title: Biosynthetic studies on the tropane ring system of the tropane alkaloids from Datura stramonium.
abstract: Isotopic labelling experiments have been carried out in Datura stramonium root cultures with the following isotopically labelled precursors; [2H3]- [2-13C, 2H3]-, [1-13C, 18O2]-acetates, 2H2O, [2H3-methyl]-methionine, [2-13C]-phenyllactate, [3-2H]-tropine and [2'-13C, 3-2H]-littorine. The study explored the incorporation of isotope into the tropane ring system of littorine 1 and hyoscyamine 2 and revealed that deuterium from acetate is incorporated only into C-6 and C-7, and not into C-2 and C-4 as previously reported. Oxygen-18 was not retained at a detectable level into the C(3)-O bond from [1-13C, 18O2]-acetate. The intramolecular nature of the rearrangement of littorine 1 to hyoscyamine 2 is revealed again by a labelling study using [2'-13C, 3-2H]-littorine, [2-13C]-phenyllactate and [3-2H]-tropine.
authors.affiliation: Department of Chemistry, University of Durham Science Laboratories, UK.
authors.forename: R
authors.initials: R
authors.lastname: Duran-Patron
authors.forename: D
authors.initials: D
authors.lastname: O'Hagan
authors.forename: J T
authors.initials: JT
authors.lastname: Hamilton
authors.forename: C W
authors.initials: CW
authors.lastname: Wong
mesh_terms: D000470:Alkaloids / Q000096:biosynthesis* / Q000737:chemistry; D013286:Datura stramonium / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010946:Plants, Medicinal; D010947:Plants, Toxic; D014326:Tropanes / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D014326:Tropanes