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Deltonin

$896

  • Brand : BIOFRON

  • Catalogue Number : BD-P0126

  • Specification : 98.0%(HPLC)

  • CAS number : 55659-75-1

  • Formula : C45H72O17

  • Molecular Weight : 885.04

  • PUBCHEM ID : 441884

  • Volume : 25mg

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Catalogue Number

BD-P0126

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

885.04

Appearance

Powder

Botanical Source

Structure Type

Steroid Saponins and its Sapogenins

Category

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

Synonyms

IUPAC Name

(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Applications

Deltonin induced both apoptosis and autophagy in head and neck squamous carcinoma FaDu cell. PUMID/DOI:DOI:10.4149/neo_2015_050 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. PUMID/DOI:DOI:10.1016 / j.steroids.2014.12.019 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. Deltonin isolated from Dioscorea zingiberensis inhibits cancer cell growth through inducing mitochondrial apoptosis and suppressing Akt and mitogen activated protein kinase signals. PUMID/DOI: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 Study on steroidal saponins from Dioscorea zingiberensis and their platelet aggregation activities PUMID/DOI:25612440 Zhongguo Zhong Yao Za Zhi. 2014 Oct;39(19):3782-7. Using the absorbent resin, silica gel and ODS column chromatography as well as semi-preparative HPLC, ten compounds were isolated from 70% ethanol extract of tubers of Dioscorea zingiberensis C. H. Wright, and their structures were elucidated as trigoneoside XIIIa (1), parvifloside (2), trigoneoside IVa (3), deltoside (4), protobioside (5), lilioglycoside k (6), zingiberensis newsaponin I (7), deltonin (8), prosapogenin A of dioscin (9), and trillin (10) on the basis of NMR and MS spectral data analysis. Among these compounds, 1, 3, 5 and 6 were isolated from this plant for the first time. In the screening test on platelet aggregation, compounds 7 and 8 exhibited induction effect on platelet aggregation, while compound 9 exhibited significant inhibitory effect on platelet aggregation in vitro.

Density

1.4±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

InChl

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

InChl Key

OLAMGHNQGZIWHZ-YIKYYZBWSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:55659-75-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

25554580

Abstract

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.

KEYWORDS

AKT/MAPK; Antiangiogenesis; Deltonin; HUVECs; VEGFR2.

Title

Deltonin inhibits angiogenesis by regulating VEGFR2 and subsequent signaling pathways in endothelial cells

Author

Qingyi Tong 1, Qingbing Zhao 1, Yong Qing 2, Xiaojuan Hu 2, Lei Jiang 2, Xiaohua Wu 3

Publish date

2015 Apr

PMID

24636066

Abstract

Aim: To investigate the chemical constituents of Dioscorea zingiberensis C. H. Wright.

Methods: The compounds were isolated by various chromatographic techniques, and the structures of the new steroidal saponins were elucidated by extensive 1D- and 2D-NMR, MS, and IR spectral analysis.

Results: The 70% EtOH extract of the rhizomes of Dioscorea zingiberensis afforded two new steroidal saponins, zingiberenosides A (1) and B (2), along with eight known analogues, 3β, 26-dihydroxy-25(R)-furosta-Δ(5, 20(22))-diene-3-O-α-L- rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside (3), methyl parvifloside (4), deltoside (5), methyl deltoside (6), zingiberensis new saponin (7), deltonin (8), progenin III (9) and diosgenin-diglucoside (10).

Conclusion: Two new steroidal saponins were isolated from Dioscorea zingiberensis and their structures determined.

KEYWORDS

Dioscorea zingiberensis; Dioscoreaceae; Steroidal saponins; Zingiberenoside.

Title

Two new steroidal saponins from the rhizomes of Dioscorea zingiberensis

Author

Lu Zheng 1, Yuan Zhou 1, Jia-Yu Zhang 2, Min Song 1, Ye Yuan 1, Yan-Jiao Xiao 1, Ting Xiang 3

Publish date

2014 Feb

PMID

23747424

Abstract

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 (150mm×2.1mm, 5μm), 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 200μL/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).

Copyright © 2013 Elsevier B.V. All rights reserved.

Title

Determination of deltonin in rat plasma by using HPLC-MS/MS and the application of this method in pharmacokinetic studies

Author

Dan Du 1, Bo Gao, Guang Xin, Aimin Sun, Baozhan Huang, Rui Zhang, Zhihua Xing, Qianming Chen, Yang He, Wen Huang

Publish date

2013 Jul 15