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Akuammine

From Wikipedia, the free encyclopedia

Akuammine
Names
Other names
Vincamajoridine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C22H26N2O4/c1-4-13-11-24-8-7-21-16-9-14(25)5-6-17(16)23(2)22(21)18(24)10-15(13)20(21,12-28-22)19(26)27-3/h4-6,9,15,18,25H,7-8,10-12H2,1-3H3/b13-4+/t15-,18?,20?,21+,22-/m1/s1 checkY
    Key: YILKZADAWNUTTB-OCTHBTNBSA-N checkY
  • COC(=O)C46CO[C@]35N(C)c1ccc(O)cc1[C@]56CCN2C/C(=C\C)[C@H]4CC23
Properties
C22H26N2O4
Molar mass382.460 g·mol−1
Melting point225 °C (437 °F; 498 K)[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Akuammine (vincamajoridine[2]) is anindole alkaloid. It is the most abundant alkaloid found in the seeds from the treePicralima nitida,[3] commonly known as akuamma, comprising 0.56% of the dried powder. It has also been isolated fromVinca major.[2] Akuammine is structurally related toyohimbine,mitragynine and more distantlyVoacangine, all of which are alkaloid plant products with pharmacological properties.

Pharmacology

[edit]

Akuammine hasantimalarial activity,[3] and may be the primary constituent ofP. nitida seeds responsible for this activity.[4]

Akuammine is anopioid agonist with low affinity, selective for themu-opioid receptor, when testedin vitro.[5][6]

References

[edit]
  1. ^Merck Index (12th ed.). 200.
  2. ^abJanot MM, Le Men J, Aghoramurthy K, Robinson R (September 1955)."The identity of vincamajoridine and akuammine".Experientia.11 (9): 343.doi:10.1007/BF02159911.PMID 13262018.
  3. ^abKapadia GJ, Angerhofer CK, Ansa-Asamoah R (December 1993). "Akuammine: an antimalarial indolemonoterpene alkaloid of Picralima nitida seeds".Planta Medica.59 (6):565–6.doi:10.1055/s-2006-959764.PMID 8302957.S2CID 260253044.
  4. ^Neuwinger HD (1996).African Ethnobotany: Poisons and Drugs : Chemistry, Pharmacology, Toxicology. CRC Press. p. 123.ISBN 9783826100772.
  5. ^Menzies JR, Paterson SJ, Duwiejua M, Corbett AD (May 1998). "Opioid activity of alkaloids extracted from Picralima nitida (fam. Apocynaceae)".European Journal of Pharmacology.350 (1):101–8.doi:10.1016/s0014-2999(98)00232-5.PMID 9683021.
  6. ^Lewin G, Le Ménez P, Rolland Y, Renouard A, Giesen-Crouse E (March 1992). "Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors".Journal of Natural Products.55 (3):380–4.doi:10.1021/np50081a017.PMID 1317407.
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
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