Structural Elucidation and Biological Activity of Acyl-homoserine Lactones from the Phytopathogen Pantoea ananatis Serrano 1928
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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.
KeywordsPantoea ananatis Acyl-homoserine lactones Absolute configuration Quorum-sensing Agrobacterium tumefaciens reporter assay
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.
- Bodman, S. B. V. and Farrand, S. K. 1995. Capsular polysaccharide biosynthesis and pathogenicity in Erwinia stewartii require induction by an N-acylhomoserine lactone autoinducer. J. Bacteriol. 177:5000–5008.Google Scholar
- Horng, Y. T., Deng, S. C., Daykin, M., Soo, P. C., Wei, J. R., Luh, K. T., Ho, S. W., Swift, S., Lai, H. C., and Williams, P. 2002. The LuxR family protein SpnR functions as a negative regulator of N-acylhomoserine lactone-dependent quorum sensing in Serratia marcescens. Mol. Microbiol. 45:1655–1671.PubMedCrossRefGoogle Scholar
- Jones, S., Yu, B., Bainton, N. J., Birdsall, M., Bycroft, B. W., Chhabra, S. R., Cox, A. J. R., Golby, P., Reeves, P. J., Stephens, S., Winson, M. K., Salmond, G. P. C., Stewart, G. S. A. B., and Williams, P. 1993. The lux autoinducer regulates the production of exoenzyme virulence determinants in Erwinia carotovora and Pseudomonas aeruginosa. EMBO J. 12:2477–2482.PubMedGoogle Scholar
- Serrano, F. B. 1928. Bacterial fruitlet brown-rot of pineapple in the Philippines. Philipp. J. Sci. 36:271–305.Google Scholar