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Coptisine chloride

$155

  • Brand : BIOFRON

  • Catalogue Number : BF-C1014

  • Specification : 98%

  • CAS number : 6020-18-4

  • Formula : C19H14ClNO4

  • Molecular Weight : 355.77

  • PUBCHEM ID : 72321

  • Volume : 20mg

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Catalogue Number

BF-C1014

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

355.77

Appearance

Red crystal

Botanical Source

Chelidonium majus,Coptis chinensis

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.[Cl-]

Synonyms

6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquinolino[3,2-a]isoquinolin-5-ium chloride/Coptisine chloride/Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium, 6,7-dihydro-, chloride/6,7-dihydrobis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium chloride/[1,3]Benzodioxolo[5,6-a]-1,3-benzodioxolo[4,5-g]quinolizinium, 6,7-dihydro-, chloride (1:1)/6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinolin-5-ium chloride/Coptisine (chloride)

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;chloride

Applications

Coptisine chloride 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

1.51g/cm3

Solubility

Methanol; Wter containing soda

Flash Point

190.4ºC

Boiling Point

601.5ºC at 760 mmHg

Melting Point

>258ºC (dec.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2934990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:6020-18-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31400784

Abstract

Isoquinoline alkaloids possess broad pharmacological activities. In this study, the antifungal activity of twelve isoquinoline alkaloids, including berberine (1), jatrorrhizine (2), coptisine (3), corydaline (4), tetrahydroberberine (5), chelidonine (6), dihydrosanguinarine (7), chelerythrine (8), sanguinarine (9), palmatine (10), tetrahydropalmatine (11) and columbamine (12) were evaluated against eight plant pathogenic fungi in vitro. All the tested compounds showed varying degrees of inhibition against the eight tested plant fungi. Among them, sanguinarine exhibited high antifungal activity (EC50 ranging from 6.96-59.36 μg/mL). It displayed the best inhibitory activity against Magnaporthe oryzae (EC50 = 6.96 μg/mL), compared with azoxystrobin (EC50 = 12.04 μg/mL), and significantly suppressed spore germination of M. oryzae with the inhibition rate reaching 100% (50 μg/mL). The optical microscopy and scanning electron microscopy observations revealed that after treating M. oryzae mycelia with sanguinarine at 10 μg/mL, the mycelia appeared curved, collapsed and the cell membrane integrity was eventually damaged. Furthermore, the reactive oxygen species production, mitochondrial membrane potential and nuclear morphometry of mycelia had been changed, and the membrane function and cell proliferation of mycelia were destroyed. These results will enrich our insights into action mechanisms of antifungal activity of sanguinarine against M. oryzae.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Fungicidal activity; Isoquinoline alkaloids; Sanguinarine

Title

Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine.

Author

Zhao ZM1, Shang XF2, Lawoe RK1, Liu YQ3, Zhou R1, Sun Y1, Yan YF1, Li JC1, Yang GZ1, Yang CJ1.

Publish date

2019 Sep

PMID

31382302

Abstract

Pyrrolizidine alkaloids are secondary plant constituents that became a subject of public concern because of their hepatotoxic, pneumotoxic, genotoxic, and cytotoxic effects. Due to disregardful harvesting and/or contamination with pyrrolizidine alkaloid-containing plants, there is a high risk of ingesting these substances with plant extracts or natural products. The limit for the daily intake was set to 0.007 µg/kg body weight. If contained in an extract, cleanup methods may help to minimize the pyrrolizidine alkaloid concentration. For this purpose, a material for depleting pyrrolizidine alkaloids in herbal preparations was developed based on the approach of molecular imprinting using monocrotaline. Molecular imprinted polymers are substances with specific binding characteristics, depending on the template used for imprinting. By means of group imprinting, only one molecule is used for creating selective cavities for many molecular pyrrolizidine alkaloid variations. Design of Experiment was used for the development using a 25 screening plan resulting in 64 polymers (32 MIPs/32 NIPs). Rebinding trials revealed that the developed material can compete with common cation exchangers and is more suitable for depleting pyrrolizidine alkaloids than C18- material. Matrix trials using an extract from Chelidonium majus show that there is sufficient binding capacity for pyrrolizidine alkaloids (80%), but the material is lacking in selectivity towards pyrrolizidine alkaloids in the presence of other alkaloids with similar functional groups such as berberine, chelidonine, and coptisine. Beyond this interaction, the selectivity could be proven for other structurally different compounds on the example of chelidonic acid.

Georg Thieme Verlag KG Stuttgart · New York.

Title

Development of a Selective Adsorbing Material for Binding of Pyrrolizidine Alkaloids in Herbal Extracts, Based on Molecular Group Imprinting.

Author

Kopp T1,2, Abdel-Tawab M1, Khoeiklang M1, Mizaikoff B2.

Publish date

2019 Sep;

PMID

31279667

Abstract

Many drugs with anti-diabetic effects regulate glucose consumption in peripheral tissues. Via cellular glucose consumption assays, we identified that coptisine, a main effective constituent from the plant Coptis chinensis, enhanced hepatic and skeletal muscle glucose consumption. We further explored its effects on glucose metabolism in diabetic animals to elucidate its mechanism of action. Our results showed that coptisine did not show cytotoxicity. Intragastric administration of coptisine for ten days in normal ICR mice markedly decreased fasting blood-glucose levels without significant effects on body weight. In alloxan-induced type 1 diabetic mice, intragastric administration of coptisine for 28 days decreased fasting and non-fasting blood-glucose levels as well. In type 2 diabetic KKAy mice, intragastric administration of coptisine for nine weeks improved glucose tolerance. It decreased fasting/non-fasting blood-glucose and fructosamine levels. Coptisine decreased low-density lipoprotein and total cholesterol levels, however, had no significant effect on triglyceride levels. Coptisine increased AMPK phosphorylation while decreasing Akt phosphorylation in HepG2 hepatic cells and C2C12 myotubes. Coptisine also reduced mitochondrial respiration in isolated and cellular mitochondria, suggesting that coptisine lowered cellular energy levels. In particularly, coptisine administration (10-6 M) decreased the mitochondrial oxygen consumption rate (OCR) with a greater extracellular acidification rate (ECAR), resulting in an oxidative-to-glycolysis phosphorylation shifted for cellular energy generation. Our results demonstrate that coptisine acts as an enhancer of peripheral glucose consumption could improve glucose metabolism in diabetic animals. Coptisine may serve as a novel anti-diabetic agent and warrant further evaluation.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

AMPK; Coptisine; Diabetes; Glucose consumption; Mitochondrion; Natural compound

Title

Glucose consumption assay discovers coptisine with beneficial effect on diabetic mice.

Author

Shi LL1, Jia WH1, Zhang L1, Xu CY2, Chen X1, Yin L1, Wang NQ1, Fang LH1, Qiang GF1, Yang XY3, Du GH4.

Publish date

2019 Sep 15