Dioscin Chemical Properties

Melting point:

275～277℃

alpha 

D13 -115° (c = 0.373 in ethanol)

Density 

1.39±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

pka

12?+-.0.70(Predicted)

form 

Solid

color 

White to Off-White

Safety Information

Safety Statements 

24/25

HS Code 

29389090

Toxicity

mouse,LD50,subcutaneous,> 300mg/kg (300mg/kg),Japanese Kokai Tokyo Koho Patents. Vol. #91-271224,

Dioscin Usage And Synthesis

Description

Dioscin is extracted from Dioscorea nipponica. Rhizoma Dioscoreae Nipponicae is the dry rhizome of this plant. It can be orally used to treat joint pain, arthritis, malaria, and chronic bronchitis. In addition, it can also be used externally to treat sore carbuncle swollen. Rhizoma Dioscoreae Nipponicae is commonly used in the northeast region, Shanxi province, and Shandong province of China.

Physical properties

Appearance: white powder. Solubility: insoluble in water, petroleum ether, and benzene; soluble in methanol, ethanol, and acetic acid; slightly soluble in acetone and amyl alcohol. Melting point: 294–296℃. Specific optical rotation: ?115° (c?=?0.373, ethanol).

History

Japanese scientists firstly reported and analyzed the structure of dioscin isolated from the saponins of Japanese Dioscoreaceae. V . However, the biological activities of dioscin have not attracted the interests of scientists until the late 1990s and the beginning of this century. It is now believed that dioscin may have therapeutic effects on reducing blood lipids and protecting the liver, as well as antivirus, antiinflammatory, and antitumor effects. After the implementation of standardization of traditional Chinese medicine, dioscin as the quality control specification of Dioscorea nipponica Makino and other traditional Chinese medicine has attracted more attentions and researches. In China, dioscin tablets have been used to treat hyperlipidemia in the clinical practice. However, no corresponding drugs are available on the market in other countries. In addition, dioscin is also an important predecessor for synthesizing steroid hormones . Dioscorea nipponica Makino, which is used to extract dioscin, primarily comes from wild plants, whose resources are limited.

Uses

Dioscin, a natural steroid saponin that has been shown to promote anticancer activity against several forms of cancers. Dioscin induces cancer cell apoptosis through elevated oxidative stress mediated by downregulation of peroxiredoxins.

Definition

ChEBI: Dioscin is a spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc attached to position 3 of diosgenin via a glycosidic linkage. It has a role as a metabolite, an antifungal agent, an antiviral agent, an antineoplastic agent, an anti-inflammatory agent, a hepatoprotective agent, an apoptosis inducer and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a spirostanyl glycoside, a spiroketal, a hexacyclic triterpenoid and a trisaccharide derivative. It is functionally related to a diosgenin. It derives from a hydride of a spirostan.

Indications

This drug was recorded in the national standards for chemical drugs, volume 5. Dioscin tablets, containing total dioscin, are used to treat coronary heart disease, coronary insufficiency, as well as control hyperlipidemia.

Pharmacology

Studies showed that compound preparations containing dioscin can increase coronary blood flow, reduce myocardial oxygen consumption, and protect myocardial ischemia and ischemia-reperfusion injury, which is beneficial for alleviating myocardial ischemia and angina. In addition, dioscin can regulate the lipid metabolism and improve hemodynamics. Dioscin can also prevent atherosclerosis by reducing serum total cholesterol, triglyceride, low-density lipoprotein, and oxidized lowdensity lipoprotein, reducing the whole blood viscosity and plasma viscosity at high and low shear rates, and relieving arterial wall lipid infiltration and plaque formation. Furthermore, dioscin can reduce liver fat deposition, which may be related to promoting cholesterol secretion metabolism.
It has also been reported that dioscin can induce the apoptosis of a variety of tumor cells, including gastric cancer cells, breast cancer cells, lung cancer cells, oral squamous cell carcinoma, and cervical cancer cells. The mechanisms are related to reducing the oxidative stress and inhibiting some cellular survival signaling pathways
Dioscin can induce antioxidant enzymes, lower blood lipids, improve insulin resistance, inhibit the inflammatory response, reduce the damage of alcoholic hepatitis, and decrease the hepatic injury induced by acetaminophen .

Dioscin(19057-60-4)Related Product Information

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• Chonglou Saponin II
• Matrine
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• Icariin
• POLYPHYLLIN E (RG)
• Paris saponin V palmitate
• POLYPHYLLIN D
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• Prosapogenin A 【dioscin】
• 27-Hydroxycholesterol
• PROTOGRACELLIN
• methyl protodioscin
• Diosgenin glucoside
• Diosgenin
• Protodioscin