19057-67-1

Usage

Uses

Used in Pharmaceutical Industry:
(25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene is used as a potential medicinal compound for its bioactive properties. (25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene's anti-inflammatory, anti-cancer, and cholesterol-lowering effects make it a candidate for the development of new therapeutic agents.
Used in Nutraceutical Industry:
In the nutraceutical industry, (25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene is used as a dietary supplement ingredient, leveraging its cholesterol-lowering and health-promoting properties to support overall well-being.
Used in Cosmetic Industry:
(25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene is used as an active ingredient in cosmetic products, particularly for its potential anti-inflammatory effects, which can be beneficial for skin care formulations aimed at reducing inflammation and promoting skin health.

Upstream product

• 53846-52-9 diosgenin 3-O-<α-L-rhamnopyranosyl(1<*>2)>-<β-D-glucopyranosyl(1<*>4)>-β-D-glucopyranoside 
• 50773-41-6 (3β,25R)-spirost-5-en-3-ol-3-O-α-L-arabinofuranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside 
• 60478-68-4 dioscin 
• 573700-76-2 diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 573700-75-1 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide 
• 573700-74-0 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose 
• 211797-94-3 diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside 
• 211797-93-2 diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 161007-95-0 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 
• 92418-39-8 1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose 
• 55916-50-2 (25R)-26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,22ξ,26-triol 3-O-2)-O-β-D-glucopyranoside> 
• 335591-64-5 diosgenyl 2,3,4-tri-O-benzoyl-α–L-rhamnopyranosyl-(1→2)-3,6-di-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 

Downstream Products

• 14144-06-0 trillin 
• 512-04-9 diosgenin 

Relevant academic research and scientific papers

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.

Synthesis of spirostanol saponins via gold(I)-catalyzed glycosylation in the presence of Ga(OTf)3, In(OTf)3, or HOTf

An effective approach relying on a Lewis acid- or Br?nsted acid-assisted gold(I)-catalyzed glycosylation has been reported in the synthesis of a panel of the representative natural spirostanol saponins, namely polyphyllin D (1), polyphyllin V (2), dioscin (3), formosanin C (4), and a derivative of polyphyllin D bearing a terminal azide group (5). This approach highlights the engagement of low loadings of Ph3AuPOTf (≤ 0.5 mol%) in the presence of Ga(OTf)3, In(OTf)3, or HOTf (~10mol%) as a co-catalyst, at practical reaction rates as an alternative to the conventional ~10 mol% loadings of the gold(I) catalyst in the glycosylation. Polyphyllin D (1) was obtained in 41% overall yield over six steps compared to the maximum 30% yield in previous syntheses where conventional donors and promoters were used. By exploiting a regioselective rhamnosylation, a “one-pot” approach was adopted to assemble 1 and 5, thus further strengthening the efficiency of the gold(I)-catalyzed glycosylation.

STEROID SAPONINS WITH ANTI-CANCER ACTIVITY

The present invention relates to a new class of steroid saponins that have interesting biological activity. In particular the present invention relates to a class of steroid saponins in which the sugar moiety has been selectively functionalised to introdu

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.

Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin

A new steroidal saponin-β-glucosidase from Aspergillus flavus that specifically hydrolyzed the terminal β-d-glucosyl group at the C-3 position of zingiberen newsaponin, deltonin and trillin from Dioscorea zingiberensis C. H. Wright (DZW) was purified, and characterized. The optimal temperature and pH for the new steroidal saponin-β-glucosidase was 50 C and pH 5.0. The steroidal saponin-β-glucosidase was stable at 30-60 C, and retained more than 80% activity. Further, the purified protein was analyzed by ESI-Q-TOF proteomic analyzer. The results indicated that this enzyme is a β-glucosidase of the type glycosidase hydrolase 3 (GH3). Using a combination of the steroidal saponin-β-glucosidase and steroidal saponin-α-1,2-rhamnosidase from Curvularia lunata obtained previously in our lab, the saponins zingieren newsaponin and deltonin could be converted to diosgenin. The pathways of converting zingiberen newsaponin and deltonin into diosgenin by the two key enzymes were elucidated in this study.

Synthesis of novel spirostanic saponins and their cytotoxic activity

This study was carried out to assess the cytotoxicity of several new synthetic steroidal saponins against the human myeloid leukemia cell lines (HL-60 and U937) and against human melanoma cells (SK-MEL-1). Several diosgenyl glycosides analyzed showed strong cell growth inhibition which was associated with alterations in cell cycle progression and induction of apoptosis. Studies of cytochrome c release and caspase-9 activation suggest a main role of the intrinsic pathway of apoptosis in the mechanism of cytotoxicity caused by this kind of compounds.

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.

Synthesis of diosgenyl α-L-rhamnopyranosyl-(1 → 2)-[β-D- glucopyranosyl-(1 → 3)]-β-D-glucopyranoside (gracillin) and related saponins

Diosgenyl α-L-rhamnopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 3)]- β-D-glucopyranoside (gracillin), a monodesmosidic saponin isolated from paris, dioscorea, and costacea species with promising cardiovascular and antitumor activities, was synthesized by s

A SULFATED GLYCOSIDE FROM THE PREPARATION "TRIBESTAN"

The chemical composition and structures of the steroid glycosides forming the active principle of the preparation "tribestan", which is used for treating impotence and female infertility, have been studied.It has been shown that together with trillin, prosapogenin A of dioscin, trillarin, dioscin, gracillin, protodioscin and protogracillin, tribestane contains a diosgenin rhamnoglucoside sulfated in position 4 of the glucose residue, the structure of which has been shown by chemical and physicochemical methods.