Affinisine Explained

Affinisine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana.^{[1] [2]} Structurally, it can be considered a member of the sarpagine alkaloid family and may be synthesized from tryptophan via a Pictet-Spengler reaction.^{[3] [4]}

Pharmacology

Limited pharmacological testing has indicated that affinisine may effectively inhibit acetylcholinesterase and butyrylcholinesterase.^[5]

See also

• Affinine
• 19-Epivoacristine

Notes and References

1. Andrade. Marcelo T.. Lima. Josélia A.. Pinto. Angelo C.. Rezende. Claudia M.. Carvalho. Meriane P.. Epifanio. Rosângela A.. Indole alkaloids from Tabernaemontana australis (Müell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorganic & Medicinal Chemistry. June 2005. 13. 12. 4092–4095. 10.1016/j.bmc.2005.03.045. 15911323.
2. Clivio. Pascale. Richard. Bernard. Deverre. Jean-Robert. Sevenet. Thierry. Zeches. Monique. Le Men-Oliver. Louisette. Alkaloids from leaves and root bark ofErvatamia hirta. Phytochemistry. January 1991. 30. 11. 3785–3792. 10.1016/0031-9422(91)80111-D.
3. Liu. Xiaoxiang. Wang. Tao. Xu. Qingge. Ma. Chunrong. Cook. James M. Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine. Tetrahedron Letters. August 2000. 41. 33. 6299–6303. 10.1016/S0040-4039(00)01061-3.
4. Liao. Xuebin. Zhou. Hao. Yu. Jianming. Cook. James M.. An Improved Total Synthesis of (+)-Macroline and Alstonerine as Well as the Formal Total Synthesis of (−)-Talcarpine and (−)-Anhydromacrosalhine−methine. The Journal of Organic Chemistry. November 2006. 71. 23. 8884–8890. 10.1021/jo061652u. 17081019.
5. Vieira. Ivo J.C.. Medeiros. Walter L.B.. Monnerat. Cecilia S.. Souza. Jucimar J.. Mathias. Leda. Braz-Filho. Raimundo. Pinto. Angelo C.. Sousa. Priscila M.. Rezende. Claudia M.. Epifanio. Rosângela De A.. Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. Anais da Academia Brasileira de Ciências. September 2008. 80. 3. 419–426. 10.1590/S0001-37652008000300003. 18797794. free.