65914-17-2

Basic information

• Product Name: Polydatin
• Synonyms: 4',5-DIHYDROXYSTILBENE-3-O-BETA-D-GLUCOSIDE;3-HYDROXY-5-(2-(4-HYDROXYPHENYL)ETHENYL)PHENYL-BETA-D-GLUCOSIDE;3,4',5-TRIHYDROXYSTILBENE-3-BETA-MONOGLUCOSIDE;3,4'-5-TRIHYDROXYSTILBENE-3-BETA-D-GLUCOPYRANOSIDE;TRANS-RESVERATROL 3-O-BETA-D-GLUCURONIDE;TRANS-RESVERATROL-O-BETA-GLUCOSIDE;PICEID;RESVERATROL GLUCOSIDE
• CAS NO: 65914-17-2
• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 407.39
• Product Categories: Natural Plant Extract;Improve Organism Immunity;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;plant extract;Herb extract;natural product;Inhibitors
• Mol File: 65914-17-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 223-226 °C(lit.)
• Boiling Point: 707.7 °C at 760 mmHg
• Flash Point: 381.8 °C
• Appearance: /
• Density: 1.521 g/cm³
• Vapor Pressure: 1.34E-20mmHg at 25°C
• Refractive Index: 1.69
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly), Water (Slightly)
• PKA: 9.31±0.10(Predicted)
• BRN: 54837
• CAS DataBase Reference: Polydatin(CAS DataBase Reference)
• NIST Chemistry Reference: Polydatin(65914-17-2)
• EPA Substance Registry System: Polydatin(65914-17-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 65914-17-2(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 65914-17-2 differently. You can refer to the following data:
1. Polydatin (PD) is a major chemical component of Polygonum cuspidatum and it could also be found in a variety of other sources. PD is a polyphenol belonging to the chemical family of stilbenoids. Previous studies have shown that PD exhibits many pharmacological activities, including cardioprotective, neuroprotective, and antioxidative activities. With vascular dementia (VaD) rat models, PD markedly attenuated cognitive deficits. Biochemical analysis revealed that PD decreased the production of malondialdehyde (MDA) and significantly increased superoxide dismutase and catalase activities. Additionally, PD effectively alleviated the injuries of cultured neurons induced by oxygen–glucose deprivation. The therapeutic potential of PD for VaD seems related to its antioxidative activity and the direct protection of neurons. Furthermore, PD could also effectively inhibit the polymerization of amyloid-β peptides, which is a major mark in the progression of pathogenesis in Alzheimer’s disease (AD). These results suggest that PD is a promising drug candidate or nutraceutical for the treatment of VaD and AD.
2. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside is a stilbene glucoside that has been found in V. vinifera and has diverse biological activities. It reduces the growth of SKOV3 ovarian cancer cell 3D aggregates in a concentration-dependent manner. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside (10 and 20 μg/ml) inhibits IL-17 production in activated peripheral blood mononuclear cells (PBMCs). It inhibits the loss of glutathione peroxidase 4 (GPX4) activity induced by the ferroptosis inducer hemin in Neuro2a neuroblastoma cells. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside (50 mg/kg) reduces escape latency in a rat model of vascular dementia induced by four-vessel occlusion (4-VO).

Uses

Different sources of media describe the Uses of 65914-17-2 differently. You can refer to the following data:
1. Polydatin, a type of polyphenolic phytoalexin, has many physiological and pharmacological effects including anti-inflammatory and anti-oxidative activities. Polydatin is an effective candidate drug for the protection of photo-inflammation. Polydatin exhibits therapeutic potential for vascular dementia, most likely due to its anti-oxidant activity and the direct protection of neurons.
2. Trans-piceid is a stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue. It has a role as a metabolite, a potassium channel modulator, an anti-arrhythmia drug, a hepatoprotective agent, an antioxidant and a nephroprotective agent. It is a stilbenoid, a polyphenol, a beta-D-glucoside and a monosaccharide derivative. It derives from a trans-resveratrol.
3. Polydatin is a Resveratrol glycoside and inhibitor of platelet aggregation.

Biological Functions

Stilbene found in medicinal herbs. Antioxidant, anti-inflammatory and neuroprotective.

Biological Activity

Polydatin is a natural stilbene originally isolated from the rhizome of P. cuspidatum, which is used in traditional Chinese medicine for analgesic, antipyretic, and diuretic effects.Like other stilbenes, this resveratrol glucoside has antioxidant activity.Polydatin has diverse effects in cells, tissues, and animals, including reducing cytotoxicity, inflammation, and atherosclerosis.

Biochem/physiol Actions

Stilbene found in medicinal herbs. Antioxidant, anti-inflammatory and neuroprotective.

Clinical Use

Polydatin (PD, also named pieceid, (E)-piceid, (E)-polydatin, trans-polydatin, 3,40 ,5-trihydroxystilbene-3-b-D-glucoside) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum Sieb. et Zucc. (Polygonaceae), a traditional Chinese medicine that has long been used in China as an analgesic, anti-pyretic, diuretic and expectorant. It is a glucoside of resveratrol (3,40 ,5-trihydroxystilbene) in which the glucoside group bound to the position C-3 substitutes a hydroxyl group, belonging to stilbene phytoalexins. Polydatin can also be detected in grape, peanut, hop cones, red wines, hop pellets, cocoa-containing products, chocolate products and many daily diets. Polydatin is the most abundant form of resveratrol in nature. Polydatin shows many pharmacological effects confirmed by numerous investigations, including cardiovascular protection, neuroprotection, anti-inflammation, immunoregulation, anti-oxidation, anti-tumour and liver and lung protective effects. Polydatin has found its way into clinical trials for the treatment of hemorrhagic shock and irritable bowel syndrome.

InChI:InChI=1/C21H24O8/c1-27-15-6-4-12(5-7-15)2-3-13-8-14(23)10-16(9-13)28-21-20(26)19(25)18(24)17(11-22)29-21/h2-10,17-26H,11H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1

Upstream product

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 62502-04-9 (E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene 
• 133-89-1 UDP-glucose 
• 57-50-1 Sucrose 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 197440-94-1 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{3-hydroxy-5-[(Z)-2-(4-methoxy-phenyl)-vinyl]-phenoxy}-tetrahydro-pyran-3-yl ester 
• 192710-89-7 cis-5-(4-methoxystyryl)benzene-1,3-diol 
• 21960-26-9 (4-methoxybenzylidene)triphenylphosphorane 
• 824-94-2 p-methoxybenzyl chloride 
• 187803-40-3 3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 65728-21-4 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol 
• 26153-38-8 3,5-dihydroxybenzaldehyde 
• 709030-17-1 3-acetoxy-5-iodophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 7585-39-9 β‐cyclodextrin 
• 492-61-5 β-D-glucose 

Relevant articles and documents

Enzymatic Synthesis of Resveratrol α-Glucoside by Amylosucrase of Deinococcus geothermalis

Glycosylation of resveratrol was carried out by using the amylosucrase of Deinococcus geothermalis, and the glycosylated products were tested for their solubility, chemical stability, and biological activities. We synthesized and identified these two major glycosylated products as resveratrol-4'-O- α-glucoside and resveratrol-3-O-α-glucoside by nuclear magnetic resonance analysis with a ratio of 5:1. The water solubilities of the two resveratrol-α-glucoside isomers (α-piceid isomers) were approximately 3.6 and 13.5 times higher than that of β-piceid and resveratrol, respectively, and they were also highly stable in buffered solutions. The antioxidant activity of the α-piceid isomers, examined by radical scavenging capability, showed it to be initially lower than that of resveratrol, but as time passed, the α-piceid isomers' activity reached a level similar to that of resveratrol. The α- piceid isomers also showed better inhibitory activity against tyrosinase and melanin synthesis in B16F10 melanoma cells than β-piceid. The cellular uptake of the α-piceid isomers, which was assessed by ultra-performance liquid chromatography (UPLC) analysis of the cell-free extracts of B16F10 melanoma cells, demonstrated that the glycosylated form of resveratrol was gradually converted to resveratrol inside the cells. These results indicate that the enzymatic glycosylation of resveratrol could be a useful method for enhancing the bioavailability of resveratrol.

Switching glycosyltransferase UGTBL1 regioselectivity toward polydatin synthesis using a semi-rational design

The 62nd residue of glycosyltransferase UGTBL1 was identified as a "hotspot" for glycosylation at 3-OH of resveratrol. Via semi-rational design including structure-guided alanine scanning and saturation mutations, the mutation I62G significantl

Creating a Water-Soluble Resveratrol-Based Antioxidant by Site-Selective Enzymatic Glucosylation

The phytochemical resveratrol (trans-3,5,4′-trihydroxystilbene) has drawn great interest as health-promoting food ingredient and potential therapeutic agent. However, resveratrol shows vanishingly low water solubility; this limits its uptake and complicates the development of effective therapeutic forms. Glycosylation should be useful to enhance resveratrol solubility, with the caveat that unselective attachment of sugars could destroy the molecule's antioxidant activity. UGT71A15 (a uridine 5′-diphosphate α-D-glucose-dependent glucosyltransferase from apple) was used to synthesize resveratrol 3,5-β-D-diglucoside; this was about 1700-fold more water-soluble than the unglucosylated molecule (～0.18 mM), yet retained most of the antioxidant activity. Resveratrol 3-β-D-glucoside, which is the naturally abundant form of resveratrol, was a practical substrate for perfect site-selective conversion into the target diglucoside in quantitative yield (gL-1 concentration).