Piceatannol
Piceatannol is a polyphenolic hydroxystilbene derivative of resveratrol with increased bioavailability and bioactivity compared to its parent compound. Piceatannol exhibits pro-angiogenic, anticancer, antioxidative, and anti-obesity properties. Piceatannol directly inhibits HIF-prolyl hydroxylase-2 (HPH-2), increasing levels of HIF-1α, VEGF, and heme oxygenase-1 (HO1). When complexed with copper (II), the piceatannol-Cu complex increases ROS levels and damages DNA. Additionally, piceatannol suppresses nuclear translocation of p65 and p50, preventing activation of NF-κB and downregulating expression of matrix metalloproteinase 9 (MMP9). Piceatannol also downregulates phosphorylation of Akt in prostate cancer cells. In other in vitro models, this compound increases levels of tissue inhibitor of metalloproteinase 2 (TIMP2) and inhibits phosphorylation of STAT3; it also downregulates Bcl-xl and inhibits phosphorylation of JNK. In prostate cancer cells, piceatannol decreases levels of cyclins A and D1 and also decreases cyclin-dependent kinase 2 and 4 (CDK2, CDK4) activity, inhibiting cell growth. The hydroxyl groups on piceatannol function as radical scavengers, preventing accumulation of ROS and RNS. This compound noncompetitively inhibits the insulin receptor (IR), preventing phosphorylation of the receptor, IR substrate-1 and Akt, inhibiting adipogenesis of preadipocytes; it may also directly inhibit PI3K and JAK1.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18954235
| Cas No. |
10083-24-6 |
|---|---|
| Purity |
≥98% |
| Formula |
C14H12O4 |
| Formula Wt. |
244.24 |
| Chemical Name |
3,3’,4,5’-Tetrahydroxy-trans-stilbene |
| IUPAC Name |
4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol |
| Solubility |
DMSO (20mg/ml), Ethanol (10mg/ml) |
| Appearance |
Light Pink Powder |
Yum S, Doh HJ, Hong S, et al. Piceatannol, a hydroxystilbene natural product, stabilizes HIF-1α protein by inhibiting HIF prolyl hydroxylase. Eur J Pharmacol. 2013 Jan 15;699(1-3):124-31. PMID: 23261967.
Jayasooriya RG, Lee YG, Kang CH, et al. Piceatannol inhibits MMP-9-dependent invasion of tumor necrosis factor-α-stimulated DU145 cells by suppressing the Akt-mediated nuclear factor-κB pathway. Oncol Lett. 2013 Jan;5(1):341-347. PMID: 23255946.
Li Z, Yang X, Dong S, et al. DNA breakage induced by piceatannol and copper(II): Mechanism and anticancer properties. Oncol Lett. 2012 May;3(5):1087-1094. PMID: 22783397.
Kwon JY, Seo SG, Heo YS, et al. Piceatannol, natural polyphenolic stilbene, inhibits adipogenesis via modulation of mitotic clonal expansion and insulin receptor-dependent insulin signaling in early phase of differentiation. J Biol Chem. 2012 Mar 30;287(14):11566-78. PMID: 22298784.
Kwon GT, Jung JI, Song HR, et al. Piceatannol inhibits migration and invasion of prostate cancer cells: possible mediation by decreased interleukin-6 signaling. J Nutr Biochem. 2012 Mar;23(3):228-38. PMID: 21497499.
Lee YM, Lim do Y, Cho HJ, et al. Piceatannol, a natural stilbene from grapes, induces G1 cell cycle arrest in androgen-insensitive DU145 human prostate cancer cells via the inhibition of CDK activity. Cancer Lett. 2009 Nov 28;285(2):166-73. PMID: 19487074.
Rossi M, Caruso F, Opazo C, et al. Crystal and molecular structure of piceatannol; scavenging features of resveratrol and piceatannol on hydroxyl and peroxyl radicals and docking with transthyretin. J Agric Food Chem. 2008 Nov 26;56(22):10557-66. PMID: 18959413.
Kim HJ, Lee KW, Kim MS, et al. Piceatannol attenuates hydrogen-peroxide- and peroxynitrite-induced apoptosis of PC12 cells by blocking down-regulation of Bcl-XL and activation of JNK. J Nutr Biochem. 2008 Jul;19(7):459-66. PMID: 17869087.
