PICEATANNOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H12O4
Molecular Weight	244.2427
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC(\C=C\C2=CC=C(O)C(O)=C2)=CC(O)=C1

InChI

InChIKey=CDRPUGZCRXZLFL-OWOJBTEDSA-N

InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+

HIDE SMILES / InChI

Molecular Formula	C14H12O4
Molecular Weight	244.2427
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26758628 | https://www.ncbi.nlm.nih.gov/pubmed/29214257 | https://www.ncbi.nlm.nih.gov/pubmed/29041990 | https://www.ncbi.nlm.nih.gov/pubmed/28888979

Piceatannol (3,3′,4,5′-tetrahydroxy-trans-stilbene; PIC) is a naturally occurring stilbene present in diverse plant sources. Piceatannol is a hydroxylated analog of resveratrol and produced from resveratrol by microsomal cytochrome P450 1A11/2 and 1B1 activities. Like resveratrol, Piceatannol has a broad spectrum of health beneficial effects, many of which are attributable to its antioxidative and anti-inflammatory activities. Piceatannol exerts anticarcinogenic effects by targeting specific proteins involved in regulating cancer cell proliferation, survival/death, invasion, metastasis, angiogenesis, etc. in the tumor microenvironment. Piceatannol also has other health promoting and disease preventing functions, such as anti-obese, antidiabetic, neuroprotective, cardioprotective, anti-allergic, anti-aging properties. A comprehensive review of PIC concludes that the compound has the health promoting and disease preventive potential. However, low water-solubility and bioavailability of PIC limit its pharmaceutical application and also use in functional foods. In this context, it is noticeable that beta-cyclodextrin was found to improve the bioavailability, the solubility and the stability of Piceatannol.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine-protein kinase SRC 19 Target ID: CHEMBL267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10743952	Inhibitor 8297
Tyrosine-protein kinase LCK 12 Target ID: CHEMBL258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16441060 \| https://www.ncbi.nlm.nih.gov/pubmed/22257213	Inhibitor 8297		82.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved.	2003 Apr 10	12687016
Resveratrol-induced modification of polyamine metabolism is accompanied by induction of c-Fos.	2003 Mar	12663506
Purinergic P2Y12 receptor blockade inhibits shear-induced platelet phosphatidylinositol 3-kinase activation.	2003 Mar	12606772
Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes.	2004 Aug 15	15276085
Estrogenic effects of resveratrol in breast cancer cells expressing mutant and wild-type estrogen receptors: role of AF-1 and AF-2.	2004 Mar	15120416
Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship.	2004 Nov 1	15465334
Antimycobacterial agents from selected Mexican medicinal plants.	2005 Sep	16105233
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Resveratrol attenuates oxLDL-stimulated NADPH oxidase activity and protects endothelial cells from oxidative functional damages.	2007 Apr	17194732
Calpain and caspase orchestrated death signal to accomplish apoptosis induced by resveratrol and its novel analog hydroxystilbene-1 [correction of hydroxstilbene-1] in cancer cells.	2010 Aug	20484155
Control of eotaxin-1 expression and release by resveratrol and its metabolites in culture human pulmonary artery endothelial cells.	2011	22254182
Piceatannol, a resveratrol derivative, promotes glucose uptake through glucose transporter 4 translocation to plasma membrane in L6 myocytes and suppresses blood glucose levels in type 2 diabetic model db/db mice.	2012 Jun 8	22579688
Involvement of SIRT1 in hypoxic down-regulation of c-Myc and β-catenin and hypoxic preconditioning effect of polyphenols.	2012 Mar 1	22245592
Anti-HIV-1 activity of resveratrol derivatives and synergistic inhibition of HIV-1 by the combination of resveratrol and decitabine.	2012 Nov 1	23010273
Piceatannol inhibits mast cell-mediated allergic inflammation.	2013 Apr	23426871

Patents

Sample Use Guides

In Vivo Use Guide

The pharmacokinetics of Piceatannol were investigated in male Sprague-Dawley rats after single intravenous doses of 10 mg/kg body weight.

Route of Administration: Intravenous

In Vitro Use Guide

The 96-hole culture plates was used to seed WM266-4 and A2058 cells with 1 x 10 cells/well, and the plate was placed in incubation box at 37 °C with 5% CO2. The cells were treated with different concentrations of piceatannol and after 24-h culture, MTT assay (Gibco) was performed to determine the cell apoptosis. The culture media were placed and 20 μl MTT assay (5 mg/ml) was added to each well prior to 4 h incubation. 150 μl DMSO were added to dissolve the formazan crystals. After 10 min oscillation, the optical density (OD) values were measured with a microplate reader (Beckmann Coulters) at 490 nm. Cell viability was presented as a percent of MTT reduction in the treated cells versus the controls (cells incubated in serumfree DMEM without extracts).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:21:23 UTC 2023` Edited by `admin` on `Sat Dec 16 08:21:23 UTC 2023`
Record UNII	6KS3LS0D4F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PICEATANNOL

Official Name

English

C05901

Code

English

1,2-BENZENEDIOL, 4-(2-(3,5-DIHYDROXYPHENYL)ETHENYL)-, (E)-

Systematic Name

English

1,2-BENZENEDIOL, 4-((1E)-2-(3,5-DIHYDROXYPHENYL)ETHENYL)-

Systematic Name

English

NSC-365798

Code

English

TRANS-PICEATANNOL

Common Name

English

J61.264B

Code

English

PICEATANNOL [INCI]

Common Name

English

3,3',4,5'-TETRAHYDROXY-TRANS-STILBENE

Systematic Name

English

3-HYDROXYRESVERATOL

Common Name

English

ASTRINGENIN

Common Name

English

3,3',4,5'-STILBENETETROL, (E)-

Systematic Name

English

4-((E)-2-(3,5-DIHYDROXYPHENYL)VINYL)-1,2-BENZENEDIOL

Systematic Name

English

TRANS-3,3',4,5'-TETRAHYDROXYSTILBENE

Systematic Name

English

(E)-PICEATANNOL

Common Name

English

4-((E)-2-(3,5-DIHYDROXYPHENYL)ETHENYL)BENZENE-1,2-DIOL

Systematic Name

English

NSC-622471

Code

English

DB08399

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1967