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
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.	2001	11962253
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	11681415
Piceatannol inhibits TNF-induced NF-kappaB activation and NF-kappaB-mediated gene expression through suppression of IkappaBalpha kinase and p65 phosphorylation.	2002 Dec 1	12444159
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	12038794
Short constrained peptides that inhibit HIV-1 entry.	2002 Nov 12	12417739
Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved.	2003 Apr 10	12687016
Resveratrol-induced modification of polyamine metabolism is accompanied by induction of c-Fos.	2003 Mar	12663506
Purinergic P2Y12 receptor blockade inhibits shear-induced platelet phosphatidylinositol 3-kinase activation.	2003 Mar	12606772
Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes.	2004 Aug 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 Mar	15120416
Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship.	2004 Nov 1	15465334
Effects of resveratrol, piceatannol, tri-acetoxystilbene, and genistein on the inflammatory response of human peripheral blood leukocytes.	2005 May	15779068
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	16178010
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
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	17935960
Upregulation of I-CAM1 in response to beryllium exposure in small airway epithelial cells.	2008 Jul 10	18539414
Inhibition of proliferation and migration by piceatannol in vascular smooth muscle cells.	2009 Oct	19631264
Piceatannol enhances TRAIL-induced apoptosis in human leukemia THP-1 cells through Sp1- and ERK-dependent DR5 up-regulation.	2011 Apr	21167276
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
Piceatannol inhibits mast cell-mediated allergic inflammation.	2013 Apr	23426871
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	23712764
Piceatannol suppresses the metastatic potential of MCF10A human breast epithelial cells harboring mutated H-ras by inhibiting MMP-2 expression.	2013 Oct	23877152
Direct activation of ATM by resveratrol under oxidizing conditions.	2014	24933654
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
Inhibition of CYP17A1 activity by resveratrol, piceatannol, and synthetic resveratrol analogs.	2014 Jun	24610083
Natural products induce a G protein-mediated calcium pathway activating p53 in cancer cells.	2015 Nov 1	26341291

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