Affinisine

Affinisine
Names
	IUPAC name ((6S,7R,10R,11R,11aS,E)-9-ethylidene-5-methyl-5,6,8,9,10,11,11a,12-octahydro-6,10-methanoindolo[3,2-b]quinolizin-11-yl)methanol
	Other names 1-Methylsarpagan-17-ol, De(hydroxymethyl)voachalotinol
Identifiers
CAS Number	2912-11-0;
3D model (JSmol)	Interactive image;
ChemSpider	10172574;
PubChem CID	12000107;
CompTox Dashboard (EPA)	DTXSID201045726 ;
	InChI InChI=1S/C20H24N2O/c1-3-12-10-22-18-9-15-13-6-4-5-7-17(13)21(2)20(15)19(22)8-14(12)16(18)11-23/h3-7,14,16,18-19,23H,8-11H2,1-2H3/b12-3-/t14-,16+,18-,19-/m0/s1 Key: UVWQYWHKTZABSO-ILADVTTDSA-N; InChI=1S/C20H24N2O/c1-3-12-10-22-18-9-15-13-6-4-5-7-17(13)21(2)20(15)19(22)8-14(12)16(18)11-23/h3-7,14,16,18-19,23H,8-11H2,1-2H3/b12-3-/t14-,16+,18-,19-/m0/s1 Key: UVWQYWHKTZABSO-ILADVTTDSA-N;
	SMILES CN1C2=C(C=CC=C2)C3=C1[C@@](C[C@@]4([H])/C(C5)=C\C)([H])[N@]5[C@@]([C@@]([H])4CO)([H])C3;
Properties
Chemical formula	C20H24N2O
Molar mass	308.425 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

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 it may be an effective inhibitor of both acetylcholinesterase and butyrylcholinesterase.^[1]^[5]

References

^ ^a ^b Andrade, Marcelo T.; Lima, Josélia A.; Pinto, Angelo C.; Rezende, Claudia M.; Carvalho, Meriane P.; Epifanio, Rosângela A. (June 2005). "Indole alkaloids from Tabernaemontana australis (Müell. Arg) Miers that inhibit acetylcholinesterase enzyme". Bioorganic & Medicinal Chemistry. 13 (12): 4092–4095. doi:10.1016/j.bmc.2005.03.045. PMID 15911323.
^ Clivio, Pascale; Richard, Bernard; Deverre, Jean-Robert; Sevenet, Thierry; Zeches, Monique; Le Men-Oliver, Louisette (January 1991). "Alkaloids from leaves and root bark ofErvatamia hirta". Phytochemistry. 30 (11): 3785–3792. doi:10.1016/0031-9422(91)80111-D.
^ Liu, Xiaoxiang; Wang, Tao; Xu, Qingge; Ma, Chunrong; Cook, James M (August 2000). "Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine". Tetrahedron Letters. 41 (33): 6299–6303. doi:10.1016/S0040-4039(00)01061-3.
^ Liao, Xuebin; Zhou, Hao; Yu, Jianming; Cook, James M. (November 2006). "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. 71 (23): 8884–8890. doi:10.1021/jo061652u. PMID 17081019.
^ 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. (September 2008). "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. 80 (3): 419–426. doi:10.1590/S0001-37652008000300003. PMID 18797794.

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[source1-1] Andrade, Marcelo T.; Lima, Josélia A.; Pinto, Angelo C.; Rezende, Claudia M.; Carvalho, Meriane P.; Epifanio, Rosângela A. (June 2005). "Indole alkaloids from Tabernaemontana australis (Müell. Arg) Miers that inhibit acetylcholinesterase enzyme". Bioorganic & Medicinal Chemistry. 13 (12): 4092–4095. doi:10.1016/j.bmc.2005.03.045. PMID 15911323.

[2] Clivio, Pascale; Richard, Bernard; Deverre, Jean-Robert; Sevenet, Thierry; Zeches, Monique; Le Men-Oliver, Louisette (January 1991). "Alkaloids from leaves and root bark ofErvatamia hirta". Phytochemistry. 30 (11): 3785–3792. doi:10.1016/0031-9422(91)80111-D.

[3] Liu, Xiaoxiang; Wang, Tao; Xu, Qingge; Ma, Chunrong; Cook, James M (August 2000). "Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine". Tetrahedron Letters. 41 (33): 6299–6303. doi:10.1016/S0040-4039(00)01061-3.

[4] Liao, Xuebin; Zhou, Hao; Yu, Jianming; Cook, James M. (November 2006). "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. 71 (23): 8884–8890. doi:10.1021/jo061652u. PMID 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. (September 2008). "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. 80 (3): 419–426. doi:10.1590/S0001-37652008000300003. PMID 18797794.

[1]

[2]

[3]

[4]

[5]

Pharmacology

See also

References