Axillaridine

CAS# 23506-96-9

Axillaridine

2D Structure

Catalog No. BCN2060----Order now to get a substantial discount!

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3D structure

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Axillaridine

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Chemical Properties of Axillaridine

Cas No. 23506-96-9 SDF Download SDF
PubChem ID 179398 Appearance Cryst.
Formula C18H27NO6 M.Wt 353.41
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CCC1(C(C(C(=O)OC2CCN3C2C(=CC3)COC1=O)C(C)C)O)O
Standard InChIKey PHBXHCOARFTKGZ-VFCJXBEMSA-N
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 Axillaridine

The herbs of Pachysandra axillaris

Biological Activity of Axillaridine

Description1. Axillaridine shows significant activity as antiestrogen binding site-inhibitory agents. 2. The complexation of AChE with Axillaridine-A, results in the reduction of gorge size due to interaction between the ligand and the active site residues.
TargetsAChR | Estrogen receptor | Progestogen receptor

Axillaridine Dilution Calculator

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Axillaridine Molarity Calculator

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Preparing Stock Solutions of Axillaridine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8296 mL 14.1479 mL 28.2957 mL 56.5915 mL 70.7394 mL
5 mM 0.5659 mL 2.8296 mL 5.6591 mL 11.3183 mL 14.1479 mL
10 mM 0.283 mL 1.4148 mL 2.8296 mL 5.6591 mL 7.0739 mL
50 mM 0.0566 mL 0.283 mL 0.5659 mL 1.1318 mL 1.4148 mL
100 mM 0.0283 mL 0.1415 mL 0.283 mL 0.5659 mL 0.7074 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 Axillaridine

Activity-guided isolation of steroidal alkaloid antiestrogen-binding site inhibitors from Pachysandra procumbens.[Pubmed:9784163]

J Nat Prod. 1998 Oct;61(10):1257-62.

Four novel steroidal alkaloids, (+)-(20S)-20-(dimethylamino)-3-(3'alpha-isopropyl)-lactam-5alpha-+ ++preg n-2-en-4-one (1), (+)-(20S)-20-(dimethylamino)-16alpha-hydroxy-3-(3'alpha-isopropyl) -la ctam-5alpha-pregn-2-en-4-one (2), (+)-(20S)-3-(benzoylamino)-20-(dimethylamino)-5alpha-pregn-2-en-++ +4beta -yl acetate (3), and (+)-(20S)-2alpha-hydroxy-20-(dimethylamino)-3beta-phthalimido-5 alpha- pregnan-4beta-yl acetate (4), as well as five known compounds, (-)-pachyaximine A (5), (+)-spiropachysine (6), (+)-Axillaridine A (7), (+)-epipachysamine D (8), and (+)-pachysamine B (9), were isolated from Pachysandra procumbens, using a bioassay-guided fractionation based on inhibition of 3H-tamoxifen binding at the antiestrogen binding site (AEBS). Compounds 1-7 and 9 demonstrated significant activity as AEBS-inhibitory agents, and compounds 3, 5 and 9 were found to potentiate significantly the antiestrogenic effect mediated by tamoxifen in cultured Ishikawa cells. The structure elucidation of compounds 1-4 was carried out by spectral data interpretation.

Molecular dynamics simulation of Axillaridine-A: a potent natural cholinesterase inhibitor.[Pubmed:19555175]

J Enzyme Inhib Med Chem. 2009 Oct;24(5):1101-5.

Molecular Dynamics (MD) simulations were carried out for human acetylcholinesterase (hAChE) and its complex with Axillaridine-A, in order to dynamically explore the active site of the protein and the behaviour of the ligand at the peripheral binding site. Simulation of the enzyme alone showed that the active site of AChE is located at the bottom of a deep and narrow cavity whose surface is lined with rings of aromatic residues while Tyr72 is almost perpendicular to the Trp286, which is responsible for stable pi -pi interactions. The complexation of AChE with Axillaridine-A, results in the reduction of gorge size due to interaction between the ligand and the active site residues. The gorge size was determined by the distance between the center of mass of Glu81 and Trp286. As far as the geometry of the active site is concerned, the presence of ligand in the active site alters its specific conformation, as revealed by stable hydrogen bondings established between amino acids. With the increasing interaction between ligand and the active amino acids, size of the active site of the complex decreases with respect to time. Axillaridine-A, forms stable pi -pi interactions with the aromatic ring of Tyr124 that results in inhibition of catalytic activity of the enzyme. This pi -pi interaction keeps the substrate stable at the edge of the catalytic gorge by inhibiting its catalytic activity. The MD results clearly provide an explanation for the binding pattern of bulky steroidal alkaloids at the active site of AChE.

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