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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22O8
Molecular Weight 390.3839
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of POLYDATIN

SMILES

OC[C@H]1O[C@@H](OC2=CC(\C=C\C3=CC=C(O)C=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=HSTZMXCBWJGKHG-CUYWLFDKSA-N
InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.webmedcentral.com/article_view/5000

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.

CNS Activity

Curator's Comment: It has shown that PD can cross the blood–brain barrier to protect brain tissues from ischemia–reperfusion injury or cerebral ischemia

Approval Year

PubMed

PubMed

TitleDatePubMed
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.
2001
Cellular uptake and efflux of trans-piceid and its aglycone trans-resveratrol on the apical membrane of human intestinal Caco-2 cells.
2005 Feb 9
In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes.
2005 Mar 23
Anti-HIV activities of the compounds isolated from Polygonum cuspidatum and Polygonum multiflorum.
2010 Jun
Polydatin (PD) inhibits IgE-mediated passive cutaneous anaphylaxis in mice by stabilizing mast cells through modulating Ca²⁺ mobilization.
2012 Nov 1
Polydatin attenuated food allergy via store-operated calcium channels in mast cell.
2013 Jul 7
The stilbenes resveratrol, pterostilbene and piceid affect growth and stress resistance in mammalian cells via a mechanism requiring estrogen receptor beta and the induction of Mn-superoxide dismutase.
2014 Feb
Investigation of the effects of some phenolic compounds on the activities of glucose-6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase from human erythrocytes.
2014 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: can also be used as oral tablets; 200 mg PEA+20 mg polydatin; 2 tablets/day; 12 weeks https://clinicaltrials.gov/ct2/show/NCT01370720
Shock treatment: dilute two 100mg/5mL vials of HW6 (Polydatin) into 500mL 0.9% NaCl injection and administer as i.v. infusion over 2 hours. The drug should be given as early as possible right after the IC Form is signed on Day 1, and once every 24 hours for additional 4 doses.
Route of Administration: Intravenous
Polydatin attenuated phenylephrine-induced inhibition of hypertrophy of murine cardiomyocytes in a concentration-dependent manner with a complete inhibition of hypertrophy at the concentration of 50 uM.
Name Type Language
POLYDATIN
INCI  
INCI  
Official Name English
3,4'-5-TRIHYDROXYSTILBENE-3-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)-1,3-BENZENEDIOL-3-.BETA.-MONO-D-GLUCOSIDE
Common Name English
PICEID
Common Name English
TRANS-POLYDATIN
Common Name English
3-Hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenyl β-D-glucopyranoside
Common Name English
GLUCOPYRANOSIDE, 3-HYDROXY-5-(P-HYDROXYSTYRYL)PHENYL, .BETA.-D-
Common Name English
RESVERATROL 3-.BETA.-MONO-D-GLUCOSIDE [MI]
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, 3-HYDROXY-5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)PHENYL
Common Name English
POLYDATIN [INCI]
Common Name English
Polydatin [WHO-DD]
Common Name English
POLYDATIN [USP-RS]
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, 3-HYDROXY-5-(2-(4-HYDROXYPHENYL)ETHENYL)PHENYL
Common Name English
Classification Tree Code System Code
DSLD 4329 (Number of products:1)
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
Code System Code Type Description
RXCUI
1364277
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PRIMARY RxNorm
DAILYMED
XM261C37CQ
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PRIMARY
FDA UNII
XM261C37CQ
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PRIMARY
CAS
27208-80-6
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PRIMARY
MERCK INDEX
m9549
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PRIMARY Merck Index
WIKIPEDIA
PICEID
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EVMPD
SUB34035
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PUBCHEM
5281718
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PRIMARY
DRUG BANK
DB11263
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PRIMARY
EPA CompTox
DTXSID001030555
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PRIMARY
RS_ITEM_NUM
1546194
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PRIMARY
MESH
C058229
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CHEBI
8198
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PRIMARY
DRUG CENTRAL
4613
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PRIMARY
SMS_ID
100000127888
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PRIMARY