50773-41-6

Basic information

• Product Name: POLYPHYLLIN D
• Synonyms: POLYPHYLLIN D;Polyphyllin;Polyphyllin I;Polyphyllin C;Paris saponin Pa;Polyphillin D;Polyphyllin A;Chonglou Saponin I(Polyphyllin A)
• CAS NO: 50773-41-6
• Molecular Formula: C₄₄H₇₀O₁₆
• Molecular Weight: 855.021
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 50773-41-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.40
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly)
• PKA: 12?+-.0.70(Predicted)
• CAS DataBase Reference: POLYPHYLLIN D(CAS DataBase Reference)
• NIST Chemistry Reference: POLYPHYLLIN D(50773-41-6)
• EPA Substance Registry System: POLYPHYLLIN D(50773-41-6)

Safety Data

• Hazardous Substances Data: 50773-41-6(Hazardous Substances Data)

Usage

Description

Polyphyllin I is a steroid saponin that has been found in P. polyphylla and has anticancer activity. It decreases proliferation of, and induces apoptosis in, MCF-7 and MDA-MB-231 cells (IC50s = 5 and 2.5 μM, respectively). It disrupts the mitochondrial membrane potential, activates caspase-3, and increases protein levels of the caspase-3 substrate poly(ADP-ribose) polymerase (PARP) in HepG2 and drug-resistant R-HepG2 cells. Polyphyllin I (2.05 and 2.73 mg/kg for 10 days) reduces tumor growth in an MCF-7 mouse xenograft model.

Uses

Polyphylin II is a natural saponin extracted from the plant, Paris polyphylla, and displays antiproliferative activity in vivo. Used in the treatment of lung and cervical cancers.

Upstream product

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• 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 
• 56272-01-6 1,2,3,5-tetra-O-acetyl-L-arabinofuranose 
• 222719-12-2 diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside 
• 512-04-9 diosgenin 

Downstream Products

• 2280-44-6 D-Glucose 
• 73-34-7 L-rhamnose 
• 532-20-7 L-arabinose 
• 14144-06-0 trillin 
• 19057-67-1 ophiopogonin C 
• 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.

An improved synthesis of the saponin, polyphyllin D

Polyphyllin D, namely diosgenyl α-L-rhamnopyranosyl-(1→2)-[(α-L-arabinofuranosyl)- (1→4)]-β-D-glucopyranoside, was synthesized from diosgenyl-β-D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and

A facile synthetic approach to a group of structurally typical diosgenyl saponins

A facile approach was developed for synthesizing an important group of plant diosgenyl saponins, three members (dioscin, polyphyllin D, and balanitin 7) with promising bioactivities were prepared.