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 8504
Tyrosine-protein kinase LCK 14 Target ID: CHEMBL258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16441060 \| https://www.ncbi.nlm.nih.gov/pubmed/22257213	Inhibitor 8504		82.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Ischemic stroke 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Natural products induce a G protein-mediated calcium pathway activating p53 in cancer cells.	2015-11-01	26341291
Keratinocyte-derived IL-24 plays a role in the positive feedback regulation of epidermal inflammation in response to environmental and endogenous toxic stressors.	2014-10-15	25168428
Inhibition of CYP17A1 activity by resveratrol, piceatannol, and synthetic resveratrol analogs.	2014-06	24610083
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.	2014-02-25	24398169
Direct activation of ATM by resveratrol under oxidizing conditions.	2014	24933654
Piceatannol suppresses the metastatic potential of MCF10A human breast epithelial cells harboring mutated H-ras by inhibiting MMP-2 expression.	2013-10	23877152
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.	2013-08	23712764
Piceatannol inhibits mast cell-mediated allergic inflammation.	2013-04	23426871
Anti-HIV-1 activity of resveratrol derivatives and synergistic inhibition of HIV-1 by the combination of resveratrol and decitabine.	2012-11-01	23010273
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.	2012-06-08	22579688
Piceatannol, natural polyphenolic stilbene, inhibits adipogenesis via modulation of mitotic clonal expansion and insulin receptor-dependent insulin signaling in early phase of differentiation.	2012-03-30	22298784
First-in-class small molecule inhibitors of the single-strand DNA cytosine deaminase APOBEC3G.	2012-03-16	22181350
Involvement of SIRT1 in hypoxic down-regulation of c-Myc and β-catenin and hypoxic preconditioning effect of polyphenols.	2012-03-01	22245592
Piceatannol enhances TRAIL-induced apoptosis in human leukemia THP-1 cells through Sp1- and ERK-dependent DR5 up-regulation.	2011-04	21167276
Resveratrol, a phytoestrogen found in red wine, down-regulates protein S expression in HepG2 cells.	2011-01	20926118
Control of eotaxin-1 expression and release by resveratrol and its metabolites in culture human pulmonary artery endothelial cells.	2011	22254182
Inhibition of aryl hydrocarbon receptor-dependent transcription by resveratrol or kaempferol is independent of estrogen receptor α expression in human breast cancer cells.	2010-12-28	20846786
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.	2010-08	20584749
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.	2010-08	20484155
Syk is a novel target of arsenic trioxide (ATO) and is involved in the toxic effect of ATO in human neutrophils.	2010-04	19925860
Inhibition of proliferation and migration by piceatannol in vascular smooth muscle cells.	2009-10	19631264
Piceatannol inhibits phorbol ester-induced NF-kappa B activation and COX-2 expression in cultured human mammary epithelial cells.	2009	20155627
Resveratrol and piceatannol inhibit iNOS expression and NF-kappaB activation in dextran sulfate sodium-induced mouse colitis.	2009	20155626
Upregulation of I-CAM1 in response to beryllium exposure in small airway epithelial cells.	2008-07-10	18539414
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.	2007-11	17935960
Yeast glucan particles activate murine resident macrophages to secrete proinflammatory cytokines via MyD88- and Syk kinase-dependent pathways.	2007-08	17572156
Resveratrol attenuates oxLDL-stimulated NADPH oxidase activity and protects endothelial cells from oxidative functional damages.	2007-04	17194732
Characterization of immunological activities of peanut stilbenoids, arachidin-1, piceatannol, and resveratrol on lipopolysaccharide-induced inflammation of RAW 264.7 macrophages.	2007-03-21	17316017
The small polyphenolic molecule kaempferol increases cellular energy expenditure and thyroid hormone activation.	2007-03	17327447
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Resveratrol oligomers are potent MRP1 transport inhibitors.	2006-07-11	16827148
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.	2006-02-01	16178010
Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways.	2006-02	16243536
Resveratrol promotes clearance of Alzheimer's disease amyloid-beta peptides.	2005-11-11	16162502
Antimycobacterial agents from selected Mexican medicinal plants.	2005-09	16105233
Effects of resveratrol, piceatannol, tri-acetoxystilbene, and genistein on the inflammatory response of human peripheral blood leukocytes.	2005-05	15779068
Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship.	2004-11-01	15465334
Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes.	2004-08-15	15276085
Estrogenic effects of resveratrol in breast cancer cells expressing mutant and wild-type estrogen receptors: role of AF-1 and AF-2.	2004-03	15120416
Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved.	2003-04-10	12687016
Resveratrol-induced modification of polyamine metabolism is accompanied by induction of c-Fos.	2003-03	12663506
Purinergic P2Y12 receptor blockade inhibits shear-induced platelet phosphatidylinositol 3-kinase activation.	2003-03	12606772
Piceatannol inhibits TNF-induced NF-kappaB activation and NF-kappaB-mediated gene expression through suppression of IkappaBalpha kinase and p65 phosphorylation.	2002-12-01	12444159
Short constrained peptides that inhibit HIV-1 entry.	2002-11-12	12417739
Functional role of p38 mitogen activated protein kinase in platelet activation induced by a thromboxane A2 analogue and by 8-iso-prostaglandin F2alpha.	2002-05	12038794
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.	2001-11	11681415
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.	2001	11962253
Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis.	1999	10370868

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 `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

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Name

Type

Language

C05901

Preferred Name

English

PICEATANNOL

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