19057-67-1

Basic information

• Product Name: (25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene
• Synonyms: Progenin III(Prosapogenin A);(25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene;[(25R)-Spirost-5-en-3β-yl]2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside;Progenin III;Prosapogenin A 【dioscin】;Prosapogenin A【Dioscorea tokoro】;Prosapogenin D'1;Polyphyllin E (= Prosapogenin A)
• CAS NO: 19057-67-1
• Molecular Formula: C₃₉H₆₂O₁₂
• Molecular Weight: 722.90238
• Product Categories: reagent;standard substance
• Mol File: 19057-67-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 212℃
• Boiling Point: 838.82 °C at 760 mmHg
• Flash Point: 461.102 °C
• Appearance: /
• Density: 1.34
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.85±0.70(Predicted)
• CAS DataBase Reference: (25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene(19057-67-1)
• EPA Substance Registry System: (25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene(19057-67-1)

Safety Data

• Hazardous Substances Data: 19057-67-1(Hazardous Substances Data)

Usage

Description

(25R)-3β-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene is a complex organic chemical compound that belongs to the class of steroidal saponins. It features a spirostane skeleton (spirosta-5-ene), which is a common structural element in steroidal saponins, and is adorned with sugar moieties, specifically rhamnose and glucose (2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy), attached to the steroid backbone. This natural product is typically found in various plant species and is known for its bioactive properties, such as anti-inflammatory, anti-cancer, and cholesterol-lowering effects.

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

• 335591-64-5 diosgenyl 2,3,4-tri-O-benzoyl-α–L-rhamnopyranosyl-(1→2)-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 53846-52-9 diosgenin 3-O-<α-L-rhamnopyranosyl(1<*>2)>-<β-D-glucopyranosyl(1<*>4)>-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 
• 512-04-9 diosgenin 
• 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 
• 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 
• 573700-75-1 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl 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 
• 573700-76-2 diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 211797-94-3 diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside 
• 60478-68-4 dioscin 
• 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> 

Downstream Products

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

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.

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

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.