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Structural Elucidation and Biological Activity of Acyl-homoserine Lactones from the Phytopathogen Pantoea ananatis Serrano 1928

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Abstract

In Gram-negative bacteria, the acyl-homoserine lactones (acyl-HSLs) are the main signaling substances employed in cell-to-cell communication systems. This paper describes the chemical characterization of acyl-HSLs produced by the worldwide-spread phytopathogen Pantoea ananatis (Serrano 1928) by using gas chromatography-electron impact mass spectrometry. The absolute configuration of the major identified substance, (S)-(−)-N-hexanoyl-HSL, was determined with gas chromatography-flame ionization detection with a chiral capillary column. Biological activities of extracts, fractions, and synthetic products were evaluated with the specific reporter Agrobacterium tumefaciensNTL4(pZLR4) in β-galactosidase expression assays.

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Acknowledgments

The authors are indebted to FAPESP for financial support and for a scholarship awarded to A. M. Pomini (process n. 03/09357-7). We wish to express our gratitude to Carol H. Collins (IQ/Unicamp) for revising the manuscript.

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Authors and Affiliations

  1. Chemistry Institute, State University of Campinas, CP 6154, CEP 13083-970, Campinas,SP, Brazil

    Armando M. Pomini & Anita J. Marsaioli

  2. Genetic Department, ESALQ, State University of São Paulo, CP 83, CEP 13400-970, Piracicaba,SP, Brazil

    Welington L. Araújo

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  1. Armando M. Pomini
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  2. Welington L. Araújo
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  3. Anita J. Marsaioli
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Correspondence to Anita J. Marsaioli.

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Pomini, A.M., Araújo, W.L. & Marsaioli, A.J. Structural Elucidation and Biological Activity of Acyl-homoserine Lactones from the Phytopathogen Pantoea ananatis Serrano 1928. J Chem Ecol 32, 1769–1778 (2006). https://doi.org/10.1007/s10886-006-9108-x

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  • DOI: https://doi.org/10.1007/s10886-006-9108-x

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