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

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

Uses

Used in Pharmaceutical Industry:
Polydatin is used as a therapeutic agent for vascular dementia due to its antioxidant activity and direct protection of neurons. It also shows potential in treating Alzheimer's disease by inhibiting the polymerization of amyloid-β peptides.
Used in Neuroprotection:
Polydatin is used as a neuroprotective agent, as it effectively alleviates injuries of cultured neurons induced by oxygen-glucose deprivation.
Used in Cardiovascular Protection:
Polydatin is used as a cardioprotective agent, exhibiting many pharmacological activities that benefit the cardiovascular system.
Used in Antioxidant Applications:
Polydatin is used as an antioxidant, reducing the production of malondialdehyde (MDA) and significantly increasing superoxide dismutase and catalase activities.
Used in Anti-Inflammatory Applications:
Polydatin is used as an anti-inflammatory agent, effective for the protection of photo-inflammation.
Used in Platelet Aggregation Inhibition:
Polydatin is used as an inhibitor of platelet aggregation, contributing to its cardiovascular protective effects.
Used in Cancer Treatment:
Polydatin is used in the reduction of SKOV3 ovarian cancer cell 3D aggregate growth in a concentration-dependent manner.
Used in Immunomodulation:
Polydatin is used to inhibit IL-17 production in activated peripheral blood mononuclear cells (PBMCs), demonstrating its immunomodulatory potential.
Used in Neurodegenerative Disease Treatment:
Polydatin is used to inhibit the loss of glutathione peroxidase 4 (GPX4) activity induced by the ferroptosis inducer hemin in Neuro2a neuroblastoma cells, suggesting its potential in treating neurodegenerative diseases.
Used in Cognitive Enhancement:
Polydatin is used to reduce escape latency in a rat model of vascular dementia induced by four-vessel occlusion (4-VO), indicating its potential in improving cognitive function.

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

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• 133-89-1 UDP-glucose 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 197440-96-3 (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene 

Downstream Products

• 106822-44-0 (E)-1-(3-methoxy-5-(β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxyphenyl)ethene 
• 148766-36-3 cis-piceid 
• 7585-39-9 β‐cyclodextrin 
• 29884-49-9 (E)-astringin 
• 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

Hybrid of Resveratrol and Glucosamine: An Approach to Enhance Antioxidant Effect against DNA Oxidation

Resveratrol exhibits various pharmacological activities, which are dependent upon phenolic hydroxyl groups. In this work, glucosamine, lipoic acid, or adamantanamine moiety was applied for attaching to ortho-position of hydroxyl group in resorcinol moiety of resveratrol (known as position-2). Antioxidant effects of the obtained hybrids were characterized using DNA oxidative systems mediated by ?OH, Cu2+/glutathione (GSH), and 2,2′-azobis(2-amidinopropanehydrochloride) (AAPH), respectively. The glucosyl-appended imine and amine at position-2 of resveratrol were found to show higher inhibitory effects than other resveratrol derivatives against AAPH-induced DNA oxidation. The antioxidative effect was quantitatively expressed by stoichiometric factor (n, the number of radical-propagation terminated by one molecule of antioxidant). The stoichiometric factors of glucosyl-appended imine and amine of resveratrol increased to 4.74 (for imine) and 4.97 (for amine), respectively, higher than that of resveratrol (3.70) and glucoside of resveratrol (3.49). It was thereby concluded that the combination of resveratrol with glucosamine at position-2 represented a novel pathway for modifying resveratrol structure in the protection of DNA against peroxyl radical-mediated oxidation.

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

The stilbene compound resveratrol was glycosylated to give its 4′-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4′-O-β-D-glucoside, and converted pinostilbene to its 4′-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested.

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).

Exploring the catalytic promiscuity of a new glycosyltransferase from Carthamus tinctorius

The catalytic promiscuity of a new glycosyltransferase (UGT73AE1) from Carthamus tinctorius was explored. UGT73AE1 showed the capability to glucosylate a total of 19 structurally diverse types of acceptors and to generate O-, S-, and N-glycosides, making it the first reported trifunctional plant glycosyltransferase. The catalytic reversibility and regioselectivity were observed and modeled in a one-pot reaction transferring a glucose moiety from icariin to emodin. These findings demonstrate the potential versatility of UGT73AE1 in the glycosylation of bioactive natural products.

Assessing the regioselectivity of oleD-catalyzed glycosylation with a diverse set of acceptors

To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavonesnY (daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2- methoxyestradiol)- were determined. This study highlights the first synthesis of flavopiridol and 2-methoxyestradiol glucosides and confirms the ability of OleD to glucosylate both aromatic and aliphatic nucleophiles. In all cases, molecular dynamics simulations were consistent with the determined product distribution and suggest the potential to develop a virtual screening model to identify additional OleD substrates.

Glycosylation of trans-resveratrol by plant-cultured cells

Plant-cultured cells of Catharanthus roseus converted trans-resveratrol into its 3-O-β-D-glucopyranoside, 40-O-β-D-glucopyranoside, 3-O-(6-O-β-D-xylopyranosyl)-β-Dglucopyranoside, and 3-O-(6-O-α-L-arabinopyranosyl)-β- D-glucopyranoside. The 3-O-(6-O-β-D-x

Substrate specificities of family 1 UGTs gained by domain swapping

Family 1 glycosyltransferases are a group of enzymes known to embrace a large range of different substrates. This study devises a method to enhance the range of substrates even further by combining domains from different glycosyltransferases to gain impro

Synthesis of mono- and di-O-β-D-glucopyranoside conjugates of (E)-resveratrol

Starting from the commercially available natural product (E)-resveratrol (1), the four selectively tert-butyldimethylsilyl (TBS) protected (E)-resveratrols 6-9 were prepared by one reaction. Using 6-9 as glucosyl acceptors and trifluoroacetimidate 11 as glucosyl donor, three bioactive natural glucopyranoside conjugates of (E)-resveratrol 2-4 and one novel compound (5) were efficiently prepared in two steps. Georg Thieme Verlag Stuttgart.