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Corynoxeine

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-C2010

  • Specification : 98%

  • CAS number : 630-94-4

  • Formula : C22H26N2O4

  • Molecular Weight : 382.45

  • PUBCHEM ID : 44568160

  • Volume : 20mg

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Catalogue Number

BF-C2010

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

382.45

Appearance

White crystalline powder

Botanical Source

herbs of Uncaria rhynchophylla.

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

COC=C(C1CC2C3(CCN2CC1C=C)C4=CC=CC=C4NC3=O)C(=O)OC

Synonyms

(+/-)-corynoxeine/Corynoxeine/()-corynoxeine/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,3R,6'R,7'S,8'aS)-/ISOCORYNOXEINE/Methyl (7β,16E,20α)-17-methoxy-2-oxocorynoxa-16,18-dien-16-carboxylate

IUPAC Name

methyl (E)-2-[(3R,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

Density

1.3±0.1 g/cm3

Solubility

Methanol

Flash Point

294.1±30.1 °C

Boiling Point

562.7±50.0 °C at 760 mmHg

Melting Point

210℃

InChl

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

InChl Key

MUVGVMUWMAGNSY-KAXDATADSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:630-94-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30073385

Abstract

This study was designed to investigate the vasorelaxant effects and underlying mechanism of isocorynoxeine (ICN), one of the indole alkaloids from Uncaria hooks, on isolated mesenteric arteries in vitro. The myograph system was applied for isometric tension recording in the vascular rings. ICN relaxed both endothelium-intact and endothelium-denuded rat vascular rings precontracted with phenylephrine or KCl in a dose-dependent manner. Propranolol, tetraethylammonium, BaCl2, and glibenclamide had no influence on the vasodilator effect of ICN on phenylephrine-primed vascular rings, while 4-aminopyridine decreased the maximum relaxation. Furthermore, ICN produced a significant drop in maximum response in the PE log concentration-response curve without shifting to the right. In the Ca2+-free Kreb’s-Henseleit buffer, ICN inhibited the contraction in vascular rings evoked by PE, but not by KCl. The phasic contractions of segments in the Ca2+-free Kreb’s-Henseleit buffer induced by CaCl2 were restrained by ICN, while contractions elicited by caffeine displayed no differences. Furthermore, the phasic vasodilation of ICN was significantly lower than controls when pretreated with nifedipine and heparin. Both BAYK8644- and PE-evoked responses were significantly inhibited in the presence of 100 μM of ICN in human vascular smooth muscle cells loaded with the fluorescent Ca2+ indicator Fluo-4-AM. All these results suggest that ICN act in an endothelium-independent manner on the mesenteric artery. Its mechanisms of vasorelaxant action were produced by the inhibition of L-type calcium channel-mediated external Ca2+ influx and α1A-adrenoceptor-mediated intracellular Ca2+ release in vascular smooth muscle cells, and the participation of the Kv channel.

KEYWORDS

Calcium channel; Isocorynoxeine (ICN); Rat mesenteric artery; Vasorelaxation; α1A-Adrenoceptor antagonist

Title

Endothelium-independent vasodilator effect of isocorynoxeine in vitro isolated from the hook of Uncaria rhynchophylla (Miquel).

Author

Li T1,2, Xu K1,2, Che D1,3, Huang Z4, Jahan N1,2, Wang S5,6.

Publish date

2018 Nov

PMID

29747744

Abstract

BACKGROUND:
We recently focused on alkaloids in Uncaria hook (a constituent of the Kampo medicine, yokukansan) and identified the pharmacological action of geissoschizine methyl ether on several G protein-coupled receptors. However, the functions of other identified alkaloids in Uncaria hook, including hirsutine, hirsuteine, rhynchophylline, isorhynchophylline, corynoxeine, isocorynoxeine, are not clear.

PURPOSE:
To evaluate the effect of seven alkaloids in Uncaria hook (hirsutine, hirsuteine, rhynchophylline, isorhynchophylline, corynoxeine, isocorynoxeine and geissoschizine methyl ether) on the hydroxytryptamine type-3 (5-HT3) receptor ion channel.

STUDY DESIGN:
We examined the effect of these alkaloids on the current of human 5-HT3 receptors expressed in Xenopus laevis oocytes.

METHODS:
The human 5-HT3A subunit alone for the 5-HT3A receptor, or 5-HT3A and 5-HT3B subunits for the 5-HT3AB receptor, were expressed in Xenopus laevis oocytes. The 5-HT current was measured with or without alkaloid application using a two-electrode voltage clamp.

RESULTS:
Each alkaloid, except for geissoschizine methyl ether, weakly inhibited the 5-HT-mediated 5-HT3A and/or 5-HT3AB receptor current, but co-application of these seven alkaloids inhibited the current strongly.

CONCLUSION:
Each alkaloid contributes to antagonism of the 5-HT3 receptor.

Copyright © 2018 Elsevier GmbH. All rights reserved.

KEYWORDS

5-HT(3); Antagonist; Ion channel; Serotonin receptor; Yi-Gan San; Yokukansan

Title

Yokukansan contains compounds that antagonize the 5-HT3 receptor.

Author

Nakamura Y1, Ishida Y2, Kondo M2, Shimada S2.

Publish date

2018 Apr 1

PMID

27302594

Abstract

An effective separation and simultaneous determination of corynoxeine and its metabolites using high-performance liquid chromatography with tandem mass spectrometry was developed and validated. The method was applied to pharmacokinetics and in vivo distribution investigations in rats after oral (0.105 mmol kg(-1)) and intravenous (0.0105 mmol kg(-1)) doses of corynoxeine. Its brain uptake index was of 3.08 × 10(-11) mol g(-1) at 3 h and 3.75 × 10(-11) mol g(-1) at 74 min after oral and intravenous doses, respectively.

Title

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.

Author

Wang W1, Luo S, Chen Y, Li B, Hattori M.

Publish date

2016


Description :

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.