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

Author(s): S. Patterson, D. O'Hagan

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.

Full version: Available here

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ISBN: 0031-9422
Publication Year: 2002
Periodical: Phytochemistry
Periodical Number: 3
Volume: 61
Pages: 323-329
Author Address: