Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable in vivo and is not derived from littorine via a vicinal interchange process

David O'Hagan, Stephen Patterson

Research output: Other contribution

Abstract

The conversion of littorine to hyoscyamine has been investigated by feeding deuterium labelled (RS)-[2-H-2]-, [3, 3-H-2(2)]-, [2, 3, 3-H-2(3)]- phenyllactic acids to transformed root cultures of Datura stramonium. Isolation and GC-MS analyses of the isotope incorporation into the resultant hyoscyamine does not support the involvement of a vicinal interchange process operating during the isomerisation of littorine to hyoscyamine. Additionally a metabolism study with [1'-C-13, 3', 3'-H-2(2)]-hyoscyamine has established that the alkaloid is metabolically stable at C-3' with no evidence for a reversible in vivo oxidation process to the corresponding aldehyde. The data do not support an S-adenosy-L-methionine (SAM 5)/co-enzyme-B-12, mediated process for the isomerisation of littorine to hyoscyamine. (C) 2002 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Volume61
Publication statusPublished - Oct 2002

Keywords

  • Datura stramonium
  • Solanaceae
  • transformed root culture
  • biosynthesis
  • secondary metabolism
  • tropane alkaloids
  • hyoscyamine
  • littorine
  • tropic acid
  • TRANSFORMED ROOT CULTURES
  • TROPIC ACID
  • STEREOCHEMICAL COURSE
  • REARRANGEMENT
  • PHENYLLACTATE
  • PHENYLALANINE
  • CHEMISTRY

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