Original Paper

Analytical and Bioanalytical Chemistry

, Volume 389, Issue 5, pp 1447-1457

Uptake, degradation and chiral discrimination of N-acyl-D/L-homoserine lactones by barley (Hordeum vulgare) and yam bean (Pachyrhizus erosus) plants

  • Christine GötzAffiliated withDepartment Microbe-Plant Interactions, GSF-National Research Center for Environment and Health
  • , Agnes FeketeAffiliated withInstitute of Ecological Chemistry, GSF-National Research Center for Environment and Health
  • , Istvan GebefuegiAffiliated withInstitute of Ecological Chemistry, GSF-National Research Center for Environment and Health
  • , Sándor T. ForczekAffiliated withInstitute of Experimental Botany, Academy of Sciences of the Czech Republic
  • , Květoslava FuksováAffiliated withFirst Faculty of Medicine, Charles University
  • , Xiaojing LiAffiliated withInstitute of Ecological Chemistry, GSF-National Research Center for Environment and HealthMinistry of Education Key Laboratory of Analysis and Detection Technology for Food Safety, Fuzhou UniversityDepartment of Chemistry, Fuzhou University
  • , Matthias EnglmannAffiliated withInstitute of Ecological Chemistry, GSF-National Research Center for Environment and Health
  • , Milan GryndlerAffiliated withInstitute of Microbiology, Academy of Sciences of the Czech Republic
  • , Anton HartmannAffiliated withDepartment Microbe-Plant Interactions, GSF-National Research Center for Environment and Health
    • , Miroslav MatuchaAffiliated withInstitute of Experimental Botany, Academy of Sciences of the Czech Republic
    • , Philippe Schmitt-KopplinAffiliated withInstitute of Ecological Chemistry, GSF-National Research Center for Environment and Health
    • , Peter SchröderAffiliated withDepartment Microbe-Plant Interactions, GSF-National Research Center for Environment and Health Email author 

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Abstract

Bacterial intraspecies and interspecies communication in the rhizosphere is mediated by diffusible signal molecules. Many Gram-negative bacteria use N-acyl-homoserine lactones (AHLs) as autoinducers in the quorum sensing response. While bacterial signalling is well described, the fate of AHLs in contact with plants is much less known. Thus, adsorption, uptake and translocation of N-hexanoyl- (C6-HSL), N-octanoyl- (C8-HSL) and N-decanoyl-homoserine lactone (C10-HSL) were studied in axenic systems with barley (Hordeum vulgare L.) and the legume yam bean (Pachyrhizus erosus (L.) Urban) as model plants using ultra-performance liquid chromatography (UPLC), Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) and tritium-labelled AHLs. Decreases in AHL concentration due to abiotic adsorption or degradation were tolerable under the experimental conditions. The presence of plants enhanced AHL decline in media depending on the compounds’ lipophilicity, whereby the legume caused stronger AHL decrease than barley. All tested AHLs were traceable in root extracts of both plants. While all AHLs except C10-HSL were detectable in barley shoots, only C6-HSL was found in shoots of yam bean. Furthermore, tritium-labelled AHLs were used to determine short-term uptake kinetics. Chiral separation by GC-MS revealed that both plants discriminated D-AHL stereoisomers to different extents. These results indicate substantial differences in uptake and degradation of different AHLs in the plants tested.

Keywords

UPLC FTICR-MS Tritium autoradiography Chiral separation Hordeum vulgare Pachyrhizus erosus