Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Antifeedants and feeding stimulants in bark extracts of ten woody non-host species of the pine weevil, Hylobius abietis
2008 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 34, no 10, 1290-1297 p.Article in journal (Refereed) Published
Abstract [en]

Bark of ten woody species, known to be rejected as a food source by the pine weevil, Hylobius abietis, were sequentially extracted by a Soxhlet apparatus with pentane followed by methanol. Species were alder (Alnus glutinosa), aspen (Populus tremula), beech (Fagus sylvatica), guelder rose (Viburnum opulus), holly (Ilex aquifolium), horse chestnut (Aesculus hippocastanum), lilac (Syringa vulgaris), spindle tree (Evonymus europaeus), walnut (Juglans regia), and yew (Taxus baccata). Bark of each species was collected in southern Scandinavia during the summer. Resulting extracts were tested for antifeedant activity against the pine weevil by a micro-feeding choice assay. At a dose corresponding to that in the bark, methanol extracts from Aesculus, Taxus, Ilex, and Populus were antifeedant active, while pentane extracts of Aesculus, Fagus, Syringa, and Viburnum were stimulatory. Four known antifeedants against H. abietis, the straight-chained carboxylic acids, hexanoic and nonanoic acid (C6 and C9), carvone, and carvacrol were identified by gas chromatography (GC)-mass spectrometry (MS) in several extracts. The major constituents were identified and tested for feeding deterrence. The aromatic compounds benzyl alcohol and 2-phenylethanol are new non-host plant-derived feeding deterrents for the pine weevil. Additionally, two feeding stimulants, beta-sitosterol and 5-(hydroxymethyl)-2-furaldehyde, were identified. One active methanol extract of Aesculus bark was sequentially fractionated by liquid chromatography, and major compounds were tentatively identified as branched alcohols and esters of hexanoic acid. Five commercially available hexanoate esters and two commercially available branched alcohols were identified as new active antifeedants. Both stimulatory and inhibiting compounds were found in the same extracts and co-eluted in the same or adjacent fractions. The mix of semiochemicals of opposite activity in each extract or fraction could explain the stimulatory-, inhibitory-, or sometimes neutral activity. Generally, such co-occurrence confounds the isolation of antifeedants.

Place, publisher, year, edition, pages
2008. Vol. 34, no 10, 1290-1297 p.
Keyword [en]
Phagostimulant, Carboxylic acid, Bark extract, Limonene, Carvone, Carvacrol, Eugenol, Benzyl alcohol, Benzoic acid, 2-Phenylethanol, beta-Sitosterol, Hexanoate esters, Branched alcohols
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-5600DOI: 10.1007/s10886-008-9525-0ISI: 000259910800005OAI: oai:DiVA.org:kth-5600DiVA: diva2:10018
Note
QC 20110124. Uppdaterad från manuskript till artikel(20110124)Available from: 2006-04-11 Created: 2006-04-11 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Isolation, Synthesis and Structure-Activity Relationships of Antifeedants against the Pine Weevil, Hylobius Abietis
Open this publication in new window or tab >>Isolation, Synthesis and Structure-Activity Relationships of Antifeedants against the Pine Weevil, Hylobius Abietis
2006 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

The large pine weevil, Hylobius abietis L., is a major insect pest on conifer seedlings in northern Europe. Due to its feeding newly planted trees get girdled, resulting in high seedling mortality (up to 80%). As a consequence great financial losses to the forest industry occur. Today the seedlings are protected with the pyrethroid insecticide cypermethrin. This insecticide is toxic to aquatic organisms and is, from 2010, prohibited for use in Sweden by the Swedish Chemicals Inspectorate. An alternative to insecticides is to protect the seedlings with antifeedants, compounds that, either through taste or smell or both, deter the weevils from feeding. This thesis describes the search for and the synthesis of such antifeedant compounds.

Bark extracts of several woody species, known to be non-palatable to the weevil, were prepared and found to display antifeedant activity against H. abietis. The major chemical constituents of the extracts were tested for antifeedant activity. Antifeedants such as eugenol, 2-phenylethanol and benzylalcohol, but also feeding stimulants such as β-sitosterol and linoleic acid, were identified. An extract of linden bark, Tilia cordata, was shown to contain nonanoic acid, a highly active antifeedant. Other aliphatic carboxylic acids were also found to display high antifeedant activities against the weevil, both in laboratory and in field tests.

The enantiomers of dihydropinidine, a piperidine alkaloid present in several conifer species, were prepared by dimethylzinc mediated allylation of 2- methyltetrahydropyridine-N-oxide. When tested in micro feeding assays, no difference in antifeedant activity was found for the enantiomers. In a field test high antifeedant activity, comparable with that of the presently used insecticide cypermethrin, was found for (±)-dihydropindine. Other naturally occurring piperidine alkaloids were synthesised and also found to display high antifeedant activities in laboratory tests.

Structure-activity relationships were evaluated for methoxy substituted benzaldehydes, benzoic acids and cinnamic aldehydes, -acids, -esters and -alcohols. While the carboxylic acids were inactive or even feeding stimulants, the aldehydes were the most active antifeedants

Place, publisher, year, edition, pages
Stockholm: KTH, 2006. ix, 53 p.
Series
Trita-IOK, ISSN 1100-7974 ; 2006:101
Keyword
Pine weevil, Hylobius abietis, semiochemicals, antifeedant, feeding deterrent, feeding stimulant, bark extract, carboxylic acid, piperidine alkaloids, structure-activity, cinnamic aldehyde, benzaldehyde
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-3919 (URN)91-7178-301-6 (ISBN)
Public defence
2006-04-28, Sal 0102, Åkroken, Mittuniversitetet, Sundsvall, 14:00
Opponent
Supervisors
Note
QC 20110124Available from: 2006-04-11 Created: 2006-04-11 Last updated: 2011-01-24Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text
In the same journal
Journal of Chemical Ecology
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 84 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf