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Erythravine

From Wikipedia, the free encyclopedia
Erythravine
Names
IUPAC name
15,16-Dimethoxy-1,2,6,7-tetradehydroerythrinan-3β-ol
Systematic IUPAC name
(9bS,11R)-7,8-Dimethoxy-4,5,10,11-tetrahydro-2H-indolo[7a,1-a]isoquinolin-11-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C18H21NO3/c1-21-16-9-12-5-7-19-8-6-13-3-4-14(20)11-18(13,19)15(12)10-17(16)22-2/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-/m0/s1 ☒N
    Key: JEBFJSHKHYDVNP-KSSFIOAISA-N ☒N
  • COC1=C(C=C2C(=C1)CCN3[C@]24C[C@H](C=CC4=CC3)O)OC
Properties
C18H21NO3
Molar mass299.370 g·mol−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

Erythravine is atetrahydroisoquinolinealkaloid found in the plantErythrina mulungu and other species of the genusErythrina.

Biological activity

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Some laboratory research has investigated thebiological activity of erythravine, but the relevance to effects in humans is unknown.

Nicotinic acetylcholine receptor

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It has been shown to be a potentnicotinic receptorantagonist in animal models with anIC50 of 6μM at theα7 site and 13 nM for theα4β2 receptor.[1]

Anxiolytic

[edit]

It appears to haveanxiolytic effects inanimal models of anxiety. Further studies suggest that theanxiolytic effects are only reproducible with the whole extract ofErythrina mulungu but not with the pure alkaloids.[2][3]

Anticonvulsant

[edit]

Erythravine inhibited seizures evoked bybicuculline,pentylenetetrazole, andkainic acid as well as increasing the latency of seizures induced byNMDA. Treatment with erythravine prevented death in all the animals tested with the fourconvulsants except a few of those treated with kainic acid.[4]

See also

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References

[edit]
  1. ^Setti-Perdigão, Pedro; Serrano, Maria A. R.; Flausino, Otávio A.;Bolzani, Vanderlan S.; Guimarães, Marília Z. P.; Castro, Newton G. (2013-01-01)."Erythrina mulungu alkaloids are potent inhibitors of neuronal nicotinic receptor currents in mammalian cells".PLOS ONE.8 (12): e82726.Bibcode:2013PLoSO...882726S.doi:10.1371/journal.pone.0082726.ISSN 1932-6203.PMC 3862643.PMID 24349349.
  2. ^Flausino Jr, O; Santos Lde, A; Verli, H; Pereira, AM;Bolzani Vda, S; Nunes-De-Souza, RL (2007). "Anxiolytic effects of erythrinian alkaloids from Erythrina mulungu".Journal of Natural Products.70 (1):48–53.doi:10.1021/np060254j.PMID 17253849.
  3. ^Flausino Jr, OA; Pereira, AM;Da Silva Bolzani, V; Nunes-De-Souza, RL (2007)."Effects of erythrinian alkaloids isolated from Erythrina mulungu (Papilionaceae) in mice submitted to animal models of anxiety".Biological & Pharmaceutical Bulletin.30 (2):375–8.doi:10.1248/bpb.30.375.hdl:11449/34195.PMID 17268084.
  4. ^Faggion, Silmara Aparecida; Cunha, Alexandra Olimpio Siqueira; Fachim, Helene Aparecida; Gavin, Amanda Salomão; dos Santos, Wagner Ferreira; Pereira, Ana Maria Soares; Beleboni, Renê Oliveira (2011-03-01)."Anticonvulsant profile of the alkaloids (+)-erythravine and (+)-11-α-hydroxy-erythravine isolated from the flowers of Erythrina mulungu Mart ex Benth (Leguminosae-Papilionaceae)".Epilepsy & Behavior.20 (3):441–446.doi:10.1016/j.yebeh.2010.12.037.ISSN 1525-5069.PMID 21277832.
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)
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