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W4394

Sigma-Aldrich

Withaferin A

≥95% (HPLC)

Synonyme(s) :

5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide, Withaferine A

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About This Item

Formule empirique (notation de Hill):
C28H38O6
Numéro CAS:
5119-48-2
Poids moléculaire :
470.60
Numéro MDL:
MFCD10687098
Code UNSPSC :
12352211
ID de substance PubChem :
329830709
Nomenclature NACRES :
NA.77

Source biologique

plant (Withania somnifera)

Niveau de qualité

200

Essai

≥95% (HPLC)

Forme

powder

Pf

252-253 °C

Groupe fonctionnel

epoxy
ketone

Conditions d'expédition

ambient

Température de stockage

2-8°C

Chaîne 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

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

Clé InChI

DBRXOUCRJQVYJQ-CKNDUULBSA-N

Application

Withaferin A was used to treat HEK293 cells to study its effect on cystic fibrosis inflammation.

Actions biochimiques/physiologiques

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.

Notes préparatoires

Withaferin A yields a clear, colorless solution in methanol at 1 mg/ml.

Code de la classe de stockage

13 - Non Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

438.8 °F

Point d'éclair (°C)

226 °C

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Certificats d'analyse (COA)

Lot/Batch Number
SLCN2765
SLCN0222
SLCM7668
SLCM9129
SLCM8033

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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
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
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)
Hee Jung Um et al.
Biochemical and biophysical research communications, 427(1), 24-29 (2012-09-18)
Withaferin A, the active component of Withania somnifera, causes cytotoxicity in a variety of tumor cell lines. In this study, we show that withaferin A inhibits constitutive and IL-6-induced phosphorylation of STAT3 (on Tyr705), but not IFN-γ-induced STAT1 phosphorylation. Withaferin
Wim Vanden Berghe et al.
Biochemical pharmacology, 84(10), 1282-1291 (2012-09-18)
Herbal medicine which involves the use of plants for their medicinal value, dates as far back as the origin of mankind and demonstrates an array of applications including cardiovascular protection and anti-cancer activities, via antioxidant, anti-inflammatory and metabolic activities. Even
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