Norcoronatine and N-coronafacoyl-L-valine,phytotoxic analogues of coronatine produced by a strain of Pseudomonas syringae pv. glycinea

Compounds in liquid cultures of the phytopathogenic bacterium Pseudomonas syringae pv. glycinea that cause chlorosis after application to young bean leaves have been investigated. Known compounds that were isolated and identified were coronatine, the major component, and N-coronafacoyl-L-valine, which are both biologically active, and coronafacic acid which is inactive. In addition a new minor component was isolated and purified. Mass spectrometry indicated that this was an amide of coronafacic acid, bearing one less methylene group than coronatine. Mass spectral and NMR data, together with a study of the products from acid hydrolysis of the new compound, established its structure to be norcoronatine (i.e. a methyl substituent in place of the 2-ethyl substituent on the cyclopropyl moiety of coronatine). The probable biosynthetic derivation of norcoronatine is discussed.