chysopine family of Amadori-type crown gall opines

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 re...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 1995, Vol.40 (3), p.619-628
Main Authors: Chilton, W.S, Stomp, A.M, Beringue, V, Bouzar, H, Vaudequin-Dransart, V, Petit, A, Dessaux, Y
Format: Article
Language:English
Subjects:
Agrobacterium tumefaciens
amadori reaction
chemical composition
chemical reactions
Datura stramonium
galls
geographical variation
glucose
glutamine
metabolites
molecular conformation
neoplasms
pathogenicity
spectral analysis
strain differences
tropane alkaloids
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Summary: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, Nalpha-(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, psedo-nopaline.
ISSN:0031-9422
1873-3700