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Structure elucidation of semiochemicals related to: Polygraphus poligraphus, Polygraphus punctifrons, Trioza apicalis, Whittleia retiella, Neodiprion edulicolus, Neodiprion scutellatus, Neodiprion knereri and Neodiprion virginianus
Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
2019 (English)Doctoral thesis, comprehensive summary (Other academic)
Place, publisher, year, edition, pages
Sundsvall: Mid Sweden University , 2019. , p. 60
Series
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 293
National Category
Chemical Engineering
Identifiers
URN: urn:nbn:se:miun:diva-36850ISBN: 978-91-88527-88-2 (print)OAI: oai:DiVA.org:miun-36850DiVA, id: diva2:1342767
Public defence
2019-03-12, O102, Sundsvall, 10:15 (English)
Supervisors
Note

Vid tidpunkten för disputationen var följande delarbeten opublicerade: delarbete 2 (accepterat), delarbete 3 (accepterat), delarbete 4 (inskickat), delarbete 5 (inskickat), delarbete 6 (manuskript).

At the time of the doctoral defence the following papers were unpublished: paper 2 (accepted), paper 3 (accepted), paper 4 (submitted), paper 5 (submitted), paper 6 (manuscript).

Available from: 2019-08-14 Created: 2019-08-14 Last updated: 2019-08-16Bibliographically approved
List of papers
1. SPME collection and GC-MS analysis of volatiles emitted during the attack of male Polygraphus poligraphus (Coleoptera, Curcolionidae) on Norway spruce
Open this publication in new window or tab >>SPME collection and GC-MS analysis of volatiles emitted during the attack of male Polygraphus poligraphus (Coleoptera, Curcolionidae) on Norway spruce
2015 (English)In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 70, no 9-10, p. 265-273Article in journal (Refereed) Published
Abstract [en]

Tree mortality caused by bark beetles has increased in recent decades in both Europe and North America. In a large recent outbreak in central Sweden the bark beetle Polygraphus poligraphus was often found together with the spruce bark beetle Ips typographus in killed trees. To increase the understanding of the aggregation behavior of P. poligraphus we used solid phase microextraction (SPME) to collect volatile organic compounds (VOCs) released from single P. poligraphus males, with and without added females, colonizing Norway spruce stem sections and analyzed the sampled compounds by combined gas chromatography and mass spectrometry (GC-MS). High amounts of terpinen-4-ol, a substance found in the hindguts of P. poligraphus males in earlier studies, were released by colonizing males. The emission of both enantiomers of terpinen-4-ol was monitored by GC-MS over time as the males aged in the absence and presence of females. Single males emitted (R)-(-)-terpinen-4-ol for up to 60 days in high enantiomeric purity but the enantiomeric excess (ee) varied between males, and also for the same individual, over time from 96.3% to 99.3% ee. In the presence of females, males also emitted terpinen-4-ol for up to 50 days but now in lower amounts and with lower enantiomeric purity varying from 67.7% ee to 99.3% ee. Small quantities of other volatile compounds were emitted from the colonizing beetles including cis-and trans-4-thujanol, both of which were previously shown to be present in the hindguts of males. In earlier studies frontalin was found to attract P. poligraphus, but in our study it was not identified among emitted compounds from colonizing beetles.

Keywords
analysis, enantiomers, forest pest, pheromone, terpinen-4-ol, volatile organic compounds
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-26874 (URN)10.1515/znc-2015-5035 (DOI)000366258700006 ()26461842 (PubMedID)2-s2.0-84946213121 (Scopus ID)
Available from: 2016-01-15 Created: 2016-01-15 Last updated: 2019-08-14Bibliographically approved
2. Identification and Field Assay of Two Aggregation Pheromone Components Emitted by Males of the Bark Beetle Polygraphus punctifrons (Coleoptera: Curculionidae)
Open this publication in new window or tab >>Identification and Field Assay of Two Aggregation Pheromone Components Emitted by Males of the Bark Beetle Polygraphus punctifrons (Coleoptera: Curculionidae)
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2019 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 45, no 4, p. 356-365Article in journal (Refereed) Published
Abstract [en]

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. 

Keywords
(+)-(1R, 2S)-Grandisol, (−)-(R)-Terpinen-4-ol, Enantiomeric separation, Picea abies, Preparative fraction collection, SPME
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-35836 (URN)10.1007/s10886-019-01056-6 (DOI)000467745400003 ()30796678 (PubMedID)2-s2.0-85061967619 (Scopus ID)
Available from: 2019-03-20 Created: 2019-03-20 Last updated: 2019-08-14Bibliographically approved
3. Optimizing the attractiveness of pheromone baits used for trapping the four-eyed spruce bark beetle Polygraphus poligraphus
Open this publication in new window or tab >>Optimizing the attractiveness of pheromone baits used for trapping the four-eyed spruce bark beetle Polygraphus poligraphus
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2019 (English)In: Journal of applied entomology, ISSN 0931-2048, E-ISSN 1439-0418, Vol. 143, no 7, p. 721-730Article in journal (Refereed) Published
Abstract [en]

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.

Keywords
enantiomers, field study, frontalin, pheromone, synergism, terpinen‐4‐ol
National Category
Ecology
Identifiers
urn:nbn:se:miun:diva-36659 (URN)10.1111/jen.12641 (DOI)000475465300003 ()2-s2.0-85064480153 (Scopus ID)
Available from: 2019-07-08 Created: 2019-07-08 Last updated: 2019-10-16Bibliographically approved
4. Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Forster)
Open this publication in new window or tab >>Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Forster)
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2019 (English)In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 29, no 3, p. 103-110Article in journal (Refereed) Published
Abstract [en]

The Carrot psyllid, Trioza apicalis Forster (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 -sesquiphellandrene and -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 theformula of C15H24 and together with GC-MS, H-1 and C-13 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.

Keywords
Synthesis, beta-Sesquiphellandrene, alpha-cis-Bergamotene, Preparative gas chromatography, Single-sensillum recording, Analysis
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-36651 (URN)10.1007/s00049-019-00280-6 (DOI)000469799200002 ()2-s2.0-85063037685 (Scopus ID)
Available from: 2019-07-08 Created: 2019-07-08 Last updated: 2019-10-16Bibliographically approved

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Rahmani, Rizan

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