W4394
Withaferin A
≥95% (HPLC)
Synonym(s):
5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide, Withaferine A
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About This Item
Empirical Formula (Hill Notation):
C28H38O6
CAS Number:
Molecular Weight:
470.60
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
biological source
plant (Withania somnifera)
Quality Level
assay
≥95% (HPLC)
form
powder
mp
252-253 °C
functional group
epoxy, ketone
shipped in
ambient
storage temp.
2-8°C
SMILES string
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
InChI
1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
InChI key
DBRXOUCRJQVYJQ-CKNDUULBSA-N
Application
Withaferin A was used to treat HEK293 cells to study its effect on cystic fibrosis inflammation.
Biochem/physiol Actions
Steroidal lactone that exhibits cytotoxicity towards tumor cells. Protective effects attributed to anti-lipid peroxidative, antioxidant and detoxifying functionality.
Withaferin A is a steroidal lactone that is isolated from the plant Withania somnifera. It has potent anti-inflammatory properties as it inhibits the activation of NF-κ B signaling pathway. The anti-tumor activity of Withaferin A is due to its ability to alter cytoskeletal architecture by binding annexin II and disrupting F actin cross-links. Withaferin A also inhibits angiogenesis by binding to vimentin and F-actin.
Preparation Note
Withaferin A yields a clear, colorless solution in methanol at 1 mg/ml.
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Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
438.8 °F
flash_point_c
226 °C
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Inhibition of NFκB by the natural product Withaferin A in cellular models of Cystic Fibrosis inflammation
Maitra R et al
Journal of Inflammation (London, England), 6, doi: 10-doi: 10 (2009)
Paola Bargagna-Mohan et al.
Chemistry & biology, 14(6), 623-634 (2007-06-23)
The natural product withaferin A (WFA) exhibits antitumor and antiangiogenesis activity in vivo, which results from this drug's potent growth inhibitory activities. Here, we show that WFA binds to the intermediate filament (IF) protein, vimentin, by covalently modifying its cysteine
Silvia D Stan et al.
Nutrition and cancer, 60 Suppl 1, 51-60 (2008-11-15)
Withaferin A (WA) is derived from the medicinal plant Withania somnifera that has been safely used for centuries in the Indian Ayurvedic medicine for treatment of various ailments. We now demonstrate that WA treatment causes G2 and mitotic arrest in