Biosynthetic studies on the tropane ring system of the tropane alkaloids from Datura stramonium

Phytochemistry

Volumn 53, Issue 7, 2000, Pages 777-784

  Duran Patron, Rosa ^a   O'Hagan, David ^a   Hamilton, John T G ^b   Wong, Chi W ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b AGRI FOOD AND BIOSCIENCES INSTITUTE   (United Kingdom)

Author keywords

Biosynthesis; Datura stramonium; Hyoscyamine; Littorine; Tropane alkaloids

Indexed keywords

ALKALOID; DATURA STRAMONIUM; HYOSCYAMINE; LITTORINE; STRAMONIUM; TROPANE ALKALOID; TROPANE DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMISTRY; ISOTOPE LABELING; METABOLISM; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE;

ALKALOIDS; DATURA STRAMONIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANTS, MEDICINAL; PLANTS, TOXIC; TROPANES;

DATURA STRAMONIUM;

EID: 0034616322     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(00)00022-4     Document Type: Article

References (15)

1. Abraham T.W., Leete E. New intermediate in the biosynthesis of the tropane alkaloids in Datura innoxia. J. Am. Chem. Soc. 117:1995;8100-8105.
2. Berger R.S., Jacobson A.E., Kondritzer A.A. p-Fluorotropic acid and p-fluoroatropine. J. Org. Chem. 22:1957;451-452.
3. Cane D.E., Liang T.-C., Hasler H. Polyether biosynthesis. Part II: Origin of the oxygen atoms of monensin A. J. Am. Chem. Soc. 104:1982;7274-7281.
4. Chesters N.C.J.E., O'Hagan D., Robins R.J. The biosynthesis of tropic acid in plants: evidence for the direct rearrangement of 3-phenyllactate to tropate. J. Chem. Soc. Perkin Trans. 1:1994;1159-1162.
5. Chesters, N. C. J. E., O'Hagan, D., & Robins, R. J. (1995). The biosynthesis of tropic acid. The (R)-D-phenyllactyl moiety is processed by the mutase involved in hyoscyamine biosynthesis in Datura Stramonium. J. Chem. Soc., Chem. Commun., 127-128.
6. 2 ] acetate. J. Am. Chem. Soc. 114:1992;5472-5473.
7. O'Hagan D., Robins R.J. Tropic acid ester biosynthesis in Datura stramonium and related species. Chem. Soc. Rev. 27:1998;207-212.
8. O'Hagan, D., Robinson, J. A., & Turner, D. L. (1983). Biosynthesis of the macrolide antibiotic tylactone. Origin of the oxygen atoms in tylactone. J. Chem. Soc. Chem. Commun., 1337-1340.
9. Ollagnier S., Kervio E., Retey J. The role and source of 5′-deoxyadenosyl radical in a carbon skeleton rearrangement catalysed by a plant enzyme. FEBS Letts. 437:1998;309-312.
10. Robins R.J., Abraham T.W., Parr A.J., Eagles J., Walton N.J. The biosynthesis of tropane alkaloids in Datura stramonium: the identity of the intermediates between N-methylpyrrolinium salt and tropinone. J. Am. Chem. Soc. 119:(45):1997;10929-10934.
11. Robins R.J., Bachmann P., Woolley J.G. Biosynthesis of hyoscyamine involves an intramolecular rearrangement of littorine. J. Chem. Soc. Perkin Trans. 1:1994;615-619.
12. Robins R.J., Parr A.J., Bent E.G., Rhodes M.J.C. Studies on the biosynthesis of tropane alkaloids in Datura stramonium L D15/5 transformed root cultures. Part I: The kinetics of alkaloid production and the influence of feeding intermediate metabolites. Planta. 183:1991;185-195.
13. 2 ]-acetate into tropane alkaloids in Hyoscyamus albus. Chem. Pharm. Bull. 38:(7):1990;2066-2068.
14. 13C ]-acetate into tropane alkaloids by hairy root cultures of Hyoscyamus albus. Phytochemistry. 32:(4):1993;905-909.
15. Zabetakis I., Edwards R., O'Hagan D. Elicitation of tropane alkaloid biosynthesis in transformed root cultures of Datura stramonium. Phytochemistry. 50:1999;53-56.