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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

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

Endres, H.|Grassmann, W.|Mathes, H.
1
Sources: Chemische Berichte (1958), 91, 141-3

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
 82.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.
2001
Resveratrol-induced modification of polyamine metabolism is accompanied by induction of c-Fos.
2003 Mar
Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes.
2004 Aug 15
Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship.
2004 Nov 1
Antimycobacterial agents from selected Mexican medicinal plants.
2005 Sep
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Piceatannol inhibits phorbol ester-induced NF-kappa B activation and COX-2 expression in cultured human mammary epithelial cells.
2009
Resveratrol and piceatannol inhibit iNOS expression and NF-kappaB activation in dextran sulfate sodium-induced mouse colitis.
2009
Anti-HIV-1 activity of resveratrol derivatives and synergistic inhibition of HIV-1 by the combination of resveratrol and decitabine.
2012 Nov 1
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
Patents

Patents

JP01038009
1

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).
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 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
Code System Code Type Description
CAS
10083-24-6
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
NSC
365798
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
WIKIPEDIA
Piceatannol
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
CHEBI
28814
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
PUBCHEM
667639
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
NSC
622471
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
FDA UNII
6KS3LS0D4F
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID6040587
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
DRUG BANK
DB08399
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
NCI_THESAURUS
C1195
Created by admin on Sat Dec 16 08:21:23 GMT 2023 , Edited by admin on Sat Dec 16 08:21:23 GMT 2023
PRIMARY
PARENT (METABOLITE)
Structure of RESVERATROL
SUBSTANCE RECORD
Structure of PICEATANNOL
NIH
NCATS
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