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IUPAC name
Methyl (19E)-2,16-didehydrocur-19-en-17-oate
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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).
|
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]
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]
As with other indole alkaloids, the biosynthesis of akuammicine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration. [4]
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]
Plant metabolites have long been studied for their biological activity and alkaloids in particular are major subjects for ethnobotanical research. [15] Akuammicine is reported to have effects on glucose uptake [2] and be a κ- and μ-opioid receptor agonist. [3] [16]
Names | |
---|---|
IUPAC name
Methyl (19E)-2,16-didehydrocur-19-en-17-oate
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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]
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]
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]
As with other indole alkaloids, the biosynthesis of akuammicine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration. [4]
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]
Plant metabolites have long been studied for their biological activity and alkaloids in particular are major subjects for ethnobotanical research. [15] Akuammicine is reported to have effects on glucose uptake [2] and be a κ- and μ-opioid receptor agonist. [3] [16]