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

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

Uses

Used in Pharmaceutical Industry:
Dioscin is used as a therapeutic agent for its anti-inflammatory, anti-cancer, and anti-diabetic properties. It is employed to inhibit the growth of cancer cells, improve insulin sensitivity, and reduce inflammation.
Used in Health Supplements:
Dioscin is used as a dietary supplement to promote overall health and well-being. It is consumed for its potential benefits in improving heart health and protecting the liver.
Used in Traditional Chinese Medicine:
Dioscin is used as a traditional medicine for its potential health benefits, including anti-inflammatory, anti-cancer, and anti-diabetic properties. It is utilized in various formulations to treat a range of health conditions.

Upstream product

• 161659-82-1 methyl protodioscin 
• 21494-98-4 trigonelloside C 
• 512-04-9 diosgenin 
• 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 
• 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 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

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

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.

N-Pentenyl-Type Glycosides for Catalytic Glycosylation and Their Application in Single-Catalyst One-Pot Oligosaccharide Assemblies

We have developed a new type of n-pentenyl-type glycosides that can be activated by catalytic amounts of promoter, Hg(NTf2)2 or PPh3AuCl/AgNTf2, at room temperature. The mild activation conditions and outstanding stability of common protection/deprotection manipulations enable the enynyl donors to have broad applications in constructing various glycosidic bonds. Furthermore, under the Hg(NTf2)2-catalyzed conditions, the sequential activation of different types of donors was achieved, based on which a gentiotetrasaccharide was synthesized via the newly developed single-catalyst one-pot strategy.

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.

Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity

Natural steroidal glycosides containing α-l-rhamnopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-β-d-glucopyranose (chacotriose) at the oligosaccharide moiety exhibit anti-cancer and anti-herpes activities. To investigate the structure-activity relationships of the aglycone parts of chacotriosides, we developed a synthesis method for chacotriosyl glycosides having various aglycones. In the process, it was revealed that α-chacotriosyl glycosides could be obtained mainly by using a trichloroacetimidate donor, while β-chacotriosyl glycosides were afforded by using phosphite and phosphate donors. In cytotoxicity tests using the A549 and HepG2 cell lines, naturally occurring β-chacotriosyl diosgenin and cholestanol exhibited higher activities than the corresponding α-chacotriosyl glycosides.

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.

Facile sythesis of dioscin and its analogues

Three representative spirostanol saponins that have typical structure of the sugar moiety, diosgenyl 2,3-di-O-α-L-rhamnopyranosyl-β-D- glucopyranoside, diosgenyl 2,4-di-O-α-L-rhamnopyranosyl-β-D- glucopyranoside (dioscin), and diosgenyl 2,6-di-O-α-L-rhamnopyranosyl- β-D-glucopyranoside, were synthesized in a facile way. An approach to selectively mask the C3-hydroxyl of diosgenyl 4,6-O-benzylidene β-D-glucopyranoside was described. A procedure using cerium(IV) ammonium nitrate for selective removal of tert-butyldimethylsilyl group while retaining levulinyl group is afforded. Copyright

Fluorophore-appended steroidal saponin (dioscin and polyphyllin D) derivatives

(Chemical Equation Presented) The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 μM) against the HeLa carcinoma cell line evaluated by standard MTT assay.

The synthesis of gracillin and dioscin: Two typical representatives of spirostanol glycosides

Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]- β-D-glucopyranoside (gracillin) and diosgenyl α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]- β-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described.

A facile approach to diosgenin and furostan type saponins bearing a 3β-chacotriose moiety

Combination of a one-pot coupling technique and the use of benzyl ethers as permanent protecting groups offered a short and simple route to dioscin-type saponins. This strategy in combination with a mild reductive opening procedure of the spiroketal function in diosgenin also offered a convenient approach to bidesmosidic furostan type saponins. Me3N·BH3/AlCl3 promoted acetal opening of 3-O-TBDMS-protected diosgenin gave the 26-OH acceptor 9 into which a benzylated β-glucose moiety was introduced by a SN2-type imidate coupling. After cleavage of the silyl ether, the 3β-O-glucose and the 4-O-linked rhamnose of the chacotriose unit were introduced by a NIS/AgOTf-promoted one-pot coupling sequence utilising thioglycoside donors and their different reactivity in different solvents. After removal of a benzoyl group, the same coupling conditions were also used for the coupling of the second 2-O-linked rhamnose unit. The target substance was obtained after cleavage of the protecting benzyl ethers under Birch-type conditions, which did not affect the double bond in the steroid skeleton.