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Uncarine E

CAS# 5171-37-9

Uncarine E

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Chemical structure

Uncarine E

3D structure

Chemical Properties of Uncarine E

Cas No. 5171-37-9 SDF Download SDF
PubChem ID 9885603 Appearance White-beige powder
Formula C21H24N2O4 M.Wt 368.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Isopteropodine
Solubility Soluble in chloroform and methan
Chemical Name methyl (1S,4aS,5aS,6S,10aS)-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate
SMILES CC1C2CN3CCC4(C3CC2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
Standard InChIKey JMIAZDVHNCCPDM-PFDNRQJHSA-N
Standard InChI InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14-,18-,21-/m0/s1
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 Uncarine E

The herbs of Uncaria rhynchophylla

Biological Activity of Uncarine E

DescriptionIsopteropodine has antimicrobial activity, it shows strong apoptotic effects on acute leukaemic lymphoblasts, it also shows an ability to stimulate the immune system.
TargetsAntifection
In vitro

Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells.[Pubmed: 16445836 ]

Br J Haematol. 2006 Mar;132(5):615-22.

Natural products are still an untapped source of promising lead compounds for the generation of antineoplastic drugs.
METHODS AND RESULTS:
Here, we investigated for the first time the antiproliferative and apoptotic effects of highly purified oxindole alkaloids, namely Isopteropodine (A1), pteropodine (A2), isomitraphylline (A3), uncarine F (A4) and mitraphylline (A5) obtained from Uncaria tomentosa, a South American Rubiaceae, on human lymphoblastic leukaemia T cells (CCRF-CEM-C7H2). Four of the five tested alkaloids inhibited proliferation of acute lymphoblastic leukaemia cells. Furthermore, the antiproliferative effect of the most potent alkaloids pteropodine (A2) and uncarine F (A4) correlated with induction of apoptosis. After 48 h, 100 micromol/l A2 or A4 increased apoptotic cells by 57%. CEM-C7H2 sublines with tetracycline-regulated expression of bcl-2, p16ink4A or constitutively expressing the cowpox virus protein crm-A were used for further studies of the apoptosis-inducing properties of these alkaloids. Neither overexpression of bcl-2 or crm-A nor cell-cycle arrest in G0/G1 phase by tetracycline-regulated expression of p16INK4A could prevent alkaloid-induced apoptosis.
CONCLUSIONS:
Our results show the strong apoptotic effects of pteropodine and uncarine F on acute leukaemic lymphoblasts and recommend the alkaloids for further studies in xenograft models.

Antimicrobial activity of isopteropodine.[Pubmed: 16042336 ]

Z Naturforsch C. 2005 May-Jun;60(5-6):385-8.


METHODS AND RESULTS:
Bioassay-directed fractionation for the determination of antimicrobial activity of Uncaria tomentosa, has led to the isolation of Isopteropodine (0.3%), a known Uncaria pentacyclic oxindol alkaloid that exhibited antibacterial activity against Gram positive bacteria.

In vivo

Cat's Claw: an herb from the Peruvian Amazon.[Pubmed: 11363206]

Sidahora. 1995 Apr-May:35-6.

Uncaria tomentosa, also known as cat's claw, an herb from the highlands of the Peruvian Amazon, has been used by natives for hundreds of years to treat immunologic and digestive disorders. Research began in the 1970s to discover the benefits of this plant in relieving symptoms of cancers, arthritis, and other ailments.
METHODS AND RESULTS:
It has the ability to cleanse the digestive tract, aiding victims of Crohn's, colitis, gastritis and more. In a 1989 study by Klaus Keplinger, several alkaloid oxidants found in the plant's roots showed an ability to stimulate the immune system. The principal alkaloids are Isopteropodine and rynchophyiline.
CONCLUSIONS:
Extracts of cat's claw mixed with AZT in an experimental drug, called Krallendom, were effective in reducing symptoms in AIDS patients in Austria. The plant has been useful in reducing secondary effects of radiation and chemotherapy in cancer victims as well.

Protocol of Uncarine E

Structure Identification
Biomed Chromatogr. 2017 Aug;31(8).

Rapid determination of oxindole alkaloids in cat's claw by HPLC using ionic liquid-based microwave-assisted extraction and silica monolithic column.[Pubmed: 28009448]

Cat's claw is a large woody vine with hook-like thorns, and has been traditionally used to treat inflammatory disorders in South and Central America.
METHODS AND RESULTS:
In this study, a rapid, validated high-performance liquid chromatographic (HPLC) method using a silica monolithic column was developed for the simultaneous determination of oxindole alkaloids, namely rhynchophylline, pteropodine, isomitraphylline and Isopteropodine, in cat's claw. The ionic liquid-based microwave-assisted extraction (ILMAE), considered as an environmentally friendly and powerful tool, was first applied in the extraction of oxindole alkaloids. To optimize the HPLC method, the stationary phases, pH values of mobile phase and flow rates were investigated. The validated HPLC method using a Monolithic RP18e column (100 × 4.6 mm) enables these analytes to be separated almost twice as fast as with a conventional particulate column (~16 vs ~30 min) with limits of quantification and detection of 0.5 and 0.15 μg/mL, respectively. The ILMAE conditions were optimized by the Taguchi orthogonal array design. In comparison with conventional water boiling extraction, ILMAE offers almost four times higher yields within an extremely short extraction time.
CONCLUSIONS:
The developed HPLC coupled with ILMAE method could be efficient and practical for rapid determination of oxindole alkaloids in cat's claw.

Uncarine E Dilution Calculator

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Preparing Stock Solutions of Uncarine E

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7144 mL 13.5722 mL 27.1444 mL 54.2888 mL 67.861 mL
5 mM 0.5429 mL 2.7144 mL 5.4289 mL 10.8578 mL 13.5722 mL
10 mM 0.2714 mL 1.3572 mL 2.7144 mL 5.4289 mL 6.7861 mL
50 mM 0.0543 mL 0.2714 mL 0.5429 mL 1.0858 mL 1.3572 mL
100 mM 0.0271 mL 0.1357 mL 0.2714 mL 0.5429 mL 0.6786 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 Uncarine E

Effects of Uncaria tomentosa total alkaloid and its components on experimental amnesia in mice: elucidation using the passive avoidance test.[Pubmed:11197086]

J Pharm Pharmacol. 2000 Dec;52(12):1553-61.

The effects of Uncaria tomentosa total alkaloid and its oxindole alkaloid components, Uncarine E, uncarine C, mitraphylline, rhynchophylline and isorhynchophylline, on the impairment of retention performance caused by amnesic drugs were investigated using a step-down-type passive avoidance test in mice. In this test, the retention performance of animals treated with the amnesic and test drugs before training was assessed 24 h after training. Uncaria tomentosa total alkaloid (10-20 mg kg(-1), i.p.) and the alkaloid components (10-40 mg kg(-1), i.p.), as well as the muscarinic receptor agonist oxotremorine (0.01 mg kg(-1), i.p.), significantly attenuated the deficit in retention performance induced by the muscarinic receptor antagonist scopolamine (3 mg kg(-1), i.p.). The effective doses of uncarine C and mitraphylline were larger than those of other alkaloid components. Uncarine E (20 mg kg(-1), i.p.) also blocked the impairment of passive avoidance performance caused by the nicotinic receptor antagonist mecamylamine (15 mg kg(-1), i.p.) and the N-methyl-D-aspartate (NMDA) receptor antagonist (+/-)-3-(2-carboxypiperazin-4-yl)-propyl-1-phosphonic acid (CPP; 7.5 mg kg(-1), i.p.), but it failed to affect the deficit caused by the benzodiazepine receptor agonist diazepam (2 mg kg(-1), i.p.). Rhynchophylline significantly reduced the mecamylamine-induced deficit in passive avoidance behaviour, but it failed to attenuate the effects of CPP and diazepam. These results suggest that Uncaria tomentosa total alkaloids exert a beneficial effect on memory impairment induced by the dysfunction of cholinergic systems in the brain and that the effect of the total alkaloids is partly attributed to the oxindole alkaloids tested. Moreover, these findings raised the possibility that the glutamatergic systems are implicated in the anti-amnesic effect of Uncarine E.

Description

Isopteropodine is heteroyohimbine-type oxindole alkaloid components of Uncaria tomentosa (Willd.) DC. Isopteropodine acts as positive modulators of muscarinic M1 and 5-HT2 receptors.

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