IsocorynoxeineCAS# 51014-29-0 |
- Corynoxeine
Catalog No.:BCN5002
CAS No.:630-94-4
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 51014-29-0 | SDF | Download SDF |
| PubChem ID | 3037448 | Appearance | Powder |
| Formula | C22H26N2O4 | M.Wt | 382.45 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Synonyms | 7-Isocorynoxeine | ||
| Solubility | DMSO : 50 mg/mL (130.74 mM; Need ultrasonic) | ||
| Chemical Name | 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 | ||
| SMILES | COC=C(C1CC2C3(CCN2CC1C=C)C4=CC=CC=C4NC3=O)C(=O)OC | ||
| Standard InChIKey | MUVGVMUWMAGNSY-VKCGGMIFSA-N | ||
| Standard InChI | InChI=1S/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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Isocorynoxeine, an isorhynchophylline-related alkaloid, exhibits a dose-dependent inhibition of 5-HT2A receptor-mediated current response with an IC50 of 72.4 μM. Isocorynoxeine shows the effects of lowering blood pressure, vasodilatation, and protection against ischemia-induced neuronal damage, it exhibits a significant neuroprotective effect against glutamate-induced HT22 cell death at the maximum concentration. |
| Targets | 5-HT2A receptor | NO |
| In vivo | Isolation and identification of twelve metabolites of isocorynoxeine in rat urine and their neuroprotective activities in HT22 cell assay.[Pubmed: 25519834]Planta Med. 2015 Jan;81(1):46-55.Isocorynoxeine, one of the major alkaloids from Uncaria Hook, shows the effects of lowering blood pressure, vasodilatation, and protection against ischemia-induced neuronal damage.
|
| Kinase Assay | Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: behavioural and electrophysiological studies.[Pubmed: 15963493]Eur J Pharmacol. 2005 Jul 11;517(3):191-9.Isorhynchophylline is a major oxindole alkaloid found in Uncaria species which have long been used in traditional Chinese medicine. |
| Animal Research | Metabolites of isocorynoxeine in rats after its oral administration.[Pubmed: 25633191]J Asian Nat Prod Res. 2015;17(4):384-90.This work presents the metabolites of Isocorynoxeine (ICOR), which is one of four bioactive tetracyclic oxindole alkaloids isolated from Uncaria hooks used commonly in the traditional Chinese medicines and Kampo medicines.
|
| Structure Identification | J Nat Prod. 2008 Jul;71(7):1271-4.Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia.[Pubmed: 18588343]Two new isomeric alkaloids, 18,19-dehydrocorynoxinic acid B (1) and 18,19-dehydrocorynoxinic acid (2), were isolated from the CHCl3 extract of the leaves of Uncaria rhynchophylla, together with four known rhynchophylline-type alkaloids, corynoxeine (3), Isocorynoxeine (4), rhynchophylline (5), and isorhynchophylline (6), and an indole alkaloid glucoside, vincoside lactam (7).
|
Isocorynoxeine Dilution Calculator
Isocorynoxeine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6147 mL | 13.0736 mL | 26.1472 mL | 52.2944 mL | 65.368 mL |
| 5 mM | 0.5229 mL | 2.6147 mL | 5.2294 mL | 10.4589 mL | 13.0736 mL |
| 10 mM | 0.2615 mL | 1.3074 mL | 2.6147 mL | 5.2294 mL | 6.5368 mL |
| 50 mM | 0.0523 mL | 0.2615 mL | 0.5229 mL | 1.0459 mL | 1.3074 mL |
| 100 mM | 0.0261 mL | 0.1307 mL | 0.2615 mL | 0.5229 mL | 0.6537 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
Isocorynoxeine, an isorhynchophylline-related alkaloid, exhibits a dose-dependent inhibition of 5-HT2A receptor-mediated current response with an IC50 of 72.4 μM.
In Vitro:Isocorynoxeine inhibits 5-HT2A receptor-mediated 5-HT currents. Isocorynoxeine prefer to interact with 5-HT2A receptors rather than with 5-HT2C receptors in the brain.Isocorynoxeine exhibits less potent inhibitory activity (with IC50 values of > 100 μM) against the 5-HT2C receptor-mediated response than the 5-HT2A receptor-mediated response in oocytes. Isocorynoxeine dose-dependently and competitively inhibits 5-HT-evoked currents in Xenopus oocytes expressing 5-HT2A receptors, but has less of a suppressive effect on those in oocytes expressing 5-HT2C receptors[1].
In Vivo: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][1].
References:
[1]. Matsumoto K, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: behavioural and electrophysiological studies. Eur J Pharmacol. 2005 Jul 11;517(3):191-9.
- 6''-O-Malonylgenistin
Catalog No.:BCN2772
CAS No.:51011-05-3
- Minecoside
Catalog No.:BCN5627
CAS No.:51005-44-8
- Galanthaminone
Catalog No.:BCN2867
CAS No.:510-77-0
- AMI-193
Catalog No.:BCC6679
CAS No.:510-74-7
- Echinocystic acid
Catalog No.:BCN5628
CAS No.:510-30-5
- Belladonnine
Catalog No.:BCN1892
CAS No.:510-25-8
- Voacangine
Catalog No.:BCN3224
CAS No.:510-22-5
- Trachelanthine
Catalog No.:BCN2042
CAS No.:510-19-0
- Tetramethylammonium
Catalog No.:BCN1816
CAS No.:51-92-3
- (2-Acetoxyethyl)trimethylammonium
Catalog No.:BCN1743
CAS No.:51-84-3
- Carbamoylcholine chloride
Catalog No.:BCC7492
CAS No.:51-83-2
- Tyramine
Catalog No.:BCN6776
CAS No.:51-67-2
- Demethylcephalotaxinone
Catalog No.:BCN7070
CAS No.:51020-45-2
- (+)-Licarin A
Catalog No.:BCC9008
CAS No.:51020-86-1
- (-)-Licarin B
Catalog No.:BCN1241
CAS No.:51020-87-2
- Salbutamol Sulfate
Catalog No.:BCC4338
CAS No.:51022-70-9
- Acipimox
Catalog No.:BCC4884
CAS No.:51037-30-0
- Flurbiprofen
Catalog No.:BCC3781
CAS No.:5104-49-4
- Z-GABA-OH,Z-gama-Abu-OH
Catalog No.:BCC2644
CAS No.:5105-78-2
- alpha-Lipomycin
Catalog No.:BCN1842
CAS No.:51053-40-8
- Wogonoside
Catalog No.:BCN1200
CAS No.:51059-44-0
- ATC 0065
Catalog No.:BCC7666
CAS No.:510732-84-0
- ATC 0175 hydrochloride
Catalog No.:BCC7657
CAS No.:510733-97-8
- Boc-Lys(Z)-pNA
Catalog No.:BCC3419
CAS No.:51078-31-0
Metabolites of isocorynoxeine in rats after its oral administration.[Pubmed:25633191]
J Asian Nat Prod Res. 2015;17(4):384-90.
This work presents the metabolites of Isocorynoxeine (ICOR), which is one of four bioactive tetracyclic oxindole alkaloids isolated from Uncaria hooks used commonly in the traditional Chinese medicines and Kampo medicines. After oral administration of 40 mg kg(-1) ICOR to rats, bile was drained and analyzed by LC-MS. Two phase I metabolites, namely 11-hydroxyIsocorynoxeine (M1) and 10-hydroxyIsocorynoxeine (M2), and two phase II metabolites, namely 11-hydroxyIsocorynoxeine 11-O-beta-D-glucuronide (M3) and 10-hydroxyIsocorynoxeine 10-O-beta-D-glucuronide (M4), were isolated from rat excreta and bile, respectively, whose structures were elucidated on the basis of CD, NMR, and MS.
Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia.[Pubmed:18588343]
J Nat Prod. 2008 Jul;71(7):1271-4.
Two new isomeric alkaloids, 18,19-dehydrocorynoxinic acid B (1) and 18,19-dehydrocorynoxinic acid (2), were isolated from the CHCl3 extract of the leaves of Uncaria rhynchophylla, together with four known rhynchophylline-type alkaloids, corynoxeine (3), Isocorynoxeine (4), rhynchophylline (5), and isorhynchophylline (6), and an indole alkaloid glucoside, vincoside lactam (7). The structures of compounds 1 and 2 were elucidated by spectroscopic methods including UV, IR, HREIMS, 1D and 2D NMR, and CD experiments. The activity assay showed that compounds 3-6, with a C-16 carboxylic ester group, and 7 exhibited inhibitory activity on lipopolysaccharide (LPS)-induced NO release in primary cultured rat cortical microglia (IC 50: 13.7-19.0 microM). However, only weak inhibitory activity was observed for compounds 1 and 2, with a C-16 carboxylic acid group (IC 50: >100 microM).
Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: behavioural and electrophysiological studies.[Pubmed:15963493]
Eur J Pharmacol. 2005 Jul 11;517(3):191-9.
Isorhynchophylline is a major oxindole alkaloid found in Uncaria species which have long been used in traditional Chinese medicine. Here, we investigated the effects of isorhynchophylline and isorhynchophylline-related alkaloids on 5-hydroxytryptamine (5-HT) receptor-mediated behavioural responses in mice and 5-HT-evoked current responses in Xenopus oocytes expressing 5-HT2A or 5-HT2C receptors. Isorhynchophylline dose-dependently inhibited 5-HT2A receptor-mediated head-twitch but not 5-HT1A receptor-mediated head-weaving responses evoked by 5-methoxy-N,N-dimethyltryptamine. Pretreatment with reserpine, a monoamine-depleting agent, enhanced the head-twitching, but did not influence the effect of isorhynchophylline on the behavioural response. Isocorynoxeine, an isorhynchophylline-related alkaloid in which the configuration of the oxindole moiety is the same as in isorhynchophylline, also reduced the head-twitch response in reserpinized mice over the same dose range as isorhynchophylline, while both rhynchophylline and corynoxeine, stereoisomers of isorhynchophylline and Isocorynoxeine, did not. None of the alkaloids tested had an effect on meta-chlorophenylpiperazine-induced hypolocomotion, a 5-HT2C receptor-mediated behavioural response. In experiments in vitro, isorhynchophylline and Isocorynoxeine dose-dependently and competitively inhibited 5-HT-evoked currents in Xenopus oocytes expressing 5-HT2A receptors, but had less of a suppressive effect on those in oocytes expressing 5-HT2C receptors. These results indicate that isorhynchophylline and Isocorynoxeine preferentially suppress 5-HT2A receptor function in the brain probably via a competitive antagonism at 5-HT2A receptor sites and that the configuration of the oxindole moiety of isorhynchophylline is essential for their antagonistic activity at the 5-HT2A receptor.
Isolation and identification of twelve metabolites of isocorynoxeine in rat urine and their neuroprotective activities in HT22 cell assay.[Pubmed:25519834]
Planta Med. 2015 Jan;81(1):46-55.
Isocorynoxeine, one of the major alkaloids from Uncaria Hook, shows the effects of lowering blood pressure, vasodilatation, and protection against ischemia-induced neuronal damage. In this paper, the metabolism of Isocorynoxeine was investigated in rats. Twelve metabolites and the parent drug were isolated by using solvent extraction and repeated chromatographic methods, and determined by spectroscopic methods including UV, MS, NMR, and CD experiments. Seven new compounds were identified as 11-hydroxyIsocorynoxeine, 5-oxoisocorynoxeinic acid-22-O-beta-D-glucuronide, 10-hydroxyIsocorynoxeine, 17-O-demethyl-16,17-dihydro-5-oxoIsocorynoxeine, 5-oxoisocorynoxeinic acid, 21-hydroxy-5-oxoIsocorynoxeine, and oxireno[18, 19]-5-oxoIsocorynoxeine, together with six known compounds identified as Isocorynoxeine, 18,19-dehydrocorynoxinic acid, 18,19-dehydrocorynoxinic acid B, corynoxeine, Isocorynoxeine-N-oxide, and corynoxeine-N-oxide. Possible metabolic pathways of Isocorynoxeine are proposed. Furthermore, the activity assay for the parent drug and some of its metabolites showed that Isocorynoxeine exhibited a significant neuroprotective effect against glutamate-induced HT22 cell death at the maximum concentration. However, little or weak neuroprotective activities were observed for M-3, M-6, M-7, and M-10. Our present study is important to further understand their metabolic fate and disposition in humans.
