R. Duran-patron et al., Biosynthetic studies on the tropane ring system of the tropane alkaloids from Datura stramonium, PHYTOCHEM, 53(7), 2000, pp. 777-784
Isotopic labelling experiments have been carried out in Dautura stramonium
root cultures with the Following isotopically labelled precursors; [H-2(3)]
-, [2-C-13, H-2(3)], [1-C-13, O-18(2)]-acetates, 2H(2)O, [H-2(3)-methyl]-me
thionine, [2-C-13]-phenyllacetate, [3-H-3]-tropine and [2'-C-13, 3-H-2]-lit
torine. The study explored the incorporation of isotope into the tropane ri
ng 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-C-13, O-18(2)]-acetate. The intramolecular nature
of the rearrangement of littorine 1 to hyoscyamine 2 is revealed again by a
labelling study using [2'-C-13, 3-H-2]-littorine, [2-C-13]-phenyllactate a
nd [3-H-2]-tropine. (C) 2000 Elsevier Science Ltd. All rights reserved.