| 1. |
- Abreu, Ilka, et al.
(författare)
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UHPLC-ESI/TOFMS Determination of Salicylate-like Phenolic Gycosides in Populus tremula Leaves
- 2011
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 37:8, s. 857-70
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Tidskriftsartikel (refereegranskat)abstract
- Associations of salicylate-like phenolic glycosides (PGs) with biological activity have been reported in Salix and Populus trees, but only for a few compounds, and in relation to a limited number of herbivores. By considering the full diversity of PGs, we may improve our ability to recognize genotypes or chemotype groups and enhance our understanding of their ecological function. Here, we present a fast and efficient general method for salicylate determination in leaves of Eurasian aspen that uses ultra-high performance liquid chromatography-electrospray ionization/time-of-flight mass spectrometry (UHPLC-ESI/TOFMS). The time required for the liquid chromatography separations was 13.5 min per sample, compared to around 60 min per sample for most HPLC protocols. In leaf samples from identical P. tremula genotypes with diverse propagation and treatment histories, we identified nine PGs. We found the compound-specific mass chromatograms to be more informative than the UV-visible chromatograms for compound identification and when quantitating samples with large variability in PG content. Signature compounds previously reported for P. tremoloides (tremulacin, tremuloidin, salicin, and salicortin) always were present, and five PGs (2'-O-cinnamoyl-salicortin, 2'-O-acetyl-salicortin, 2'-O-acetyl-salicin, acetyl-tremulacin, and salicyloyl-salicin) were detected for the first time in P. tremula. By using information about the formic acid adduct that appeared for PGs in the LTQ-Orbitrap MS environment, novel compounds like acetyl-tremulacin could be tentatively identified without the use of standards. The novel PGs were consistently either present in genotypes regardless of propagation and damage treatment or were not detectable. In some genotypes, concentrations of 2'-O-acetyl-salicortin and 2'-O-cinnamoyl-salicortin were similar to levels of biologically active PGs in other Salicaceous trees. Our study suggests that we may expect a wide variation in PG content in aspen populations which is of interest both for studies of interactions with herbivores and for mapping population structure.
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| 2. |
- Anderbrant, Olle, et al.
(författare)
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Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden
- 2010
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 36:9, s. 969-977
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Tidskriftsartikel (refereegranskat)abstract
- The pine sawfly Neodiprion sertifer (Geoffroy) uses the acetate or propionate of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) as pheromone components, with the (2S,3R,7R)-isomer being antagonistic, synergistic, or inactive according to the population tested. In this study, we tested the attraction of males to the acetates of three analogs of diprionol, each missing one methyl group, viz. (2S,7S)-7-methyl-2-pentadecanol, (2S,6S)-2,6-dimethyl-1-tetradecanol, and (2S,3S)-3-methyl-2-pentadecanol. None of the analogs alone, or in combination with diprionol acetate, was attractive in Sweden, even at 100 times the amount of diprionol acetate attractive to N. sertifer. In Japan, the acetate of (2S,3S)-3-methyl-2-pentadecanol attracted males when tested in amounts 10–20 times higher than the acetate pheromone component. The acetate esters of the (2S,3R)-analog and the (2S,3R,7R)-isomer of diprionol also were tested in combination with the pheromone compound (acetate ester). Both compounds caused an almost total trap-catch reduction in Sweden, whereas in Japan they appear to have relatively little effect on trap capture when added to diprionol acetate. Butyrate and iso-butyrate esters of diprionol were unattractive to N. sertifer in Sweden. In summary, there exists geographic variation in N. sertifer in responses to both diprionyl acetate and some of its analogs.
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| 3. |
- Anderbrant, Olle, et al.
(författare)
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Field response of the pine sawfly Neodiprion sertifer to controlled release of diprionyl acetate, diprionyl propionate and trans-perillenal
- 1992
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 18:10, s. 1707-1725
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Tidskriftsartikel (refereegranskat)abstract
- Two dispenser types for pine sawfly (Hymenoptera: Diprionidae) pheromones-glass capillaries and dental cotton rolls-are described, and release rates reported. Glass capillaries of different diameters were used in field tests to determine dose-response relationships of (2 S,3 S,7 S)-3,7-dimethylpentadecan-2-yl acetate (diprionyl acetate), diprionyl propionate, and trans-perillenal on the trap catch of male Neodiprion sertifer. A linear relationship between the logarithm of the capillary cross-sectional area and the logarithm of the release rate was found. However, capillaries of the same diameter could vary in the amount released by as much as a factor of 10. Both the acetate and propionate were attractive alone, but no synergistic effect was found. trans-Perillenal did not show any behavioral activity. Dental cotton rolls have been used extensively in diprionid pheromone research without knowledge about release rates. The release rate from rolls loaded with different amounts of diprionyl acetate was determined by extracting rolls after different times under constant temperature and wind conditions or after use in field tests. Quantification of diprionyl acetate was done on GC. The release rate was found to be proportional to the amount applied over several orders of magnitude, and persisted for several weeks. Capillaries and rolls with similar release rates caught similar numbers of sawflies.
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| 4. |
- Andersson, J., et al.
(författare)
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Antiaphrodisiacs in pierid butterflies : A theme with variation!
- 2003
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Ingår i: Journal of Chemical Ecology. - 0098-0331 .- 1573-1561. ; 29:6, s. 1489-1499
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Tidskriftsartikel (refereegranskat)abstract
- Male Pieris napi butterflies previously have been shown to synthesize and transfer an antiaphrodisiac, methyl salicylate (MeS), to females at mating. This substance curtails courtship and decreases the likelihood of female remating. Here, we show that similar systems occur in Pieris rapae and Pieris brassicae. In P. rapae, C-13-labeling studies showed that males utilize the amino acids phenylalanine and tryptophan as precursors to MeS and indole, respectively. These volatiles are transferred to females at mating and function as antiaphrodisiacs, as demonstrated by field tests entailing painting MeS, indole, or a mixture on the abdomens of virgin females and assessing their attractiveness to wild males. With P. brassicae, C-13-labeling studies showed that males use phenylalanine as a precursor to synthesize benzyl cyanide, which was demonstrated to function as an antiaphrodisiac by field tests similar to those for P. rapae. This communication system exhibits both similarities and differences among the three species; in P. napi and P. rapae, males are fragrant but transfer a volatile antiaphrodisiac to females that is completely different from the male odor, whereas in P. brassicae the antiaphrodisiac transferred by male to female is identical with male odor.
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| 5. |
- Andersson, Martin, et al.
(författare)
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Identification of Sex Pheromone Components of the Hessian Fly, Mayetiola destructor
- 2009
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 35, s. 81-95
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Tidskriftsartikel (refereegranskat)abstract
- Coupled gas chromatographic (GC)-electroantennographic detection (EAD) analyses of ovipositor extract of calling Hessian fly, Mayetiola destructor, females revealed that seven compounds elicited responses from male antennae. Four of the compounds-(2S)-tridec-2-yl acetate, (2S,10Z)-10-tridecen-2-yl acetate, (2S,10E)-10-tridecen-2-yl acetate, and (2S,10E)-10-tridecen-2-ol-were identified previously in female extracts. Two new EAD-active compounds, (2S,8Z,10E)-8,10-tridecadien-2-yl acetate and (2S,8E,10E)-8,10-tridecadien-2-yl acetate, were identified by GC-mass spectroscopy (MS) and the use of synthetic reference samples. In a Y-tube bioassay, a five-component blend (1 ng (2S)-tridec-2-yl acetate, 10 ng (2S,10E)-10-tridecen-2-yl acetate, 1 ng (2S,10E)-10-tridecen-2-ol, 1 ng (2S,8Z,10E)-8,10-tridecadien-2-yl acetate, and 1 ng (2S,8E,10E)-8,10-tridecadien-2-yl acetate) was as attractive to male Hessian flies as a similar amount of female extract (with respect to the main compound, (2S,10E)-10-tridecen-2-yl acetate). The five-component blend was more attractive to male flies than a three-component blend lacking the two dienes. Furthermore, the five-component blend was more attractive than a blend with the same compounds but that contained one tenth the concentration of (2S,8E,10E)-8,10-tridecadien-2-yl acetate (more accurately mimicking the ratios found in female extract). This suggests that the ratios emitted by females might deviate from those in gland extracts. In a field-trapping experiment, the five-component blend applied to polyethylene cap dispensers in a 100:10 mu g ratio between the main component and each of the other blend components attracted a significant number of male Hessian flies. Also, a small-plot field test demonstrated the attractiveness of the five-component blend to male Hessian flies and suggests that this pheromone blend may be useful for monitoring and predicting Hessian fly outbreaks in agricultural systems.
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| 6. |
- Andersson, Martin N, et al.
(författare)
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Attraction modulated by spacing of pheromone components and anti-attractants in a bark beetle and a moth
- 2011
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 1573-1561 .- 0098-0331. ; 37, s. 899-911
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Tidskriftsartikel (refereegranskat)abstract
- Orientation for insects in olfactory landscapes with high semiochemical diversity may be a challenging task. The partitioning of odor plumes into filaments that are interspersed with pockets of ‘clean air’ may help filament discrimination and upwind flight to attractive sources in the face of inhibitory signals. We studied the effect of distance between odor sources on trap catches of the beetle, Ips typographus, and the moth, Spodoptera littoralis. Insects were tested both to spatially separated pheromone components [cis-verbenol and 2-methyl-3-buten-2-ol for Ips; (Z,E)- 9,11-tetradecadienyl acetate and (Z,E)-9,12-tetradecadienyl acetate for Spodoptera], and to separated pheromone and anti-attractant sources [non-host volatile (NHV) blend for Ips; (Z)-9-tetradecenyl acetate for Spodoptera]. Trap catch data were complemented with simulations of plume structure and plume overlap from two separated sources using a photo ionization detector and soap bubble generators. Trap catches of the beetle and the moth were both affected when odor sources in the respective traps were increasingly separated. However, this effect on trap catch occurred at smaller (roughly by an order of magnitude) odor source separation distances for the moth than for the beetle. This may reflect differences between the respective olfactory systems and central processing. For both species, the changes in trap catches in response to separation of pheromone components occurred at similar spacing distances as for separation of pheromone and anti-attractant sources. Overlap between two simulated plumes depended on distance between the two sources. In addition, the number of detected filaments and their concentration decreased with downwind distance. This implies that the response to separated odor sources in the two species might take place under different olfactory conditions. Deploying multiple sources of anti-attractant around a pheromone trap indicated long-distance (meter scale) effects of NHVon the beetle and a potential use for NHV in forest protection.
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| 7. |
- Azeem, Muhammad, et al.
(författare)
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Penicillium expansum Volatiles Reduce Pine Weevil Attraction to Host Plants
- 2013
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 39:1, s. 120-128
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Tidskriftsartikel (refereegranskat)abstract
- The pine weevil Hylobius abietis (L.) is a severe pest of conifer seedlings in reforested areas of Europe and Asia. To identify minimally toxic and ecologically sustainable compounds for protecting newly planted seedlings, we evaluated the volatile metabolites produced by microbes isolated from H. abietis feces and frass. Female weevils deposit feces and chew bark at oviposition sites, presumably thus protecting eggs from feeding conspecifics. We hypothesize that microbes present in feces/frass are responsible for producing compounds that deter weevils. Here, we describe the isolation of a fungus from feces and frass of H. abietis and the biological activity of its volatile metabolites. The fungus was identified by morphological and molecular methods as Penicillium expansum Link ex. Thom. It was cultured on sterilized H. abietis frass medium in glass flasks, and volatiles were collected by SPME and analyzed by GC-MS. The major volatiles of the fungus were styrene and 3-methylanisole. The nutrient conditions for maximum production of styrene and 3-methylanisole were examined. Large quantities of styrene were produced when the fungus was cultured on grated pine bark with yeast extract. In a multi-choice arena test, styrene significantly reduced male and female pine weevils' attraction to cut pieces of Scots pine twigs, whereas 3-methylanisole only reduced male weevil attraction to pine twigs. These studies suggest that metabolites produced by microbes may be useful as compounds for controlling insects, and could serve as sustainable alternatives to synthetic insecticides.
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| 8. |
- 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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| 9. |
- Becher, Paul, et al.
(författare)
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The Scent of the Fly
- 2018
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 44:5, s. 431-435
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Tidskriftsartikel (refereegranskat)abstract
- (Z)-4-undecenal (Z4-11Al) is the volatile pheromone produced by females of the vinegar fly Drosophila melanogaster. Female flies emit Z4-11Al for species-specific communication and mate-finding. A sensory panel finds that synthetic Z4-11Al has a characteristic flavour, which can be perceived even at the small amounts produced by a single female fly. Since only females produce Z4-11Al, and not males, we can reliably distinguish between single D. melanogaster males and females, according to their scent. Females release Z4-11Al at 2.4 ng/h and we readily sense 1 ng synthetic Z4-11Al in a glass of wine (0.03 nmol/L), while a tenfold concentration is perceived as a loud off-flavour. This corroborates the observation that a glass of wine is spoilt by a single D. melanogaster fly falling into it, which we here show is caused by Z4-11Al. The biological role of Z4-11Al or structurally related aldehydes in humans and the basis for this semiochemical convergence remains yet unclear.
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| 10. |
- Bengtsson, Göran, et al.
(författare)
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Selective odor perception in the soil collembola Onychiurus armatus
- 1991
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 17:11, s. 2113-2125
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Tidskriftsartikel (refereegranskat)abstract
- The olfactorial response of the fungivorous soil collembolan Onychiurus armatus was examined in a bioassay covering volatile compounds identified in the odor blends of two of its preferred fungal species Monierella isabellina and Verticillium bulbillosum. The odor of the fungi was trapped using activated carbon filters, extracted with diethyl ether, and subjected to GC-MS analysis. About 50% of the compounds resolved by GC were identified by a combination of electron impact and chemical ionization mass spectrometry. In a Y-shaped olfactometer the collembolans were attracted to a variety of common odors, such as CO2 and 2-methyl-1-propanol, and a species-specific odor, such as 1-heptene, and arrested by, for example, decanal and 2-octene. The response was not improved by pairwise combinations of common and specific odors. An amount of 0.5 ng of ethyl acetate or 3 pg of 1-pentanol was sufficient to attract the collembolans. The specific compounds of V. bulbillosum, 1-heptene and 1-octen-3-ol, may be key stimuli explaining why O. armatus prefers V. bulbillosum.
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