Akuammicine

Source: Wikipedia, the free encyclopedia.
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

Picralima nitida,[1][2]
Vinca minor and the Aspidosperma.[3]

History

The

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

Picralima nitida, a source of akuammicine

Akuammicine is found in plants of the

Picralima nitida.[1][2] It has also been reported in Catharanthus roseus.[9]

Synthesis

Biosynthesis

Main article: Indole alkaloid § 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

Strychnine

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]

Research

Plant

κ- and μ-opioid receptor agonist.[3][16]

See also

References

  1. ^
    ISSN 0368-1769
    .
  2. ^
    ISSN 1874-3900
    .
  3. ^
    S2CID 260251185
    .
  4. ^
    ISBN 0-471-49640-5
    .
  5. doi:10.1039/NP9840100021
    .
  6. doi:10.1039/JR9600000792
    .
  7. S2CID 28255077
    .
  8. PMID 29152344
    .
  9. doi:10.1016/0031-9422(80)83216-X
    .
  10. PMID 21753848
    .
  11. PMID 11506556
    .
  12. PMID 20408591
    .
  13. ISBN 978-0-08-099362-1
    .
  14. PMID 28170147
    .
  15. doi:10.1039/C5RA01912E
    .
  16. PMID 9683021
    .
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