Name | corynoxeine |
Synonyms | corynoxeine Isocorynoxeine Isocorynoxeine, BR Isocorynoxeine (7-Isocorynoxeine) methyl (16E,20alpha)-16-(methoxymethylidene)-2-oxocorynox-18-en-17-oate (16E,20α)-16,17,18,19-Tetradehydro-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester methyl (E)-2-[(3S,6'R,7'S,8'aS)-6'-ethenyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethenyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, methyl ester, (αE,1'S,6'R,7'S,8'aS)- (alphaE,1'S,6'R,7'S,8'aS)-6'-ethenyl-1,2,2',3',6',7',8',8'a-octahydro-alpha-(methoxymethylene)-2-oxospiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid methyl ester |
CAS | 51014-29-0 630-94-4 |
InChI | InChI=1/C22H26N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h4-8,13-15,19H,1,9-12H2,2-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22-/m0/s1 |
Molecular Formula | C22H26N2O4 |
Molar Mass | 382.46 |
Density | 1.25 |
Melting Point | 210°C |
Boling Point | 562.7±50.0 °C(Predicted) |
Specific Rotation(α) | (CHCl3)-21;(c, 1 in Py)+23 |
Flash Point | 294.1°C |
Solubility | Soluble in chloroform, soluble in acetone, ethanol, benzene, slightly soluble in ether and ethyl acetate, insoluble in petroleum ether. |
Vapor Presure | 1.09E-12mmHg at 25°C |
Appearance | Light yellow powder |
pKa | 13.54±0.60(Predicted) |
Storage Condition | 2-8℃ |
Refractive Index | 1.605 |
MDL | MFCD20527288 |
Physical and Chemical Properties | White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Uncaria. |
In vitro study | Isocorynoxeine inhibits 5-HT 2A receptor-mediated 5-HT currents. Isocorynoxeine prefer to interact with 5-HT 2A receptors rather than with 5-HT 2C receptors in the brain.Isocorynoxeine exhibits less potent inhibitory activity (with IC 50 values of > 100 μM) against the 5-HT 2C receptor-mediated response than the 5-HT 2A receptor-mediated response in oocytes. Isocorynoxeine dose-dependently and competitively inhibits 5-HT-evoked currents in Xenopus oocytes expressing 5-HT 2A receptors, but has less of a suppressive effect on those in oocytes expressing 5-HT 2C receptors. |
In vivo study | The effects of Rhynchophylline, Corynoxeine, and Isocorynoxeine, isorhynchophylline-related alkaloids present are tested in Uncaria species, on 5-MeO-DMT-induced head-twitch behaviour in reserpinized mice. Neither Rhynchophylline [H=1.369, P=0.504] nor Corynoxeine [H=0.242, P=0.886] affects the behaviour, while Isocorynoxeine significantly attenuates it at 30 mg/kg (i.p.) [H=7.582, P<0.01]. |
Reference Show more | 1. Guo Xiaomin, Huang Baoyuan, Zeng Chang Qing. Screening of Uncaria alkaloid extract and its monomer to reverse drug resistance activity of HepG2/ADM cells [J]. Journal of Guangdong Pharmaceutical College, 2018, 034(004):447-451. 2. [IF = 3.935] Shuanglu Xie et al."Systematic identification and quantification of tectyclic monoterpenoid oxindole alkaloids in Uncaria rhynchophylla and their fragmentations in Q-TOF-MS spectra." J Pharmaceut Biomed. 2013 Jul;81-82:56 3. [IF = 4.759] Keyu Feng et al."Configuration of the ion exchange chromatography, and reversed-phase chromatography as off-line three-dimensional chromatography coupled with high-resolution quadrupole-Orbitrap mass spectrometry fo 4. [IF=3.935] Wenwen Huang et al."Rapid discovery of potentially vasodilative compounds from Uncaria by UHPLC/Q-Orbitrap-MS based metabolomics and correlation analysis."J Pharmaceut Biomed. 2021 Nov;206:114384 |