| 1. |
- Anderbrant, Olle, et al.
(författare)
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Article sex pheromone of the introduced pine sawfly, diprion similis, revisited to define a useful monitoring lure : Deviating chiral composition and behavioural responses compared to earlier reports
- 2021
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Ingår i: Insects. - : MDPI. - 2075-4450. ; 12:10
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Tidskriftsartikel (refereegranskat)abstract
- Extracts of Diprion similis females contained about 15 ng of the sex pheromone precursor 3,7‐dimethylpentadecan‐2‐ol per female. After derivatisation with (S)‐2‐acetoxypropanoyl chloride, we found that the major stereoisomer in the extract was (2S,3R,7R)‐3,7‐dimethylpentadecan‐2‐ol. Small amounts of other stereoisomers of 3,7‐dimethylpentadecan‐2‐ol were also identified in the extract, namely 1% of (2R,3S,7S), 0.3% (2R,3R,7R) and 0.4% of (2R,3R,7S). An unknown fifth substance showed a very similar spectrum to 3,7‐dimethylpentadecan‐2‐ol, both in SIM and full scan mode. None of the earlier suggested behavioural synergistic isomers ((2S,3S,7S), (2S,3S,7R) and (2S,3R,7S)) were detected in the extracts. In field tests in Ontario, Canada, the earlier identified main pheromone component, viz. the propanoate of (2S,3R,7R)‐3,7‐dimethylpentadecan‐2‐ol, was tested alone and in combination with other stereoisomers, earlier reported to be synergistic. No synergistic effects were detected and the threo four‐isomer blend was as attractive as the pure main compound. Thus, one of the few examples of a diprionid sawfly using more than one substance in its sex pheromone could not be confirmed. The results also suggest that monitoring programs can use the more easily synthesized threo‐blend without losing efficiency. Furthermore, the study suggests that other diprionid pheromones may benefit from a reinvestigation, to clarify possible synergistic effects of stereoisomers.
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| 2. |
- Anderbrant, Olle, et al.
(författare)
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Attraction of Male Pine Sawflies, Diprion jingyuanensis, to Synthetic Pheromone Candidates: Synergism between Two Stereoisomers
- 2023
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Ingår i: Forests. - : MDPI. - 1999-4907. ; 14:6
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Tidskriftsartikel (refereegranskat)abstract
- The pine sawfly Diprion jingyuanensis Xiao and Zhang (Hymenoptera: Diprionidae) is a serious pest of Pinus tabulaeformis Carr. in the Shanxi, Gansu, and Inner Mongolia provinces in P. R. China. The sex pheromone of D. jingyuanensis was shown to be the propionate ester of 3,7-dimethyl-2-tridecanol. Virgin females contained an approximate 1:3 blend of the pheromone precursors erythro-(2S,3S,7R/S and 2R,3R,7R/S)-3,7-dimethyl-2-tridecanol and threo-(2S,3R,7R/S and 2R,3S,7R/S)-3,7-dimethyl-2-tridecanol, but the exact stereoisomers were not determined. Males responded the strongest to the propionate ester of the two threo-isomers, (2S,3R,7R) and (2S,3R,7S), in electroantennogram (EAG) recordings, followed by a significant EAG response to the (2S,3R,7R) propionate of diprionol (pheromone component of D. similis), whereas the remaining two isomers (2S,3S,7S and 2S,3S,7R) of the propionate ester of 3,7-dimethyl-2-tridecanol and the acetate of the (2S,3R,7R) isomer (one of the two pheromone components of D. pini) did not elicit any significant increase in antennal response. In the field, the strongly EAG-active (2S,3R,7R)-isomer alone was only weakly (but significantly) attractive to D. jingyuanensis males at 100 & mu;g, while the equally EAG- active (2S,3R,7S)-isomer alone at the same loading was 8-14 times more attractive than was the (2S,3R,7R)-isomer alone. Traps baited with the same amounts of the two threo-isomers ((2S,3R,7R) and (2S,3R,7S), 100 & mu;g + 100 & mu;g) caught significantly more males than did traps baited with other isomers, either of the two isomers alone or other proportions of the two isomers. Thus, the (2S,3R,7S)-isomer is considered as a strong and essential sex-attractant component for D. jingyuanensis males, whereas the (2S,3R,7R)-isomer is a weak but synergistic sex-attractant. This is one of the few examples of a pine sawfly responding significantly stronger to a binary blend of stereoisomers in a synergistic fashion than to a single stereoisomer alone.
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| 3. |
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| 4. |
- 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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| 5. |
- Borrero, Felipe, et al.
(författare)
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Yeast Volatomes Differentially Affect Larval Feeding in an Insect Herbivore
- 2019
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Ingår i: Applied and Environmental Microbiology. - 0099-2240 .- 1098-5336. ; 85
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Tidskriftsartikel (refereegranskat)abstract
- Yeasts form mutualistic interactions with insects. Hallmarks of this interaction include provision of essential nutrients, while insects facilitate yeast dispersal and growth on plant substrates. A phylogenetically ancient chemical dialogue coordinates this interaction, where the vocabulary, the volatile chemicals that mediate the insect response, remains largely unknown. Here, we used gas chromatography-mass spectrometry, followed by hierarchical cluster and orthogonal partial least-squares discriminant analyses, to profile the volatomes of six Metschnikowia spp., Cryptococcus nemorosus, and brewer's yeast (Saccharomyces cerevisiae). The yeasts, which are all found in association with insects feeding on foliage or fruit, emit characteristic, species-specific volatile blends that reflect the phylogenetic context. Species specificity of these volatome profiles aligned with differential feeding of cotton leafworm (Spodoprera littoralis) larvae on these yeasts. Bioactivity correlates with yeast ecology; phylloplane species elicited a stronger response than fruit yeasts, and larval discrimination may provide a mechanism for establishment of insect-yeast associations. The yeast volatomes contained a suite of insect attractants known from plant and especially floral headspace, including (Z)-hexenyl acetate, ethyl (2E,4Z)-deca-2,4-dienoate (pear ester), (3E)-4,8-dimethylnona-1,3,7-triene (DMNT), linalool, alpha-terpineol, beta-myrcene, or (E,E)-alpha-farnesene. A wide overlap of yeast and plant volatiles, notably floral scents, further emphasizes the prominent role of yeasts in plant-microbe-insect relationships, including pollination. The knowledge of insect-yeast interactions can be readily brought to practical application, as live yeasts or yeast metabolites mediating insect attraction provide an ample tool-box for the development of sustainable insect management.IMPORTANCE Yeasts interface insect herbivores with their food plants. Communication depends on volatile metabolites, and decoding this chemical dialogue is key to understanding the ecology of insect-yeast interactions. This study explores the volatomes of eight yeast species which have been isolated from foliage, from flowers or fruit, and from plant-feeding insects. These yeasts each release a rich bouquet of volatile metabolites, including a suite of known insect attractants from plant and floral scent. This overlap underlines the phylogenetic dimension of insect-yeast associations, which according to the fossil record long predate the appearance of flowering plants. Volatome composition is characteristic for each species, aligns with yeast taxonomy, and is further reflected by a differential behavioral response of cotton leafworm larvae, which naturally feed on foliage of a wide spectrum of broad-leaved plants. Larval discrimination may establish and maintain associations with yeasts and is also a substrate for designing sustainable insect management techniques.
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| 6. |
- Ding, Bao Jian, et al.
(författare)
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Biosynthesis of the sex pheromone component (E,Z)-7,9-Dodecadienyl acetate in the European Grapevine Moth, Lobesia botrana, involving ∆11 desaturation and an elusive ∆7 desaturase
- 2021
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 47:3, s. 248-264
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Tidskriftsartikel (refereegranskat)abstract
- The European grapevine moth, Lobesia botrana, uses (E,Z)-7,9-dodecadienyl acetate as its major sex pheromone component. Through in vivo labeling experiments we demonstrated that the doubly unsaturated pheromone component is produced by ∆11 desaturation of tetradecanoic acid, followed by chain shortening of (Z)-11-tetradecenoic acid to (Z)-9-dodecenoic acid, and subsequently introduction of the second double bond by an unknown ∆7 desaturase, before final reduction and acetylation. By sequencing and analyzing the transcriptome of female pheromone glands of L. botrana, we obtained 41 candidate genes that may be involved in sex pheromone production, including the genes encoding 17 fatty acyl desaturases, 13 fatty acyl reductases, 1 fatty acid synthase, 3 acyl-CoA oxidases, 1 acetyl-CoA carboxylase, 4 fatty acid transport proteins and 2 acyl-CoA binding proteins. A functional assay of desaturase and acyl-CoA oxidase gene candidates in yeast and insect cell (Sf9) heterologous expression systems revealed that Lbo_PPTQ encodes a ∆11 desaturase producing (Z)-11-tetradecenoic acid from tetradecanoic acid. Further, Lbo_31670 and Lbo_49602 encode two acyl-CoA oxidases that may produce (Z)-9-dodecenoic acid by chain shortening (Z)-11-tetradecenoic acid. The gene encoding the enzyme introducing the E7 double bond into (Z)-9-dodecenoic acid remains elusive even though we assayed 17 candidate desaturases in the two heterologous systems.
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| 7. |
- Dupaul, Gabriel, et al.
(författare)
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Fiberbanks as substrate and feedstock for biological remediation : A practical analytical method development for organic pollutants analysis
- 2020
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Ingår i: Book of Abstracts. - : ABA Publishing. - 9789189081031
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Konferensbidrag (refereegranskat)abstract
- Fiberbanksfrom the pulp and paper industry are typically contaminated with a wide range ofchlorinated aromatic and aliphatic toxins such as HCB and other chlorinated benzenes, PCB,HCH, DDT, PCDD, PCDF and Chlorophenols. This poses a formidable challenge for theanalyst to develop appropriate analytical methodology for the monitoring of the progress ofremediation.In preparation to this undertaking, an examination of a practical analytical method using oneextraction method, one clean-up and one analysis method for the aforementioned targetcompounds found in the fibrous sediment. This method was performed using acceleratedsolvent extraction (ASE), a modified silica gel column and GC-FID/ECD. Additionally,an assessment of the levels of organic pollutants was conducted,with the purposeofmeasuringthe potential alteration in contaminantswhenfreeze-drying, air-drying andautoclavingpretreatments are applied to the sediment samples, prior to be used as a media forbiological remediation.The results showed that the ASE is a very fast and reliable method of extraction, with yieldscomparableorhigher than the reference Soxhlet extraction method. Theactivatedsilica gelcolumn demonstrated adequate purification of the sediment extract for analysisusingthe twodetectors, FID and ECD, whichwere able to identify the target analytes fromonlyone purifiedextract. The method employed in this study has the potentialto reduceboth processing timeand materialusedfor analytical sample preparation. Lastly, some modifications inconcentrations anddistribution of target analyteswere revealedin thesediments pre-treated byautoclave and air-driedwhencompared withthefreeze-dried sediments, which can helpunderstanding the development of the biological remediation process.
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| 8. |
- Frey, T., et al.
(författare)
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The human odorant receptor OR10A6 is tuned to the pheromone of the commensal fruit fly Drosophila melanogaster
- 2022
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Ingår i: iScience. - : Elsevier BV. - 2589-0042. ; 25:11
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Tidskriftsartikel (refereegranskat)abstract
- All living things speak chemistry. The challenge is to reveal the vocabulary, the odorants that enable communication across phylogenies and to translate them to physiological, behavioral, and ecological function. Olfactory receptors (ORs) interface animals with airborne odorants. Expression in heterologous cells makes it possible to interrogate single ORs and to identify cognate ligands. The cosmopolitan, anthropophilic strain of the vinegar fly Drosophila melanogaster depends on human resources and housing for survival. Curiously, humans sense the pheromone (Z)-4-undecenal (Z4-11Al) released by single fly females. A screening of all human ORs shows that the most highly expressed OR10A6 is tuned to Z4-11Al. Females of an ancestral African fly strain release a blend of Z4-11Al and Z4-9Al that produces a different aroma, which is how we distinguish these fly strains by nose. That flies and humans sense Z4-11Al via dedicated ORs shows how convergent evolution shapes communication channels between vertebrate and invertebrate animals.
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| 9. |
- Haller, Henrik, 1977-, et al.
(författare)
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Appropriate technology for soil remediation in tropical low-income countries - a pilot scale test of three different amendments for accelerated biodegradation of diesel fuel in Ultisol
- 2020
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Ingår i: Cogent Environmental Science. - : Informa UK Limited. - 2331-1843. ; 6:1
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Tidskriftsartikel (refereegranskat)abstract
- Polluted land in marginalized regions, such as tropical low-incomecountries and sparsely populated regions in industrialised countries, demand specialremediation strategies that are energy-efficient, locally adapted, economicallyviable. Strategies for appropriate bioremediation technology under such circumstancescan be based on locally available resources in combination with in situbioremediation technologies to keep energy and material costs down. A pilot scaleexperiment was set up to test the application of three organic by-products from thelocal industry (whey, pyroligneous acid and compost tea) to enhance the naturalbiodegradation of diesel in ultisol. Biweekly applications of 6 mL whey kg−1 soilsignificantly increased the degradation rate but no positive effect on degradationwas found with any of the other amendments. Tropical climate is favourable forbiodegradation but many tropical soils are rich in clay which can inhibit the bioavailabilityof the pollutant which in turn may be decisive for biodegradation kinetics. If low cost is a crucial factor, our results indicate that whey treatment has the potential to be an appropriate technology for treating petroleum-contaminated soils in tropical regions.
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| 10. |
- Haller, Henrik, 1977-, et al.
(författare)
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Polluted lignocellulose-bearing sediments as a resource for marketable goods—a review of potential technologies for biochemical and thermochemical processing and remediation
- 2023
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Ingår i: Clean Technologies and Environmental Policy. - : Springer Science and Business Media LLC. - 1618-954X .- 1618-9558. ; 25, s. 409-425
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Tidskriftsartikel (refereegranskat)abstract
- Lignocellulose-bearing sediments are legacies of the previously unregulated wastewater discharge from the pulp and paper industry, causing large quantities of toxic organic waste on the Baltic Sea floor and on the bottom of rivers and lakes. Several km2 are covered with deposits of lignocellulosic residues, typically heavily contaminated with complex mixtures of organic and inorganic pollutants, posing a serious threat to human and ecological health. The high toxicity and the large volume of the polluted material are challenges for remediation endeavours. The lignocellulosic material is also a considerable bioresource with a high energy density, and due to its quantity, it could appeal to commercialization as feedstock for various marketable goods. This study sets out to explore the potential of using this polluted material as a resource for industrial production at the same time as it is detoxified. Information about modern production methods for lignocellulosic material that can be adapted to a polluted feedstock is reviewed. Biochemical methods such as composting, anaerobic digestion, as well as, thermochemical methods, for instance, HTC, HTL, pyrolysis, gasification and torrefaction have been assessed. Potential products from lignocellulose-bearing sediment material include biochar, liquid and gaseous biofuels, growing substrate. The use of a contaminated feedstock may make the process more expensive, but the suggested methods should be seen as an alternative to remediation methods that only involve costs. Several experiments were highlighted that support the conception that combined remediation and generation of marketable goods may be an appropriate way to address polluted lignocellulose-bearing sediments. Graphic abstract: [Figure not available: see fulltext.]
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| 11. |
- Haller, Henrik, 1977-, et al.
(författare)
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Polluted lignocellulose waste as a resource for marketable products
- 2020
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Ingår i: Proceedings Linnaeus ECO-TECH 2020. - 9789189081031
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Konferensbidrag (refereegranskat)abstract
- Fiberbanks and fiber-rich sediments are legacies of the previously unregulated wastewater discharge from the pulp and paper industry that have accumulated large quantities of toxic organic waste on the Baltic Sea floor and on the bottom of rivers and lakes. Several km2 are covered with deposits of fibrous residues that are, typically, heavily polluted with a number of organic and inorganic substances, posing a serious threat to human and ecological health. High toxicity and the large volume of the polluted material are challenges for remediation endeavors. However, since the fibrous material is a bioresource with a high energy density, the sheer quantity of it could appeal to commercialization as feedstock for various marketable products. This study sets out to explore the potential of using this polluted material as a resource for industrial production, by reviewing and synthesizing data about modern production methods or reuse alternatives for lignocellulose material that can be adapted to a polluted feedstock. Biochemical methods such as composting, anaerobic digestion, as well as, thermochemical methods, for instance, HTC, HTL, pyrolysis, gasification etc. have been assessed. Potential end products from fiber bank material include biochar, liquid and gaseous biofuels, growth media, and fatty acids and proteins produced by white-rot fungi.
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| 12. |
- Harvey, Deborah J., et al.
(författare)
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Making the invisible visible : Determining an accurate national distribution of Elater ferrugineus in the United Kingdom using pheromones
- 2017
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Ingår i: Insect Conservation and Diversity. - : Wiley. - 1752-458X .- 1752-4598. ; 10:4, s. 1-11
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Tidskriftsartikel (refereegranskat)abstract
- To date, conservation-status saproxylic beetle species in the UK have been monitored by chance findings or by monitor-based observational studies. Here, using Elater ferrugineus as our target species, we present the first national distribution survey carried out in the UK or across mainland Europe on such a species using chemicals produced by the insect. Over 3 years, mark-release-recapture studies were performed across the UK, using 416 lured (pheromone) traps monitored by volunteer recorders; the first survey in Europe to do so. Traps were baited with 7-methyloctyl- (Z)-4-decenoate, a compound previously identified as a female sex pheromone. The results were used to plot a distribution map and investigate factors that may influence the distribution, including summer temperatures, possible habitat availability and larval food source. The survey revealed a south-eastern distribution of E. ferrugineus in the UK, which was suggested by previous casual studies. A correlative model was fitted to the data, indicating that 55% of the variation in the distribution of E. ferrugineus was explained by climatic variables (temperature and wind speed).
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| 13. |
- Harvey, Deborah J., et al.
(författare)
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Use of novel attraction compounds increases monitoring success of a rare beetle, Elater ferrugineus
- 2017
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Ingår i: Insect Conservation and Diversity. - : Wiley. - 1752-458X .- 1752-4598. ; 10:2, s. 161-170
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Tidskriftsartikel (refereegranskat)abstract
- The use of pheromones to determine distributions of rare saproxylic insects is an increasingly popular technique. Pheromones may, however, also be used to elucidate the biology of these cryptic species, a vital requirement if they are to be accurately monitored and conserved. We used non-invasive aerial trapping to compare the effectiveness of chemicals produced by Elater ferrugineus L (Coleoptera: Elateridae), namely 7-methyloctyl (Z)-4-decenoate (the female-produced sex pheromone), and male compounds (geranyl and neryl acetone and 6-methyl-5-heptene-2-one). The male compounds were identified using headspace analysis by solid phase micro-extraction gas chromatography-mass spectrometry. We discovered that males only produce these two compounds after having been attracted to a female, and that this serves to attract further males to a female. Such compounds do not appear to attract females but for a species that has a short activity period and is non-feeding in the adult stage, may ensure breeding success when populations are low. By marking all beetles caught, we were able to demonstrate that recapture rate using this method is low (approximately 11% of total captures annually). Therefore, the method does not limit dispersal or breeding opportunities, making it a valuable tool for monitoring endangered saproxylic beetle species.
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| 14. |
- Hedenström, Erik, 1955-, et al.
(författare)
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6-(4-Methylpent-3-en-1-yl)naphthalene-1,4-dione, a behaviorally active semivolatile in tibial perfumes of orchid bees
- 2018
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Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 28:4-5, s. 131-135
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Tidskriftsartikel (refereegranskat)abstract
- Male neotropical orchid bees (Euglossini) collect volatiles from varied sources in their environment to compile complex, species-specific tibial perfumes, which are later released at mating sites. A major compound prominent in tibial extracts of Euglossa allosticta was purified, as well as isolated and its structure was elucidated by analytical methods including GC–MS, GC–FTIR, HRMS and 1H and 13C NMR. After synthesis, the compound with the proposed structure was finally identified as 6-(4-methylpent-3-en-1-yl)naphthalene-1,4-dione. At field sites in Panama and Costa Rica, the synthetic compound attracted males of E. allosticta, but no other euglossines. This strengthens the view that semivolatiles play an important role in conveying specificity to perfume signals of orchid bees.
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| 15. |
- Jiang, Bingyi, et al.
(författare)
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A novel approach to enhance CO biomethanation by semi-disaggregation of anaerobic granular sludge
- 2023
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Ingår i: Energy Conversion and Management. - : Elsevier BV. - 0196-8904 .- 1879-2227. ; 276
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Tidskriftsartikel (refereegranskat)abstract
- The syngas produced from biomass gasification is a great potential energy resource, which can well be utilized to produce biomass-based substitute natural gas (BioSNG) via syngas biomethanation. CO biomethanation is one of the key issues in the biomethanation process and was studied experimentally in this work with respect to the effect of anaerobic granular sludge semi-disaggregation. The results show 1.07 times higher averaged CH4 production rate with the semi-disaggregated granular sludge than the whole granular sludge at 35 °C, and 1.69 times higher at 55 °C. The main mechanisms behind the enhanced CH4 production rate, especially under the thermophilic condition, are the improvement of microbial interspecific syntrophic association caused by the higher electron and substrate transfer rate, and more active cell growth and metabolism as reflected in higher abundance of functional genes and enzymes and less useless extracellular polymeric substances. The CO biomethanation enhancement occurs in the conversion of the substrate to the intermediate products. The semi-disaggregation of anaerobic granular sludge or similar way to strengthen interspecific association is an effective approach to improve the ability and tolerance of microbial cultures under the CO atmosphere. This technique can well be applied for the energy conversion from the CO-rich gas substrates into BioSNG via CO biomethanation under the thermophilic condition, or for the production of intermediates as fuels/chemicals under the mesophilic condition.
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| 16. |
- Jiang, Bingyi, et al.
(författare)
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Low-Grade Syngas Biomethanation in Continuous Reactors with Respect to Gas–Liquid Mass Transfer and Reactor Start-Up Strategy
- 2023
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Ingår i: Fermentation. - : MDPI AG. - 2311-5637. ; 9:1
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Tidskriftsartikel (refereegranskat)abstract
- In order to utilize a wider range of low-grade syngas, the syngas biomethanation was studied in this work with respect to the gas–liquid mass transfer and the reactor start-up strategy. Two reactors, a continuous stirred tank (CSTR) and a bubble column with gas recirculation (BCR-C), were used in the experiment by feeding an artificial syngas of 20% H2, 50% CO, and 30% CO2 into the reactors at 55 °C. The results showed that the CH4 productivity was slightly increased by reducing the gas retention time (GRT), but was significantly improved by increasing the stirring speed in the CSTR and the gas circulation rate in the BCR-C. The best syngas biomethanation performance of the CSTR with a CH4 productivity of 22.20 mmol·Lr−1·day−1 and a yield of 49.01% was achieved at a GRT of 0.833 h and a stirring speed of 300 rpm, while for the BCR-C, the best performance with a CH4 productivity of 61.96 mmol·Lr−1·day−1 and a yield of 87.57% was achieved at a GRT of 0.625 h and a gas circulation rate of 40 L·Lr−1·h−1. The gas–liquid mass transfer capability provided by gas circulation is far superior to mechanical stirring, leading to a much better performance of low-grade syngas biomethanation in the BCR-C. Feeding H2/CO2 during the startup stage of the reactor can effectively stimulate the growth and metabolism of microorganisms, and create a better metabolic environment for subsequent low-grade syngas biomethanation. In addition, during the thermophilic biomethanation of syngas, Methanothermobacter is the dominant genus.
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| 17. |
- Lebreton, Sebastien, et al.
(författare)
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A Drosophila female pheromone elicits species-specific long-range attraction via an olfactory channel with dual specificity for sex and food
- 2017
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Ingår i: BMC Biology. - : Springer Science and Business Media LLC. - 1741-7007. ; 15:1
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Tidskriftsartikel (refereegranskat)abstract
- Background: Mate finding and recognition in animals evolves during niche adaptation and involves social signals and habitat cues. Drosophila melanogaster and related species are known to be attracted to fermenting fruit for feeding and egg-laying, which poses the question of whether species-specific fly odours contribute to long-range premating communication. Results: We have discovered an olfactory channel in D. melanogaster with a dual affinity to sex and food odorants. Female flies release a pheromone, (Z)-4-undecenal (Z4-11Al), that elicits flight attraction in both sexes. Its biosynthetic precursor is the cuticular hydrocarbon (Z,Z)-7,11-heptacosadiene (7,11-HD), which is known to afford reproductive isolation between the sibling species D. melanogaster and D. simulans during courtship. Twin olfactory receptors, Or69aB and Or69aA, are tuned to Z4-11Al and food odorants, respectively. They are co-expressed in the same olfactory sensory neurons, and feed into a neural circuit mediating species-specific, long-range communication; however, the close relative D. simulans, which shares food resources with D. melanogaster, does not respond to Z4-11Al. Conclusion: The Or69aA and Or69aB isoforms have adopted dual olfactory traits. The underlying gene yields a collaboration between natural and sexual selection, which has the potential to drive speciation.
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| 18. |
- Ljunggren, Joel, et al.
(författare)
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Antifungal efficiency of individual compounds and evaluation of non-linear effects by recombining fractionated turpentine
- 2020
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Ingår i: Microchemical journal (Print). - : Elsevier BV. - 0026-265X .- 1095-9149. ; 153
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Tidskriftsartikel (refereegranskat)abstract
- A combination between a reductive and a holistic assay was employed to investigate whole fraction, synergistic, antagonistic and individual compound efficacy of vacuumdistilled turpentine fractions against the economically important brown-rot fungus Coniophora puteana. The fungus was subjected to recombinations of turpentine fractions at a concentration of 1000 ppm. All combinations exhibited useful antifungal properties, but some antifungal mixtures showed a more pronounced effect than the expected level of inhibition. Synergistic effects by a two-fold factor and minor antagonistic effects were observed. Complete growth inhibition of C. puteana was observed by a fraction obtained after distilling 1 L turpentine at 111–177°C (0.5 mbar) as well as by mixing it with another fraction withdrawn at 70–79°C (0.5 mbar). Chemical compositions of distilled fractions were determined through GC–MS analysis and Orthogonal Partial Least Squares (OPLS) multivariate data analysis of GC–MS chromatograms was employed to zoom in on the most active compounds responsible for antifungal activity. Isomers of epicubenol, the hydrocarbon aromatic compound ar-himachalene and α-cadinol are suggested as effective antifungal compounds. In addition, a subsequent fractionation of the most effective fraction was performed with preparatory gas chromatography and subfractions showed similar or better efficacy than previously observed. Our work demonstrates the possibility to retain adequate synergistic antifungal efficiency and offers an opportunity to explore the effects of individual compounds originating from the same crude sample.
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| 19. |
- Ljunggren, Joel, et al.
(författare)
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Evaluation of fractionally distilled Picea abies TMP-turpentine on wood-decaying fungi : in vitro, microcosm and field experiments
- 2020
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Ingår i: Wood Science and Technology. - : Springer Science and Business Media LLC. - 0043-7719 .- 1432-5225. ; 54, s. 847-868
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Tidskriftsartikel (refereegranskat)abstract
- Synthetic and heavy metal antifungals are frequently used as wood preservatives. However, they exhibit relatively inert biodegradation and toxic properties when leached; this makes their replacement with environmentally degradable yet functional alternatives a key target in the wood protection industry. In this context, distilled fractions of raw thermomechanical pulp turpentine (TMP-T) from Picea abies were assessed for their wood protecting capabilities against wood-decaying fungi. Antifungal bioactivity of fractions and some of their combinations were screened on agar-plates against the brown-rot fungus Coniophora puteana. Addition of TMP-T fractions showed a significant fungal growth rate reduction, while mixtures indicated the presence of synergistic and antagonistic effects. One fraction, obtained after distilling 1 L TMP-T at 111–177 °C at 0.5 mbar, showed complete growth inhibition of Antrodia sinuosa, Serpula lacrymans, Serpula himantioides and significant inhibition of Antrodia serialis, Antrodia xantha, Gloeophyllum sepiarium, Heterobasidion parviporum at a concentration of 1000 ppm. This fraction was further examined for long- and medium-term effects on wood decay in microcosm soil-jar and field experiment, respectively. The known antifungal compounds benzisothiazolinone, 2-octyl-4-isothiazolin-3-one, 3-iodo-2-propynyl N-butylcarbamate and two commercial wood preservatives were used as reference treatments. Commercial preservatives instilled long-term efficacy against C. puteana wood decay in a soil-jar microcosm experiment, but no noticeable protection with antifungal compounds or the present treatments was found. However, a moderate effect by the TMP-T fraction from the in vitro assay was observed and the TMP-turpentine distillation residue showed a similar fungal inhibition effect to the most potent commercial treatment after 29 months in the field.
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| 20. |
- Ljunggren, Joel
(författare)
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Some Approaches to Eco-Friendly Products from Natural Matrices
- 2020
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Doktorsavhandling (övrigt vetenskapligt/konstnärligt)abstract
- Since the onset of the industrial and chemical revolution, humans have caused immense damages to the surrounding flora and fauna. Effective methods for wood protection measures proved to be toxic; fossil fuels contribute to global warming and pesticides can be detected in the air, water, and soil. It is abundantly clear that efforts to find eco-friendly products are needed, while simultaneously providing the necessary incentives for sustainable worldwide development. Using renewable resources play a critical role in this shift towards circular economies.Wood has long been used as a renewable resource in high demand, but its susceptibility to attack by wood-decaying fungi mean that most European woods need to be protected against these fungi before outdoor use. We showed that fractionating turpentine, a pulp and paper mill by-product, increased antifungal efficacy by concentrating bioactive oxygenated sesquiterpenes. Based on this result, recombinations of the fractions were shown to exhibit synergistic effects that enable a more efficient product utilisation. In addition, this approach enabled putative identifications of previously unknown Picea abies turpentine constituents present at low levels.For a carbon-neutral society, production of biofuels using oleaginous yeast to convert lignocellulosic biomass into fuel has been hailed as a next-generation source of bioenergy. However, lignocellulose biofuel production by microorganisms is not straightforward and one challenge is the formation of microbe-toxic monomers, such as vanillin, during lignin degradation. The oleaginous yeast Cystobasidium laryngis and other potential oil-producing yeasts were screened for their viability and vanillin biotransformation capabilities. To this end, a mass chromatographic peak extraction tool termed TMATE was developed. Vanillyl alcohol was found to be the main product following vanillin degradation.The detrimental health and ecological effects of pesticides highlight the urgency for alternative crop protection measures, such as biological insect control and semiochemicals. In this regard, we present an essential step towards understanding the varied chemical ecology of microbe-insect interactions. Our methodology and findings provide cues with high information value that can be used to develop well-informed and potentially sustainable pest management regimes by, for example, the push-pull methodology using live yeasts.
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| 21. |
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| 22. |
- Rahmani, Rizan, et al.
(författare)
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Identification and Field Assay of Two Aggregation Pheromone Components Emitted by Males of the Bark Beetle Polygraphus punctifrons (Coleoptera: Curculionidae)
- 2019
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 45:4, s. 356-365
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Tidskriftsartikel (refereegranskat)abstract
- The bark beetle Polygraphus punctifrons (Coleoptera: Curculionidae) is a species that feeds on Norway spruce (Picea abies) and is found in the Northern parts of Europe and Russia. The release of volatile organic compounds (VOCs) produced by males and females of P. punctifrons when the beetles bore into spruce stem sections in a laboratory environment was studied using solid phase microextraction (SPME). The sampled VOCs emitted by boring beetles were analysed by gas chromatography and mass spectrometry (GCMS). (+)-2-[(1R,2S)-1-Methyl-2-(prop-1-en-2-yl)cyclobutyl]ethanol [(+)-(1R,2S)-grandisol] and (−)-(R)-1-isopropyl-4-methyl-3-cyclohexen-1-ol [(−)-(R)-terpinen-4-ol] were identified to be male specific volatiles. The identity of the compounds was confirmed by comparison with synthetic samples. Field trials with synthetic compounds in Sweden showed that racemic grandisol per se was strongly attractive for both males and females, while (−)-(R)-terpinen-4-ol was not. Further, when adding (−)-(R)-terpinen-4-ol to rac-grandisol, a synergistic effect was observed as the trap catch of P. punctifrons was fourfold. (−)-(R)-Terpinen-4-ol by its own did not attract P. punctifrons but Polygraphus poligraphus, and the latter was also attracted to traps baited with a 10:90 mixture of the two compounds. Thus, we have identified (+)-(1R,2S)-grandisol as a main component and (−)-(R)-terpinen-4-ol as a minor component of the aggregation pheromone of P. punctifrons. This opens future possibilities to monitor and, if necessary, manage populations of P. punctifrons.
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| 23. |
- Rahmani, Rizan, et al.
(författare)
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Identification and synthesis of putative pheromone components of the threatened salt marsh bagworm moth, Whittleia retiella (Lepidoptera: Psychidae)
- 2020
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 46, s. 115-127
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Tidskriftsartikel (refereegranskat)abstract
- Whittleia retiella (Newman, 1847) is a threatened salt marsh species of the bagworm moth family Psychidae. For its preservation it is necessary to develop efficient tools to survey its distribution and habitat requirements in order to use appropriate conservation methods. Such tools may be pheromone-based monitoring systems, which have documented efficacy in establishing the occurrence of cryptic insect species in nature. By using gas chromatography combined with electroantennographic detection (GC-EAD), we found two compounds in female W. retiella headspace samples and whole-body extracts that elicited electrophysiological activity in male antennae. Gas chromatograpy coupled with mass spectrometry (GC-MS) operating in electron impact (EI) mode and comparison of the analytical data with those of synthetic reference compounds showed the chemical structures of these putative pheromone components to be (1S)-1-methylpropyl (5Z)-dec-5-enoate and 1-methylethyl (5Z)-dec-5-enoate. Field assays using baits loaded with synthetic compounds revealed that conspecific males were attracted to (1S)-1-methylpropyl (5Z)-dec-5-enoate alone or in combination with 1-methylethyl (5Z)-dec-5-enoate, whereas 1-methylethyl (5Z)-dec-5-enoate neither attracted nor repelled males in the field assays when tested alone. This study shows the potential of using (1S)-1-methylpropyl (5Z)-dec-5-enoate for monitoring W. retiella to gather more detailed information about the geographic distribution and habitat needs of this rare moth.
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| 24. |
- Rahmani, Rizan, et al.
(författare)
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Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Förster)
- 2019
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Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 29:3, s. 103-110
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Tidskriftsartikel (refereegranskat)abstract
- The Carrot psyllid, Trioza apicalis Förster (Homoptera: Psylloidea: Triozidae) is one of the major insect pests of carrots (Daucus carota L.) in parts of northern and central Europe. Gas chromatography–single-sensillum recording (GC–SSR) previously confirmed several active compounds in a carrot leaf extract, but the most active compound remained unidentified. Mass fragmentation patterns observed from the unidentified active compound when analyzed by gas chromatography and mass spectrometry (GC–MS) was used to propose β-sesquiphellandrene and α-cis-bergamotene to be candidates as the unidentified compound. The compounds were synthesized and their mass spectra were nearly identical with the unknown active compound. But, the retention times differed from the compound in the carrot leaf extract. Thus, to obtain the unidentified compound pure enough and in adequate amounts for nuclear magnetic resonance (NMR) analysis, preparative gas chromatography was applied to separate and concentrate this biologically active compound. Analysis by liquid chromatography quadrupole time of flight mass spectrometry (LC–QTOF) confirmed the unidentified compound to be a compound with the formula of C 15 H 24 and together with GC–MS, 1 H and 13 C NMR analysis sesquisabinene B was identified as the unidentified compound in the extract. GC–SSR was then used to finally confirm the biological activity of sesquisabinene B isolated from the carrot leaf extract via preparative GC.
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| 25. |
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| 26. |
- Rönnander, Jonas, et al.
(författare)
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Biotransformation of vanillin into vanillyl alcohol by a novel strain of Cystobasidium laryngis isolated from decaying wood
- 2018
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Ingår i: AMB Express. - : Springer Science and Business Media LLC. - 2191-0855. ; 8:1
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Tidskriftsartikel (refereegranskat)abstract
- Vanillin is an aromatic aldehyde found as a component of lignocellulosic material, and in the cured pods of orchidaceae plants. Like other phenolic substances, vanillin has antimicrobial activity and can be extracted from lignin either by a thermo-chemical process or through microbial degradation. Vanillin, can serve as a model monomer in biodegradation studies of lignin. In the present study, a yeast isolated from decaying wood on the Faroe Islands, was identified as Cystobasidium laryngis strain FMYD002, based on internal transcribed spacer sequence analysis. It demonstrated the ability to convert vanillin to vanillyl alcohol, as detected by ultra-high performance liquid chromatography–quadrupole-time-of-flight. Structural analysis of vanillyl alcohol was carried out by using gas chromatography–mass spectrometry and 1H NMR spectroscopy, and further verified by synthesis. The reduction of vanillin to vanillyl alcohol has been documented for only a few species of fungi. However, to our knowledge, this biotransformation has not yet been reported for basidiomycetous yeast species, nor for any representative of the subphylum Pucciniomycotina. The biotransformation capability of the present strain might prove useful in the industrial utilisation of lignocellulosic residues.
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| 27. |
- Viklund, Lina, 1984-
(författare)
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Aggregation pheromones in the four-eyed bark beetles Polygraphus poligraphus, Polygraphus punctifrons, Polygraphus subopacus and Polygraphus proximus
- 2024
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Doktorsavhandling (övrigt vetenskapligt/konstnärligt)abstract
- Some bark beetle species can cause considerable damage and mortality in their host trees, resulting in major economic and environmental losses. Beetles of the genus Polygraphus, four-eyed bark beetles, have been involved in large bark beetle outbreaks in Sweden together with the European spruce bark beetle Ips typographus. Three species of Polygraphus are present in Swedish spruce forests: P. poligraphus, P. punctifrons and P. subopacus. Polygraphus poligraphus has been associated with tree mortality whereas little is known about the two other species. In other parts of the world, other Polygraphus species are well-known pest insects; these include Polygraphus rufipennis, which attacks black spruce in North America, and Polygraphus proximus, which is an invasive pest in Russia where it has killed large volumes of Siberian fir. Polygraphus proximus is spreading westwards towards the European Union. Bark beetles use aggregation pheromones to coordinate mass attacks on their host trees as well as for the males to attract females. Traps baited with aggregation pheromones offer a promising way of monitoring pest species and may, in combination with other measures, contribute to pest control. Aggregation pheromones of P. rufipennis and P. poligraphus were identified over 30 years ago, but for the other Polygraphus species, no aggregation pheromones were known. The aim of this work was to investigate the chemical communication of P. poligraphus, P. subopacus, P. punctifrons and P. proximus. Beetles were allowed to bore into the bark of their host trees at the laboratory, and the emitted volatiles were sampled with SPME and analysed with GC-MS. Several sex-specific compounds were identified in all four species. Electroantennographic studies as well as field experiments were conducted in order to evaluate the biological role of these compounds. Attractive compounds which werevipresumed to be parts of the aggregation pheromones produced by the males were found for all four species, as well as some repellant compounds. Species-specific pheromone lures were developed for P. punctifrons and optimised for P. poligraphus. In P. subopacus and P. proximus, the composition of their aggregation pheromones turned out to be surprisingly similar. Both species appear to use the same main compound in their pheromones, and when this compound was used as a bait in traps, both species were caught as well as P. poligraphus. Several other compounds were also found in the emissions of volatiles collected from boring males of P. proximus and P. subopacus, but despite several field studies which were conducted in Russia and Sweden, no species-specific formulation was identified for P. subopacus. For P. proximus, one compound which was collected from the males in minor amounts appeared to be attractive to P. proximus specifically, but this effect should be confirmed in future studies. The presented work should be a good starting point for anyone who wishes to study the chemical communication of these species.
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| 28. |
- Viklund, Lina, et al.
(författare)
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Identification of male produced compounds in the bark beetle Polygraphus subopacus and establishment of (Z)-2-(3,3-dimethylcyclohexylidene)-ethanol as an aggregation pheromone component
- 2021
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Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 31:6, s. 367-376
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Tidskriftsartikel (refereegranskat)abstract
- Bark beetles of the genus Polygraphus have recently been involved in large bark beetle outbreaks in central Sweden, together with the European spruce bark beetle Ips typographus. Three species of Polygraphus can be found in this region; Polygraphus poligraphus, Polygraphus punctifrons and Polygraphus subopacus. Efficient pheromone traps would facilitate further investigations of these species and their role in bark beetle outbreaks. Pheromone compounds have previously been identified in P. poligraphus and P. punctifrons, but not in P. subopacus. Thus, we allowed males and females of P. subopacus to bore in the bark of stem sections of Norway spruce (Picea abies) in the laboratory. Volatile organic compounds from boring insects were sampled with SPME and analysed with GC–MS and several male-specific compounds were observed. The male specific compounds were 3-methyl-3-buten-1-ol, 3-methyl-2-buten-1-ol, 3-methyl-2-butenal, grandisol, fragranol, (Z)-2-(3,3-dimethylcyclohexylidene)-ethanol, (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, (Z)-2-(3,3-dimethylcyclohexylidene)-acetaldehyde, (E)-2-(3,3-dimethylcyclohexylidene)-acetaldehyde, geranial and γ-isogeraniol. (Z)-2-(3,3-dimethylcyclohexylidene)-ethanol, [(Z)-DMCHE], was identified from GC–MS analysis to be the major male-specific compound while the (E)-isomer, [(E)-DMCHE], was found as a minor compound. These two compounds gave positive responses in EAG analyses with antennae from males and females of P. subopacus. Thus, (Z)- and (E)-DMCHE were used in a field experiment in central Sweden but only (Z)-DMCHE was found to be attractive to males and females of P. subopacus. Consequently, (Z)-DMCHE was established to be a component of P. subopacus aggregation pheromone.
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| 29. |
- Viklund, Lina, et al.
(författare)
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Identification of sex-specific compounds in the invasive four-eyed fir bark beetle Polygraphus proximus
- 2022
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Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 32:6, s. 183-195
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Tidskriftsartikel (refereegranskat)abstract
- Polygraphus proximus, a four-eyed fir bark beetle, is an invasive bark beetle species which has caused extensive damage to forests of Abies sibirica in southern and western Siberia and to Abies species in the European part of Russia. There is a high risk that the pest insect will spread to areas where it is currently not considered present, such as the European Union. In these areas, it threatens to attack conifer forests of various species which may result in major environmental and economic impact. The aim of this study was to identify pheromone components of P. proximus that can be used as pheromone baits. Males and females of P. proximus were allowed to bore into the bark of stem sections of Abies sibirica at the laboratory, and volatiles were collected with solid-phase microextraction (SPME). Analyses of these extracts with gas chromatography-mass spectrometry (GC–MS) revealed several sex-specific compounds. In total, twelve male-specific compounds and one female-specific compound were identified. The major male-specific compound determined by GC peak area was (Z)‐2‐(3,3‐dimethylcyclohexylidene)‐ethanol [(Z)-DMCHE] and the minor male-specific compounds were 3-methyl-3-buten-1-ol, 3-methyl-2-buten-1-ol, 3-methyl-2-butenal, benzyl alcohol, fragranol, 7-methyl-3-methylene-6-octen-1-ol, (Z)- and (E)-2-(3,3-dimethylcyclohexylidene)-acetaldehyde, geraniol, geranial and papayanol. The only female-specific compound was identified as 1-hexanol. Two of the male-specific compounds, (Z)‐DMCHE and 3-methyl-2-buten-1-ol were shown to attract males and females of P. proximus in field studies. Thus, we now for the first time can present the structures of two male-specific components that are biologically active parts of P. proximus aggregation pheromone. However, some chemical communication overlap between P. proximus and P. subopacus needs to be further investigated as (Z)‐DMCHE also attracted males and females of P. subopacus.
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| 30. |
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| 31. |
- Viklund, Lina, et al.
(författare)
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Optimizing the attractiveness of pheromone baits used for trapping the four-eyed spruce bark beetle Polygraphus poligraphus
- 2019
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Ingår i: Journal of applied entomology. - : Wiley. - 0931-2048 .- 1439-0418. ; 143:7, s. 721-730
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Tidskriftsartikel (refereegranskat)abstract
- Bark beetles have caused extensive damage to forests in central Sweden during the past decade, and the four-eyed spruce bark beetle, Polygraphus poligraphus, seems to be involved. However, its role in these bark beetle outbreaks is still not clear. The purpose of this study was to develop an efficient pheromone bait for P. poligraphus, which would make it possible to study the species more carefully and thereby contribute to protect exposed forests in an environmentally friendly way. Three field studies were conducted in 2015, 2016 and 2018 in Medelpad, county of Västernorrland, Sweden. The pheromone of P. poligraphus, (−)-terpinen-4-ol, was tested at different release rates and in different enantiomeric purities, to find the most attractive formulation for the beetles. It was also tested in combination with racemic frontalin, a compound which has previously been shown to produce a synergistic effect together with (−)-terpinen-4-ol of low enantiomeric purity; 52% ee. Other compounds, chosen based on responses from electroantennographic studies, were also tested in an attempt to find additional attractants and repellents for P. poligraphus. The most attractive treatment tested was enantiomerically pure (−)-terpinen-4-ol (99% ee). When the enantiomeric purity was lower (50% ee), the trap catches was lowered to levels comparable to the catches for unbaited control traps. A strong synergistic effect with frontalin was observed for (−)-terpinen-4-ol of low enantiomeric purity (50% ee) but not for the enantiomerically pure compound (99% ee). The release rate of (−)-terpinen-4-ol (99% ee) was shown to be an important factor. For the combination of frontalin and (−)-terpinen-4-ol (50% ee), the attraction seemed strongest when (−)-terpinen-4-ol was released at a higher rate than frontalin. An interesting and novel result was that a repellent compound, α-terpineol, was identified in our studies. Our results from field studies and electroantennography recordings also indicate that (+)-terpinen-4-ol is a repellent for P. poligraphus.
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| 32. |
- Wallin, Erika A., 1985-, et al.
(författare)
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Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella
- 2020
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Ingår i: Scientific Reports. - : Springer Science and Business Media LLC. - 2045-2322. ; 10:1
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Tidskriftsartikel (refereegranskat)abstract
- The bumblebee wax moth, Aphomia sociella, is a parasite of bumblebees. In this species, males produce sexual pheromone to attract females, while females produce an aphrodisiac pheromone that initiates male courtship. Both pheromones contain 6,10,14-trimethylpentadecan-2-one (TMPD-one) and the corresponding alcohol, 6,10,14-trimethylpentadecan-2-ol (TMPD-ol) in sex specific quantities. Male sex pheromone consists of 7 components with TMPD-one as a minor one and traces of TMPD-ol. In female aphrodisiac pheromone, TMPD-ol is the major component, while TMPD-one is present in traces. Here we report on the absolute configuration of TMPD-one in male sex pheromone and TMPD-ol in female aphrodisiac pheromone of A. sociella. The configuration was determined from GC/MS of prepared (S)-acetoxypropionyl esters of TMPD-ol. TMPD-one was first reduced to the alcohol that was then derivatized with (S)-acetoxypropionyl chloride. The GC/MS data of obtained diastereoisomers were compared with synthetic standards. The absolute configuration of TMPD-one in the male pheromone was (6R,10R). The configuration of TMPD-ol in the female pheromone was (2R,6R,10R). Electrophysiological experiments showed that TMPD-one and TMPD-ol are perceived by both sexes. The synthetic standards of naturally produced stereoisomers elicited higher responses than mixtures of all stereoisomers.
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| 33. |
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