5119-48-2 Usage
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
Different sources of media describe the Uses of 5119-48-2 differently. You can refer to the following data:
1. 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).
2. 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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 5119-48-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,1,1 and 9 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5119-48:
(6*5)+(5*1)+(4*1)+(3*9)+(2*4)+(1*8)=82
82 % 10 = 2
So 5119-48-2 is a valid CAS Registry Number.
InChI:InChI=1/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
5119-48-2Relevant articles and documents
2,3-Dihydrowithaferin A-3β-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera
Xu, Ya-ming,Marron, Marilyn T.,Seddon, Emily,McLaughlin, Steven P.,Ray, Dennis T.,Whitesell, Luke,Leslie Gunatilaka
, p. 2210 - 2214 (2009)
Preparations of the roots of the medicinal plant Withania somnifera (L.) Dunal commonly called ashwagandha have been used for millennia in the Ayurvedic medical tradition of India as a general tonic to relieve stress and enhance health, especially in the
BIOSYNTHESIS OF WITHANOLIDES IN ACNISTUS BREVIFLORUS
Veleiro, Adriana S.,Burton, Gerardo,Gros, Eduardo G.
, p. 2263 - 2266 (2007/10/02)
Acnistus breviflorus; Solanaceae; withaferin A; withanolide; biosynthesis.Administration of mevalonolactone to excised leaves of Acnistus breviflorus produced labelled withaferin A and jaborosalactone A.The former was degraded leading to the isolation of glyceric acid from C-25-C-27 of the withanolide.These carbons represented only 2percent of the total radioactivity of withaferin A.The relative radioactivity of these carbons indicated that C-26 is directly derived from C-2 of mevalonolactone suggesting that the 25-pro-R-methyl group of cholesterol or any other sterol intermediate had been oxidized to form the lactone ring of the withanolide.The total radioactivity value found for C-25-C27 was much lower than the expected 20percent of the total value for the withanolide indicating that the side chain of the sterol precursor had been partially cleaved during the biosynthetic process.
