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 8146
Tyrosine-protein kinase LCK 10 Target ID: CHEMBL258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16441060 \| https://www.ncbi.nlm.nih.gov/pubmed/22257213	Inhibitor 8146		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 266 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown
Obesity 204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis.	1999	10370868
Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved.	2003 Apr 10	12687016
Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes.	2004 Aug 15	15276085
Effects of resveratrol, piceatannol, tri-acetoxystilbene, and genistein on the inflammatory response of human peripheral blood leukocytes.	2005 May	15779068
Resveratrol oligomers are potent MRP1 transport inhibitors.	2006 May-Jun	16827148
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
Characterization of immunological activities of peanut stilbenoids, arachidin-1, piceatannol, and resveratrol on lipopolysaccharide-induced inflammation of RAW 264.7 macrophages.	2007 Mar 21	17316017
Piceatannol inhibits phorbol ester-induced NF-kappa B activation and COX-2 expression in cultured human mammary epithelial cells.	2009	20155627
Piceatannol, a catechol-type polyphenol, inhibits phorbol ester-induced NF-{kappa}B activation and cyclooxygenase-2 expression in human breast epithelial cells: cysteine 179 of IKK{beta} as a potential target.	2010 Aug	20584749
Inhibition of aryl hydrocarbon receptor-dependent transcription by resveratrol or kaempferol is independent of estrogen receptor α expression in human breast cancer cells.	2010 Dec 28	20846786
Control of eotaxin-1 expression and release by resveratrol and its metabolites in culture human pulmonary artery endothelial cells.	2011	22254182
Piceatannol enhances TRAIL-induced apoptosis in human leukemia THP-1 cells through Sp1- and ERK-dependent DR5 up-regulation.	2011 Apr	21167276
Resveratrol, a phytoestrogen found in red wine, down-regulates protein S expression in HepG2 cells.	2011 Jan	20926118
Involvement of SIRT1 in hypoxic down-regulation of c-Myc and β-catenin and hypoxic preconditioning effect of polyphenols.	2012 Mar 1	22245592
First-in-class small molecule inhibitors of the single-strand DNA cytosine deaminase APOBEC3G.	2012 Mar 16	22181350
Effects of hydroxylated resveratrol analogs on oxidative stress and cancer cells death in human acute T cell leukemia cell line: prooxidative potential of hydroxylated resveratrol analogs.	2014 Feb 25	24398169

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 17 22:58:42 UTC 2022` Edited by `admin` on `Sat Dec 17 22:58:42 UTC 2022`
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