POLYPHYLLIN D

Base Information

• Chemical Name: POLYPHYLLIN D
• CAS No.: 50773-41-6
• Molecular Formula: C44H70O16
• Molecular Weight: 855.03
• Hs Code.: 29389090
• Mol file: 50773-41-6.mol

Synonyms:(+)-Polyphyllin D;Spiro[8H-naphth[2',1':4,5]indeno[2,1-b]furan-8,2'-[2H]pyran], β-D-glucopyranoside deriv.;Spirostan, β-D-glucopyranoside deriv.;17-Deoxyparis H;2)]-b-D-glycopyranoside;Paris saponinI;Paris saponin Pa;Polyphillin D;Polyphyllin D;Polyphyllin I;Saponin Pa;

Chemical Property of POLYPHYLLIN D

Chemical Property:

• PKA: 12?+-.0.70(Predicted)
• PSA: 235.68000
• Density: 1.4
• LogP: 0.85320
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Polyphyllin I ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of POLYPHYLLIN D

There total 16 articles about POLYPHYLLIN D which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

diosgenyl 2,4,5-tri-O-acetyl-α-L-arabinofuranosyl-(1→4)-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)]-3,6-di-O-pivaloyl-β-D-glucopyranoside → (3β,25R)-spirost-5-en-3-ol-3-O-α-L-arabinofuranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside (50773-41-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 40 ℃;

DOI:10.1016/S0008-6215(01)00014-3

Reference yield: 85.0%

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 (222719-12-2) → (3β,25R)-spirost-5-en-3-ol-3-O-α-L-arabinofuranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside (50773-41-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 50 ℃; for 2h;

DOI:10.1016/S0040-4039(98)01354-9

Reference yield:

C51H84O22 (78101-18-5) → C44H70O16 (50773-41-6)

Guidance literature:

With almond emulsin; In water; at 37 ℃; for 8h;

DOI:10.1248/cpb.30.712

upstream raw materials:

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

1,2,3,5-tetra-O-acetyl-L-arabinofuranose

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

(2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate

Downstream raw materials:

D-Glucose

L-rhamnose

L-arabinose

trillin

Refernces

• 1、 Yang, Zhiqi,Wong, Ella Lai-Ming,Shum, Tina Yuen-Ting,Che, Chi-Ming,Hui, Yongzheng. "Fluorophore-appended steroidal saponin (dioscin and polyphyllin D) derivatives". . p. 669 - 672. Retrieved 2007/10/03.
• 2、 Deng, Shaojiang,Yu, Biao,Hui, Yongzheng,Yu, Hai,Han, Xiuwen. "Synthesis of three diosgenyl saponins: Dioscin, polyphyllin D, and balanitin 7". . p. 53 - 62. Retrieved 2007/10/03.