DIOSCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C45H72O16
Molecular Weight	869.0436
Optical Activity	UNSPECIFIED
Defined Stereocenters	26 / 26
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]6(CC[C@@H](C)CO6)O2)O[C@]7([H])O[C@H](CO)[C@@H](O[C@]8([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@]9([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]9O

InChI

InChIKey=VNONINPVFQTJOC-ZGXDEBHDSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28677156
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25993784 | https://www.ncbi.nlm.nih.gov/pubmed/28796245 | https://www.ncbi.nlm.nih.gov/pubmed/28849197 | https://www.ncbi.nlm.nih.gov/pubmed/28435431

Dioscin is a natural steroid saponin derived from several plants, showing the potent anti-cancer effect against a variety of tumor cell lines. Pharmacological studies have shown that dioscin processes anti-cerebral ischemia/reperfusion injury, anti-liver fibrosis and anti-obesity effects. Dioscin markedly inhibited cell viability, colony formation, motility and induced apoptosis in prostate cancer cells. Dioscin remarkably suppressed the migratory and invasive capacities of melanoma cells. In preclinical models, dioscin showed significant anti-metastatic effects and suppress the tumor cell malignancy.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
PI3K-Akt signaling pathway 24 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28689917	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Liver fibrosis 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28689917	Primary		Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28677156	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Mice 80 mg/kg/day for 21 days

Route of Administration: Oral

In Vitro Use Guide

The PC3 cells were seeded in 96-well plates (5000 cells/well) in DMEM/F12 medium and incubated overnight, and the PC3 cell-derived mammospheres were seeded in growth medium for 5 days culturing. Subsequently, various concentrations of dioscin (0.18–92 μM for PC3 monolayers; 0.36–184 μM for mammospheres) were added in each well. After PC3 cells were incubated for 24 h, the cell viability was analyzed using the MTT assay kit

Name

Type

Language

DIOSCIN

Common Name

English

.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,25R)-SPIROST-5-EN-3-YL O-6- DEOXY-ALPHA-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L- MANNOPYRANOSYL-(1->4))-

Systematic Name

English

POLYPHYLLIN III

Common Name

English

DIOSCINE

Common Name

English

(+)-DIOSCIN

Common Name

English

(3.BETA.,25R)-SPIROST-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

DIOSGENIN 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-(1->2)-(.ALPHA.-L-RHAMNOPYRANOSYL-(1->4))-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

COLLETTISIDE III

Common Name

English

PARIS III

Common Name

English

DIOSCIN [MI]

Common Name

English

Dioscin [WHO-DD]

Common Name

English

Code System Code Type Description

FDA UNII

3B95U4OLWV