65914-17-2 Usage
Description
Polydatin (PD) is a major chemical component of Polygonum cuspidatum, also found in various other sources, and belongs to the chemical family of stilbenoids. It is a polyphenol with diverse pharmacological activities, including cardioprotective, neuroprotective, and antioxidative properties.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 65914-17-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,9,1 and 4 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 65914-17:
(7*6)+(6*5)+(5*9)+(4*1)+(3*4)+(2*1)+(1*7)=142
142 % 10 = 2
So 65914-17-2 is a valid CAS Registry Number.
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
65914-17-2Relevant articles and documents
Enzymatic Synthesis of Resveratrol α-Glucoside by Amylosucrase of Deinococcus geothermalis
Cha, Jaeho,Lee, Seola,Moon, Keumok,Park, Hyunsu
, p. 1692 - 1700 (2022/02/03)
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
Fan, Bo,Dong, Wenxin,Chen, Tianyi,Chu, Jianlin,He, Bingfang
supporting information, p. 2464 - 2469 (2018/04/12)
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
Lepak, Alexander,Gutmann, Alexander,Kulmer, Sandra T.,Nidetzky, Bernd
, p. 1870 - 1874 (2015/09/02)
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).
