Axillaridine | CAS:23506-96-9 | Manufacturer ChemFaces

Axillaridine

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Description:

Axillaridine shows significant activity as antiestrogen binding site-inhibitory agents. 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.

Targets:

AChR | Estrogen receptor | Progestogen receptor

In vitro:

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

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

METHODS AND RESULTS:
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).
CONCLUSIONS:
Compounds 1-7 and 9 demonstrated significant activity as AEBS-inhibitory agents.

Axillaridine Description

Source:	The herbs of Pachysandra axillaris
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

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

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

METHODS AND RESULTS:
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.
CONCLUSIONS:
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.

Product Name	Axillaridine
Price:
CAS No.:	23506-96-9
Catalog No.:	CFN00348
Molecular Formula:	C₁₈H₂₇NO₆
Molecular Weight:	353.41 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Cryst.
Source:	The herbs of Pachysandra axillaris
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Anti-estrogenic effect Compound Library Alkaloids Compound Library Progestogen receptor Inhibitor Library Estrogen receptor Inhibitor Library AChR Inhibitor Library

	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

CFN00347	Axillarine	19637-66-2	369.41	C₁₈H₂₇NO₇
CFN00348	Axillaridine	23506-96-9	353.41	C₁₈H₂₇NO₆
CFN00349	Othonnine	119565-25-2	353.41	C₁₈H₂₇NO₆
CFN00356	Croalbidine	41714-30-1	371.43	C₁₈H₂₉NO₇
CFN00371	Grantaline	83482-61-5	351.40	C₁₈H₂₅NO₆
CFN00381	17-Methylparsonsianidine	135637-68-2	469.53	C₂₃H₃₅NO₉
CFN00383	Spiracine	77156-24-2	485.53	C₂₃H₃₅NO₁₀
CFN00397	Parsonsianidine	135601-81-9	455.50	C₂₂H₃₃NO₉
CFN00398	Parsonsianine	131683-36-8	441.48	C₂₁H₃₁NO₉
CFN00433	Trichodesmine	548-90-3	353.41	C₁₈H₂₇NO₆