Antennal responses of a moth to single lilac aldehyde stereoisomers, using micro-preparative enantioselective MDGC and GC-MS/EAD methods

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Burkhardt, Dirk ; Mosandl, Armin ; Dötterl, Stefan ; Jürgens, Andreas ; Weißbecker, Bernhard ; Schütz, Stefan:
Antennal responses of a moth to single lilac aldehyde stereoisomers, using micro-preparative enantioselective MDGC and GC-MS/EAD methods.
2005
Veranstaltung: Entomologentagung in Dresden der DGaaE , 21.-24.3.2005 , Dresden.
(Veranstaltungsbeitrag: Kongress/Konferenz/Symposium/Tagung , Poster )

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Abstract

Lilac aldehydes are typical flower scent compounds, which are emitted in high amounts especially in nocturnal plants. They are known to be very effective in attracting nocturnal Lepidoptera such as the noctuid moths Hadena bicruris Hufnagel and Autographa gamma L. These oxygenated monoterpenoids possess three chirality centres, and therefore, eight different stereoisomers are conceivable. However, it is not known whether the moths can electrophysiologically detect all the stereoisomers, or whether the moths are equally attracted by the different stereoisomers. Lilac aldehydes were synthesised, analysed, and collected using enantioselective multidimensional gas chromatography/mass spectrometry (enantio-MDGC/MS), in order to investigate the impact of the different stereoisomers. The flow of the chiral main column was splitted and the single stereoisomers were collected by stir bar sorptive extraction (SBSE) as individual eluent fractions. All the eight stereoisomers were reeluted from the stir bars. Subsequently, the single stereoisomers were tested to H. bicruris using GC-MS/EAD analyses displaying a differentiated pattern of sensitivity to different enantiomers.