title: Norlittorine and norhyoscyamine identified as products of littorine and hyoscyamine metabolism by (13)C-labeling in Datura innoxia hairy roots.
abstract: The presence of two compounds, norlittorine and norhyoscyamine, has been reported in leaves and roots of Datura innoxia; however their metabolic origin in the tropane alkaloid pathway has remained unknown. Precise knowledge of this pathway is a necessary pre-requisite to optimize the production of hyoscyamine and scopolamine in D. innoxia hairy root cultures. The exact structure of norlittorine and norhyoscyamine was confirmed by LC-MS/MS and NMR analyses. Isotopic labeling experiments, using [1-(13)C]-phenylalanine, [1'-(13)C]-littorine and [1'-(13)C]-hyoscyamine, combined with elicitor treatments, using methyl jasmonate, coronalon and 1-aminocyclopropane-1-carboxylic acid, were used to investigate the metabolic origin of the N-demethylated tropane alkaloids. The results suggest that norlittorine and norhyoscyamine are induced under stress conditions by conversion of littorine and hyoscyamine. We propose the N-demethylation of tropane alkaloids as a mechanism to detoxify cells in overproducing conditions.
authors.affiliation: Unité de Biologie des Plantes et Insectes ravageurs, Université de Picardie Jules Verne, 33 rue Saint Leu, F-80039 Amiens Cedex, France.
authors.forename: Mohamad Houssam
authors.initials: MH
authors.lastname: Al Balkhi
authors.forename: Séverine
authors.initials: S
authors.lastname: Schiltz
authors.forename: David
authors.initials: D
authors.lastname: Lesur
authors.forename: Arnaud
authors.initials: A
authors.lastname: Lanoue
authors.forename: Anne
authors.initials: A
authors.lastname: Wadouachi
authors.forename: Michèle
authors.initials: M
authors.lastname: Boitel-Conti
mesh_terms: D000085:Acetates / Q000378:metabolism; D000222:Adaptation, Physiological; D000598:Amino Acids, Cyclic / Q000378:metabolism; D001285:Atropine / Q000378:metabolism*; D001286:Atropine Derivatives / Q000378:metabolism*; D002247:Carbon Isotopes; D018929:Cell Culture Techniques; D003517:Cyclopentanes / Q000378:metabolism; D032302:Datura / Q000378:metabolism*; D007532:Isoleucine / Q000031:analogs & derivatives / Q000378:metabolism; D008745:Methylation; D015394:Molecular Structure; D054883:Oxylipins / Q000378:metabolism; D018517:Plant Roots / Q000378:metabolism; D012601:Scopolamine / Q000378:metabolism; D013194:Staining and Labeling; D013312:Stress, Physiological
chemical_list: D000085:Acetates; D000598:Amino Acids, Cyclic; D001286:Atropine Derivatives; D002247:Carbon Isotopes; D003517:Cyclopentanes; D054883:Oxylipins; C484935:coronalon; C572831:norlittorine; D007532:Isoleucine; C063158:littorine; C023863:1-aminocyclopropane-1-carboxylic acid; D001285:Atropine; C072239:methyl jasmonate; D012601:Scopolamine; C038490:noratropine