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The Scents of Nature: Identification and Synthesis of Bioactive Compounds Used in Insect Communication
Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering. (Eko-kemi)
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Pest insects cause great financial losses in the forest and food industry every year. To fight these pests industries have used insecticides, which are sometimes harmful to nature and humans. One potential way of avoiding insecticides is the use of integrated pest management based on insect communication, which would offer species-specific methods for protecting forest and food resources. Insects use chemicals known as semiochemicals for both intra- and interspecies communication. By learning how insects use these semio-chemicals to talk to each other we can eavesdrop and mimic their communication for our benefit. One research area dealing with these questions is chemical ecology, which is an interdisciplinary area as knowledge in chemistry and biology is required. Collaborations between groups within and outside of Sweden are essential in order to make progress in this field of research.

This thesis presents the identification and synthesis of semiochemicals from several insect species, most of which are considered to be pests. Synthesised compounds have been sent to collaboration partners around Sweden and Europe for biological evaluations.

Studies of the African butterfly, Bicyclus anynana, have unravelled particular biological phenomena that may aid in the understanding of the Bicyclus genus, though recognizing individual species variation is crucial. In 2008 the putative male sex pheromone of B. anynana was determined to consist of three compounds: hexadecanal, (Z)-9-tetradecenol and 6,10,14-trimethylpentadecan-2-ol, and the specific stereoisomer for 6,10,14-trimethylpentadecan-2-ol has been determined in this thesis. The ratio of 6,10,14-trimethylpentadecan-2-ol and the corresponding ketone were investigated for seventeen Bicyclus species (including B. anynana) that live in overlapping regions in Africa. The stereochemistry was determined for most of the species and may provide a way to chemically distinguish them.

The orchid bees, Euglossa spp, are important pollinators of many orchids in Central America. Insight about pollination and conservation of endangered orchid species may be possible by gathering more information about the Euglossa genus. Males of the Euglossa genus have pouch-like structures on their hind legs where they store compounds collected from their surroundings. 6,10,14-Trimethyl-pentadecan-2-one is a common component of leg extracts from Euglossa imperialis, E. crassipunctata and E. allosticta, the specific stereochemistry of which has been determined in this thesis. Another, different compound was found in high amounts in E. viridissima and its structure has been elucidated; several synthetic pathways are under investigation to obtain the target compound.

Bed bugs (Cimex lectularius and C. hemipterus) are an ectoparasite that feed on human blood, and the number of reported infestations of these parasites has increased considerably during the last decade. Two 5th instar nymph-specific compounds, 4-oxo-hexenal and 4-oxo-octenal, were identified and synthesised.

Utilizing domestic dogs (Canis lupus familiaris) in the identification of bed bug infestations has become popular during recent years. Their training is usually conducted using live bed bugs, however this thesis describes an alternative method of teaching dogs to find infestations. This alternative method is based on synthetic compounds and dogs trained in this manner have achieved a high positive indication rate.

Two species of the tiny, Acacia leaf-eating insect pests in Australia known as thrips, Kladothrips nicolsoni and K. rugosus, have been investigated by means of larval extracts and have been shown to contain large amount of (Z)-3-dodecenoic acid which was synthesised and tested in bioassays.

Fruit flies are common pests on fruit in almost every private household. Even though fruit flies has been investigated extensively, their chemical communication has not been completely elucidated. (Z)-4-undecenal was identified as a compound emitted by females, it was synthesised in high stereoisomeric purity and evaluated in biological assays.

Place, publisher, year, edition, pages
Sundsvall: Mittuniversitetet , 2014. , 90 p.
Series
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 200
Keyword [en]
Semiochemicals, Sex pheromone, Bicyclus spp, Euglossa spp, Cimex hemipterus, Cimex lectularius, Kladothrips nicolsoni, Kladothrips rugosus, Drosophila melanogaster
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-22821ISBN: 978-91-87557-84-2 (print)OAI: oai:DiVA.org:miun-22821DiVA: diva2:744789
Public defence
2014-09-19, M102, Mittuniversitetet, Sundsvall, 16:08 (English)
Opponent
Supervisors
Projects
FORE
Available from: 2014-09-09 Created: 2014-09-08 Last updated: 2015-03-13Bibliographically approved
List of papers
1. Cracking the olfactory code of a butterfly: the scent of ageing.
Open this publication in new window or tab >>Cracking the olfactory code of a butterfly: the scent of ageing.
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2012 (English)In: Ecology Letters, ISSN 1461-023X, E-ISSN 1461-0248, Vol. 15, no 5, 415-424 p.Article in journal (Refereed) Published
Abstract [en]

Ecology Letters (2012) 15: 415-424 ABSTRACT: Although olfaction is a primary mode of communication, its importance in sexual selection remains understudied. Here, using the butterfly Bicyclus anynana, we address all the parameters of importance to sexual selection for a male olfactory signal. We show that variation in the male sex pheromone composition indicates male identity and male age. Courting males of different ages display small absolute (c. 200 ng) but large relative (100%) change of one specific pheromone component (hexadecanal) which, unlike the other components, showed no heritability. Females prefer to mate with mid-aged over younger males and the pheromone composition is sufficient to determine this preference. Surprisingly refined information is thus present in the male olfactory signal and is used for sexual selection. Our data also reveal that there may be no 'lek paradox' to resolve once the precise signal of importance to females is identified, as hexadecanal is, as expected, depleted in additive genetic variation.

Keyword
(2R, 6R, 10R)-6, 10, 14-trimethylpentadecan-2-ol, (Z)-9-tetraenol, 16:Al, 6, 10, 14-trime-15-2-ol, age, Bicyclus anynana, butterfly, hexadecanal, identity, Lepidoptera, male sex pheromone, mate choice, olfoctory communication, sexual selection, synthesis, Z9-14:=H
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-16092 (URN)10.1111/j.1461-0248.2012.01748.x (DOI)000302288900003 ()22390373 (PubMedID)2-s2.0-84859424161 (Scopus ID)
Available from: 2012-04-17 Created: 2012-04-17 Last updated: 2016-09-29Bibliographically approved
2. Stereoisomeric Analysis of 6,10,14-Trimethylpentadecan-2-ol and the Corresponding Ketone in Wing Extracts from African Bicyclus Butterfly Species
Open this publication in new window or tab >>Stereoisomeric Analysis of 6,10,14-Trimethylpentadecan-2-ol and the Corresponding Ketone in Wing Extracts from African Bicyclus Butterfly Species
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2015 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 41, no 1, 44-51 p.Article in journal (Refereed) Published
Abstract [en]

Gas chromatography (GC) and mass spectrometry (MS) were used to determine the stereoisomeric compositions of 6,10,14-trimethylpentadecan-2-ol and 6,10,14-trimethylpentadecan-2-one in wing extracts from 17 Bicyclus butterfly species from different regions of Africa. All samples were purified using solid phase extraction (SPE). Since some species contained both alcohol and ketone, these were separated and the ketone was reduced to the alcohol before analysis as either (R)-trans-chrysanthemoyl or (S)-2-acetoxypropionyl esters. A novel asymmetric synthesis was developed for a reference mixture of (2R/S,6S,10R)-6,10,14-trimethylpentadecan-2-ol with known composition of the eight stereoisomers. The mixture then was used as the (R)-trans-chrysanthemoyl esters to correlate each of the eight gas chromatographic peaks to a specific stereoisomer of the extracted wing compounds. Seven butterfly species showed (2R,6R,10R)-configuration of the alcohol, four species contained minute amounts of alcohol too small to determine the stereochemistry, nine species showed (6R,10R)-configuration of the ketone, and one species contained minute amounts of ketone too small to determine the stereochemistry. No other stereoisomers of alcohol or ketone could be detected in the extracts, and the quantities of the compounds in the wing extracts varied from 5 to 900 ng per sample for each species.

Keyword
6, 10, 14-Trimethylpentadecan-2-one, Asymmetric synthesis, GC/MS, Stereoisomers, Wing compounds
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-23026 (URN)10.1007/s10886-014-0539-5 (DOI)000348424800006 ()2-s2.0-84925537674 (Scopus ID)
Note

Published online 20 Dec 2014.

Available from: 2014-09-19 Created: 2014-09-19 Last updated: 2016-09-29Bibliographically approved
3. (6R,10R)-6,10,14-Trimethylpentadecan-2-one, a Dominant and Behaviorally Active Component in Male Orchid Bee Fragrances
Open this publication in new window or tab >>(6R,10R)-6,10,14-Trimethylpentadecan-2-one, a Dominant and Behaviorally Active Component in Male Orchid Bee Fragrances
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2010 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 36, no 12, 1322-1326 p.Article in journal (Refereed) Published
Abstract [en]

6,10,14-Trimethylpentadecan-2-one (Hexahydrofarnesyl acetone; HHA) previously has been found to be a major component in tibial fragrances of male orchid bees, Euglossa spp. HHA is a chiral molecule with four possible stereoisomers, (6R,10R)-, (6R,10S)-, (6S,10R)-, and (6S,10S)-6,10,14-trimethylpentadecan-2-one. In the present study, we characterized HHA extracted from Euglossa as the pure enantiomer (6R,10R)-6,10,14-trimethylpentadecan-2-one. During bioassays in Mexico and Panama, the synthetic RR-isomer attracted males of six species of orchid bees, including three that were known to contain HHA in their tibial fragrances. Possible sources of HHA for wild bees are flowers of euglossophilous orchids and aroids. With a molecular weight of 268, HHA is the largest natural molecule known to attract male orchid bees in pure form. Its attractiveness to males suggests that low-volatility compounds have a function in male signals, e.g., serve as a "base note" in complex odor bouquets. © 2010 Springer Science+Business Media, LLC.

Keyword
(6R, 10R)-6, 10, 14-trimethylpentadecan-2-one; Euglossa; Euglossini; Hexahydrofarnesyl acetone; Hymenoptera; Pheromone; Stereoisomer; Synthesis
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-12203 (URN)10.1007/s10886-010-9873-4 (DOI)000285986500006 ()2-s2.0-78650518354 (Scopus ID)
Available from: 2010-11-03 Created: 2010-11-03 Last updated: 2016-09-29Bibliographically approved
4. Alarm pheromones and chemical communication in nymphs of the tropical bed bug Cimex hemipterus (Hemiptera: Cimicidae)
Open this publication in new window or tab >>Alarm pheromones and chemical communication in nymphs of the tropical bed bug Cimex hemipterus (Hemiptera: Cimicidae)
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2011 (English)In: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 6, no 3, e18156- p.Article in journal (Refereed) Published
Abstract [en]

The recent resurge of bed bug infestations (Cimex spp.; Cimicidae) and their resistance to commonly used pesticides calls for alternative methods of control. Pheromones play an important role in environmentally sustainable methods for the management of many pest insects and may therefore be applicable for the control of bed bugs. The tropical bed bug, Cimex hemipterus, is a temporary ectoparasite on humans and causes severe discomfort. Compared to the common bed bug, Cimex lectularius, little is known about the chemical signalling and pheromone-based behaviour of the tropical species. Here, we show that the antennal morphology and volatile emission of C. hemipterus closely resembles those of C. lectularius and we test their behavioural responses to conspecific odour emissions. Two major volatiles are emitted by male, female and nymph C. hemipterus under stress, (E)-2-hexenal and (E)-2-octenal. Notably, nymph emissions show contrasting ratios of these compounds to adults and are further characterized by the addition of 4-oxo-(E)-2-hexenal and 4-oxo-(E)-2-octenal. The discovery of this nymph pheromone in C. hemipterus is potentially the cause of a repellent effect observed in the biotests, where nymph odours induce a significantly stronger repellent reaction in conspecifics than adult odours. Our results suggest that pheromone-based pest control methods developed for C. lectularius could be applicable to C. hemipterus, with the unique nymph blend showing promising practical properties.

Keyword
LECTULARIUS L; INSECTICIDE RESISTANCE; SYSTEM; HETEROPTERA; COMPONENTS; BEHAVIOR; BEDBUGS
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-12716 (URN)10.1371/journal.pone.0018156 (DOI)000289055700035 ()2-s2.0-79953298213 (Scopus ID)
Available from: 2010-12-14 Created: 2010-12-14 Last updated: 2016-10-26Bibliographically approved
5. Chemical tools for training domestic dogs (Canis lupus familiaris) to detect bed bugs
Open this publication in new window or tab >>Chemical tools for training domestic dogs (Canis lupus familiaris) to detect bed bugs
(English)Manuscript (preprint) (Other academic)
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-23027 (URN)
Available from: 2014-09-19 Created: 2014-09-19 Last updated: 2016-09-29Bibliographically approved
6. (Z)-3-Dodecenoic Acid Is the Main Component of Full-Body n-Hexane Extracts from Two Acacia Gall-Inducing Thrips (Thysanoptera) and May Function as an Alarm Pheromone
Open this publication in new window or tab >>(Z)-3-Dodecenoic Acid Is the Main Component of Full-Body n-Hexane Extracts from Two Acacia Gall-Inducing Thrips (Thysanoptera) and May Function as an Alarm Pheromone
2014 (English)In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, Vol. 69C, no 7-8, 335-345 p.Article in journal (Refereed) Published
Abstract [en]

A major interest in the gall-inducing thrips of Australia began with the discovery that some species have eusocial colonies. The origin of social castes remains one of the outstanding questions in evolutionary biology. The inference of the ancestral stage from study of solitary species is important to understanding the evolutionary history of semiochemicals in the social species. Here we investigated two solitary species, Kladothrips nicolsoni and K. rugosus. Whole body extracts revealed that (Z)-3-dodecenoic acid, here reported for the first time in a thrips species, is the main component. (Z)-3-Dodecenoic acid and (E)-3-dodecenoic acid were synthesized in high stereoisomeric purity (> 99.8 %) and exposed to K. nicolsoni 2nd-instar larvae in a contact chemoreception bioassay to test for potential bioactivity. Both isomers decreased the average time spent in the treated area per entry suggesting repellence at the tested dose. (Z)-3-Dodecenoic acid may function as alarm pheromone. (E)-3-Dodecenoic acid increased also the absolute change in direction of larvae compared to an n-hexane control and could potentially function as a repellent.

Keyword
Kladothrips, Semiochemicals, (E)-3-Dodecenoic Acid
National Category
Chemical Sciences Biological Sciences
Identifiers
urn:nbn:se:miun:diva-22608 (URN)10.5560/ZNC.2014-0049 (DOI)000343191800009 ()2-s2.0-84907354875 (Scopus ID)
Available from: 2014-08-20 Created: 2014-08-20 Last updated: 2016-09-29Bibliographically approved

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