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Groenlandicine

CAS# 38691-95-1

Groenlandicine

Catalog No. BCN8189----Order now to get a substantial discount!

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Chemical structure

Groenlandicine

3D structure

Chemical Properties of Groenlandicine

Cas No. 38691-95-1 SDF Download SDF
PubChem ID 3084708 Appearance Powder
Formula C19H16NO4 M.Wt 322.10
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES COC1=C(C=C2CC[N+]3=C(C2=C1)C=C4C=CC5=C(C4=C3)OCO5)O
Standard InChIKey PGIOBGCIEGZHJH-UHFFFAOYSA-O
Standard InChI InChI=1S/C19H15NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,6-9H,4-5,10H2,1H3/p+1
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.

Source of Groenlandicine

The herbs of Coptis groenlandica

Biological Activity of Groenlandicine

Description1. Groenlandicine has bitter, and also has antibacterial activity on E. coli and S. aureus, there was close relationship between the bitter degree and antibacterial activity of bitter components. 2. Groenlandicine may be a promising anti-Alzheimer's disease agent due to its potent inhibitory activity of both ChEs and beta-amyloids formation, as well as marked ONOO(-) scavenging and good ROS inhibitory capacities. 3. Groenlandicine exhibits moderate inhibitory effects with the IC(50) value of 140.1 microM for rat lens aldose reductase (RLAR) and 154.2 microM for human recombinant AR (HRAR), it has beneficial uses in the development of therapeutic and preventive agents for diabetic complications and diabetes mellitus. 4. Groenlandicine is a active principle with topoisomerase I-mediated DNA cleavage activity in vitro.
TargetsROS | AChR | BChE | Antifection | Topoisomerase

Groenlandicine Dilution Calculator

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Preparing Stock Solutions of Groenlandicine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1046 mL 15.5231 mL 31.0463 mL 62.0925 mL 77.6156 mL
5 mM 0.6209 mL 3.1046 mL 6.2093 mL 12.4185 mL 15.5231 mL
10 mM 0.3105 mL 1.5523 mL 3.1046 mL 6.2093 mL 7.7616 mL
50 mM 0.0621 mL 0.3105 mL 0.6209 mL 1.2419 mL 1.5523 mL
100 mM 0.031 mL 0.1552 mL 0.3105 mL 0.6209 mL 0.7762 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.

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References on Groenlandicine

Anti-Alzheimer and antioxidant activities of Coptidis Rhizoma alkaloids.[Pubmed:19652386]

Biol Pharm Bull. 2009 Aug;32(8):1433-8.

Coptidis Rhizoma and its isolated alkaloids are reported to possess a variety of activities, including neuroprotective and antioxidant effects. Thus, the anti-Alzheimer and antioxidant effects of six protoberberine alkaloids (berberine, palmatine, jateorrhizine, epiberberine, coptisine, and Groenlandicine) and one aporphine alkaloid (magnoflorine) from Coptidis Rhizoma were evaluated via beta-site amyloid precursor protein (APP) cleaving enzyme 1 (BACE1), acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) assays, along with peroxynitrite (ONOO(-)) scavenging and total reactive oxygen species (ROS) inhibitory assays. Six protoberberine alkaloids exhibited predominant cholinesterases (ChEs) inhibitory effects with IC(50) values ranging between 0.44-1.07 microM for AChE and 3.32-6.84 microM for BChE; only epiberberine (K(i)=10.0) and Groenlandicine (K(i)=21.2) exerted good, non-competitive BACE1 inhibitory activities with IC(50) values of 8.55 and 19.68 microM, respectively. In two antioxidant assays, jateorrhizine and Groenlandicine exhibited significant ONOO(-) scavenging activities with IC(50) values of 0.78 and 0.84 microM, respectively; coptisine and Groenlandicine exhibited moderate total ROS inhibitory activities with IC(50) values of 48.93 and 51.78 microM, respectively. These results indicate that Coptidis Rhizoma alkaloids have a strong potential of inhibition and prevention of Alzheimer's disease (AD) mainly through both ChEs and beta-amyloids pathways, and additionally through antioxidant capacities. In particular, Groenlandicine may be a promising anti-AD agent due to its potent inhibitory activity of both ChEs and beta-amyloids formation, as well as marked ONOO(-) scavenging and good ROS inhibitory capacities. As a result, Coptidis Rhizoma and the alkaloids contained therein would clearly have beneficial uses in the development of therapeutic and preventive agents for AD and oxidative stress-related disease.

Inhibitory activities of the alkaloids from Coptidis Rhizoma against aldose reductase.[Pubmed:19023536]

Arch Pharm Res. 2008 Nov;31(11):1405-12.

As part of our ongoing search of natural sources for therapeutic and preventive agents for diabetic complications, the rat lens aldose reductase (RLAR) inhibitory effect of Coptidis Rhizoma (the rhizome of Coptis chinensis Franch) was evaluated. Its extract and fractions exhibited broad and moderate RLAR inhibitory activities of 38.9 approximately 67.5 microg/mL. In an attempt to identify bioactive components, six quaternary protoberberine-type alkaloids (berberine, palmatine, jateorrhizine, epiberberine, coptisine, and Groenlandicine) and one quaternary aporphine-type alkaloid (magnoflorine) were isolated from the most active n-BuOH fraction, and the chemical structures therein were elucidated on the basis of spectroscopic evidence and comparison with published data. The anti-diabetic complications capacities of seven C. chinensis-derived alkaloids were evaluated via RLAR and human recombinant AR (HRAR) inhibitory assays. Although berberine and palmatine were previously reported as prime contributors to AR inhibition, these two major components exhibited no AR inhibitory effects at a higher concentration of 50 microg/ml in the present study. Conversely, epiberberine, coptisine, and Groenlandicine exhibited moderate inhibitory effects with IC(50) values of 100.1, 118.4, 140.1 microM for RLAR and 168.1, 187.3, 154.2 microM for HRAR. The results clearly indicated that the presence of the dioxymethylene group in the D ring and the oxidized form of the dioxymethylene group in the A ring were partly responsible for the AR inhibitory activities of protoberberine-type alkaloids. Therefore, Coptidis Rhizoma, and the alkaloids contained therein, would clearly have beneficial uses in the development of therapeutic and preventive agents for diabetic complications and diabetes mellitus.

Protective role of Coptidis Rhizoma alkaloids against peroxynitrite-induced damage to renal tubular epithelial cells.[Pubmed:15807993]

J Pharm Pharmacol. 2005 Mar;57(3):367-74.

A study was conducted to elucidate and compare the protective activity of alkaloids from Coptidis Rhizoma (berberine, coptisine, palmatine, epiberberine, jatrorhizine, Groenlandicine and magnoflorine) using an LLC-PK(1) cell under peroxynitrite (ONOO(-)) generation model. Treatment with 3-morpholinosydnonimine (SIN-1) led to an increase in cellular ONOO(-) generation in comparison with non-treated cells. However, Coptidis Rhizoma extract and its alkaloids, except for berberine, reduced the cellular ONOO(-) level. In addition, DNA fragmentation induced by SIN-1 was significantly decreased by the extract, and also by coptisine, epiberberine, jatrorhizine, Groenlandicine and magnoflorine. Moreover, treatment with berberine, coptisine, palmatine and epiberberine exerted a protective effect against G(0)/G(1)phase arrest of cell cycle induced by SIN-1. The increase in cellular ONOO(-) generation, DNA damage and disturbance of the cell cycle by SIN-1 resulted in a decrease in cell viability. However, Coptidis Rhizoma extract, epiberberine, jatrorhizine, Groenlandicine and magnoflorine significantly increased cell viability even at a concentration as low as 10 microg mL(-1). These findings demonstrate that Coptidis Rhizoma extract and its alkaloids can ameliorate the cell damage associated with ONOO(-) generation in renal tubular LLCPK(1) cells, and that the various alkaloids have distinctive mechanisms of action, such as ONOO(-) scavenging, protection from DNA damage and control of the cell cycle. Furthermore, the data suggest that among the Coptidis Rhizoma alkaloids, coptisine is the most effective for protection against SIN-1-induced cellular injury in terms of its potency and content.

[Research on bitter components from Coptis chinensis based on electronic tongue].[Pubmed:25522621]

Zhongguo Zhong Yao Za Zhi. 2014 Sep;39(17):3326-9.

Isolated alkaloids from Coptis chinensis Franch. The compounds were identified as berberine, columbamine, Groenlandicine, jatrorrhizine, magnoflorine, corydaldine and ferulic acid methylester. Then measured their bitter degree based on the electronic tongue and evaluated the antibacterial. The results based on the Electronic Tongue showed that berberine, columbamine, Groenlandicine and jatrorrhizine have higher bitter degree than magnoflorine and corydaldine. And they also appeared better antibacterial activity on E. coli and S. aureus. The correlation coefficients between bitter degree and the two bacteria antibacterial activity were 0.983 and 0.911. So there was close relationship between the bitter degree and antibacterial activity of bitter components. Thus, it is confirmed further that bitter components are the material foundation of medicinal effectiveness of bitter herbs.

Description

Groenlandicine is a protoberberine alkaloid isolated from Coptidis Rhizoma. Groenlandicine exhibits moderate inhibitory effect with IC50 value of 154.2 μM for human recombinant aldose reductase (HRAR). Groenlandicine selectively induces topoisomerase I-mediated DNA cleavage.

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