Structural elucidation and biological activity of acyl-homoserine lactones from the phytopathogen Pantoea ananatis Serrano 1928.
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 beta-galactosidase expression assays.
Pomini
Armando M
AM
Chemistry Institute, State University of Campinas, CP 6154, CEP 13083-970, Campinas,SP, Brazil.
Araújo
Welington L
WL
Marsaioli
Anita J
AJ
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D016960:Agrobacterium tumefaciens; D005410:Flame Ionization; D008401:Gas Chromatography-Mass Spectrometry; D007783:Lactones / Q000032:analysis / Q000737:chemistry*; D015394:Molecular Structure; D020636:Pantoea / Q000737:chemistry*; D010935:Plant Diseases; D013329:Structure-Activity Relationship
D007783:Lactones; C088386:homoserine lactone; D015107:4-Butyrolactone