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Chemical Signals in Arthropods – New Structural Motifs Von Der PDFMAILER.DE autorisierter Distributor SienerSoft AG Tel.: 0 67 21 / 30 5-0 Softwareversand www.sienersoft.de Chemical Signals in Arthropods – New structural Motifs Von der Fakultät für Lebenswissenschaften der Technischen Universität Carolo-Wilhelmina zu Braunschweig zur Erlangung des Grades eines Doktors der Naturwissenschaften (Dr. rer. nat.) genehmigte D i s s e r t a t i o n von Stephan Goller aus Hildesheim PDFMAILER.DE autorisierter Distributor SienerSoft AG Tel.: 0 67 21 / 30 5-0 Softwareversand www.sienersoft.de 1. Referent: Professor Dr. Stefan Schulz 2. Referentin: Professor Dr. Monika Mazik eingereicht am: 16.01.2008 mündliche Prüfung (Disputation) am: 04.04.2008 Druckjahr 2008 Vorveröffentlichungen der Dissertation Teilergebnisse aus dieser Arbeit wurden mit Genehmigung der Fakultät für Lebenswissenschaften, vertreten durch den Mentor dieser Arbeit, in folgenden Beiträgen vorab veröffentlicht: Posterbeiträge: 09/2004 ORCHEM in Bad Nauheim, Titel: Chiral siloxanes for the gaschromatographic analysis of natural diols 09/2005 1.Deutsch-Französischer Kongreß für Organische Chemie in Goslar, Titel: New chiral silylating reagents for the determination of the absolute configuration of natural diols 07/2006 22.Kongreß der „International Society of Chemical Ecology“ in Barcelona, Titel: Biosynthesis of (3Z,6Z,9Z)-octadecatriene: A compound of the pheromone blend of Erannis bajaria 07/2007 23.Kongreß der „International Society of Chemical Ecology“ in Jena Titel: Altered pheromone blend of the winter moth Erannis bajaria (Lepidoptera: Geometridae) Vorträge: 07/2005 Organisch-Chemische Kolloquium des Instituts für Organische Chemie der Technischen Universität Braunschweig, Titel: Chirale Silylierungsreagentien für die gaschromatographische Analyse natürlicher Diole 12/2006 GDCh-Kolloquium Ortsverband Braunschweig, Titel: Strukturaufklärung neuartiger Spinnenlipide aus Argyrodes elevatus Veröffentlichung: S. Goller, G. Szöcs, W. Francke, S. Schulz 2007. Biosynthesis of (3Z,6Z,9Z)-octadecatriene: A compound of the pheromone blend of Erannis bajaría (Lepidoptera: Geometridae). J. Chem. Ecol. 33:1505-1509. Danksagungen Als erstens möchte ich mich bei meinem Mentor, Herrn Prof. Dr. Stefan Schulz, für die Aufnahme in den Arbeitskreis, für die Bereitstellung des interessanten Themas und die Begutachtung dieser Arbeit bedanken. Durch seinen Führungsstil hat er es mir ermöglicht, diese Arbeit in einem großen wissenschaftlichen Freiraum unter ständiger Gesprächsbereitschaft zu entwickeln. Dadurch konnte ich meine Persönlichkeit deutlich erweitern, was mich auch nun in meiner weiteren beruflichen Entwicklung voranbringt. Auch möchte ich erwähnen, daß er die Korrekturen zu dieser Arbeit sehr schnell erledigt hat, was ich bei all seinen Verpflichtungen nicht für selbstverständlich halte. Daneben bedanke ich mich bei Frau Prof. Dr. Mazik, Frau Prof. Dr. Mischnick und Herrn Prof. Dr. Gericke für die Begutachtung meiner Arbeit und die Teilnahme an der Prüfungskommission. Des Weiteren gilt mein Dank Herrn PD Dr. Jahn für die gute Zusammenarbeit während der Praktika Organische Chemie für Biotechnologen. Durch die Überlassung vieler Kompetenzen konnte ich auch hier mein Profil erweitern. Außerdem gilt mein Dank den Kooperationspartnern, Prof Dr. Franke, Prof. Dr. Gnatzy, Prof. Dr. Schütz, Prof. Dr. Riechert, Dr. Francke, Dr. Szöcs, PD Dr. Uhl, Dr. Weissbecker, S. Funke und A. B. Payne, die durch ihre Mitarbeit die Arbeit in diesem Umfang möglich gemacht haben. Für eine wohltuende Arbeitsatmosphäre möchte ich mich auch bei meinen ehemaligen Kollegen aus der Arbeitsgruppe bedanken, namentlich: Elena Barcari, Dr. Katalin Böröczky, Dr. Gregor Brasse, Birte Flachsbarth, Matthias Fritzsche, Christopher Häberlein, Andreas Hennig, Nico Klewer, Dr. Karsten Krückert, Jasmin Müller, Dr. Edyta Nagrodzka, Nicole Schlüter, Andreas Schmidt, Thies Schulze, Paul Sobik, Verena Thiel, Nicole Tiesing und Frau Weiß. Besonders hervorheben möchte ich folgende Personen: Wiebke Jacobs und Selma Yildizhan danke ich für eine gute Zusammenarbeit bei den Arbeiten zu der chiralen Analyse natürlicher Diole. Satya Chinta danke ich für eine gute Zusammenarbeit bei den Arbeiten zur Lipidanalytik bei Argyrodes elevatus. Björn Hahn und Thorben Nawrath möchte ich danken, da sie mich während meiner Dissertation in den Zeiten, als ich mit Lehraufgaben beschäftigt war, in der Betreuung meiner Praktikanten unterstützt haben. Nur so konnte ich in dieser Zeit die praktischen Arbeiten an meiner Dissertation konsequent weiterführen. Dr. Jeroen Sidney Dickschat danke ich für umfangreiche wissenschaftliche Diskussionen. Entscheidend für die Entwicklung dieser Arbeit waren auch zahlreiche Praktikanten. Bei diesen möchte ich mich auch bedanken. Frau Gödecke, als Vorsitzende des Freundeskreises des Instituts für Organische Chemie (FIOC), danke ich für die finanzielle Unterstützung. Nur dadurch konnte ich an wissenschaftlichen Tagungen teilnehmen und Teile meiner Ergebnisse in einem wissenschaftlichen Forum präsentieren. Ebenso gilt mein Dank dem Glasbläser, sämtlichen Mitarbeitern der MS-Abteilung, der NMR-Abteilung und des zentralen Chemikalienlagers. Meinem Onkel, Karl-Heinz Hodur, danke ich für das Binden dieser Arbeit. Abschließend gilt mein größter Dank meinen Eltern, meinem Bruder und meiner Oma, die mich durch ihre Persönlichkeit auf diesem Weg begleitet haben. Danke ! Table of contents Table of contents 1. Introduction 1-4 2. Chemical analysis of the parasitic wasps Ampulex compressa and Liris niger 5 2.1 Aim 5 2.2 Taxonomy of wasps and their lifestyle 5-7 2.3 Semiochemicals and mating strategies of hymenoptera 8-10 2.4 Analysis of cuticular waxes of female and male Ampulex compressa and those of the female Dufour gland 11-16 2.4.1 Structure elucidation of (6Z,9Z)-6,9-heptacosadiene 16-21 2.4.2 Determination of double-bond positions in alkenes of Ampulex compressa 21-23 2.4.3 Presence of 2-methyl-3-pentanone in the Dufour gland of Ampulex compressa females 23-24 2.4.4 (Z)-3-Nonenal, an unusual aldehyde on the cuticle of male Ampulex compressa 24-25 2.4.4.1 Biosynthesis of (Z)-3-nonenal in plants 25-26 2.4.4.2 (6Z,9Z)-6,9-Heptacosadiene as precursor for the biosynthesis of (Z)-3-nonenal in Ampulex compressa males? 26-28 2.4.5 Long-chain alkyl benzoates in Ampulex compressa males 28-30 2.4.6 17-Methylhentriacontan-10-one on the cuticle of Ampulex compressa males 31-34 2.5 Volatiles released by females and males of the digger wasp Liris niger 34 2.5.1 Previous investigations of Liris niger 34-36 2.5.2 Head space analysis of Liris niger females and males 37-41 2.5.3 Compounds preferentially occurring in unmated females and EAG-experiments 41 2.5.3.1 Structure elucidation of 3,6-dimethyl-2-isobutylyrazine and EAG-experiments 41-44 2.5.3.2 Structure elucidation of tridecyl and tetradecyl acetate and EAG-experiments 45-46 2.5.4 EAG-experiments with (9Z,12Z)-9,12-octadecadienyl acetate 46 Table of contents 2.5.5 EAG-experiments with saturated and unsaturated hydrocarbons of the Dufour gland 46-49 2.5.6 EAG-experiments with extracts of the Dufour gland 49-50 3. Identification of novel spider lipids from Argyrodes elevatus and Diplocephalus permixtus 51 3.1 New cuticular lipids of Argyrodes elevatus 51 3.1.1 Lifestyle of spiders of the genus Argyrodes 51-52 3.1.2 Composition of the male and female cuticle of Argyrodes elevatus 52-57 3.1.3 Structure elucidation of the wax esters by derivatizations 57 3.1.3.1 Flow scheme for the analysis of wax esters 57-62 3.1.3.2 Methyl esters and pyridylmethyl esters of Argyrodes elevatus 62-67 3.1.3.3 Trimethylsilyl ethers and nicotinic esters of the alcohol parts of the wax esters of Argyrodes elevatus 67-73 3.1.3.4 Wax esters of the head extracts of Argyrodes elevatus 74-75 3.2 New methoxyalkanes in spiders: 2-methoxyalkanes from the spider Diplocephalus permixtus 75 3.2.1 Evolution of peculiar head structures in erigoninae males 75 3.2.2 Occurrence of 1- and 2-methoxyalkanes in Diplocephalus permixtus 76 3.2.2.1 Analysis of 1-methoxyalkanes 76-79 3.2.2.2 Analysis of 2-methoxyalkanes 79-86 3.2.2.3 Composition of the methyl ethers in females of Diplocephalus permixtus 86-87 3.2.2.4 Biosynthesis of 2-methoxyalkanes 88-89 4. Pheromone biosynthesis in the winter moth Erannis bajaria and identification of novel compounds in its pheromone gland 90 4.1 Introduction into the biosynthesis of butterfly pheromones 90-95 4.2 Biosynthesis of (3Z,6Z,9Z)-3,6,9-octadecatriene in Erannis bajaria (Lepidoptera:Geometridae) 95 4.2.1 Considerations about its biosynthesis 95-97 4.2.2 Syntheses of labeled pheromone precursors 97-101 4.2.3 Results of labeling experiments and discussion 101-103 Table of contents 4.3 Identification of novel compounds in the pheromone gland of Erannis bajaria 104 4.3.1 Comparison of a pheromone gland extract of Erannis bajaria in the year 1996 and 2006 104-105 4.3.2 Structure elucidation of the novel compounds 106-110 5. The catalepsis pheromone of the male desert spider Agelenopsis aperta and a female pheromone of the wasp spider Argiope bruennichi 111 5.1 Spider pheromones 111 5.2 The catalepsis pheromone of Agelenopsis aperta males 112 5.2.1 Previous investigations 112-113 5.2.2 Investigation of male body extracts of Agelenopsis aperta 113-116 5.2.3 Head space experiments with Agelenopsis aperta 116-127 5.3 A new female spider pheromone of the wasp spider Argiope bruennichi 127 5.3.1 Preface 127-128 5.3.2 Analysis of body extracts of Argiope bruennichi females 128-136 5.3.3 Chemical composition of web extracts of Argiope bruennichi females
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