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Coronaridine

Names

[ CAS No. ]:
467-77-6

[ Name ]:
Coronaridine

[Synonym ]:
cornigerine
1,2-(methylenedioxy)-1,2-dimethylcolchicine
Dihydrocatharanthin
(+-)-Coronaridin
(-)-1,2-(Methylenedioxy)-1,2-didemethoxycolchicine
ibogamine-18-carboxylic acid methyl ester
Acetamide,N-(6,7,8,10-tetrahydro-4,11-dimethoxy-10-oxoheptaleno(1,2-e)-1,3-benzodioxol-8-yl)-,(S)
n-(4,11-dimethoxy-10-oxo-6,7,8,10-tetrahydroheptaleno[1',2':3,4]benzo[1,2-d][1,3]dioxol-8-yl)acetamide
Catharanthin
EINECS 207-398-7

Biological Activity

[Description]:

Coronaridine, an iboga type alkaloid, inhibits the wnt signaling pathway by decreasing β-catenin expression[1].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Stem Cell/Wnt >> Wnt
Research Areas >> Neurological Disease

[In Vitro]

Coronaridine (0-40 μM; 24 hours) is against non-cancer cells with IC50 values >40 μM. It agaisnt wnt-dependent cells with IC50 values of 10.4, 11.6 and 24.4 μM for SW480, HCT116 and DLD1cells, respectively[1]. Coronaridine (0-40 μM; 24 hours) inhibits β-catenin expression, but the protein levels of p-β--catenin at Ser33, Ser37, and Thr41 and p-β-catenin at Ser 45 [p-b-catenin (S45)] are unchanged[1]. In whole-cell patch clamp recordings,Catharanthine (1-300 μM) are respectively co-applied with GABA at concentrations corresponding to the EC30 value for each receptor subtype. Both congeners potentiated different GABAARs in a concentration-dependent manner[2]. At higher concentrations, however, Catharanthine starts to inhibit GABA-activated currents due to the reduced amplitude and rebound current, where the threshold concentration depended on the receptor subtype (e.g., > 30 μM for hα1β2; > 100 μM for hα1β2γ2 and hα2β2γ2). The PAM activity of Catharanthine's are depended on the receptor subtype: hα1β2 (4.6±0.8 μM), >hα2β2γ2 (12.6±3.8 μM), hα1β2γ2 (14.4 ± 4.6 μM)[2].

[References]

[1]. Kensuke Ohishi, et al. Coronaridine, an iboga type alkaloid from Tabernaemontana divaricata, inhibits the Wnt signaling pathway by decreasing β-catenin mRNA expression. Bioorg Med Chem Lett. 2015 Sep 15;25(18):3937-40.

[2]. Hugo R Arias, et al. Coronaridine congeners potentiate GABA A receptors and induce sedative activity in mice in a benzodiazepine-insensitive manner. Prog Neuropsychopharmacol Biol Psychiatry. 2020 Jul 13;101:109930

Chemical & Physical Properties

[ Density]:
1.24g/cm3

[ Boiling Point ]:
488.1ºC at 760 mmHg

[ Melting Point ]:
92-93 ºC

[ Molecular Formula ]:
C21H26N2O2

[ Molecular Weight ]:
338.44300

[ Flash Point ]:
249ºC

[ Exact Mass ]:
338.19900

[ PSA ]:
45.33000

[ LogP ]:
3.19310

[ Vapour Pressure ]:
1.12E-09mmHg at 25°C

[ Index of Refraction ]:
1.642

[ Water Solubility ]:
Practically insoluble (0.024 g/L) (25 ºC)

Related Compounds