A naturally-occurring structural analogue of the phytotoxin coronatine

Chlorosis-inducing compounds in liquid cultures of the phytopathogenic bacterium Pseudomonas syringae pv. atropurpurea have been investigated. In addition to coronatine as previously reported, a new compound was discovered. This gave a mass spectral fragmentation pattern which indicated that it was, like coronatine, an amide of coronafacic acid. Acid-hydrolysis of the new toxin liberated the amino acid valine. This observation, together with mass spectral and NMR data, established the structure of the new toxin as N-coronafacoylvaline. Some implications to biosynthesis are discussed. Along with the two chlorosis-inducing compounds, the biologically inactive coronafacic acid was also isolated from the growth medium.