POLYDATIN

First approved in 2010

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 Search

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

Molecular Formula	C20H22O8
Molecular Weight	390.3839
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23862567
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
lipid metabolic process 20 Target ID: GO:0006629 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23862567	Modulator 828
Free radical scavenging 5 Target ID: Free radical scavenging Sources: https://www.ncbi.nlm.nih.gov/pubmed/27526125	Activator 1430
Pyruvate kinase isozymes M1/M2 12 Target ID: CHEMBL1075189 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26951145	Inhibitor 8297	128.0 µM [IC50]
Leishmania amazonensis 8 Target ID: CHEMBL612877 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26517558	Inhibitor 8297	95.0 µM [IC50]
Sirt1, UniProtKB - A0A0G2JZ79 1 Target ID: Sirt1, UniProtKB - A0A0G2JZ79 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26301045	Activator 1430
Sulfonylurea receptors; K-ATP channels 11 Target ID: CHEMBL2095152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22277937 \| https://www.ncbi.nlm.nih.gov/pubmed/23862567 \| https://www.ncbi.nlm.nih.gov/pubmed/16369084	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Shock 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23241098	Primary		Phase II 1132	Unknown Approved Use Unknown
Irritable bowel syndrome 60 Sources: https://clinicaltrials.gov/ct2/show/NCT01370720	Primary		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.	2001	11962253
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	15686436
Role of peptide primary sequence in polyphenol-protein recognition: an example with neurotensin.	2005 Nov 30	16249055
Transport, deglycosylation, and metabolism of trans-piceid by small intestinal epithelial cells.	2006 Oct	17009167
Anti-HIV activities of the compounds isolated from Polygonum cuspidatum and Polygonum multiflorum.	2010 Jun	20112182
Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFκB and AhR and EGFR-ERK pathway.	2011 Sep 1	21756928
Plant polyphenols regulate chemokine expression and tissue repair in human keratinocytes through interaction with cytoplasmic and nuclear components of epidermal growth factor receptor system.	2012 Feb 15	21967610
Polydatin (PD) inhibits IgE-mediated passive cutaneous anaphylaxis in mice by stabilizing mast cells through modulating Ca²⁺ mobilization.	2012 Nov 1	22959927
Polydatin attenuated food allergy via store-operated calcium channels in mast cell.	2013 Jul 7	23840142
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	24361291
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	25130191

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:36:56 GMT 2023` Edited by `admin` on `Fri Dec 15 17:36:56 GMT 2023`
Record UNII	XM261C37CQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

POLYDATIN

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)