Dioscin

Names

[ CAS No. ]:
19057-60-4

[ Name ]:
Dioscin

[Synonym ]:
(3β,25R)-Spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[6-deoxy-α-L-mannopyranosyl-(1->4)]-β-D-glucopyranoside
collettisideiii
(25R)-Spirost-5-en-3b-yl O-6-Deoxy-a-L-mannopyranosyl-(1®2)-O-[6-deoxy-a-L-mannopyranosyl-(1®4)]-b-D-glucopyranoside
β-D-Glucopyranoside, (3β,25R)-spirost-5-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1->2)-O-[6-deoxy-α-L-mannopyranosyl-(1->4)]-
Dioscin
polyphyllin III
Diosgenin Bis-a-L-rhamnopyranosyl-(1®2 And 1®4)-b-D-Glucopyranoside

Biological Activity

[Description]:

Dioscin(CCRIS 4123; Collettiside III) is a natural steroid saponin derived from several plants, showing potent anti-cancer effect against a variety of tumor cell lines. IC50 value:Target: Anticancer agentin vitro: dioscin (1, 2 and 4 μmol/L) could significantly inhibit the viability of LNCaP cells in a time- and concentration-dependent manner. Flow cytometry revealed that the apoptosis rate was increased after treatment of LNCaP cells with dioscin for 24 h, indicating that apoptosis was an important mechanism by which dioscin inhibited cancer [1]. dioscin abrogated AKT phosphorylation, which subsequently impaired RANKL-induced nuclear factor-kappaB (NF-κB) signaling pathway and inhibited NFATc1 transcriptional activity. Moreover, in vivo studies further verified the bone protection activity of dioscin in osteolytic animal model [2]. Dioscin reduced cell death and lactate dehydrogenase (LDH) release in cells subjected to I/R. I/R induced apoptosis and cytochrome c release from mitochondria to the cytosol and this was prevented by dioscin. In support, dioscin decreased Bax but increased Bcl-2 mRNA expression. Dioscin prevented I/R induced dissipation of ΔΨm [3].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Cancer

Natural Products >> Steroids

[References]

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
294-296 â„ƒ

[ Molecular Formula ]:
C₄₅H₇₂O₁₆

[ Molecular Weight ]:
869.044

[ Exact Mass ]:
868.482056

[ PSA ]:
235.68000

[ LogP ]:
7.24

[ Index of Refraction ]:
1.614

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ6405000

CHEMICAL NAME :: 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))-

CAS REGISTRY NUMBER :: 19057-60-4

LAST UPDATED :: 199703

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C45-H72-O16

MOLECULAR WEIGHT :: 869.17

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #91-271224

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
24/25

[ HS Code ]:
29389090

Related Compounds

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