Identification of bacterial <Emphasis Type="Italic">N</Emphasis>-acylhomoserine lactones (AHLs) with a combination of ultra-performance liquid chromatography (UPLC), ultra-high-resolution mass spectrometry,and in-situ biosensors |
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Authors: | Agnes Fekete Moritz Frommberger Michael Rothballer Xiaojing Li Matthias Englmann Jenoe Fekete Anton Hartmann Leo Eberl Philippe Schmitt-Kopplin |
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Institution: | Institute of Ecological Chemistry, GSF - National Research Center for Environment and Health, 85764, Neuherberg, Germany. |
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Abstract: | N-Acylated homoserine lactones (AHLs) are produced by Gram-negative bacteria as communication signals and are frequently studied
as mediators of the “quorum sensing” response of bacterial communities. Several reports have recently been published on the
identification of AHLs from different species and attempts have been made to study their role in natural habitats, for example
the surface of plant roots in the rhizosphere. In this article, different analytical methods, including bacterial biosensors
and chromatographic techniques, are reviewed. A concept for assignment of the structures of AHLs is also presented. The retention
behaviour of derivatives of AHLs containing β-keto or hydroxyl groups and/or double bonds has been evaluated in relation to
the separation behaviour of AHLs with saturated and unsubstituted alkanoyl chains. Samples have also been analysed by high
resolution mass spectrometry (Fourier-transform ion-cyclotron-resonance mass spectrometry, FTICR-MS), nano liquid chromatography–electrospray
ionization ion trap mass spectrometry (nano-LC–MS) and by the aid of a biosensor. The results obtained from ultra performance
liquid chromatography (UPLC), FTICR-MS, nano-LC–MS, and bioassays have been compared to attempt structural characterisation
of AHL without chemical synthesis of analytical standards. The method was used to identify the major AHL compound produced
by the rhizosphere bacterium Acidovorax sp. N35 as N-(3-hydroxydecanoyl)homoserine lactone. |
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Keywords: | N-Acylhomoserine lactones Biosensing Chromatography UPLC FTICR-MS |
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