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
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+
Molecular Formula | C14H12O4 |
Molecular Weight | 244.2427 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27671818Curator'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
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 |
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Target ID: CHEMBL267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10743952 |
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Target ID: CHEMBL258 |
82.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis. | 1999 |
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Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved. | 2003 Apr 10 |
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Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. | 2004 Aug 15 |
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Effects of resveratrol, piceatannol, tri-acetoxystilbene, and genistein on the inflammatory response of human peripheral blood leukocytes. | 2005 May |
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Resveratrol oligomers are potent MRP1 transport inhibitors. | 2006 May-Jun |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Resveratrol attenuates oxLDL-stimulated NADPH oxidase activity and protects endothelial cells from oxidative functional damages. | 2007 Apr |
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Characterization of immunological activities of peanut stilbenoids, arachidin-1, piceatannol, and resveratrol on lipopolysaccharide-induced inflammation of RAW 264.7 macrophages. | 2007 Mar 21 |
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Piceatannol inhibits phorbol ester-induced NF-kappa B activation and COX-2 expression in cultured human mammary epithelial cells. | 2009 |
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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 |
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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 |
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Control of eotaxin-1 expression and release by resveratrol and its metabolites in culture human pulmonary artery endothelial cells. | 2011 |
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Piceatannol enhances TRAIL-induced apoptosis in human leukemia THP-1 cells through Sp1- and ERK-dependent DR5 up-regulation. | 2011 Apr |
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Resveratrol, a phytoestrogen found in red wine, down-regulates protein S expression in HepG2 cells. | 2011 Jan |
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Involvement of SIRT1 in hypoxic down-regulation of c-Myc and β-catenin and hypoxic preconditioning effect of polyphenols. | 2012 Mar 1 |
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First-in-class small molecule inhibitors of the single-strand DNA cytosine deaminase APOBEC3G. | 2012 Mar 16 |
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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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671818
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29041990
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
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Record UNII |
6KS3LS0D4F
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Record Status |
Validated (UNII)
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C1967
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Piceatannol
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