19057-60-4

Basic information

• Product Name: Dioscin
• Synonyms: DIOSCIN;beta-d-glucopyranoside,(3-beta,25r)-spirost-5-en-3-ylo-6-deoxy-alpha-l-mannop;Dioscin(Collettiside III);Dioscin / Diosgenyl 2,4-Di-O-α-L-rhamnopyranosyl-β-D-glucopyranoside;collettisideiii;dioscine;yranosyl-(1-2)-o-(6-deoxy-alpha-l-mannopyranosyl)-(1-4))-;DIOSCIN(P)
• CAS NO: 19057-60-4
• Molecular Formula: C₄₅H₇₂O₁₆
• Molecular Weight: 869.04
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Miscellaneous Natural Products;Natural Plant Extract;The group of Dioscin
• Mol File: 19057-60-4.mol

Chemical Properties

• Melting Point: 275～277℃
• Appearance: /
• Density: 1.39 g/cm³
• Refractive Index: 1.613
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 12?+-.0.70(Predicted)
• CAS DataBase Reference: Dioscin(CAS DataBase Reference)
• NIST Chemistry Reference: Dioscin(19057-60-4)
• EPA Substance Registry System: Dioscin(19057-60-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 19057-60-4(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 19057-60-4 differently. You can refer to the following data:
1. 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.
2. 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.

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 .

InChI:InChI=1/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

Upstream product

• 161659-82-1 methyl protodioscin 
• 54522-52-0 26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,26-diol 3-O-β-chacotrioside 
• 54522-52-0 methyl protoneodioscin 
• 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 
• 335591-71-4 diosgenin-3β-yl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl)-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 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 
• 335591-72-5 diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→4)-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)]-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 55056-80-9 protodioscin 
• 50-99-7 D-glucose 
• 339204-55-6 allyl 3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 339204-58-9 allyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 339204-60-3 (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)]-3,6-di-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate 
• 105376-04-3 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 

Downstream Products

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

Related news

Dioscin (cas 19057-60-4) ameliorates intestinal ischemia/reperfusion injury via adjusting miR-351-5p/MAPK13-mediated inflammation and apoptosis07/27/2019

Inflammatory reaction and cell apoptosis are two important processes in intestinal ischemia/reperfusion (II/R) injury, and exploration of effective lead compounds against II/R injury via regulating inflammation and apoptosis is critical important. In this paper, the results indicated that diosci...detailed

Protective effects of Dioscin (cas 19057-60-4) against cartilage destruction in a monosodium iodoacetate (MIA)-indcued osteoarthritis rat model07/26/2019

BackgroundOsteoarthritis (OA) is a disabling disease of joint with no clear treatment. The finding of medicine be of benefit to joint is an important topic for osteoarthritis prevention and treatment. The present study was designed to explore the therapeutic effects and possible underlying mecha...detailed

Protective effects of Dioscin (cas 19057-60-4) against systemic inflammatory response syndromevia adjusting TLR2/MyD88/NF‑κb signal pathway07/25/2019

Development of active compounds to control inflammation against systemic inflammatory response syndrome (SIRS) is critical important. Dioscin shows anti-inflammatory effects in our previous works. However, the action of the compound on SIRS still remained unknown. In the present paper, zymosan i...detailed

Dioscin (cas 19057-60-4) ameliorates cardiac hypertrophy through inhibition of the MAPK and Akt/GSK3β/mTOR pathways07/24/2019

Cardiac hypertrophy occurs in response to multiple stimuli and develops into congestive heart failure with morbidity and mortality. Dioscin exerts protective effects against tumor growth and ischemia/reperfusion injury. However, whether and how dioscin attenuates angiotensin II (AngII)-induced c...detailed

Molecular mechanism and inhibitory targets of Dioscin (cas 19057-60-4) in HepG2 cells07/23/2019

Dioscin has been known for its anti-cancer activity; however, its detailed molecular mechanisms have not been studied so far. Herein, we evaluated the anti-cancer activity of dioscin for proliferation inhibition and apoptosis in HepG2 cancer cells. Initially, dioscin was purified and identified ...detailed

Dioscin (cas 19057-60-4) inhibits intimal hyperplasia in rat carotid artery balloon injury model through inhibition of the MAPK-FoxM1 pathway07/22/2019

Vascular smooth muscle cell (VSMC) proliferation and migration are crucial events in the pathological course of atherosclerosis and restenosis after percutaneous coronary intervention (PCI). Dioscin has been shown to exhibit powerful cardiovascular protective effects and potent therapeutic poten...detailed

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.

Heterologous expression of furostanol glycoside 26-O-β-glucosidase of Costus speciosus in Nicotiana tabacum

Furostanol glycoside 26-O-β-glucosidase (F26G) is a specific β- glucosidase converting a furostanol glycoside (FG) to its corresponding spirostanol glycoside (SG). A cDNA encoding F26G from Costus speciosus was introduced into a heterologous plant, Nicotiana tabacum via Agrobacterium tumefaciens using a binary vector method. Successful integration of the cDNA into tobacco chromosomal DNA was confirmed by PCR analysis. F26G activity was also detected in cell-free extracts of the transgenic plantlets.

Studies on the constituents of palmae plants. VI. Steroid saponins and flavonoids of leaves of Phoenix canariensis hort. ex CHABAUD, P. humilis ROYLE var. hanceana BECC., P. dactylifera L., and Licuala spinosa WURMB.

Steroid saponins and flavonoids of the leaves of Phoenix canariensis hort. ex CHABAUD, P. humilis ROYLE var. hanceana BECC., P. dactylifera L., and Licuala spinosa WURMB. have been investigated. Tricin 7-O-β-D-glucopyranoside (1), isorhamnetin 3-O-β-D-glucopyranoside (2), isoquercitrin (3), isorhamnetin 3-O-β-rutinoside (4), rutin (5), and methyl (25S)-proto-Pb (6) from P. canariensis, 1, 6, glucoluteolin (7), tricin 7-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside (8), and methyl (25S)-proto-loureiroside (9) from P. humilis var. hanceana, 1, 2, 8, methyl proto-prosapogenin A of dioscin (10), methyl proto-reclinatoside (11) and methyl proto-Pb (12) from P. dactylifera, and vitexin (13) and methyl (25S)-proto-dioscin (14) from Licuala spinosa have been isolated and identified.

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.