60478-68-4

Basic information

• Product Name: Dioscin
• Synonyms: Collettinside III;a-D-Glucopyranoside,(3a,25S)-spirost-5-en- 3-yl O-6-deoxy-R-L-mannopyranosyl- (1f2)-O-[6-deoxy-R-L-mannopyranosyl- (1f4)]-;Yamoscin;Dioscin
• CAS NO: 60478-68-4
• Molecular Formula: C₄₅H₇₂O₁₆
• Molecular Weight: 869.057
• Mol File: 60478-68-4.mol
• Article Data: 18

Chemical Properties

• Density: 1.39 g/cm³
• CAS DataBase Reference: Dioscin(CAS DataBase Reference)
• NIST Chemistry Reference: Dioscin(60478-68-4)
• EPA Substance Registry System: Dioscin(60478-68-4)

Safety Data

• Hazardous Substances Data: 60478-68-4(Hazardous Substances Data)

Usage

General Description

Dioscin is a natural steroid saponin that is found in various plants, including Dioscorea villosa, Trigonella foenum-graecum, and Tribulus terrestris. It has been traditionally used in Chinese medicine for its potential health benefits, including anti-inflammatory, anti-cancer, and anti-diabetic properties. Dioscin has also been studied for its potential to inhibit the growth of cancer cells, improve insulin sensitivity, and reduce inflammation. Additionally, it has shown potential for promoting heart health and protecting the liver. Overall, Dioscin is a promising compound with potential therapeutic applications, although more research is needed to fully understand its mechanisms of action and potential side effects.

Upstream product

• 161659-82-1 methyl protodioscin 
• 243454-96-8 diosgenyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside 
• 21494-98-4 trigonelloside C 
• 54522-52-0 methyl protoneodioscin 
• 54522-52-0 26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,26-diol 3-O-β-chacotrioside 
• 512-04-9 diosgenin 
• 211797-89-6 diosgenyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 213753-23-2 diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside 
• 213753-22-1 diosgenyl 2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside 
• 222719-08-6 diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3-O-pivaloyl-β-D-glucopyranoside 
• 213753-20-9 diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 213753-21-0 diosgenyl 4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside 
• 149563-08-6 (2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate 
• 122089-71-8 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 

Downstream Products

• 503314-24-7 diosgenyl 3,6-di-O-benzyl-2,4-di-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside 
• 14144-06-0 trillin 
• 19057-68-2 diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside 
• 1061-54-7 diosgenin acetate 
• 18615-48-0 L-arabino-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 534-97-4 glucosazone 
• 2280-44-6 D-Glucose 
• 1061-54-7 Diosgenin monoacetate 
• 1061-54-7 yamogenin-acetate 
• 73-34-7 L-rhamnose 
• 6014-42-2 L-rhamnose 
• 512-04-9 diosgenin 
• 19057-67-1 ophiopogonin C 

Relevant articles and documents

Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity

Diosgenyl saponins, as a type of natural products derived from plants, are the main active component of traditional chinese medicine. Inspiringly, a large number of natural diosgensyl saponins have been shown to exert excellent toxicity to hepatocellular cancer (HCC) cells. In order to better understand the relationship between the structures and their biological effects, a group of diosgenyl saponins (1–4 as natural products and 5 and 6 as their analogs) were efficiently synthesized. The cytotoxic activity of these compounds was evaluated on human hepatocellular carcinoma (HepG2) cells. Structure–activity relationship studies showed that the pentasaccharide or hexasaccharide saponin analogs were relatively less active than their corresponding disaccharide analogue or dioscin. The extension of 4-branched rhamnose moiety on these saponin does not exhibit significant effect on their cytotoxic activity, which disclosed that a certain number and the linkage mode of rhamnose moieties could influence the cytotoxicity of steroid saponins on HepG2 cells.

IMPROVED SYNTHESIS

The present invention provides an improved synthesis of a class of steroid saponins. Furthermore, the present invention provides a method of selectively discriminating between the C2 and C3 hydroxyl groups of a mono-glycosylated steroid saponin – a key step in the preparation of this class of compounds. Additionally, the present invention provides a range of steroid saponin derivatives, and methods of making them.

Synthesis of neosaponins and neoglycolipids containing a chacotriosyl moiety

α-l-Rhamnopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-β-d-glucopyranose (chacotriose) is the oligosaccharide moiety of dioscin. Chacotriosyl trichloroacetimidate was synthesized from d-glucose and l-rhamnose, and glycosylated to mevalonate (diosgenin, cholesterol, and glycyrrhetic acid) to yield dioscin and neosaponins. In order to simplify the structure of the aglycone part, the mevalonate moiety was replaced with double-chain neoglycolipids that mimicked glycosyl ceramides. A cytotoxicity test revealed the importance of the glycosidic linkage of the naturally occurring β-form and that dioscin and the neoglycolipid with the longest chain showed a moderate activity.