Oleandrin

• CAT Number: I003613
• CAS Number: 465-16-7
• Molecular Formula: C32H48O9
• Molecular Weight: 576.72
• Purity: ≥95%
• Target: NF-κB
• Solubility: 10 mM in DMSO
• Storage: Store at -20°C

Oleandrin (a toxic cardiac glycoside of N. oleander L.) inhibits the activity of NF-κB in various cultured cell lines (U937, CaOV3, human epithelial cells and T cells) as well as it induces programmed cell death in PC3 cell line culture.Target: NF-κBin vitro: Oleandrin inhibits proliferation of tumor cells and inhibits the excretion of fibroblast growth factor-2 (FGF-2) through membrane interaction and through inhibition of the Na, K-ATPase pump. In PANC-1 cells (human pancreatic cancer cell line), cell death occurs not through apoptosis, but rather through autophagy and it has been noticed that Oleandrin at low nanomolar concentrations potently inhibited cell proliferation associated with induction of a profound G(2)/M cell cycle arrest. Inhibition of cell cycle is not accompanied by any significant sub G1 accumulation of cells, suggesting a non-apoptotic mechanism of Oleandrin. [1] Oleandrin suppresses the activity of Wnt/β-catenin signaling pathway. Oleandrin downregulates the target gene expression of the Wnt/β-catenin pathway at both the mRNA and protein levels. Oleandrin inhibits the protein expression of β-catenin and reduces its nuclear localization. In addition, Oleandrin suppresses the activities of MMP-2 and MMP-9. Oleandrin also induces apoptosis in human leukemia cells through the dephosphorylation of Akt and expression of Fas L, as well as by altering the membrane fluidity. [2]in vivo: Oleandrin has lipophilic property and it can be easily absorbed in the gastrointestinal tract after oral dosing. Oleandrin is metabolized into oleandrigenin in mice. Oleandrin is rapidly absorbed after oral dosing (Cmax at 20 min) although the elimination half-life is longer (2.3 ± 0.5 h) than that after i.v. dosing (0.4 ± 0.1 h). In mouse studies, Oleandrin rapidly accumulates in brain tissue as it can pass through the blood-brain barrier. [1]

Reference

1:Simultaneous determination of eight alkaloids and oleandrin in herbal cosmetics by dispersive solid-phase extraction coupled with ultra high performance liquid chromatography and tandem mass spectrometry. Xun Z, Liu D, Huang R, He S, Hu D, Guo X, Xian Y.J Sep Sci. 2017 May;40(9):1966-1973. doi: 10.1002/jssc.201601427. Epub 2017 Apr 19. PMID: 28317265 2:The Glycoside Oleandrin Reduces Glioma Growth with Direct and Indirect Effects on Tumor Cells. Garofalo S, Grimaldi A, Chece G, Porzia A, Morrone S, Mainiero F, D/’Alessandro G, Esposito V, Cortese B, Di Angelantonio S, Trettel F, Limatola C.J Neurosci. 2017 Apr 5;37(14):3926-3939. doi: 10.1523/JNEUROSCI.2296-16.2017. Epub 2017 Mar 14. PMID: 28292827 3:Retraction: Oleandrin: A Cardiac Glycosides with Potent Cytotoxicity. [No authors listed]Pharmacogn Rev. 2016 Jul-Dec;10(20):147. doi: 10.4103/0973-7847.194050. PMID: 28082799 Free PMC Article4:Synthetic Approach to the Core Structure of Oleandrin and Related Cardiac Glycosides with Highly Functionalized Ring D. Michalak K, Morawiak M, Wicha J.Org Lett. 2016 Dec 2;18(23):6148-6151. Epub 2016 Nov 22. PMID: 27934370 5:Regulation of Intrinsic and Extrinsic Apoptotic Pathways in Osteosarcoma Cells Following Oleandrin Treatment. Ma Y, Zhu B, Yong L, Song C, Liu X, Yu H, Wang P, Liu Z, Liu X.Int J Mol Sci. 2016 Nov 23;17(11). pii: E1950. PMID: 27886059 Free PMC Article6:Oleandrin induces DNA damage responses in cancer cells by suppressing the expression of Rad51. Bao Z, Tian B, Wang X, Feng H, Liang Y, Chen Z, Li W, Shen H, Ying S.Oncotarget. 2016 Sep 13;7(37):59572-59579. doi: 10.18632/oncotarget.10726. PMID: 27449097 Free PMC Article7:Inhibition of oleandrin on the proliferation show and invasion of osteosarcoma cells in vitro by suppressing Wnt/β-catenin signaling pathway. Ma Y, Zhu B, Liu X, Yu H, Yong L, Liu X, Shao J, Liu Z.J Exp Clin Cancer Res. 2015 Oct 6;34:115. doi: 10.1186/s13046-015-0232-8. PMID: 26444270 Free PMC Article8:An unusual case of oleandrin poisoning suggesting its possible antiarrhythmic activity. Palmisano P, Hadad Y, De Nuccio FA.Europace. 2015 Sep;17(9):1401. doi: 10.1093/europace/euv050. Epub 2015 Mar 29. No abstract available. PMID: 25825458 9:BDNF mediates neuroprotection against oxygen-glucose deprivation by the cardiac glycoside oleandrin. Van Kanegan MJ, He DN, Dunn DE, Yang P, Newman RA, West AE, Lo DC.J Neurosci. 2014 Jan 15;34(3):963-8. doi: 10.1523/JNEUROSCI.2700-13.2014. PMID: 24431454 Free PMC Article10:Bidirectional (negative/positive) interference of oleandrin and oleander extract on a relatively new Loci digoxin assay using Vista 1500 analyzer. Dasgupta A, Welsh KJ, Hwang SA, Johnson M, Actor JK.J Clin Lab Anal. 2014 Jan;28(1):16-20. doi: 10.1002/jcla.21637. Epub 2013 Dec 27. PMID: 24375780