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Dioscin

CAT: 0804-HY-N0124-03Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0124-03Size:10 mg
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Description
Dioscin (CCRIS 4123; Collettiside III) is a natural plant-derived steroidal saponin that has good anti-cancer activity against a variety of cancer cells. Dioscin causes DNA damage and induces apoptosis in HeLa and SiHa cells. Dioscin regulates ROS-mediated DNA damage and mitochondrial signaling pathways, exerting anticancer activity[1][2][3][4][5][6].
CAS Number
19057-60-4
Product Name Alternative
Collettiside III; CCRIS 4123
UNSPSC
12352005
Hazard Statement
H315, H319
Target
Apoptosis; Autophagy
Type
Natural Products
Related Pathways
Apoptosis; Autophagy
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/Dioscin.html
Purity
99.95
Solubility
DMSO : ≥ 100 mg/mL
Smiles
O[C@@H]1[C@@H](O)[C@H](C)O[C@@]([H])(O[C@H]2[C@H](O)[C@@H](O[C@]3([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@](O[C@@H]4CC5=CC[C@]([C@]([H])(C[C@@]6([H])[C@]7([H])[C@H](C)[C@]8(OC[C@H](C)CC8)O6)[C@]7(C)CC9)([H])[C@@]9([H])[C@@]5(C)CC4)([H])O[C@@H]2CO)[C@@H]1O
Molecular Formula
C45H72O16
Molecular Weight
869.04
Precautions
H315, H319
References & Citations
[1]Chen J, et al. Dioscin-induced apoptosis of human LNCaP prostate carcinoma cells through activation of caspase-3 and modulation of Bcl-2 protein family. J Huazhong Univ Sci Technolog Med Sci. 2014 Feb;34 (1) :125-30.|[2]Qu X, et al. Dioscin inhibits osteoclast differentiation and bone resorption though down-regulating the Akt signaling cascades. Biochem Biophys Res Commun. 2014 Jan 10;443 (2) :658-65.|[3]Qin J, et al. Dioscin prevents the mitochondrial apoptosis and attenuates oxidative stress in cardiac H9c2 cells. Drug Res (Stuttg) . 2014 Jan;64 (1) :47-52.|[4]Zhao X, et al. Dioscin Induces Apoptosis in Human Cervical Carcinoma HeLa and SiHa Cells through ROS-Mediated DNA Damage and the Mitochondrial Signaling Pathway. Molecules. 2016 Jun 4;21 (6) :730.|[5]Xu T, et al. A 90-day subchronic toxicological assessment of dioscin, a natural steroid saponin, in Sprague-Dawley rats. Food Chem Toxicol. 2012 May;50 (5) :1279-87.|[6]Tao X, et al. Dioscin attenuates hepatic ischemia-reperfusion injury in rats through inhibition of oxidative-nitrative stress, inflammation and apoptosis. Transplantation. 2014 Sep 27;98 (6) :604-11.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
Launched

Chemical Information

(+)-Dioscin

Dioscin is a spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(14)-[alpha-L-Rha-(12)]-beta-D-Glc attached to position 3 of diosgenin via a glycosidic linkage. It has a role as an antiviral agent, a metabolite, an antineoplastic agent, an antifungal agent, an EC 1.14.18.1 (tyrosinase) inhibitor, a hepatoprotective agent, an anti-inflammatory agent and an apoptosis inducer. It is a spirostanyl glycoside, a trisaccharide derivative, a hexacyclic triterpenoid and a spiroketal. It is functionally related to a diosgenin. It derives from a hydride of a spirostan.

CAS Number19057-60-4
PubChem CID119245
IUPAC Name(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(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,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Molecular FormulaC45H72O16
Molecular Weight869.0
XLogP1.3
Topological Polar Surface Area236
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count16
Rotatable Bond Count7
Heavy Atom Count61
Formal Charge0
Complexity1600
SMILES
C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C)OC1
InChI
InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
InChIKey
VNONINPVFQTJOC-ZGXDEBHDSA-N
Chemical Structure
2D Structure
2D structure of (+)-Dioscin
CAS: 19057-60-4
CID: 119245
Formula: C45H72O16
MW: 869.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight869.0
XLogP31.3
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count16
Rotatable Bond Count7
Exact Mass868.48203620
Monoisotopic Mass868.48203620
Topological Polar Surface Area236 Ų
Heavy Atom Count61
Formal Charge0
Complexity1600
Isotope Atom Count0
Defined Atom Stereocenter Count26
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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