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 |
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Authors: | Patterson Stephen O'Hagan David |
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Affiliation: | School of Chemistry, Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK. |
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Abstract: | The conversion of littorine to hyoscyamine has been investigated by feeding deuterium labelled (RS)-[2-(2)H]-, [3, 3-(2)H(2)]-, [2, 3, 3-(2)H(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'-13C, 3', 3'-(2)H(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. |
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Keywords: | Datura stramonium Solanaceae Transformed root culture Biosynthesis Secondary metabolism Tropane alkaloids Hyoscyamine Littorine Tropic acid |
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