WITHAFERIN A 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.

InChIKey

DBRXOUCRJQVYJQ-CKNDUULBSA-N

Safety Information

Hazard Codes 

T

WGK Germany 

3

RTECS 

KE7288500

HS Code 

29322090

WITHAFERIN A Usage And Synthesis

Description

Withaferin A (5119-48-2) displays potent antiangiogenesis activity inhibiting endothelial cell sprouting in vitro?(IC50?= 12 nM) and?in vivo.1?Potently inhibits NF-κB activation by preventing TNFα-induced activation of IKKβ.2?Covalently binds to the intermediate filament protein, vimentin3?inducing its disassembly and serine 56 phosphorylation4. Inhibits reactive gliosis and blocks TNFα-mediated neuronal apoptosis in?in vivo?models.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(5119-48-2)Related Product Information

• Brassinolide
• (2alpha,3beta,19alpha)-2,3,19-Trihydroxyolean-12-en-28-oic acid beta-D-glucopyranosyl ester
• HELENALIN
• 5-Aminosalicylic acid
• BAY 11-7085
• Kidney Bean Extract
• BAY 11-7082
• ROCAGLAMIDE
• 6-AMINO-4-(4-PHENOXYPHENYLETHYLAMINO)QUINAZOLINE
• 3'-Hydroxyrocaglamide
• panepoxydone
• WEDELOLACTONE
• WILFORINE
• Worenine
• WILFORDINE
• BETA-D-GLUCOPYRANOSIDURONIC ACID
• HYPERICUM PERFORATUM OIL
• WILFORGINE