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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
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.
2001
Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts.
2001 Nov
Piceatannol inhibits TNF-induced NF-kappaB activation and NF-kappaB-mediated gene expression through suppression of IkappaBalpha kinase and p65 phosphorylation.
2002 Dec 1
Functional role of p38 mitogen activated protein kinase in platelet activation induced by a thromboxane A2 analogue and by 8-iso-prostaglandin F2alpha.
2002 May
Short constrained peptides that inhibit HIV-1 entry.
2002 Nov 12
Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved.
2003 Apr 10
Resveratrol-induced modification of polyamine metabolism is accompanied by induction of c-Fos.
2003 Mar
Purinergic P2Y12 receptor blockade inhibits shear-induced platelet phosphatidylinositol 3-kinase activation.
2003 Mar
Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes.
2004 Aug 15
Estrogenic effects of resveratrol in breast cancer cells expressing mutant and wild-type estrogen receptors: role of AF-1 and AF-2.
2004 Mar
Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship.
2004 Nov 1
Effects of resveratrol, piceatannol, tri-acetoxystilbene, and genistein on the inflammatory response of human peripheral blood leukocytes.
2005 May
Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways.
2006 Feb 1
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
Subtype-specific activation of estrogen receptors by a special extract of Rheum rhaponticum (ERr 731), its aglycones and structurally related compounds in U2OS human osteosarcoma cells.
2007 Nov
Upregulation of I-CAM1 in response to beryllium exposure in small airway epithelial cells.
2008 Jul 10
Inhibition of proliferation and migration by piceatannol in vascular smooth muscle cells.
2009 Oct
Piceatannol enhances TRAIL-induced apoptosis in human leukemia THP-1 cells through Sp1- and ERK-dependent DR5 up-regulation.
2011 Apr
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
Piceatannol inhibits mast cell-mediated allergic inflammation.
2013 Apr
Involvement of heme oxygenase-1 expression in neuroprotection by piceatannol, a natural analog and a metabolite of resveratrol, against glutamate-mediated oxidative injury in HT22 neuronal cells.
2013 Aug
Piceatannol suppresses the metastatic potential of MCF10A human breast epithelial cells harboring mutated H-ras by inhibiting MMP-2 expression.
2013 Oct
Direct activation of ATM by resveratrol under oxidizing conditions.
2014
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
Inhibition of CYP17A1 activity by resveratrol, piceatannol, and synthetic resveratrol analogs.
2014 Jun
Natural products induce a G protein-mediated calcium pathway activating p53 in cancer cells.
2015 Nov 1
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 Mon Mar 31 22:01:21 GMT 2025
Edited
by admin
on Mon Mar 31 22:01:21 GMT 2025
Record UNII
6KS3LS0D4F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
C05901
Preferred Name English
PICEATANNOL
INCI  
INCI  
Official Name 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
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 Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
Code System Code Type Description
CAS
10083-24-6
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
NSC
365798
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
WIKIPEDIA
Piceatannol
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
CHEBI
28814
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
PUBCHEM
667639
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
NSC
622471
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
FDA UNII
6KS3LS0D4F
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
EPA CompTox
DTXSID6040587
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
DRUG BANK
DB08399
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
NCI_THESAURUS
C1195
Created by admin on Mon Mar 31 22:01:21 GMT 2025 , Edited by admin on Mon Mar 31 22:01:21 GMT 2025
PRIMARY
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