Withaferin A

Withaferin A
Names

IUPAC name (4β,5β,6β,22R)-4,27-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
Other names Withaferine A
Identifiers
CAS Registry Number	5119-48-2^Y
ChEBI	CHEBI:69120
ChEMBL	ChEMBL1221986
ChemSpider	233064
InChI 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 Key: DBRXOUCRJQVYJQ-CKNDUULBSA-N 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 Key: DBRXOUCRJQVYJQ-CKNDUULBBI
Jmol-3D images	Image
PubChem	265237
SMILES O=C/1O[C@H](CC(=C\1CO)\C)[C@@H](C)[C@H]6CC[C@@H]4[C@]6(C)CC[C@@H]3[C@]5(C(=O)\C=C/[C@H](O)[C@]52O[C@@H]2C[C@H]34)C
Properties
Molecular formula	C₂₈H₃₈O₆
Molar mass	470.60 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Withaferin A is a steroidal lactone which binds to and inhibits vimentin.^[1] It was first isolated from Winter cherry (Withania somnifera).^[2] and is the first member of the withanolides to be discovered. Withaferin A is a potent inhibitor of angiogenesis (the formation of new blood vessels).^[3] Withaferin A inhibits both NF-κB and Sp1 Transcription factor activity.^[3]^[4] Withaferin A also down regulates VEGF gene expression^[4] and can affect calcium signalling.^[5]

References

↑ Bargagna-Mohan, P.; Hamza, A.; Kim, Y. E.; Ho, Y. K.; Mor-Vaknin, N.; Wendschlag, N.; Liu, J.; Evans, R. M. et al. (2007). "The tumor inhibitor and antiangiogenic agent Withaferin A targets the intermediate filament protein Vimentin". Chemistry & Biology 14 (6): 623–634. doi:10.1016/j.chembiol.2007.04.010. PMC 3228641. PMID 17584610.
↑ Lavie, D.; Glotter, E.; Shvo, Y. (1965). "Constituents of Withania somnifera Dun. III. The side chain of Withaferin A". Journal of Organic Chemistry 30 (6): 1774–1778. doi:10.1021/jo01017a015.
↑ 3.0 3.1 Mohan, R; Hammers, HJ; Bargagna-Mohan, P; Zhan, XH; Herbstritt, CJ; Ruiz, A; Zhang, L; Hanson, AD et al. (2004). "Withaferin A is a potent inhibitor of angiogenesis". Angiogenesis 7 (2): 115–122. doi:10.1007/s10456-004-1026-3. PMID 15516832.
↑ 4.0 4.1 Prasanna Kumar, S; Shilpa, P; Salimath Bharati, P (2009). "Withaferin A suppresses the expression of vascular endothelial growth factor in Ehrlich ascites tumor cells via Sp1 transcription factor". Current Trends in Biotechnology and Pharmacy 3 (2): 138–148. ISSN 0973-8916.
↑ Jilani, K.; Lupescu, A.; Zbidah, M.; Shaik, N.; Lang, F. (2013). "Withaferin A-stimulated Ca²⁺ entry, ceramide formation and suicidal death of erythrocytes". Toxicology in Vitro 27 (1): 52–58. doi:10.1016/j.tiv.2012.09.004. PMID 22989414.