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W4394

Sigma-Aldrich

Withaferin A

≥95% (HPLC)

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C28H38O6
Número CAS:
Peso molecular:
470.60
Número MDL:
Código UNSPSC:
12352211
ID de substância PubChem:
NACRES:
NA.77

fonte biológica

plant (Withania somnifera)

Nível de qualidade

Ensaio

≥95% (HPLC)

forma

powder

pf

252-253 °C

grupo funcional

epoxy
ketone

Condições de expedição

ambient

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

DBRXOUCRJQVYJQ-CKNDUULBSA-N

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Nota de preparo

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

Código de classe de armazenamento

13 - Non Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

438.8 °F

Ponto de fulgor (°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)
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
Huanjie Yang et al.
PloS one, 7(8), e41214-e41214 (2012-08-23)
The medicinal plant Withania somnifera has been used for over centuries in Indian Ayurvedic Medicine to treat a wide spectrum of disorders. Withaferin A (WA), a bioactive compound that is isolated from this plant, has anti-inflammatory, immuno-modulatory, anti-angiogenic, and anti-cancer
Abhinav Grover et al.
BMC genomics, 13 Suppl 7, S20-S20 (2013-01-11)
Leishmaniasis is caused by several species of leishmania protozoan and is one of the major vector-born diseases after malaria and sleeping sickness. Toxicity of available drugs and drug resistance development by protozoa in recent years has made Leishmaniasis cure difficult

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