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Cuticular Lipids of the Parasitoid Lariophagus Distinguendus (Hymenoptera: Pteromalidae): Chemistry and Behavioural Function

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Cuticular Lipids of the Parasitoid Lariophagus Distinguendus (Hymenoptera: Pteromalidae): Chemistry and Behavioural Function Cuticular Lipids of the Parasitoid Lariophagus distinguendus (Hymenoptera: Pteromalidae): Chemistry and Behavioural Function Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) der Fakultät für Biologie und Vorklinische Medizin der Universität Regensburg vorgelegt von Stephan Kühbandner aus München im Jahr 2014 Das Promotionsgesuch wurde eingereicht am: 28.03.2014 Die Arbeit wurde angeleitet von: Prof. Dr. Joachim Ruther Unterschrift: II Lariophagus distinguendus female (Hymenoptera: Pteromalidae) Zeichnung: Ruth Kühbandner, 2011 III IV Table of contents List of abbreviations …………………………………………………………………… VI-IX Summary ……………………………………………………………………………………... 1 Zusammenfassung …………………………………………………………………………… 5 List of publications …………………………………………………………………………... 8 Chapter 1: General introduction …………………………………………………………... 9 Chapter 2: Composition of cuticular lipids in the pteromalid wasp Lariophagus distinguendus is host-dependent ………………………...…….. 29 Chapter 3: Deciphering the signature of cuticular lipids with contact sex pheromone function in a parasitic wasp ………………………… 47 Chapter 4: Elucidating structure-bioactivity relationships of methyl-branched alkanes in the contact sex pheromone of the parasitic wasp Lariophagus distinguendus ………………………………………………….. 65 Chapter 5: Solid phase micro-extraction (SPME) with in situ transesterification: An easy method for the analysis of non-volatile cuticular triacylglycerides ...85 Chapter 6: General discussion ………………………………………………………..… 107 References ……………………………………………………………………………….…129 Danksagung ……………………………………………………………………………….. 153 V List of abbreviations 0-d-old male dummies zero day old male dummies 4-d-old male dummies four day old male dummies 3-MeC25 3-methylpentacosane 3-MeC27 3-methylheptacosane 5-MeC27 5-methylheptacosane 7-MeC27 7-methylheptacosane 3,7-DiMeC27 3,7-dimethylheptacosane 4,8-DiMeC28 4,8-dimethyloctacosane 3-MeC29 3-methylnonacosane 13-MeC29 13-methylnonacosane 3,7-DiMeC29 3,7-dimethylnonacosane 3-MeC31 3-methylhentriacontane 11,21-DiMeC33 11,21-dimethyltritriacontane 3,7,11,15-TetraMeC33 3,7,11,15-tetramethyltritriacontane 13,17-DiMeC35 13,17-dimethylpentatriacontane 20-E 20-hydroxyecdysone AT Asobara tabida (Hymenoptera: Braconidae) Br2 bromine C25 pentacosane C27 heptacosane C27:1(9) heptacos-9-ene C29 nonacosane C29:1(9) nonacos-9-ene C31 hentriacontane CDCl3 deuterated chloroform VI List of abbreviations CHC cuticular hydrocarbon CH 2Cl 2 dichloromethane CH3(CH2)4COCl hexanoylchloride 13 C-NMR carbon-13 nuclear magnetic resonance spectroscopy CoA coenzyme A DCM dichloromethane DM Drosophila melanogaster (Diptera: Drosophilidae) DMSO dimethyl sulfoxide EI electron impact ionisation Et 2O diethyl ether EtOAc ethyl acetate FAME fatty acid methyl ester FFA free fatty acids GC gas chromatography GC-EAD gas chromatography coupled with an electroantennographic detector GC-MS gas chromatography coupled with mass spectrometry H2 hydrogen HCL hydrogen chloride 1H-NMR hydrogen-1 nuclear magnetic resonance spectroscopy HPLC high performance liquid chromatography JH III juvenile hormone III K2CO3 potassium carbonate LD Lariophagus distinguendus (Hymenoptera: Pteromalidae) LiBH4 lithium borohydride Li 2CuCl 4 dilithium tetrachlorocuprate (II) LMC local mate competition VII List of abbreviations LRI relative linear retention indices MALDI-MS matrix-assisted laser desorption/ionization mass spectrometry MeI methyl iodide MeOH methanol Mp melting point MS mass spectrometry MW molecular weight n-BuLi n-butyllithium Na 2CO 3 sodium carbonate NaHCO3 sodium bicarbonate NaHMDS sodium hexamethyldisilazide NaI sodium iodide Na 2SO 4 sodium sulfate NH 4Cl ammonium chloride NI Nicrophorus vespilloides (Coleoptera: Silphidae) NMDS non-metric multidimensional scaling NPMANOVA nonparametric multivariate analysis of variance NV Nasonia vitripennis (Hymenoptera: Pteromalidae) OBP odorant binding protein ODE odorant degrading enzyme ODR odorant receptor neuron OR odorant receptor PA Periplaneta americana (Blattodea: Blattidae) PBAN pheromone biosynthesis activating neuropeptide PBP pheromone binding protein PCA principal component analysis PDMS polydimethylsiloxane (coating material for SPME fibre) VIII List of abbreviations Ph 3P triphenylphosphine Ph 3PBr 2 triphenylphosphine dibromide PLS-DA partial least squares-discriminant analysis RIO resource indicating odour SE-HPLC size exclusion-high performance liquid chromatography SIMPER similarity percentage analysis SPME solid phase microextraction SPME-FAME-GC-MS SPME of TAGs with in situ transesterification into more volatile FAMEs (using TMSH) that are detectable by GC-MS TAG triacylglyceride Tf 2O trifluoromethanesulfonic anhydride THF tetrahydrofuran TMSH trimethylsulphonium hydroxide UPLC-MS ultra-performance liquid chromatography coupled with mass spectrometry UV-LDI-o-TOF MS ultraviolet laser desorption/ionisation orthogonal time-of-flight mass spectrometry IX X Summary Animals communicate with each other by means of optical, acoustic, tactile, electrical and chemical signals. This doctoral thesis deals with the contact sex pheromone of the parasitic wasp species Lariophagus distinguendus (Hymenoptera: Pteromalidae). Males respond to the cuticular lipids of conspecific females by stereotypic courtship behaviour. Young males and pupae of either sex also produce the cuticular lipids that release courtship behaviour in conspecific males. However, with increasing age, males actively remove 3-MeC27 and some other straight-chain alkanes and methylalkanes from their cuticular lipid profile. The disappearance of these components is accompanied by a loss in their attractiveness towards other males. The capability of the males to actively remove components of their cuticular lipid profile probably rendered a non-communicative barrier against water loss and pathogen attack into a species-specific contact sex pheromone. These findings from previous work led to some questions: is 3-MeC27 actually part of L. distinguendus contact sex pheromone? If this is true, is 3-MeC27 alone bioactive or only in combination with other cuticular lipids? Do L. distinguendus males respond enantioselectively towards 3-MeC27? Can the addition of synthetic 3-MeC27 onto the cuticle of aged males restore their bioactivity? Can 3-MeC27 be replaced by structurally related methylalkanes that differ in their chain length or the position of the methyl-branch? Or does the application of additional n-alkanes and structurally related methylalkanes interfere with the intact cuticular profile? During this doctoral thesis, I have shown that 3-MeC27 is the key component of the female contact sex pheromone of L. distinguendus . However, unlike in other insects studied so far, the key component 3-MeC27 alone is not attractive to L. distinguendus males. For a full behavioural response, 3-MeC27 has to be perceived by the males together with a chemical background consisting of the other cuticular hydrocarbons (CHC) and hitherto widely ignored cuticular triacylglycerides (TAG). The occurrence of cuticular TAGs has probably been underestimated in the past and a behavioural function for TAGs is described here for the first time. Behavioural experiments with fractionated wasp extracts and synthetic 3-MeC27 and other structurally related components revealed that the cuticular lipid profile of aged males can be rendered attractive again by the addition of synthetic 3-MeC27 in physiological amounts. L. distinguendus males responded specifically to even small variations of chain length or methyl-branch position of monomethylalkanes because chemically related components such 1 Summary as 3-MeC29 or 5-MeC27 could not replace 3-MeC27. On the contrary, the addition of such components rendered behaviourally active cuticular lipid profiles of females and young males unattractive. These results demonstrate that the contact sex pheromone in L. distinguendus is perceived as a whole, possibly by means of a specialized sensillum type as used by ants in the context of nestmate recognition. The males of L. distinguendus were able to differentiate between the two enantiomers of 3-MeC27, but this was only behaviourally relevant when fractionated extracts combined with (R)- or ( S)-3-MeC27 were applied onto filter paper and offered to the responding males. In experiments with three-dimensional wasp dummies, however, L. distinguendus males did not show a preference for one of the enantiomers implying that a visual component of the dummy also plays a role. During the development of parasitoids, the host is typically the only available food source. Hence, host species and quality might affect the CHC profiles of parasitoids and thus also its intraspecific communication. In this doctoral thesis it was shown that the CHC profiles of L. distinguendus wasps are host specific. CHC profiles of wasp strains reared on different host species were distinguishable by a non-metric multidimensional scaling (NMDS) and a non- parametric multivariate analysis of variance (NPMANOVA). In particular, wasps reared on Stegobium paniceum could be significantly distinguished from all wasps reared on other hosts according to their CHC profile. Remarkably, a host shift from Sitophilus granarius to Stegobium paniceum lead to a significant shift of the CHC profiles within one generation. Provided that these differences actually influence the mate recognition behaviour in L. distinguendus , these results suggest that host shifts might result in the reproductive isolation of host races and, in the long-term, end
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