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).
Infobox references

Littorine is a tropane alkaloid found in a variety of plants including Datura[1] and Atropa belladonna.[2] It is closely related in chemical structure to atropine, hyoscyamine, and scopolamine, which all share a common biosynthetic pathway.[3][4]

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. 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. doi:10.1007/s002990050565.
  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. doi:10.1007/s002990050583.
  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. doi:10.1021/np010612c. PMID 12193016.
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