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

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) Mohan?et al.?(2004),?Withaferin A is a potent inhibitor of angiogenesis; Angiogenesis, 7 115 2) Kaileh?et al.?(2007),?Withaferin A strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with inhibition of its kinase activity; J. Biol. Chem.,?282?4253 3) Bargagna-Mohan?et al.?(2007),?The tumor inhibitor and antiangiogenic agent withaferin A targets the intermediate filament protein vimentin; Chem. Biol.,?14?623 4) Thaiparambil?et al.?(2011),?Withaferin A inhibits breast cancer invasion and metastasis at sub-cytotoxic doses by inducing vimentin disassembly and serine 56 phosphorylation; Int. J. Cancer,?129?2744 5) Livne-Bar?et al.?(2016),?Pharmacologic inhibition of reactive gliosis blocks TNF-α-mediated neuronal apoptosis;?Cell Death Dis.,?7?e2386

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