| Identification | Back Directory | [Name]
WITHAFERIN A | [CAS]
5119-48-2 | [Synonyms]
nsc-101088
NSC 273757
Withaferine
WITHAFERIN A
withaferinea
Withaferin A Standard
Withaferin A 5119-48-2
delta-lactone,(20s,22r)-oxo
Withaferin A from leaves of Withania somnifera
5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide
Withaferin A, Withania somnifera - CAS 5119-48-2 - Calbiochem
Withaferin A NSC 273757 NSC 101088
5,6-beta-epoxy-4-beta,22,27-trihydroxy-1-5-beta-ergosta-24-dien-26-oicacid
(4β,5β,6β,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oicacidδ-lactone
(20S,22R)-5,6β-Epoxy-4β,22,27-trihydroxy-1-oxo-5β-ergosta-
2,24-dien-26-oic Acid δ-Lactone
Ergosta-2,24-dien-26-oicacid, 5,6-epoxy-4,22,27-trihydroxy-1-oxo-, d-lactone, (4b,5b,6b,22R)-
Ergosta-2,24-dien-26-oic acid, 5,6-epoxy-4,22,27-trihydroxy-1-oxo-, δ-lactone, (4β,5β,6β,22R)- | [EINECS(EC#)]
999-999-2 | [Molecular Formula]
C28H38O6 | [MDL Number]
MFCD01746239 | [MOL File]
5119-48-2.mol | [Molecular Weight]
470.6 |
| Chemical Properties | Back Directory | [Melting point ]
252-253℃ | [alpha ]
D28 +125° (c = 1.30 in CHCl3) | [Boiling point ]
680.7±55.0 °C(Predicted) | [density ]
1.28 | [Fp ]
226℃ | [storage temp. ]
Desiccate at -20°C | [solubility ]
Soluble in DMSO (up to 20 mg/ml) | [form ]
White solid | [pka]
13.49±0.70(Predicted) | [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 |
| Hazard Information | Back Directory | [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). | [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 |
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