Acyl-homoserine lactones produced by Pantoea sp. isolated from the "maize white spot" foliar disease.
The "maize white spot" foliar disease is a problem of increasing importance to Brazilian maize crops. A bacterium isolated from water-soaked lesions from infected maize leaves was pathogenic in biological assays in vivo. It was identified as a Gram-negative, nonsporulating, facultative anaerobic bacterium, belonging to the genus Pantoea. Chemical study of the extracts from bacterial cultivation media allowed the identification of (S)-(-)-N-butanoyl-homoserine lactone and trace amounts of N-hexanoyl-homoserine lactone, widely recognized quorum-sensing signaling substances employed in cell-to-cell communication systems. The absolute configuration of natural (S)-(-)-N-butanoyl-homoserine lactone was determined by gas chromatography-flame ionization detection with a chiral stationary phase and by comparison of circular dichroism spectroscopic data with enantiopure synthetic substances. Biological evaluations with reporter Agrobacterium tumefaciens NTL4(pZLR4) were carried out with synthetic and natural products and also with extracts from maize leaves contaminated with the isolated bacterium, as well as from healthy leaves.
Pomini
Armando M
AM
Chemistry Institute, State University of Campinas, Caixa Postal 6154, CEP 13084-971, Campinas, SP, Brazil.
Paccola-Meirelles
Luzia D
LD
Marsaioli
Anita J
AJ
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification; D002849:Chromatography, Gas; D020636:Pantoea / Q000378:metabolism*; D010935:Plant Diseases / Q000382:microbiology*; D018515:Plant Leaves / Q000737:chemistry*; D003313:Zea mays / Q000382:microbiology*
C092312:N-butyrylhomoserine lactone; C088386:homoserine lactone; D015107:4-Butyrolactone