Akuammicine

Akuammicine
Names
IUPAC name
Methyl (19E)-2,16-didehydrocur-19-en-17-oate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)17(19(23)24-2)13(12)10-16(20)22/h3-7,13,16,21H,8-11H2,1-2H3/b12-3-/t13-,16-,20+/m0/s1
    Key: AGZMFTKKLPHOMT-DUJTVWLASA-N
  • C123C(=C(C4CC1N(CC3)CC4=CC)C(OC)=O)Nc1c2cccc1
Properties[1]
C20H22N2O2
Molar mass 322.408 g·mol−1
Appearance Colourless solid
Melting point 182 °C (360 °F; 455 K)
Acidity (pKa) 7.45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida,[1][2] Vinca minor and the Aspidosperma.[3]

  1. ^ a b Robinson, Robert; Thomas, A. F. (1955). "The Alkaloids of Picralima nitida, Stapf, Th. and H. Durand. Part III. A Note on Akuammicine and pseudoAkuammicine". Journal of the Chemical Society (Resumed): 2049. doi:10.1039/jr9550002038. ISSN 0368-1769.
  2. ^ Shittu, Hafsat; Gray, Alexander; Furman, Brian; Young, Louise (2010). "Glucose uptake stimulatory effect of akuammicine from Picralima nitida (Apocynaceae)". Phytochemistry Letters. 3 (1): 53–55. Bibcode:2010PChL....3...53S. doi:10.1016/j.phytol.2009.11.003. ISSN 1874-3900.
  3. ^ Mitaine, A. C.; Mesbah, K; Richard, B; Petermann, C; Arrazola, S; Moretti, C; Zèches-Hanrot, M; Men-Olivier, L. L. (1996). "Alkaloids from Aspidosperma species from Bolivia". Planta Medica. 62 (5): 458–61. doi:10.1055/s-2006-957939. PMID 17252481. S2CID 260251185.