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W4394

Sigma-Aldrich

Withaferin A

≥95% (HPLC)

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Synonym(s):
5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide, Withaferine A
Empirical Formula (Hill Notation):
C28H38O6
CAS Number:
Molecular Weight:
470.60
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
SMB0042889910PHL89824
Withaferin A ≥95% (HPLC)

Sigma-Aldrich

W4394

Withaferin A

Resibufogenin ≥98% (HPLC)

Sigma-Aldrich

SMB00428

Resibufogenin

Withaferin A analytical standard

Supelco

89910

Withaferin A

Withaferin A phyproof® Reference Substance

PHL89824

Withaferin A

assay

≥95% (HPLC)

assay

≥98% (HPLC)

assay

≥95.0% (HPLC)

assay

≥95.0% (HPLC)

form

powder

form

powder

form

-

form

-

mp

252-253 °C

mp

-

mp

-

mp

-

functional group

epoxy, ketone

functional group

-

functional group

-

functional group

-

shipped in

ambient

shipped in

-

shipped in

-

shipped in

-

Application

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

Biochem/physiol Actions

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.
Steroidal lactone that exhibits cytotoxicity towards tumor cells. Protective effects attributed to anti-lipid peroxidative, antioxidant and detoxifying functionality.

Preparation Note

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

438.8 °F

Flash Point(C)

226 °C


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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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