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| | WITHAFERIN A Basic information |
| Product Name: | WITHAFERIN A | | Synonyms: | WITHAFERIN A;5,6-beta-epoxy-4-beta,22,27-trihydroxy-1-5-beta-ergosta-24-dien-26-oicacid;delta-lactone,(20s,22r)-oxo;nsc-101088;(4β,5β,6β,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oicacidδ-lactone;NSC 273757;Withaferine;(20S,22R)-5,6β-Epoxy-4β,22,27-trihydroxy-1-oxo-5β-ergosta-
2,24-dien-26-oic Acid δ-Lactone | | CAS: | 5119-48-2 | | MF: | C28H38O6 | | MW: | 470.6 | | EINECS: | 999-999-2 | | Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;antibiotic | | Mol File: | 5119-48-2.mol |  |
| | WITHAFERIN A Chemical Properties |
| Melting point | 252-253℃ | | alpha | D28 +125° (c = 1.30 in CHCl3) | | Boiling point | 680.7±55.0 °C(Predicted) | | density | 1.28 | | Fp | 226℃ | | storage temp. | Desiccate at -20°C | | solubility | Soluble in DMSO (up to 20 mg/ml) | | pka | 13.49±0.70(Predicted) | | form | White solid | | 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. | | InChIKey | DBRXOUCRJQVYJQ-CKNDUULBSA-N |
| Hazard Codes | T | | WGK Germany | 3 | | RTECS | KE7288500 | | HS Code | 29322090 |
| | WITHAFERIN A Usage And Synthesis |
| 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 | | Chemical Properties | Solid | | Uses | 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). | | 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. | | target | ROS | NF-kB | p53 | STAT | PARP | Bcl-2/Bax | Caspase | TGF-β/Smad | TNF-α | COX | PGE | PI3K | Akt | JNK | p38MAPK | | 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 |
| | WITHAFERIN A Preparation Products And Raw materials |
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