Littorine

Littorine
Names
Systematic IUPAC name
(1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl (R)-2-hydroxy-3-phenylpropanoate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)11-15(10-13)21-17(20)16(19)9-12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
    Key: FNRXUEYLFZLOEZ-FXUDXRNXSA-N
  • CN1[C@@H]2C[C@@H](OC([C@@H](CC3=CC=CC=C3)O)=O)C[C@H]1CC2
Properties
C17H23NO3
Molar mass 289.375 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Littorine is a tropane alkaloid found in a variety of plants including Datura and Atropa belladonna. It is closely related in chemical structure to scopolamine, atropine, and hyoscyamine, of which the latter two with littorine are isomers and which all share a common biosynthetic pathway.

See also

References

  1. ↑ Evans, W. C.; Ghani, A.; Woolley, V. A. (1972). "Distribution of littorine and other alkaloids in the roots of Datura species". Phytochemistry. 11 (8): 2527–2529. Bibcode:1972PChem..11.2527E. doi:10.1016/S0031-9422(00)88530-1.
  2. ↑ Nakanishi, F.; Sasaki, K.; Shimomura, K. (1998). "Isolation and identification of littorine from hairy roots of Atropa belladonna". Plant Cell Reports. 18 (3–4): 249–251. Bibcode:1998PCelR..18..249N. doi:10.1007/s002990050565. PMID 30744229.
  3. ↑ Zabetakis, I.; Edwards, R.; Hamilton, J. T. G.; O'Hagan, D. (1998). "The biosynthetic relationship between littorine and hyoscyamine in transformed roots of Datura stramonium". Plant Cell Reports. 18 (3–4): 341–345. Bibcode:1998PCelR..18..341Z. doi:10.1007/s002990050583. PMID 30744247.
  4. ↑ Lanoue, A.; Boitel-Conti, M.; Portais, J.-C.; Laberche, J.-C.; Barbotin, J.-N.; Christen, P.; Sangwan-Norreel, B. (2002). "Kinetic Study of Littorine Rearrangement in Datura innoxia Hairy Roots by 13C NMR Spectroscopy". Journal of Natural Products. 65 (8): 1131–1135. Bibcode:2002JNAtP..65.1131L. doi:10.1021/np010612c. PMID 12193016.