Akuammicine
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
Methyl (19E)-2,16-didehydrocur-19-en-17-oate | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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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]
The alkaloids are a large group of natural products which are classified according to the part-structure which members of a particular group contain. Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group which shares a common biosynthesis with other members, namely that they are derived from strictosidine.[4][5] It was first isolated in 1927 and had been investigated by Sir Robert Robinson and others before its structure was correctly deduced.[1][6][7] This was confirmed by X-ray crystallography in 2017.[8]
Natural occurrence
Akuammicine is found in plants of the Apocynaceae family and was first isolated from Picralima nitida.[1][2] It has also been reported in Catharanthus roseus.[9]
Synthesis
Biosynthesis
As with other indole alkaloids, the biosynthesis of akuammicine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration.[4]
Chemical synthesis
Akuammicine has been a target for total synthesis,[10] partly because of its relationship to the well-known alkaloid strychnine which has often attracted chemists in academia.[11][12][13][14]