(16E)-16,17-Didehydro-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester
corynoxine
CAS: 6877-32-3
Molecular Formula: C22H28N2O4
(16E)-16,17-Didehydro-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester - Names and Identifiers
| Name | corynoxine |
| Synonyms | corynoxine Corynoxine Corynoxine A Methyl (16E)-16-(methoxymethylene)-2-oxocorynoxan-17-oate (16E)-16,17-Didehydro-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester Corynoxan-16-carboxylicacid, 16,17-didehydro-17-methoxy-2-oxo-, methyl ester, (16E)- (E)-methyl 2-((1'S,6'S,7'S,8a'S)-6'-ethyl-2-oxo-3',5',6',7',8',8a'-hexahydro-2'H-spiro[indoline-3,1'-indolizin]-7'-yl)-3-methoxyacrylate Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, methyl ester, (αE,1'S,6'S,7'S,8'aS)- spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-alpha-(methoxymethylene)-2-oxo-, methyl ester, (alphaE,3S,6'S,7'S,8'aS)- |
| CAS | 6877-32-3 |
| EINECS | 211-708-6 |
| InChI | InChI=1/C22H28N2O4/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/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15+,19+,22+/m1/s1 |
(16E)-16,17-Didehydro-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester - Physico-chemical Properties
| Molecular Formula | C22H28N2O4 |
| Molar Mass | 384.47 |
| Density | 1.23 |
| Melting Point | 166-168℃ |
| Boling Point | 560.8±50.0 °C(Predicted) |
| Specific Rotation(α) | (CHCl3)-3；(c, 1 in Py)-14 |
| Flash Point | 292.97°C |
| Solubility | DMSO : ≥ 100 mg/mL (260.10 mM);H2O : < 0.1 mg/mL (insoluble) |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Crystallization |
| pKa | 13.61±0.60(Predicted) |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.596 |
| Physical and Chemical Properties | White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from the Rubiaceae plant Uncaria. |
| In vitro study | Corynoxine (6.25-25 μM; 6-12 h) increases the expression of LC3-II, an autophagy specific marker, in N2a and SH-SY5Y cells in a dose-dependent manner. Corynoxine (25 μM; 48 h) promotes the degradation of wild type (WT) and mutant (A53T) α-syn in inducible PC12 cells via autophagy induction. Western Blot Analysis Cell Line: N2a and SH-SY5Y cells Concentration: 6.25, 12.5, 25 μM Incubation Time: 6, 12 hours Result: Induced autophagy in neuronal cell lines. |
| In vivo study | Corynoxine (100-100 mg/kg; oral gavage) exhibits prolongation of the thiopental-induced hypnosis in mice. Corynoxine (10-100 μM for 12 h) induces autophagy in drosophila. |
(16E)-16,17-Didehydro-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester - Reference
| Reference Show more | 1. [IF=4.411] Shugen Wei et al."Molecular Identification and Targeted Quantitative Analysis of Medicinal Materials from Uncaria Species by DNA Barcoding and LC-MS/MS."Molecules. 2019 Jan;24(1):175 2. [IF=3.935] Shuanglu Xie et al."Systematic identification and quantification of tetracyclic 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, hydrophilic interaction chromatography, and reversed-phase chromatography as off-line three-dimensional chromatography coupled with high-resolution quadrupole-Orbitrap mass spectrometry fo |
(16E)-16,17-Didehydro-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester - Reference Information
| Biological activity | Corynoxine is a tetra-cyclic hydroxyindole alkaloid isolated from Uncaria macrophylla. Corynoxine is a natural autophagy enhancer, which can promote the clearance of α-synuclein through Akt/mTOR pathway. |
| in vitro study | Corynoxine (6.25-25 μM; 6-12 h) increases the expression of LC3-II, an autophagy specific marker, in N2a and SH-SY5Y cells in a pose-dependent manner. Corynoxine (25 μM; 48 h) promotes the degradation of wild type (WT) and mutant (A53T) α-syn in inducible PC12 cells via autophagy induction. Western Blot Analysis Cell Line: N2a and SH-SY5Y cells Concentration: 6.25, 12.5, 25 μ m Incubation Time: 6, 12 hours result: Induced autophagy in neuronal cell lines. |
| Cell Line: | N2a and SH-SY5Y cells |
| Concentration: | 6.25, 12.5, 25 μM |
| Incubation Time: | 6, 12 hours |
| Result: | Induced autophagy in neuronal cell lines. |
| in vivo study | Corynoxine (100-100 mg/kg; ORAL gavage) exhibits prolongation of the thiopental-induced hypnosis in mice. Corynoxine (10-100μM for 12 h) induces autophagy in drosophila. |
| chemical properties | white crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from the Rubiaceae plant Uncaria. |
| use | konosin has the effects of lowering blood pressure, resisting arrhythmia and protecting cerebral hypoxia and ischemia. used for content determination/identification/pharmacological experiment, etc. |
Last Update：2024-04-09 02:00:01
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