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

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 8297
Tyrosine-protein kinase LCK 12 Target ID: CHEMBL258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16441060 \| https://www.ncbi.nlm.nih.gov/pubmed/22257213	Inhibitor 8297		82.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis.	1999	10370868
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
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
Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways.	2006 Feb	16243536
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Yeast glucan particles activate murine resident macrophages to secrete proinflammatory cytokines via MyD88- and Syk kinase-dependent pathways.	2007 Aug	17572156
The small polyphenolic molecule kaempferol increases cellular energy expenditure and thyroid hormone activation.	2007 Mar	17327447
Characterization of immunological activities of peanut stilbenoids, arachidin-1, piceatannol, and resveratrol on lipopolysaccharide-induced inflammation of RAW 264.7 macrophages.	2007 Mar 21	17316017
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
Syk is a novel target of arsenic trioxide (ATO) and is involved in the toxic effect of ATO in human neutrophils.	2010 Apr	19925860
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	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 Aug	20484155
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	20846786

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).

Name

Type

Language

PICEATANNOL

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