Armepavine

CAS# 524-20-9

Armepavine

Catalog No. BCN8490----Order now to get a substantial discount!

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Quality Control of Armepavine

Number of papers citing our products

Chemical structure

Armepavine

3D structure

Chemical Properties of Armepavine

Cas No. 524-20-9 SDF Download SDF
PubChem ID 442169 Appearance White powder
Formula C19H23NO3 M.Wt 313.39
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Alkaloid D from Evonymus europaea; Evoeuropine
Solubility Soluble in methanol and chloroform
Chemical Name 4-[[(1~{R})-6,7-dimethoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-1-yl]methyl]phenol
SMILES CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)OC)OC
Standard InChIKey ZBKFZIUKXTWQTP-QGZVFWFLSA-N
Standard InChI InChI=1S/C19H23NO3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21H,8-10H2,1-3H3/t17-/m1/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 Armepavine

The herbs of Nelumbo nucifera

Biological Activity of Armepavine

DescriptionArmepavine exerts both in vitro and in vivo antifibrotic effects in rats, with inhibition of NF-κB, JunD and C/EBPß pathways. It also shows cytotoxic activity.
TargetsNF-κB | JunD | C/EBPß
In vitro

Phytochemical study and cytotoxic activity of alkaloids from Uvaria chamae P. Beauv.[Pubmed: 11031775]

Pharmazie. 2000 Sep;55(9):688-9.


METHODS AND RESULTS:
Phytochemical study of leaves of Uvaria chamae resulted in the isolation for the first time for the genus Uvaria of benzylisoquinoline alkaloids (+)-Armepavine (1) and racem. O,O-dimethylcoclaurine (2). The aporphines nornantenine (3), nantenine (4) and corydine (7) are new for the species.
CONCLUSIONS:
The alkaloids were found to express cytotoxic activity against L 929 transformed cells. The highest activity was shown by 1, 3, and 5. At a concentration corresponding to their IC50 against L929 cells, they were nontoxic against mouse thymocytes.

In vivo

Effects of armepavine against hepatic fibrosis induced by thioacetamide in rats.[Pubmed: 21717514 ]

Phytother Res. 2012 Mar;26(3):344-53.

The aim of this study was to investigate if Armepavine (Arm, C₁₉H₂₃O₃N) could exert inhibitory effects against hepatic fibrosis in rats.
METHODS AND RESULTS:
A cell line of rat hepatic stellate cells (HSC-T6) was stimulated with tumour necrosis factor-α (TNF-α) to evaluate the inhibitory effects of Arm. Rats were injected with thioacetamide (TAA; 300 mg/kg, intraperitoneally) thrice a week for 4 weeks to induce hepatic fibrosis, with Arm (3 or 10 mg/kg) given by gavage twice a day. Liver sections were taken for western blotting, fibrosis scoring and immunofluorescence staining. Arm (1-10 µm) concentration-dependently attenuated TNF-α-stimulated: (i) protein expressions of α-smooth muscle actin (α-SMA), collagen type I and angiopoietin-1; (ii) H₂O₂ production; and (iii) NF-κB, JunD and C/EBPß (cytidine-cytidine-adenosine-adenosine-thymidine (CCAAT)/enhancer binding protein-ß (EBPß)) nuclear translocations in HSC-T6 cells. In vivo Arm treatment significantly reduced plasma aspartate transaminase and alanine transaminase levels, hepatic α-SMA expression and collagen contents, and fibrosis scores of TAA-injected rats. Moreover, Arm treatment decreased α-SMA- and NF-κB-positive cells in immunohistochemical staining, and mRNA expression levels of IL-6, TGF-ß1, TIMP-1, col1α2, iNOS and ICAM-1 genes, but up-regulated the metallothionein gene in the livers of TAA-injected rats.
CONCLUSIONS:
Our results indicated that Arm exerted both in vitro and in vivo antifibrotic effects in rats, with inhibition of NF-κB, JunD and C/EBPß pathways.

Protocol of Armepavine

Structure Identification
Molecules. 2016 Jul 19;21(7).

Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity.[Reference: WebLink]

A quantitative analytical method for five aporphine alkaloids, nuciferine (1), nornuciferine (2), N-methylasimilobine (3), asimilobine (4), and pronuciferine (5), and five benzylisoquinoline alkaloids, Armepavine (6), norArmepavine (7), N-methylcoclaurine (8), coclaurine (9), and norjuziphine (10), identified as the constituents responsible for the melanogenesis inhibitory activity of the extracts of lotus flowers (the flower buds of Nelumbo nucifera), has been developed using liquid chromatography-mass spectrometry.
METHODS AND RESULTS:
The optimum conditions for separation and detection of these 10 alkaloids were achieved on a πNAP column, a reversed-phase column with naphthylethyl group-bonded silica packing material, with CH₃CN-0.2% aqueous acetic acid as the mobile phase and using mass spectrometry equipped with a positive-mode electrospray ionization source. According to the protocol established, distributions of these 10 alkaloids in the petal, receptacle, and stamen parts, which were separated from the whole flower, were examined.
CONCLUSIONS:
As expected, excellent correlations were observed between the total alkaloid content and melanogenesis inhibitory activity. Among the active alkaloids, nornuciferine (2) was found to give a carbamate salt (2'') via formation of an unstable carbamic acid (2') by absorption of carbon dioxide from the air.

Armepavine Dilution Calculator

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Armepavine Molarity Calculator

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Preparing Stock Solutions of Armepavine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1909 mL 15.9546 mL 31.9091 mL 63.8182 mL 79.7728 mL
5 mM 0.6382 mL 3.1909 mL 6.3818 mL 12.7636 mL 15.9546 mL
10 mM 0.3191 mL 1.5955 mL 3.1909 mL 6.3818 mL 7.9773 mL
50 mM 0.0638 mL 0.3191 mL 0.6382 mL 1.2764 mL 1.5955 mL
100 mM 0.0319 mL 0.1595 mL 0.3191 mL 0.6382 mL 0.7977 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 Armepavine

Inhibition of (S)-armepavine from Nelumbo nucifera on autoimmune disease of MRL/MpJ-lpr/lpr mice.[Pubmed:16413531]

Eur J Pharmacol. 2006 Feb 15;531(1-3):270-9.

T cell immune responses play important roles in the pathogenesis of systemic lupus erythematosus (SLE). (S)-Armepavine (C19H23O3N; MW313) from Nelumbo nucifera suppresses T cells proliferation. To study its potential benefit on SLE, we examined effects of (S)-Armepavine on MRL/MpJ-lpr/lpr mice, which have similar disease features to human SLE. MRL/MpJ-lpr/lpr mice were treated orally with (S)-Armepavine for 6 weeks and their SLE characteristics were evaluated. The results revealed that (S)-Armepavine prevented lymphadenopathy and elongated life span of MRL/MpJ-lpr/lpr mice. It seemed to be mediated by inhibition of splenocytes proliferation, suppression of interleukin-2 (IL-2), interleukin-4, interleukin-10, and interferon-gamma (IFN-gamma) gene expressions, reduction of glomerular hypercellularity and immune complexes deposition, and decrease of urinary protein and anti-double stranded DNA autoantibody production. Furthermore, the data demonstrated (S)-Armepavine impaired IL-2 and IFN-gamma transcripts in human peripheral blood mononuclear cells. We suggest that (S)-Armepavine may be an immunomodulator for the management of autoimmune diseases like SLE.

Description

Armepavine, an active compound from Nelumbo nucifera, exerts not only anti-inflammatory effects on human peripheral blood mononuclear cells, but also immunosuppressive effects on T lymphocytes and on lupus nephritic mice. Armepavine inhibits TNF-α-induced MAPK and NF-κB signaling cascades.

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