4.7 Article

Norlittorine and norhyoscyamine identified as products of littorine and hyoscyamine metabolism by 13C-labeling in Datura innoxia hairy roots

Journal

PHYTOCHEMISTRY
Volume 74, Issue -, Pages 105-114

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2011.10.010

Keywords

Tropane alkaloids; Datura innoxia; Hairy roots; Norlittorine; Norhyoscyamine; C-13-labeling; Elicitation

Funding

  1. Syrian Government
  2. University of Damascus

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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-C-13]-phenylalanine, [1'-C-13]-littorine and [1'-C-13]-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. (C) 2011 Elsevier Ltd. All rights reserved.

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