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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 of PICEATANNOL

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
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

Sources: Chemische Berichte (1958), 91, 141-3

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis.
1999
Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved.
2003 Apr 10
Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes.
2004 Aug 15
Effects of resveratrol, piceatannol, tri-acetoxystilbene, and genistein on the inflammatory response of human peripheral blood leukocytes.
2005 May
Resveratrol oligomers are potent MRP1 transport inhibitors.
2006 May-Jun
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Resveratrol attenuates oxLDL-stimulated NADPH oxidase activity and protects endothelial cells from oxidative functional damages.
2007 Apr
Characterization of immunological activities of peanut stilbenoids, arachidin-1, piceatannol, and resveratrol on lipopolysaccharide-induced inflammation of RAW 264.7 macrophages.
2007 Mar 21
Piceatannol inhibits phorbol ester-induced NF-kappa B activation and COX-2 expression in cultured human mammary epithelial cells.
2009
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
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
Control of eotaxin-1 expression and release by resveratrol and its metabolites in culture human pulmonary artery endothelial cells.
2011
Piceatannol enhances TRAIL-induced apoptosis in human leukemia THP-1 cells through Sp1- and ERK-dependent DR5 up-regulation.
2011 Apr
Resveratrol, a phytoestrogen found in red wine, down-regulates protein S expression in HepG2 cells.
2011 Jan
Involvement of SIRT1 in hypoxic down-regulation of c-Myc and β-catenin and hypoxic preconditioning effect of polyphenols.
2012 Mar 1
First-in-class small molecule inhibitors of the single-strand DNA cytosine deaminase APOBEC3G.
2012 Mar 16
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
Patents

Patents

Sample Use Guides

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
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
  • Download
Name Type Language
PICEATANNOL
INCI  
INCI  
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
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
Code System Code Type Description
CAS
10083-24-6
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
NSC
365798
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
WIKIPEDIA
Piceatannol
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
CHEBI
28814
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
PUBCHEM
667639
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
NSC
622471
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
FDA UNII
6KS3LS0D4F
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
EPA CompTox
DTXSID6040587
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
DRUG BANK
DB08399
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
NCI_THESAURUS
C1195
Created by admin on Sat Dec 17 22:58:42 UTC 2022 , Edited by admin on Sat Dec 17 22:58:42 UTC 2022
PRIMARY
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