Corynoxeine | CAS#630-94-4 | Inhibitor

MedKoo Cat#: 463046 | Name: Corynoxeine

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Corynoxeine is an alkaloid that has been found in Uncaria and has diverse biological activities. It inhibits LPS-induced production of nitric oxide in primary rat microglia. Corynoxeine inhibits PDGF-BB-induced ERK1/2 activation in, and proliferation of, rat aortic vascular smooth muscle cells. It inhibits histamine release from LAD 2 mast cells induced by compound 48/80 when used at concentrations ranging from 25 to 200 µM. In vivo, corynoxeine reduces compound 48/80-induced local anaphylaxis and mast cell degranulation in mouse hind paws. Corynoxeine also reduces methamphetamine-induced hyperlocomotion in mice.

Chemical Structure

Corynoxeine

CAS#630-94-4

Theoretical Analysis

MedKoo Cat#: 463046

Name: Corynoxeine

CAS#: 630-94-4

Chemical Formula: C22H26N2O4

Exact Mass: 382.1893

Molecular Weight: 382.46

Elemental Analysis: C, 69.09; H, 6.85; N, 7.32; O, 16.73

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Corynoxeine; Corynoxein; δ18-Rynchophylline;

IUPAC/Chemical Name

methyl (E)-3-methoxy-2-((3R,6'R,7'S,8a'S)-2-oxo-6'-vinyl-2',3',6',7',8',8a'-hexahydro-5'H-spiro[indoline-3,1'-indolizin]-7'-yl)acrylate

InChi Key

MUVGVMUWMAGNSY-KAXDATADSA-N

InChi Code

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

SMILES Code

O=C1[C@@]2([C@]3(N(CC2)C[C@H](C=C)[C@@H](/C(C(OC)=O)=C\OC)C3)[H])C4=CC=CC=C4N1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Corynoxeine, isolated from the hook of Uncaria rhynchophylla, is a potent ERK1/ERK2 inhibitor of key PDGF-BB-induced vascular smooth muscle cells (VSMCs) proliferation.

In vitro activity:

Pre-treatment of VSMCs with corynoxeine (5—50 μM) for 24 h resulted in significant decreases in cell number without any cytotoxicity; the inhibition percentages were 25.0±12.5, 63.0±27.5 and 88.0±12.5% at 5, 20 and 50 μM, respectively. Also, corynoxeine significantly inhibited the 50 ng/ml PDGF-BB-induced DNA synthesis of VSMCs in a concentration-dependent manner without any cytotoxicity; the inhibitions were 32.8±11.0, 51.8±8.0 and 76.9±7.4% at concentrations of 5, 20 and 50 μM, respectively. Reference: Biol Pharm Bull. 2008 Nov;31(11):2073-8. https://www.jstage.jst.go.jp/article/bpb/31/11/31_11_2073/_article

In vivo activity:

TBD

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	27.9	72.87

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 382.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kim TJ, Lee JH, Lee JJ, Yu JY, Hwang BY, Ye SK, Shujuan L, Gao L, Pyo MY, Yun YP. Corynoxeine isolated from the hook of Uncaria rhynchophylla inhibits rat aortic vascular smooth muscle cell proliferation through the blocking of extracellular signal regulated kinase 1/2 phosphorylation. Biol Pharm Bull. 2008 Nov;31(11):2073-8. doi: 10.1248/bpb.31.2073. PMID: 18981576.

In vitro protocol:

In vivo protocol:

TBD

1: Chen L, Ma J, Wang X, Zhang M. Simultaneous Determination of Six Uncaria Alkaloids in Mouse Blood by UPLC-MS/MS and Its Application in Pharmacokinetics and Bioavailability. Biomed Res Int. 2020 Aug 17;2020:1030269. doi: 10.1155/2020/1030269. PMID: 32879877; PMCID: PMC7448256. 2: Flores-Bocanegra L, Raja HA, Graf TN, Augustinović M, Wallace ED, Hematian S, Kellogg JJ, Todd DA, Cech NB, Oberlies NH. The Chemistry of Kratom [Mitragyna speciosa]: Updated Characterization Data and Methods to Elucidate Indole and Oxindole Alkaloids. J Nat Prod. 2020 Jul 24;83(7):2165-2177. doi: 10.1021/acs.jnatprod.0c00257. Epub 2020 Jun 29. PMID: 32597657. 3: Wu Y, Xiao H, Pi J, Zhang H, Pan A, Pu Y, Liang Z, Shen J, Du J. EGFR promotes the proliferation of quail follicular granulosa cells through the MAPK/extracellular signal-regulated kinase (ERK) signaling pathway. Cell Cycle. 2019 Oct;18(20):2742-2756. doi: 10.1080/15384101.2019.1656952. Epub 2019 Aug 29. PMID: 31465245; PMCID: PMC6773241. 4: Li T, Xu K, He J, Jahan N, Song J, Wang S. Effects of isocorynoxeine, from Uncaria, on lower urinary tract dysfunction caused by benign prostatic hyperplasia via antagonism of α1A-adrenoceptors. Toxicol Appl Pharmacol. 2019 Aug 1;376:95-106. doi: 10.1016/j.taap.2019.05.018. Epub 2019 May 27. PMID: 31145917. 5: Zou L, Lu F, Lin B, Zhou Y, Liu T, Sun Y. Stability of Alkaloids during Drying Process and Their Effect on Anticoagulating Activity of Uncariae Ramulus Cum Uncis. J Anal Methods Chem. 2019 Jan 3;2019:7895152. doi: 10.1155/2019/7895152. PMID: 30719373; PMCID: PMC6335766. 6: Zhang H, Duan S, Wang L, Liu J, Qi W, Yuan D. Identification of the absorbed components and their metabolites of Tianma-Gouteng granule in rat plasma and bile using ultra-high-performance liquid chromatography combined with quadrupole time-of-flight mass spectrometry. Biomed Chromatogr. 2019 Apr;33(4):e4480. doi: 10.1002/bmc.4480. Epub 2019 Feb 1. PMID: 30597588. 7: Li T, Xu K, Che D, Huang Z, Jahan N, Wang S. Endothelium-independent vasodilator effect of isocorynoxeine in vitro isolated from the hook of Uncaria rhynchophylla (Miquel). Naunyn Schmiedebergs Arch Pharmacol. 2018 Nov;391(11):1285-1293. doi: 10.1007/s00210-018-1536-y. Epub 2018 Aug 2. PMID: 30073385. 8: Nakamura Y, Ishida Y, Kondo M, Shimada S. Yokukansan contains compounds that antagonize the 5-HT3 receptor. Phytomedicine. 2018 Apr 1;43:120-125. doi: 10.1016/j.phymed.2018.04.034. Epub 2018 Apr 16. PMID: 29747744. 9: Tian X, Xu Z, Chen M, Hu P, Liu F, Sun Z, Liu H, Guo X, Li Z, Huang C. Simultaneous determination of eight bioactive compounds by LC-MS/MS and its application to the pharmacokinetics, liver first-pass effect, liver and brain distribution of orally administrated Gouteng-Baitouweng (GB) in rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 May 1;1084:122-131. doi: 10.1016/j.jchromb.2018.03.013. Epub 2018 Mar 9. PMID: 29597038. 10: Hou J, Feng R, Zhang Y, Pan H, Yao S, Han S, Feng Z, Cai L, Wu W, Guo DA. Characteristic Chromatogram: A Method of Discriminate and Quantitative Analysis for Quality Evaluation of Uncaria Stem with Hooks. Planta Med. 2018 Apr;84(6-07):449-456. doi: 10.1055/s-0043-123827. Epub 2017 Dec 7. PMID: 29216668. 11: Zhang YN, Yang YF, Xu W, Yang XW. The Blood-Brain Barrier Permeability of Six Indole Alkaloids from Uncariae Ramulus Cum Uncis in the MDCK-pHaMDR Cell Monolayer Model. Molecules. 2017 Nov 10;22(11):1944. doi: 10.3390/molecules22111944. PMID: 29125571; PMCID: PMC6150385. 12: Huang BY, Zeng Y, Li YJ, Huang XJ, Hu N, Yao N, Chen MF, Yang ZG, Chen ZS, Zhang DM, Zeng CQ. Uncaria alkaloids reverse ABCB1-mediated cancer multidrug resistance. Int J Oncol. 2017 Jul;51(1):257-268. doi: 10.3892/ijo.2017.4005. Epub 2017 May 17. PMID: 28534954; PMCID: PMC5467778. 13: Huang HC, Wang CF, Gu JF, Chen J, Hou XF, Zhong RL, Xia Z, Zhao D, Yang N, Wang J, Tan XB, Jia XB, Di LQ, Dong ZB, Feng L. Components of Goutengsan in Rat Plasma by Microdialysis Sampling and Its Protection on Aβ1-42-Induced PC12 Cells Injury. Evid Based Complement Alternat Med. 2017;2017:7593027. doi: 10.1155/2017/7593027. Epub 2017 Mar 2. PMID: 28348625; PMCID: PMC5352969. 14: Wang W, Luo S, Chen Y, Li B, Hattori M. Effective Separation and Simultaneous Determination of Corynoxeine and Its Metabolites in Rats by High- Performance Liquid Chromatography with Tandem Mass Spectrometry and Application to Pharmacokinetics and In Vivo Distribution in Main Organs. Anal Sci. 2016;32(6):705-7. doi: 10.2116/analsci.32.705. PMID: 27302594. 15: Zhao L, Zang B, Qi W, Chen F, Wang H, Kano Y, Yuan D. Pharmacokinetic study of isocorynoxeine metabolites mediated by cytochrome P450 enzymes in rat and human liver microsomes. Fitoterapia. 2016 Jun;111:49-57. doi: 10.1016/j.fitote.2016.04.008. Epub 2016 Apr 16. PMID: 27094112. 16: Ishida Y, Ebihara K, Tabuchi M, Imamura S, Sekiguchi K, Mizoguchi K, Kase Y, Koganemaru G, Abe H, Ikarashi Y. Yokukansan, a Traditional Japanese Medicine, Enhances the L-DOPA-Induced Rotational Response in 6-Hydroxydopamine-Lesioned Rats: Possible Inhibition of COMT. Biol Pharm Bull. 2016;39(1):104-13. doi: 10.1248/bpb.b15-00691. PMID: 26725433. 17: Feng RH, Hou JJ, Zhang YB, Pan HQ, Yang W, Qi P, Yao S, Cai LY, Yang M, Jiang BH, Liu X, Wu WY, Guo DA. An efficient and target-oriented sample enrichment method for preparative separation of minor alkaloids by pH-zone- refining counter-current chromatography. J Chromatogr A. 2015 Aug 28;1409:159-65. doi: 10.1016/j.chroma.2015.07.066. Epub 2015 Jul 17. PMID: 26209189. 18: Zhang Q, Zhao JJ, Xu J, Feng F, Qu W. Medicinal uses, phytochemistry and pharmacology of the genus Uncaria. J Ethnopharmacol. 2015 Sep 15;173:48-80. doi: 10.1016/j.jep.2015.06.011. Epub 2015 Jun 17. PMID: 26091967. 19: Zhao L, Qi W, Chen F, Sun J, Yuan D. Metabolic Profile of Isocorynoxeine in Rats Obtained by Ultra-High Performance Liquid Chromatography/Quadrupole Time- of-Flight Mass Spectrometry. Eur J Drug Metab Pharmacokinet. 2016 Oct;41(5):615-26. doi: 10.1007/s13318-015-0287-0. PMID: 26077124. 20: Chen YP, Lu MN, Hao JC, Li MH, Hattori M, Wang W. Metabolites of isocorynoxeine in rats after its oral administration. J Asian Nat Prod Res. 2015;17(4):384-90. doi: 10.1080/10286020.2014.1003182. Epub 2015 Jan 30. PMID: 25633191.