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Coptisine

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-C1013

  • Specification : 98%

  • CAS number : 3486-66-6

  • Formula : C19H14NO4

  • Molecular Weight : 320.32

  • PUBCHEM ID : 72322

  • Volume : 20mg

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Catalogue Number

BF-C1013

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

320.32

Appearance

Powder

Botanical Source

herbs of Chelidonium majus L.

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6

Synonyms

6,7-Dihydrobis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium/7,8,13,13a-Tetradehydro-2,3:9,10-bismethylenedioxyberbinium/Coptisine/Bis[methylenedioxy]protoberberine/6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinolin-5-ium/6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquinolino[3,2-a]isoquinolin-5-ium/[1,3]Benzodioxolo[5,6-a]-1,3-benzodioxolo[4,5-g]quinolizinium, 6,7-dihydro-/6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isochino[3,2-a]isochinolin-5-ium/Coptisin/coptisinium/6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinolein-5-ium

IUPAC Name

5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaene

Applications

Coptisine is an alkaloid from Chinese goldthread, and acts as an efficient uncompetitive IDO inhibitor with a Ki value of 5.8 μM and an IC50 value of 6.3 μM.

Density

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1

InChl Key

XYHOBCMEDLZUMP-UHFFFAOYSA-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#:3486-66-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30469322

Abstract

Coptisine is one of the main components of isoquinoline alkaloids in the coptidis rhizome. The effect of coptisine on allergic rhinitis has not been investigated. In this study, we report the effects and mechanisms of coptisine using monoclonal anti-2,4,6-dinitrophenyl-immunoglobulin (Ig) E/human serum albumin (DNP-IgE/HSA)-stimulated rat basophilic leukemia cells (RBL-2H3 cells) in vitro and an ovalbumin (OVA)-induced allergic rhinitis (AR) in mice. The results showed that coptisine markedly decreased the levels of β-hexosaminidase, histamine, interleukin (IL)-4, and tumor necrosis factor (TNF)-α. Coptisine also prevented morphological changes, such as restoring an elongated shape, inhibiting granule release on toluidine blue staining, and reorganizing inhibited filamentous actins (F-actin). Additionally, coptisine blocked the phosphorylation of phosphoinositide3-kinase (PI3K)/Akt (as known as protein kinase B(PKB)) in RBL-2H3 cell. Furthermore, the results showed that coptisine suppressed OVA-induced allergic rhinitis symptoms, such as nasal rubbing and OVA-specific IgE, and histamine, IL-4 and TNF-α levels in the serum of AR mice. These data suggested that coptisine should have inhibitory effects on the inflammatory responses of mast cells, and may be beneficial for the development of coptisine as a potential anti-allergic drug

KEYWORDS

allergic rhinitis; coptisine; mast cell

Title

Coptisine Suppresses Mast Cell Degranulation and Ovalbumin-Induced Allergic Rhinitis.

Author

Fu S1, Ni S2, Wang D3, Hong T4.

Publish date

2018 Nov 21

PMID

31622015

Abstract

Coptisine is a natural small-molecular compound extracted from Coptis chinensis (CC) with a history of using for thousands of years. This work aimed at summarizing coptisine’s activity and providing advice for its clinical use. We analysed the online papers in the database of SciFinder, Web of Science, PubMed, Google scholar and CNKI by setting keywords as ‘coptisine’ in combination of ‘each pivotal pathway target’. Based on the existing literatures, we find (a) coptisine exerted potential to be an anti-cancer, anti-inflammatory, CAD ameliorating or anti-bacterial drug through regulating the signalling transduction of pathways such as NF-κB, MAPK, PI3K/Akt, NLRP3 inflammasome, RANKL/RANK and Beclin 1/Sirt1. However, we also (b) observe that the plasma concentration of coptisine demonstrates obvious non-liner relationship with dosage, and even the highest dosage used in animal study actually cannot reach the minimum concentration level used in cell experiments owing to the poor absorption and low availability of coptisine. We conclude (a) further investigations can focus on coptisine’s effect on caspase-1-involved inflammasome assembling and pyroptosis activation, as well as autophagy. (b) Under circumstance of promoting coptisine availability by pursuing nano- or microrods strategies or applying salt-forming process to coptisine, can it be introduced to clinical trial.

© 2019 The Authors. Journal of Cellular and Molecular Medicine published by Foundation for Cellular and Molecular Medicine and John Wiley & Sons Ltd.

KEYWORDS

coptisine; crosstalk network; pharmacological mechanism; signalling pathways bioavailability

Title

Coptisine from Coptis chinensis exerts diverse beneficial properties: A concise review.

Author

Wu J1, Luo Y1, Deng D2, Su S1, Li S3, Xiang L1, Hu Y1, Wang P1, Meng X1.

Publish date

2019 Dec

PMID

28606475

Abstract

Coptisine is a natural occurring isoquinoline alkaloid isolated from the traditional Chinese medicinal herb Rhizoma coptidis. Coptisine has been reported to have protective effects on reperfusion injury in cardiomyocytes, however, the underlying mechanism remains uncertain. Here, we used a hypoxia/reoxygenation (H/R)-treated H9c2 cell model to study the protective effects of coptisine on cardiomyocyte. The results showed that NaS2O4 induced hypoxia/reoxygenation model increased apoptosis and up-regulated autophagy marker LC3-II and cleaved Caspase-3, Beclin1 and Sirt1 levels. Coptisine treatment increased cell survival, inhibited apoptosis, and reduced the protein level of LC3-II, cleaved Caspase-3, Beclin1 and Sirt1. Further, we showed that coptisine combined with chloroquine (CQ), the inhibitor of autolysosome, reduced LC3-II, suggesting that coptisine may inhibit autophagosome formation than induction of autolysosome in the autophagy events. Our results indicate that coptisine may protect cardiomyocyte damage by H/R through suppressing autophagy. Overall, our study provides a new mechanism for the treatment of coptisine on H/R-induced cardiomyocyte damage and death.

Copyright © 2017 Elsevier Inc. All rights reserved.

KEYWORDS

Apoptosis; Autophagy; Cardiomyocyte; Coptisine; Hypoxia/reoxygenation

Title

Coptisine protects cardiomyocyte against hypoxia/reoxygenation-induced damage via inhibition of autophagy.

Author

Wang Y1, Wang Q2, Zhang L1, Ke Z1, Zhao Y1, Wang D1, Chen H1, Jiang X1, Gu M1, Fan S3, Huang C4.

Publish date

2017 Aug 19