The Chrysopine Family of Amadori-Type Crown Gall Opines.

Abstract Crown gall tumours induced by four groups of Agrobacterium tumefaciens isolates, derived from galls from four different locations in North and South America and Europe, were found to contain mannityl opine-related metabolites derived from condensation of glucose with glutamine followed by Amadori rearrangement. The opines were characterized spectroscopically as N- (1′-deoxy- d -fructos-1′-yl)-5-oxo- l -proline , N α - (1′-deoxy- d -fructos-1′-yl)- l -glutamine and its spiropyranosyl lactone, chrysopine. Tumours induced by A. tumefaciens strain 2788 and by Ficus strains also contained nopaline, while those induced by A. tumefaciens K224, K289 and Chry9 contained l , and an unidentified opine, pseudo-nopaline.