WITHAFERIN A
Synonym(s):4β,5β,6β,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxo-ergosta-2,24-dien-26-oic acid δ-lactone;5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide;Withaferin A, Withania somnifera - CAS 5119-48-2 - Calbiochem;Withaferine;Withaferine A
- CAS NO.:5119-48-2
- Empirical Formula: C28H38O6
- Molecular Weight: 470.6
- MDL number: MFCD10687098
- EINECS: 999-999-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-17 19:25:39
What is WITHAFERIN A?
Description
Withaferin A (5119-48-2) displays potent antiangiogenesis activity inhibiting endothelial cell sprouting in vitro?(IC50?= 12 nM) and?in vivo.1?Potently inhibits NF-κB activation by preventing TNFα-induced activation of IKKβ.2?Covalently binds to the intermediate filament protein, vimentin3?inducing its disassembly and serine 56 phosphorylation4. Inhibits reactive gliosis and blocks TNFα-mediated neuronal apoptosis in?in vivo?models.5
Description
Withaferin A is a natural product with a steroidal structure. In 1962, Israeli chemists Asher Lavie and David Yarden isolated it from the leaves of the Indian plant?Withania somnifera. It is also found in other members of the Solanaceae (nightshade) family. The plant has long been used in traditional ayurvedic medicine.
Withaferin A has many potential pharmaceutical uses because of its anti-inflammatory, anticarcinogenic, and cardioprotective properties, among others. It also has been used as a flavoring and aroma agent. Its biological activity is attributed largely to its double bond and epoxide ring.
Considerable work has been done to develop withaferin A as a medicine, but this year Umut Ozcan and colleagues at Boston Children’s Hospital discovered that it may have another beneficial effect. Resistance to the hunger-regulating hormone leptin has long been known to contribute to obesity. The researchers found that withaferin A acts as a “leptin sensitizer”. Their study on obese laboratory mice showed that the animals, even on high-fat diets,?lost 20–25% of their body weight?when treated with withaferin A.
Applying these results to obese humans could be dicey. Although humans might lose weight with withaferin A, they may not change their unhealthy habits and lack of proper exercise. The problem of human obesity is complex, and many factors will have to be considered before a “magic” pill is available.
Chemical properties
Solid
The Uses of WITHAFERIN A
Withaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986).
The Uses of WITHAFERIN A
Withaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986). Withaferin A has recently been found to be a leptin sensitizer that can reduce the weight in obese mice fed in a high-fat diet (see C249500).
What are the applications of Application
Withaferin A is a steroidal lactone and apoptosis inducer that induces aggregation of vimentin intermediate filaments in cultured endothelial cells and fibroblasts.
Definition
ChEBI: A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Phys lis longifolia, it exhibits cytotoxic activity.
Biological Activity
Steroid lactone that displays anti-inflammatory, antitumor and antiangiogenic activity. Inhibits endothelial cells (HUVEC) spouting in vitro (IC 50 = 12 nM) and in vivo . Prevents NF- κ B activation by inhibiting activation of IKK β . Also inhibits chymotrypsin-like activity of the 20S proteasome.
storage
Store at -20°C
References
1) Mohan?et al.?(2004),?Withaferin A is a potent inhibitor of angiogenesis; Angiogenesis, 7 115 2) Kaileh?et al.?(2007),?Withaferin A strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with inhibition of its kinase activity; J. Biol. Chem.,?282?4253 3) Bargagna-Mohan?et al.?(2007),?The tumor inhibitor and antiangiogenic agent withaferin A targets the intermediate filament protein vimentin; Chem. Biol.,?14?623 4) Thaiparambil?et al.?(2011),?Withaferin A inhibits breast cancer invasion and metastasis at sub-cytotoxic doses by inducing vimentin disassembly and serine 56 phosphorylation; Int. J. Cancer,?129?2744 5) Livne-Bar?et al.?(2016),?Pharmacologic inhibition of reactive gliosis blocks TNF-α-mediated neuronal apoptosis;?Cell Death Dis.,?7?e2386
Properties of WITHAFERIN A
Melting point: | 252-253℃ |
Boiling point: | 680.7±55.0 °C(Predicted) |
alpha | D28 +125° (c = 1.30 in CHCl3) |
Density | 1.28 |
Flash point: | 226℃ |
storage temp. | Desiccate at -20°C |
solubility | Soluble in DMSO (up to 20 mg/ml) |
form | White solid |
pka | 13.49±0.70(Predicted) |
color | White |
Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. |
Safety information for WITHAFERIN A
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. |
Computed Descriptors for WITHAFERIN A
InChIKey | DBRXOUCRJQVYJQ-CKNDUULBSA-N |
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