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Semiochemicals related to the aphid Cinara pillicornis (Hartig) and its host, Picea abies. A method to assign diastereomers of nepetalactone
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2008 (English)In: Journal of Chromatography A, ISSN 0021-9673, E-ISSN 1873-3778, Vol. 1180, no 1-2, 165-170 p.Article in journal (Refereed) Published
Abstract [en]

Volatiles released by seedlings of Norway spruce infested with the aphid Cinara pilicornis were analyzed using SPME–GC–MS. Among the stress-induced compounds released by the host plant, citronellol, cis–trans-nepetalactone and cis–trans-nepetalactol was found. These compounds originated from the aphids and they were assumed to be pheromone components for this aphid species. To determine the relative stereochemistry of the nepetalactone, a diagnostic method was developed. The method was based on multivariate analysis of tabulated relative intensities of mass fragments of the four nepetalactone diastereomers. In the practical method described, a few pairs of fragments in the mass spectra were compared and, in combination with the Kovat's index, were used to unambiguously identify the relative stereochemistry of the nepetalactone.

Place, publisher, year, edition, pages
2008. Vol. 1180, no 1-2, 165-170 p.
Keyword [en]
Aphid, Conifer, Pheromone, Nepetalactone, Diastereomer, SPME–GC–MS, Semiochemicals
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-7043DOI: 10.1016/j.chroma.2007.12.020ISI: 000253060900018Scopus ID: 2-s2.0-38349035715OAI: oai:DiVA.org:kth-7043DiVA: diva2:11930
Note
Uppdaterad till artikel(20110214)Available from: 2007-05-04 Created: 2007-05-04 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Chemical defence in Norway spruce
Open this publication in new window or tab >>Chemical defence in Norway spruce
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Norway spruce (Picea abies) responds to stress by biosynthesis of chemical substances, which can deter invading insects or pathogens. Some of these substances are volatile and can be emitted to the surroundings while others are accumulated within the tree. Information about the susceptibility of individual plants to infestation, their volatile emissions and chemical defence is of interest, for example, in selecting plants for tree breeding programs.

The first part of this research focused on volatiles emitted by Norway spruce plants. Collection of headspace volatiles by SPME and subsequent separation and identification with GC-MS was used to investigate Norway spruce plants of different ages and stress conditions as well as trapping semiochemicals like nepetalactone emitted by the spruce shoot aphids. It was even possible to analyse the emission of single needles in vivo and obtain spatial localisation of the stress reaction to methyl jasmonate or spruce spinning mites. Seedlings of different ages showed differences in chemical composition of emitted volatiles, with the pine weevil repellent, (4S)-(-)-limonene, one of the main compounds. Wounded phloem of conventional plants emitted high amounts of monoterpenes while the phloem of mini plants emitted (3Z)-hexenal and (3Z)-hexen-1-ol. In addition, a method to separate and identify the four diastereomers of nepetalactone by GC-MS and characteristic m/z-fragments was accomplished.

The second part of the research deals with the chemical response of Norway spruce roots to inoculation with Heterobasidion annosum. Terpene concentrations increased after inoculation or wounding but the composition was mainly associated with clone identity and not to susceptibility or treatment. In contrast, inoculation with H. annosum induced a treatment-specific alteration of phenol composition. The constitutive phenol composition differed between more and less susceptible clones. The phenols astringin and astringin dimers (piceasides) as well as the terpene α-longipinene may be suitable markers of low susceptibility for P. abies to Heterobasidion.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2011. 63 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2011:13
Keyword
volatiles, terpenes, green leaf volatiles, stilbenes, stress response, nepetalactone, Picea abies, Hylobius abietis, Cinara pilicornis, Oligonychus ununguis, Heterobasidion annosum
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-31133 (URN)978-91-7415-877-9 (ISBN)
Public defence
2011-04-01, K1, Teknikringen 36, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20110314Available from: 2011-03-14 Created: 2011-03-09 Last updated: 2011-03-14Bibliographically approved
2. Stress Related Emissions of Norway Spruce Plants
Open this publication in new window or tab >>Stress Related Emissions of Norway Spruce Plants
2007 (English)Licentiate thesis, comprehensive summary (Other scientific)
Abstract [en]

The interactions between plants and insects are mediated by volatile molecules. Plants respond to stress by biosynthesis of chemical substances which can deter invading insects or pathogens. Some of these substances are volatile and are emitted to the surroundings and may attract or repel insects. Information about the susceptibility of individual plants to infestation, their volatile emissions and chemical defence is of interest, for example in selecting plants for tree breeding programs.

This research was focused on finding volatile chemical markers of resistance in Norway spruce plants that do influence insects associated to conifers. Collection of headspace volatiles by SPME followed by separation and identification with GC-MS is effective in investigating biological systems with a minimum of disturbance. This method has here been used to investigate Norway spruce plants of different ages and stress conditions as well as trapping semiochemicals like nepetalactone emitted by the spruce shoot aphids. It was even possible to analyse the emission of single needles in vivo and obtain a chemical pattern of the site of the stress reaction. Seedlings of different ages showed differences in chemical composition of emitted volatiles, with the pine weevil repellent (S)-(-)-limonene as one of the main compounds. Wounded phloem of conventional plants emitted high amounts of monoterpenes while the phloem of mini plants emitted (3Z)-hexenal and (3Z)-hexen-1-ol.

Norway spruce plants did respond to different stress elicitors with similar response, regardless of their genetic origin. The emissions from stressed Norway spruce plants mainly consist of (E)-β-farnesene, (E,E)-α-farnesene, (E)-α-bisabolene, (R)-(-)-linalool and methyl salicylate. Emissions from live spruce shoot aphids were detected during autumn periods, and a method to separate and identify the four diastereomers of nepetalactone by GC-MS and characteristic m/z-fragments was accomplished.

Place, publisher, year, edition, pages
Stockholm: Kemi, 2007
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2007:22
Keyword
volatiles, terpenes, green leaf volatiles, stress response, nepetalactone, SPME, Picea abies, Hylobius abietis, Cinara pillicornis
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-4353 (URN)978-91-7178-644-9 (ISBN)
Presentation
2007-05-09, D31, KTH, Lindstedtsvägen 5, Stockholm, 10:00
Opponent
Supervisors
Available from: 2007-05-04 Created: 2007-05-04 Last updated: 2012-03-21Bibliographically approved

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