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Stereoisomeric Analysis of 6,10,14-Trimethylpentadecan-2-ol and the Corresponding Ketone in Wing Extracts from African Bicyclus Butterfly Species
Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.ORCID iD: 0000-0002-5543-2041
Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering. (FSCN)
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
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2015 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 41, no 1, p. 44-51Article 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.

Place, publisher, year, edition, pages
2015. Vol. 41, no 1, p. 44-51
Keywords [en]
6, 10, 14-Trimethylpentadecan-2-one, Asymmetric synthesis, GC/MS, Stereoisomers, Wing compounds
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-23026DOI: 10.1007/s10886-014-0539-5ISI: 000348424800006Scopus ID: 2-s2.0-84925537674OAI: oai:DiVA.org:miun-23026DiVA, id: diva2:748383
Note

Published online 20 Dec 2014.

Available from: 2014-09-19 Created: 2014-09-19 Last updated: 2017-12-05Bibliographically approved
In thesis
1. The Scents of Nature: Identification and Synthesis of Bioactive Compounds Used in Insect Communication
Open this publication in new window or tab >>The Scents of Nature: Identification and Synthesis of Bioactive Compounds Used in Insect Communication
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. p. 90
Series
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 200
Keywords
Semiochemicals, Sex pheromone, Bicyclus spp, Euglossa spp, Cimex hemipterus, Cimex lectularius, Kladothrips nicolsoni, Kladothrips rugosus, Drosophila melanogaster
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-22821 (URN)978-91-87557-84-2 (ISBN)
Public defence
2014-09-19, M102, Mittuniversitetet, Sundsvall, 16:08 (English)
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Available from: 2014-09-09 Created: 2014-09-08 Last updated: 2015-03-13Bibliographically approved

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Hedenström, ErikWallin, ErikaAndersson, JBång, Joakim

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