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Deltonin

CAS# 55659-75-1

Deltonin

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Quality Control of Deltonin

Number of papers citing our products

Chemical structure

Deltonin

3D structure

Chemical Properties of Deltonin

Cas No. 55659-75-1 SDF Download SDF
PubChem ID 441884 Appearance Powder
Formula C45H72O17 M.Wt 885
Type of Compound Steroids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)OC1
Standard InChIKey OLAMGHNQGZIWHZ-YIKYYZBWSA-N
Standard InChI InChI=1S/C45H72O17/c1-19-8-13-45(55-18-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-35(52)33(50)31(48)21(3)56-40)37(54)38(29(17-47)59-42)60-41-36(53)34(51)32(49)28(16-46)58-41/h6,19-21,23-42,46-54H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33-,34+,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Deltonin

The rhizomes of Paris yunnanensis Franch.

Biological Activity of Deltonin

Description1. Deltonin may be a potential chemotherapeutic agent against neck squamous cell carcinoma (HNSCC), it can induce both apoptosis and autophagy in head and neck squamous carcinoma FaDu cell. 2. Deltonin exhibits induction effect on platelet aggregation. 3. Deltonin inhibits angiogenesis by regulating VEGFR2 and subsequent signaling pathways in endothelial cells. 4. Deltonin induces apoptosis in MDA-MB-231 human breast cancer cells via reactive oxygen species-mediated mitochondrial dysfunction and ERK/AKT signaling pathways.
TargetsChk | Caspase | mTOR | Akt | VEGFR | Src | FAK | ERK | p38MAPK | ROS | PARP | Bcl-2/Bax

Deltonin Dilution Calculator

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Deltonin Molarity Calculator

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Preparing Stock Solutions of Deltonin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.1299 mL 5.6497 mL 11.2994 mL 22.5989 mL 28.2486 mL
5 mM 0.226 mL 1.1299 mL 2.2599 mL 4.5198 mL 5.6497 mL
10 mM 0.113 mL 0.565 mL 1.1299 mL 2.2599 mL 2.8249 mL
50 mM 0.0226 mL 0.113 mL 0.226 mL 0.452 mL 0.565 mL
100 mM 0.0113 mL 0.0565 mL 0.113 mL 0.226 mL 0.2825 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Deltonin

Deltonin induced both apoptosis and autophagy in head and neck squamous carcinoma FaDu cell.[Pubmed:25866222]

Neoplasma. 2015;62(3):419-31.

For decades, despite the advancement of medical science, the prognosis of head and neck squamous cell carcinoma (HNSCC), has not improved. Deltonin is one of the major active components of Dioscorea Zingiberensis Wright that has been used for anthrax, rheumatic heart disease, rheumatoid arthritis etc. By employing HNSCC FaDu cell and normal human epidermal keratinocyte, we investigate Deltonin efficacy and associated mechanism in both cell culture and nude mice xenografts. Deltonin treatment selectively prevents proliferation of FaDu cells by cell-cycle arrest and induction of apoptosis, via activating checkpoint kinase Chk1and Chk2 as well as caspases 8, 9 and 3. Meanwhile, we found that treatment with Deltonin induced autophagy, which played a protective role against Deltonin-induced apoptosis. Further studies revealed that Deltonin activated autophagy by Akt-mTOR signaling. Additionally, xenograft model showed that administration of Deltonin significantly inhibited tumor growth and prolonged survival of tumor bearing mice. Our studies suggested that Deltonin might be a potential chemotherapeutic agent against HNSCC, which might contribute to clinical application and pharmacological study of Deltonin in future anti-cancer research.

Deltonin inhibits angiogenesis by regulating VEGFR2 and subsequent signaling pathways in endothelial cells.[Pubmed:25554580]

Steroids. 2015 Apr;96:30-6.

Deltonin is a steroidal saponin which could suppress tumor growth through suppressing angiogenesis, but the mechanisms have not been directly elucidated yet. In the present study, we showed that Deltonin inhibited the proliferation of primary cultured human umbilical vein endothelial cells (HUVECs) in vitro; notably, it could significantly inhibit HUVECs migration, invasion, and tube formation, which are indispensable progresses of angiogenesis. We further demonstrated that Deltonin could inhibit VEGF-induced blood vessel formation in vivo. What is more, we found that Deltonin blocked VEGF triggered phosphorylation of key intracellular angiogenic molecules, such as VEGFR2, Src family kinase, focal adhesion kinase (FAK), extracellular signal-related kinase (Erk1/2) and AKT kinase, accompanied with the increase of phosphorylated P38MAPK. Taken together, the present study demonstrates that Deltonin inhibits angiogenesis through regulating VEGFR2 signaling pathway as well as AKT/MAPK signaling pathways in endothelial cells.

Determination of deltonin in rat plasma by using HPLC-MS/MS and the application of this method in pharmacokinetic studies.[Pubmed:23747424]

J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Jul 15;931:1-5.

Deltonin is a naturally occurring spirostanol glycoside from Dioscorea zingiberensis C.H. Wright, which is used in traditional Chinese medicine. It exerts strong cytotoxic effect on C26 cells, inhibits C26 derived-tumor growth, and prolongs the survival of tumor-bearing mice after its oral administration, indicating its potential for use as an anti-tumor drug. To investigate the pharmacokinetic profiles of Deltonin, a rapid, sensitive, and simplified high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) assay was developed and validated for the determination of Deltonin in rat plasma. After acetonitrile-mediated plasma protein precipitation, chromatographic separation of Deltonin was achieved using a reversed phase Hypersil Gold column (150mmx2.1mm, 5mum), with gradient elution using 0.1% formic acid and acetonitrile. Thereafter, Deltonin was quantified using MS/MS with electrospray ionization (ESI) in positive multiple reaction monitoring (MRM) mode. The flow rate of the mobile phase was 200muL/min, and the retention time was 9.03min for Deltonin and 6.31min for the internal standard (IS: 20(S)-ginsenoside Rb1). The linear range of the calibration curve was 2-5000ng/mL (r(2)>0.99), and the limit of detection (LOD) was 0.46ng/mL. The intra- and inter-day accuracies ranged from -2.8% to 11.1% and precisions (RSD) were within 13.1%. Deltonin was found to be stable under short-term temperature conditions, post-preparative temperature conditions, and after 3 freeze-thaw cycles conditions. The validated method was successfully applied to a pharmacokinetic study in rats after oral administration of Deltonin (50 and 100mg/kg). The pharmacokinetics is characterized by high apparent clearance (CL/F) and apparent volume of distribution (Vd/F).

Deltonin induces apoptosis in MDAMB231 human breast cancer cells via reactive oxygen speciesmediated mitochondrial dysfunction and ERK/AKT signaling pathways.[Pubmed:23314115]

Mol Med Rep. 2013 Mar;7(3):1038-44.

Deltonin, a steroidal saponin isolated from Dioscorea zingiberensis Wright, exhibits high cytotoxic activity in cancer cells. In the present study, the effects of Deltonin on cell proliferation and apoptosis were evaluated in the MDAMB231 human breast carcinoma cell line. Following treatment with Deltonin, the viability of MDAMB231 cells was analyzed using MTT assay and apoptosis, mitochondrial membrane potential (Psim) alternation and intracellular reactive oxygen species (ROS) generation was determined by flow cytometry. In addition, western blot analysis was performed to examine the expression of apoptosisassociated proteins. The results demonstrated that Deltonin induced apoptosis in MDAMB231 cells in a time and concentrationdependent manner. Apoptosis was associated with depolarization of Psim and timedependent ROS generation. Deltonin treatment also resulted in Bax upregulation, Bcl-2 downregulation, activation of caspase3 and 8 and poly (ADP ribose) polymerase cleavage. Decreased levels of phosphorylated extracellular signalregulated kinase (ERK) and phosphorylated AKT were also observed. Results indicate that the proliferation inhibitory effect of Deltonin is associated with its apoptosisinducing effect, which may correlate with ROSmediated mitochondrial dysfunction as well as activation of the ERK/AKT signaling pathways. Therefore, Deltonin may be a potential chemotherapeutic agent for the treatment of breast cancer.

Deltonin isolated from Dioscorea zingiberensis inhibits cancer cell growth through inducing mitochondrial apoptosis and suppressing Akt and mitogen activated protein kinase signals.[Pubmed:21804211]

Biol Pharm Bull. 2011;34(8):1231-9.

Deltonin is an active component purified from Dioscorea zingiberensis WRIGHT (DZW), and has shown anticancer effects. However, its mechanism of action remains elusive. In the present study, we investigated the effect of Deltonin on a panel of cancer cell lines and analyzed its mechanism in C26 cells, a murine colon carcinoma cell. Our results showed that Deltonin markedly inhibited the growth of all examined cancer cell lines. Deltonin induced dose- and time-dependent apoptosis in C26 cells. The event of apoptosis was accompanied by the release of cytochrome c, depolarization of mitochondrial membrane potential, and dose- and time-dependent reactive oxygen species (ROS) generation. Deltonin also increased the expression of Bax, decreased the expression of B-cell lymphoma/lewkmia-2 (Bcl-2), and induced the activation of caspase 9, caspase 3 and poly(ADP-ribose) polymerase (PARP). Furthermore, Deltonin decreased Akt and extracellular signal-regulated kinase-1/2 (ERK(1/2)) activity. These results demonstrate that Deltonin mediates the growth inhibition of cancer cells through multiple targets, which include the generation of reactive oxygen species (ROS), mitochondrial apoptosis and the inhibition of the mitogen-activated protein kinase (MAPK) and Akt signaling pathways, suggesting Deltonin is a potent cancer preventive and therapeutic agent.

Deltonin, a steroidal saponin, inhibits colon cancer cell growth in vitro and tumor growth in vivo via induction of apoptosis and antiangiogenesis.[Pubmed:21471712]

Cell Physiol Biochem. 2011;27(3-4):233-42.

Deltonin, a steroidal saponin, isolated from Dioscorea zingiberensis Wright (DZW), has shown high-cytotoxic activity in cancer cells. However, its mechanisms and in vivo anti-cancer effects remain unknown. In the present study, we evaluated the effects and explored the anti-tumor mechanisms of Deltonin on a panel of colon cancer cell lines and in a mouse model of murine colon cancer C26. Deltonin had more cytotoxic effect on C26 cells than 5-fluorouracil had, promoting dramatic G2-M phase arrest and apoptosis in C26 cells in a concentration-dependent manner; oral administration of Deltonin significantly inhibited the tumor growth and prolonged survival of the tumor bearing mice. The Deltonin treatment caused a noticeable apoptosis in tumor tissue, which associated with increased levels of Bax, activated caspase-3, caspase-9, and cleaved poly (ADPribose) polymerase, decreased pro-caspase-8, pro-caspase-9, Bcl-2 expression levels and extracellular signal-regulated kinase-1/2 activity; and dose-dependently inhibit angiogenesis. In conclusion, the findings in this study demonstrated that Deltonin is an effective natural agent for cancer therapy, which may be mediated, in part, by induction of apoptosis, as well as involve mitogen-activated protein kinase pathways, and inhibition of angiogenesis.

Description

Deltonin, a steroidal saponin, isolated from Dioscorea zingiberensis Wright, with antitumor activity; Deltonin inhibits ERK1/2 and AKT activation.

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