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Merck

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:
5119-48-2
Molecular Weight:
470.60
NACRES:
NA.77
PubChem Substance ID:
329830709
UNSPSC Code:
12352211
MDL number:
MFCD10687098

Key Documents

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form

powder

InChI key

DBRXOUCRJQVYJQ-CKNDUULBSA-N

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

biological source

plant (Withania somnifera)

assay

≥95% (HPLC)

mp

252-253 °C

functional group

epoxy, ketone

shipped in

ambient

storage temp.

2-8°C

Quality Level

200

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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.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

438.8 °F

flash_point_c

226 °C

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Certificates of Analysis (COA)

Lot/Batch Number
0000461110
0000461110
SLCN2765
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)
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
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
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