has mainly been known for its characteristic odor, typically described as a fruity, peachlike or plumlike aroma. The odor emanating from a single beetle can sometimes be perceived from a distance of several meters. In this paper, we show that the characteristic odor from O. eremita is caused by the compound (R)-(C)-gamma-decalactone, released in large quantities mainly or exclusively by male beetles. Antennae from male and female beetles responded in a similar way to (R)-(C)-gamma-decalactone in electroantennographic recordings. Field trapping experiments showed that (R)-(C)-gamma-decalactone is a pheromone attracting female beetles. Lactones similar to (R)-(C)-gamma-decalactone are frequently used as female-released sex pheromones by phytophagous scarabs. This is, however, the first evidence of a lactone used as a male-produced pheromone in scarab beetles. We propose that the strong signal from males is a sexually selected trait used to compete for females and matings. The signal could work within trees but also act as a guide to tree hollows, which are an essential resource for O. eremita. Males may, thus, attract females dispersing from their natal tree by advertising a suitable habitat. This signal could also be exploited by other males searching for tree hollows or for females, which would explain the catch of several males in our traps.
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| 12. |
- Larsson, Mattias C, et al.
(författare)
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Specialized olfactory receptor neurons mediating intra- and interspecific chemical communication in leafminer moths Eriocrania spp. (Lepidoptera: Eriocraniidae).
- 2002
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Ingår i: Journal of Experimental Biology. - 1477-9145. ; 205:7, s. 989-998
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Tidskriftsartikel (refereegranskat)abstract
- We performed a physiological and morphological characterization of sensilla auricillica in male Eriocrania semipurpurella moths. Each auricillic sensillum contained three olfactory receptor neurons. Responding neurons (87 of 139) could be grouped into five physiological types. Type 1 responded to (R,Z)-6-nonen-2-ol and type 2 to its enantiomer (S,Z)-6-nonen-2-ol, both of which are pheromone components of E. semipurpurella. Type 3 responded to both (R)-heptan-2-ol and (R,Z)-4-hepten-2-ol, which are pheromone components of the sympatric species E. cicatricella. Types 4 and 5 responded to the ketones (Z)-6-nonen-2-one and/or nonan-2-one, which are found in the pheromone glands of female E. semipurpurella. Field-trapping showed that type 3 receptor neurons mediate strongly antagonistic effects of (R)-heptan-2-ol and (R,Z)-4-hepten-2-ol on E. semipurpurella, while nonan-2-one should possibly be included as a synergist in the sex pheromone blend of this species. The attraction of E. cicatricella and E. sparrmannella to compounds mixed with the pheromone blend of E. semipurpurella shows that the pheromone components of E. semipurpurella have little or no antagonistic effects on these species. The morphology and physiology of eriocraniid pheromone sensilla are very similar to those found in the order Trichoptera (caddisflies), suggesting a homology between pheromone detection systems in the two sister orders Lepidoptera and Trichoptera.
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| 13. |
- Lassance, Jean Marc, et al.
(författare)
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Pheromones and Barcoding Delimit Boundaries between Cryptic Species in the Primitive Moth Genus Eriocrania (Lepidoptera : Eriocraniidae)
- 2019
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 45:5-6, s. 429-439
-
Tidskriftsartikel (refereegranskat)abstract
- Animal classification is primarily based on morphological characters, even though these may not be the first to diverge during speciation. In many cases, closely related taxa are actually difficult to distinguish based on morphological characters alone, especially when there is no substantial niche separation. As a consequence, the diversity of certain groups is likely to be underestimated. Lepidoptera –moths and butterflies– represent the largest group of herbivorous insects. The extensive diversification in the group is generally assumed to have its origin in the spectacular radiation of flowering plants and the resulting abundance of ecological niches. However, speciation can also occur without strong ecological divergence. For example, reproductive isolation can evolve as the result of divergence in mate preference and the associated pheromone communication system. We combined pheromone trapping and genetic analysis to elucidate the evolutionary relationships within a complex of primitive moth species (Lepidoptera: Eriocraniidae). Mitochondrial and nuclear DNA markers provided evidence that Eriocrania semipurpurella, as currently defined by morphological characters, includes three cryptic species in Northern and Western Europe. Male moths of these cryptic species, as well as of the closely related E. sangii, exhibited relative specificity in terms of their attraction to specific ratios of two major pheromone components, (2S,6Z)-nonen-2-ol and (2R,6Z)-nonen-2-ol. Our data suggest strong assortative mating in these species in the absence of apparent niche separation, indicating that Eriocrania moths may represent an example of non-ecological speciation. Finally, our study argues in favour of combining pheromone investigations and DNA barcoding as powerful tools for identifying and delimitating species boundaries.
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| 14. |
- Löfstedt, Christer, et al.
(författare)
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Identification of a sex pheromone produced by sternal glands in females of the caddisfly Molanna angustata Curtis.
- 2008
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 1573-1561 .- 0098-0331. ; 34:2, s. 220-228
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Tidskriftsartikel (refereegranskat)abstract
- In the caddisfly Molanna angustata, females produce a sex pheromone in glands with openings on the fifth sternite. Gas chromatographic analyses of pheromone gland extracts with electroantennographic detection revealed four major compounds that stimulated male antennae. These compounds were identified by means of gas chromatography-mass spectrometry and enantioselective gas chromatography as heptan-2-one, (S)-heptan-2-ol, nonan-2-one, and (S)-nonan-2-ol in the approximate ratio of 1:1:4:10, respectively. Field tests showed that the mixture of the two alcohols was attractive to males whereas addition of the corresponding ketones reduced trap catches. The sex pheromone of M. angustata, a species in the family Molannidae within the suborder Integripalpia, is similar to the pheromones or pheromone-like compounds previously reported from six other trichopteran families, including members of the basal suborder Annulipalpia. This suggests that minimal evolutionary change of the pheromone chemistry has taken place within the leptoceroid branch of integripalpian Trichoptera compared to the ancestral character state.
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| 15. |
- Löfstedt, Christer, et al.
(författare)
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Identification of the sex pheromone of the currant shoot borer, Lampronia capitella
- 2004
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Ingår i: Journal of Chemical Ecology. - 1573-1561. ; 30:3, s. 643-658
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Tidskriftsartikel (refereegranskat)abstract
- Under an artificial light: dark cycle, females of Lampronia capitella were observed calling, with extended terminal abdominal segments, during the first 2 hr of the photoperiod. Extracts of terminal abdominal segments from females elicited large electroantennographic responses from male antennae. Gas chromatography with electroantennographic detection revealed three active peaks. Based on comparison of retention times and mass spectra of synthetic standards, these compounds were identified as (Z;Z)-9,11-tetradecadienol and the corresponding acetate and aldehyde. The electroantennographic activity of the four geometric isomers of all three compounds was investigated, and the respective (Z,Z)-isomer was found to be the most active in all cases. Aldehydes generally elicited larger antennal responses than alcohols, whereas acetates were the least active compounds. A subtractive trapping assay in the field, based on a 13: 26: 100 1 g mixture of (Z,Z)-9,11-tetradecadienal, (Z,Z)-9,11-tetradecadienyl acetate, and (Z,Z)-9,11-tetradecadienol confirmed that all three compounds are pheromone components. Subtraction of (Z,Z)-9,11-tetradecadienol from the blend completely eliminated its attractiveness, whereas the other two-component blends showed reduced activity. This is the first pheromone identification from the monotrysian superfamily Incurvarioidea, confirming that the common pheromones among ditrysian moths (long-chain fatty acid derivatives comprising alcohols, acetates, and aldehydes with one or more double bonds) is not an autapomorphy of Ditrysia, but a synapomorphy of the more advanced heteroneuran lineages.
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| 16. |
- Plepys, Dainius, et al.
(författare)
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Odour-mediated nectar foraging in the silver Y moth, Autographa gamma (Lepidoptera : Noctuidae): behavioural and electrophysiological responses to floral volatiles
- 2002
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Ingår i: Oikos. - : Wiley. - 1600-0706 .- 0030-1299. ; 99:1, s. 75-82
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Tidskriftsartikel (refereegranskat)abstract
- Naive male and female silver Y moths, Autographa gamma (Lepidoptera: Noctuidae), were attracted in a flight tunnel assay to potted creeping thistle, Cirsium arvense (Asteraceae), butterfly-orchid, Platanthera bifolia (Orchidaceae), soapwort, Saponaria officinalis (Caryophyllaceae), greater knapweed, Centaurea scabiosa (Asteraceae), red clover, Trifolium pratense (Fabaceae), and catnip, Nepeta faasseni (Labiatae), plants with flowers. The most attractive plants were C. arvense, P. bifolia and S. officinalis that elicited 87, 78 and 65%, source contacts, respectively. C. scabiosa was less attractive eliciting 43%, response. T. pratense and N. faasseni showed the least attraction eliciting 28 and 26% source contacts, respectively. A cotton plant used as control, was not attractive. Floral volatiles from the investigated plant species were collected using headspace sampling technique. Samples were analysed using gas chromatography coupled with electroantennographic detection, and electrophysiologically active compounds were identified by coupled gas chromatography/mass spectrometry. Consistent electrophysiological responses were elicited by twelve compounds from headspace of C. arvense, thirteen compounds from P. bifolia, eleven compounds from S. officinalis, nine from C. seabiosa, ten from T. pratense and two from N. faasseni. Most of the active compounds were specific for one or two species, while benzyl benzoate was present in four and benzaldehyde and benzyl alcohol in three species. Floral scents of C. arvense, P. bifolia and S. officinalis, the most attractive flowers, were dominated by aromatic compounds that were not abundant in the scent of other flowers. To conclude, the results demonstrate the absence of a common denominator of odours present in flowers of different plants visited by A. gamma.
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| 17. |
- Schiestl, F. P., et al.
(författare)
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Orchid pollination by sexual swindle [5]
- 1999
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Ingår i: Nature. - : Springer Science and Business Media LLC. - 0028-0836 .- 1476-4687. ; 399:6735, s. 421-422
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Tidskriftsartikel (refereegranskat)
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| 18. |
- Schiestl, Florian P, et al.
(författare)
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Sex pheromone mimicry in the early spider orchid (Ophrys sphegodes): patterns of hydrocarbons as the key mechanism for pollination by sexual deception
- 2000
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Ingår i: Journal of Comparative Physiology A. - : Springer Science and Business Media LLC. - 1432-1351. ; 186:6, s. 567-574
-
Tidskriftsartikel (refereegranskat)abstract
- Abstract We investigated the female-produced sex pheromone of the solitary bee Andrena nigroaenea and compared it with floral scent of the sexually deceptive orchid Ophrys sphegodes which is pollinated by Andrena nigroaenea males. We identified physiologically and behaviorally active compounds by gas chromatography with electroantennographic detection, gas chromatography-mass spectrometry, and behavioral tests in the field. Dummies scented with cuticle extracts of virgin females or of O.sphegodes labellum extracts elicited significantly more male reactions than odorless dummies. Therefore, copulation behavior eliciting semiochemicals are located on the surface of the females' cuticle and the surface of the flowers. Within bee and orchid samples, n-alkanes and n-alkenes, aldehydes, esters, all-trans-farnesol and all-trans-farnesyl hexanoate triggered electroantennographic responses in male antennae. Most of the alkanes and alkenes occurred in similar patterns both in the bees and orchids. O. sphegodes leaf extracts contained mostly the same compounds but in different proportions. In behavioral tests with synthetic compounds, blends of alkenes triggered significantly more approaches and pounces of the males whereas alkanes were not more attractive than odorless dummies. Since alkanes and alkenes together were most attractive, we conclude they constitute the bees' sex pheromone as well as the pseudocopulation-behavior releasing orchid-odor bouquet.
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| 19. |
- Tóth, Miklos, et al.
(författare)
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Pheromonal Production of and Response to Optically Active Epoxydienes in Some Ceometrid Moths (Lepidoptera: Geometridae)
- 1994
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Ingår i: Zeitschrift fur Naturforschung - Section C Journal of Biosciences. - : Walter de Gruyter GmbH. - 0939-5075. ; 49:7-8, s. 516-521
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Tidskriftsartikel (refereegranskat)abstract
- In, pheromone extracts of calling female Chiasma clathrata, L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9–heptadecatriene and (Z,Z)-6,9–cis-3,4–epoxyhepta-decadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3 R.4 S)-configuration. In field trapping tests, only the pure (3/R,4S)-enantiomer of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenaceciria Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S,4R)-enantiomer [together with a previously described minor component, (Z,Z)-3,9–cis-6,7–epoxyheptadecadiene], In trapping tests conducted iNADifferent biotope Abraxas grossu-lariata, L. (Lepidoptera: Geometridae) males were attracted by the (3S,4R)-enantiomer, whereas the (3/L4S)-enantiomer attracted a close relative. Abraxas sylvata Scop. (Lepidoptera: Geometridae). The present results suggest that one of the key mechanisms responsible for pheromone specificity among both the two alfalfa geometrids and the two Abraxas species in their respective biotops, may be the use of different enantiomers of the same polyene-derived epoxide as a sex pheromone component. It is probable that this discrimination mechanism is widespread among moth species utilizing epoxide pheromone components.
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| 20. |
- Tröger, Armin, et al.
(författare)
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Tetranorsesquiterpenoids as attractants of yucca moths to yucca flowers
- 2021
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 47:12, s. 1025-1041
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Tidskriftsartikel (refereegranskat)abstract
- The obligate pollination mutualism between Yucca and yucca moths is a classical example of coevolution. Oviposition and active pollination by female yucca moths occur at night when Yucca flowers are open and strongly scented. Thus, floral volatiles have been suggested as key sensory signals attracting yucca moths to their host plants, but no bioactive compounds have yet been identified. In this study, we showed that both sexes of the pollinator moth Tegeticula yuccasella are attracted to the floral scent of the host Yucca filamentosa. Chemical analysis of the floral headspace from six Yucca species in sections Chaenocarpa and Sarcocarpa revealed a set of novel tetranorsesquiterpenoids putatively derived from (E)-4,8-dimethyl-1,3,7-nonatriene. Their structure elucidation was accomplished by NMR analysis of the crude floral scent sample of Yucca treculeana along with GC/MS analysis and confirmed by total synthesis. Since all these volatiles are included in the floral scent of Y. filamentosa, which has been an important model species for understanding the pollination mutualism, we name these compounds filamentolide, filamentol, filamental, and filamentone. Several of these compounds elicited antennal responses in pollinating (Tegeticula) and non-pollinating (Prodoxus) moth species upon stimulation in electrophysiological recordings. In addition, synthetic (Z)-filamentolide attracted significant numbers of both sexes of two associated Prodoxus species in a field trapping experiment. Highly specialized insect-plant interactions, such as obligate pollination mutualisms, are predicted to be maintained through “private channels” dictated by specific compounds. The identification of novel bioactive tetranorsesquiterpenoids is a first step in testing such a hypothesis in the Yucca-yucca moth interaction.
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| 21. |
- Tröger, Armin, et al.
(författare)
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The Pattern of Straight Chain Hydrocarbons Released by Yucca Flowers (Asparagaceae)
- 2019
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 45:1, s. 46-49
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Tidskriftsartikel (refereegranskat)abstract
- The hydrocarbon pattern in the floral scent of Yucca species was found to comprise a group of unbranched, mid-chain alkanes, alkenes, and an alkadiene. In Y. reverchonii, highly dominant (Z)-8-heptadecene is accompanied by (6Z,9Z)-6,9-heptadecadiene and heptadecane as minor components and by traces of other saturated and unsaturated hydrocarbons with similar chain length. Some of these volatiles proved to be perceived by the antennae of Tegeticula cassandra (pollinating seed-eater of Yucca) and Prodoxus decipiens (herbivore on Yucca). The possible biosynthesis of the compounds is discussed.
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| 22. |
- Unelius, C. Rikard, 1958-, et al.
(författare)
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(4S,5S)-2,2,4-Triethyl-5-methyl-1,3-dioxolane : A New Volatile Released by a Triatomine Bug
- 2010
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Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 12:24, s. 5601-5603
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Tidskriftsartikel (refereegranskat)abstract
- Adults of the triatomine bug, Triatoma brasiliensis release 2,2,4-triethyl-5-methyl-1,3-dioxolane (1) as a mixture of the (4S,5S)- and (4R,5R)-enantiomers in a ratio of 4:1. Among the volatile acetals identified from insects so far, this is the first example resulting from an intermolecular condensation of a carbonyl moiety and a diol substructure.
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| 23. |
- Wang, Hong-Lei, et al.
(författare)
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Identification and biosynthesis of novel male specific esters in the wings of the tropical butterfly, Bicyclus martius sanaos
- 2014
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 1573-1561 .- 0098-0331. ; 40:6, s. 549-559
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Tidskriftsartikel (refereegranskat)abstract
- Representatives of the highly speciose tropical butterfly genus Bicyclus (Lepidoptera: Nymphalidae) are characterized by morphological differences in the male androconia, a set of scales and hair pencils located on the surface of the wings. These androconia are assumed to be associated with the release of courtship pheromones. In the present study, we report the identification and biosynthetic pathways of several novel esters from the wings of male B. martius sanaos. We found that the volatile compounds in this male butterfly were similar to female-produced moth sex pheromones. Components associated with the male wing androconial areas were identified as ethyl, isobutyl and 2-phenylethyl hexadecanoates and (11Z)-11-hexadecenoates, among which the latter are novel natural products. By topical application of deuterium-labelled fatty acid and amino acid precursors, we found these pheromone candidates to be produced in patches located on the forewings of the males. Deuterium labels from hexadecanoic acid were incorporated into (11Z)-11-hexadecenoic acid, providing experimental evidence of a Δ11-desaturase being active in butterflies. This unusual desaturase was found previously to be involved in the biosynthesis of female-produced sex pheromones of moths. In the male butterflies, both hexadecanoic acid and (11Z)-11-hexadecenoic acid were then enzymatically esterified to form the ethyl, isobutyl and 2-phenylethyl esters, incorporating ethanol, isobutanol, and 2-phenylethanol, derived from the corresponding amino acids L-alanine, L-valine, and L-phenylalanine.
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| 24. |
- Wang, Hong-Lei, et al.
(författare)
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Sex pheromone of the cloaked pug moth, Eupithecia abietaria (Lepidoptera: Geometridae), a pest of spruce cones
- 2015
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Ingår i: Journal of Applied Entomology. - : Wiley. - 0931-2048 .- 1439-0418. ; 139:5, s. 352-360
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Tidskriftsartikel (refereegranskat)abstract
- The sex pheromone of the cloaked pug moth, Eupithecia abietaria Götze, an important cone-feeding pest in spruce seed orchards in Europe, was investigated. Chemical and electrophysiological analyses of pheromone gland extracts of female moths and analogous analyses of synthetic hydrocarbons and epoxides of chain length C19 and C21 revealed (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) and 3Z,6Z-cis-9,10-epoxynonadecadiene (3Z,6Z-cis-9,10-epoxy-19:H) as candidate pheromone components, which were found in a gland extract in a ratio of 95 : 5. In field trapping experiments, conspecific males were only attracted to a combination of 3Z,6Z,9Z-19:H and the (9S,10R)-enantiomer of 3Z,6Z-cis-9,10-epoxy-19:H. The (9R,10S)-enantiomer was not attractive, which is in agreement with studies on other Eupithecia species, for which males have only been attracted by the (9S,10R)-enantiomer of epoxides. Subsequent experiments showed that E. abietaria males were attracted to a wide range of ratios of the two active compounds and that trap catches increased with increasing dose of the binary blend. A two-component bait containing 300 μg 3Z,6Z,9Z-19:H and 33 μg of the (9S,10R)-enantiomer of 3Z,6Z-cis-9,10-epoxy-19:H was efficient for monitoring E. abietaria in spruce seed orchards in southern Sweden, where this species has probably been overlooked as an important pest in the past. With sex pheromones recently identified for two other moths that are major pests on spruce cones, the spruce seed moth, Cydia strobilella L., and the spruce coneworm, Dioryctria abietella Denis & Schiffermüller, pheromone-based monitoring can now be achieved for the whole guild of cone-feeding moths in European spruce seed orchards.
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| 25. |
- Zhang, Dan-Dan, et al.
(författare)
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Receptor for detection of a Type II sex pheromone in the winter moth Operophtera brumata
- 2016
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Ingår i: Scientific Reports. - : Springer Science and Business Media LLC. - 2045-2322. ; 6
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Tidskriftsartikel (refereegranskat)abstract
- How signal diversity evolves under stabilizing selection in a pheromone-based mate recognitionsystem is a conundrum. Female moths produce two major types of sex pheromones, i.e., long-chainacetates, alcohols and aldehydes (Type I) and polyenic hydrocarbons and epoxides (Type II), alongdifferent biosynthetic pathways. Little is known on how male pheromone receptor (PR) genes evolvedto perceive the different pheromones. We report the identification of the first PR tuned to Type IIpheromones, namely ObruOR1 from the winter moth, Operophtera brumata (Geometridae). ObruOR1clusters together with previously ligand-unknown orthologues in the PR subfamily for the ancestralType I pheromones, suggesting that O. brumata did not evolve a new type of PR to match the novel TypeII signal but recruited receptors within an existing PR subfamily. AsegOR3, the ObruOR1 orthologuepreviously cloned from the noctuid Agrotis segetum that has Type I acetate pheromone components,responded significantly to another Type II hydrocarbon, suggesting that a common ancestor with TypeI pheromones had receptors for both types of pheromones, a preadaptation for detection of Type II sexpheromone.
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| 26. |
- Zhu, Junwei, et al.
(författare)
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Identification of a novel moth sex pheromone in Eriocrania cicatricella (Zett.) (Lepidoptera : Eriocraniidae) and its phylogenetic implications
- 1995
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 21:1, s. 29-43
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Tidskriftsartikel (refereegranskat)abstract
- Extracts from different body parts of adult female Eriocrania cicatricella (Zett.) were tested for electrophysiological activity on conspecific male antennae. Extracts from the Vth abdominal segment, containing a pair of exocrine glands, elicited the largest electroantennographic response when compared to extracts of other body parts. Female extracts were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). The EAD active peaks were identified as (Z)-4-hepten-2-one, (2 R)-heptane-2-ol, and (2 R)-(Z)-4-hepten-2-ol by coinjection on a gas chromatography and by comparison of mass spectra with those of synthetic standards. In field tests, a blend of these three pheromone components was highly attractive to conspecific males, and a subtractive assay confirmed that the unsaturated alcohol is the major pheromone component, whereas no definite behavioral activity could be assigned to the ketone or the saturated alcohol. A bait containing the two alcohols with S-configuration was attractive to male E. sparrmannella (Bosc), whereas no males of E. cicatricella were found in these traps. The sex pheromone compounds in E. cicatricella are chemically similar to pheromones reported in Trichoptera and they are produced in homologous glands.
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| 27. |
- Zhu, Jun-Wei, et al.
(författare)
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A sex pheromone component novel to the Geometridae identified from Epirrita autumnata
- 1995
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Ingår i: Entomologia Experimentalis et Applicata. - : Wiley. - 0013-8703. ; 75:2, s. 159-164
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Tidskriftsartikel (refereegranskat)abstract
- (Z,Z,Z)‐1, 3, 6, 9‐Heneicosatetraene was identified as a sex pheromone component of Epirrita autumnata (Borkhausen), (Lepidoptera: Geometridae). Gas chromatography coupled with electroantennographic detection revealed one active peak‐from female pheromone gland extracts. The chemical identification of the compound was based on gas chromatography‐mass spectrometry, chemical micro‐reactions and unambiguous synthesis. In a field test, a rubber septum loaded with 3000 μg of this compound showed highest attraction of male E. autumnata moths compared to lower doses and the control. The attraction of males to a 300 μg bait was equivalent to that obtained using live virgin females. 1995 The Netherlands Entomological Society
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