ChemicalBook Product Catalog Analytical Chemistry Analysis reagents Ion chromatography reagents WITHAFERIN A

WITHAFERIN A

Product NameWITHAFERIN A
CAS5119-48-2
MFC28H38O6
MW470.6
EINECS999-999-2
MOL File5119-48-2.mol

Chemical Properties

Melting point	252-253℃
alpha	D28 +125° (c = 1.30 in CHCl3)
Boiling point	680.7±55.0 °C(Predicted)
Density	1.28
Flash point	226℃
storage temp.	Desiccate at -20°C
solubility	Soluble in DMSO (up to 20 mg/ml)
pka	13.49±0.70(Predicted)
form	White solid
color	White
biological source	plant (Withania somnifera)
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
Major Application	food and beverages
InChIKey	DBRXOUCRJQVYJQ-CKNDUULBSA-N
SMILES	C[C@H]([C@H]1CC(C)=C(CO)C(=O)O1)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C

Safety Information

Hazard Codes	T
WGK Germany	3
RTECS	KE7288500
HS Code	29322090
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Withaferin A (5119-48-2) displays potent antiangiogenesis activity inhibiting endothelial cell sprouting in vitro(IC50= 12 nM) andin vivo.1Potently inhibits NF-κB activation by preventing TNFα-induced activation of IKKβ.2Covalently binds to the intermediate filament protein, vimentin3inducing its disassembly and serine 56 phosphorylation4. Inhibits reactive gliosis and blocks TNFα-mediated neuronal apoptosis inin vivomodels.5

Chemical Properties

Solid

Uses

Withaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986). Withaferin A has recently been found to be a leptin sensitizer that can reduce the weight in obese mice fed in a high-fat diet (see C249500).

Definition

ChEBI: A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Phys lis longifolia, it exhibits cytotoxic activity.

Biological Activity

Steroid lactone that displays anti-inflammatory, antitumor and antiangiogenic activity. Inhibits endothelial cells (HUVEC) spouting in vitro (IC 50 = 12 nM) and in vivo . Prevents NF- κ B activation by inhibiting activation of IKK β . Also inhibits chymotrypsin-like activity of the 20S proteasome.

target

ROS | NF-kB | p53 | STAT | PARP | Bcl-2/Bax | Caspase | TGF-β/Smad | TNF-α | COX | PGE | PI3K | Akt | JNK | p38MAPK

storage

Store at -20°C

References

[1] ROYCE MOHAN. Withaferin A is a potent inhibitor of angiogenesis[J]. Angiogenesis, 2004, 7 2: 115-122. DOI:10.1007/s10456-004-1026-3
[2] MARY KAILEH. Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity.[J]. The Journal of Biological Chemistry, 2007, 282 7: 4253-4264. DOI:10.1074/jbc.m606728200
[3] PAOLA BARGAGNA-MOHAN. The tumor inhibitor and antiangiogenic agent withaferin A targets the intermediate filament protein vimentin.[J]. Chemistry & biology, 2007, 14 6: 623-634. DOI:10.1016/j.chembiol.2007.04.010
[4] JOSE T. THAIPARAMBIL. Withaferin A inhibits breast cancer invasion and metastasis at sub-cytotoxic doses by inducing vimentin disassembly and serine 56 phosphorylation[J]. International Journal of Cancer, 2011, 129 11: 2744-2755. DOI:10.1002/ijc.25938
[5] IZHAR LIVNE-BAR. Pharmacologic inhibition of reactive gliosis blocks TNF-α-mediated neuronal apoptosis[J]. Cell Death & Disease, 2016, 7 9: e2386-e2386. DOI:10.1038/cddis.2016.277

WITHAFERIN A Supplier

WITHAFERIN A manufacturers

Related Product Information

Send Inquriy