19057-68-2

Usage

Uses

Used in Pharmaceutical Industry:
(25R)-3β-(4-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene is used as a therapeutic agent for its anti-inflammatory properties, making it a potential treatment for conditions characterized by inflammation.
Used in Pharmaceutical Industry:
(25R)-3β-(4-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene is used as an antidiabetic agent, leveraging its potential to manage blood sugar levels and support diabetes management.
Used in Nutraceutical Industry:
(25R)-3β-(4-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene is used as an antioxidant supplement, capitalizing on its ability to combat oxidative stress and support overall health.
Used in Pharmaceutical and Nutraceutical Industries:
(25R)-3β-(4-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene is used as a research compound for further exploration of its potential applications in therapeutic and nutritional products, given its demonstrated pharmacological properties.

Upstream product

• 60478-68-4 dioscin 
• 102115-79-7 pseudoprotodioscin 
• 55056-80-9 protodioscin 

Downstream Products

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

Relevant academic research and scientific papers

Microbial transformation of pseudoprotodioscin by Gibberella fujikuroi

Three new (6, 9, and 12) and nine known steroidal saponins were obtained from the fermentation broth of pseudoprotodioscin (PPD) incubated with a fungus Gibberella fujikuroi CGMCC 3.4663. Structures of the metabolites were elucidated by 1-D (1H, 13C), 2-D (HMBC, HSQC, NOESY) NMR, and HR-MS analyses. The biotransformation pathway of pseudoprotodioscin by Gibberella fujikuroi CGMCC 3.4663 was proposed. Compounds 1–11 were tested in vitro for their cytotoxic activities against two human cancer cell lines (HepG2 and Hela). Compounds 1, 6, 9, and 10 exhibited cytotoxic activity against HepG2 cells. Compound 10 exhibited cytotoxicity to Hela cells.

Cytotoxic activities and structure-cytotoxic relationships of steroidal saponins

We have systematically examined the cytotoxic activities of the steroidal saponins mainly isolated from the Liliaceae plants against HL-60 human promyelocytic leukemia cells and found several structure-activity relationships. Some steroidal saponins evaluated in the assay system showed considerable cytotoxic activities, which were almost as potent as that of etoposide used as a positive control. The activities were found to be sensitive to the monosaccharides constituting the sugar moieties and their sequences, as well as to the structures of the aglycons.

The substrate specificity of a glucoamylase with steroidal saponin-rhamnosidase activity from Curvularia lunata

In previous work, we studied and reported that an enzyme from Curvularia lunata 3.4381 had the novel specificity to hydrolyze the terminal rhamnosyl at C-3 position of steroidal saponin and obtained four transformed products; the enzyme was purified and ascertained as glucoamylase (EC 3.2.1.3 GA). In this work, the enzyme exhibiting steroidal saponin-rhamnosidase activity was systematically studied on 21?steroidal saponins and 6 ginsenosides. The results showed that the α-1,2-linked end-rhamnosyl residues at C-3 position of steroidal saponins could be hydrolyzed to corresponding secondary steroidal saponins, among which 18 compounds were isolated and identified, including 3 new secondary compounds. For the furostanosides having glucosyl residues at the C-26 position, hydrolysis occurred first at end-rhamnosyl at C-3 position to produce secondary furostanosides. The reaction of hydrolyzing glucosyl at C-26 position depended considerably on longer reaction times yielding the corresponding secondary spirostanosides (without rhamnosyl and glucosyl residues). The enzyme had the strict specificity for the terminal α-1,2-linked rhamnosyl residues of linear chain, or the terminal α-1,2-linked rhamnosyl residues with branched chain of 1,4-linked glycosyl residues of sugar chain at C-3 position of steroidal saponins, it was not specific for different aglycones, different glycons, and the number of glycon of sugar chain of steroidal saponin. The end-rhamnosyl of ginsenosides and p-nitrophenyl-α-l-rhamnopyranoside (pNPR) could not be hydrolyzed by the enzyme from C. lunata.

The microbiological transformation of steroidal saponins by Curvularia lunata

The microbiological transformation of polyphyllin I (compound I), polyphyllin III (compound II), polyphyllin V (compound III) and polyphyllin VI (compound IV) by Curvularia lunata into their corresponding subsaponins, for example, diosgenin-3-O-α-l-arabinofuranosyl (1→4)-β-d- glucopyranoside (compound V), diosgenin-3-O-α-l-rhamnopyranosyl (1→4)-β-d-glucopyranoside (compound VI), diosgenin-3-O-β-d- glucopyranoside (compound VII) and pennogenin-3-O-β-d-glucopyranoside (compound VIII), were studied in this paper. Curvularia lunata is able to hydrolyze terminal rhamnosyls that are linked by 1→2 C- bond to sugar residues of steroidal saponins at C-3 position with high activity and regioselectivity.