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Piceatannol Sale

(Synonyms: 白皮杉醇; Astringenin; trans-Piceatannol) 目录号 : GN10503

Piceatannol (3,3′,4,5′-trans-trihydroxystilbene) is a naturally occurring hydroxylated analogue of resveratrol .

Piceatannol Chemical Structure

Cas No.:10083-24-6

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10mM (in 1mL DMSO)
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20mg
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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Cell experiment [1]:

Cell lines

Mouse brain endothelial cell line bEnd.3

Preparation Method

The bEnd.3 cells were cultured in DMEM containing 10% FBS plus 100 U/mL penicillin and 100 U/mL streptomycin at 37 °C in a humidified atmosphere with 5% CO2. Cells were subcultured every 2-3 days. All the experiments with bEnd.3 cells were performed between passages 5 to 25 for maintaining excellent BBB characteristics in vitro. The bEnd.3 cell impaired model was induced by treating with LPS at two different concentrations and stimulation times (1 µg/mL for 24 h or 10 µg/mL for 1 h) to examine different target proteins modulating inflammatory and antioxidant responses. Piceatannol (10 or 50 µM) was added to the medium for 30 min and then LPS (10 µg/mL) was added in the existing medium containing piceatannol for 1 h. For another set of experiments, cells were pretreated with piceatannol for 4 h before LPS stimulation (1 µg/mL for 24 h) in the existing medium. Piceatannol was dissolved in 1% dimethyl sulfoxide (DMSO), and LPS was dissolved in phosphate-buffered saline (PBS).

Reaction Conditions

10 or 50 µM for 1.5 or 28 hours

Applications

The protein expression of ICAM-1 and VCAM-1 was upregulated by LPS (1 µg/mL) exposure for 24 h, whereas such upregulation was reversed by pretreatment with 50 µM piceatannol for 4 h in bEnd.3 cells

Animal experiment [2]:

Animal models

Four-week-old female BALB/c mice

Preparation Method

After given 2 weeks for adaption, 4T1-luc cells (5×104 cells) suspended in 0.1-ml matrigel/PBS (1:1, v/v) were injected into the inguinal mammary fat pad. One day after injection, the animals were randomly divided into three experimental groups. Piceatannol (10 or 20 mg/kg) in corn oil or corn oil (vehicle) alone was administered to the mice by oral gavage every day for 30 days.

Dosage form

Oral, 10 or 20 mg/kg

Applications

Tumor weights were also significantly lower in the mice administered with Piceatannol than in the control group. At the time of sacrifice, the tumor weights were 0.915±0.037 g, 0.740±0.028 g and 0.668±0.047 g in the 0-mg/kg Piceatannol, 10-mg/kg Piceatannol and 20-mg/kg Piceatannol groups, respectively.

References:

[1]: Zhou Y, Khan H, Hoi M P M, et al. Piceatannol Protects Brain Endothelial Cell Line (bEnd. 3) against Lipopolysaccharide-Induced Inflammation and Oxidative Stress[J]. Molecules, 2022, 27(4): 1206.
[2]: Song H, Jung J I, Cho H J, et al. Inhibition of tumor progression by oral piceatannol in mouse 4T1 mammary cancer is associated with decreased angiogenesis and macrophage infiltration[J]. The Journal of nutritional biochemistry, 2015, 26(11): 1368-1378.

产品描述

Piceatannol (3,3′,4,5′-trans-trihydroxystilbene) is a naturally occurring hydroxylated analogue of resveratrol [1]. Piceatannol inhibited mushroom tyrosinase with IC50 value of 1.53 mM [2]. piceatannol is a spleen tyrosine kinase (Syk) inhibitor, it is often used in studies involving Syk kinase-dependent cells [3,4], especially neutrophils [5,6], macrophages [7,8] and smooth muscle cells [9,10].

Piceatannol was used to specifically inhibit Syk, which is an important adaptor of FcγR cross-linking-induced downstream signaling. Application of Piceatannol aborted cyclin D1 expression induced by FcγR cross-linking in murine bone marrow-derived macrophages (BMM) [7]. Pre-incubation of piceatannol (100 nM for 1 h) increased neutrophil adhesion in the presence of E3MPO, reversing the non-adherent phenotype of the cells [5]. piceatannol inhibited Ang II-enhanced rat aortic smooth muscle cells (RASMCs) migration, and inhibited Ang II-stimulated phosphorylation of ERK1/2, p38 MAPK and Hsp27, pretreatment with piceatannol attenuated Ang II-increased sprout outgrowth from aortic rings [9].

Piceatannol (10 or 20 mg/kg/d, 3 weeks, oral) administration significantly decreases solid tumor growth in BALB/c mice injected with 4T1 mammary cancer cells [11]. Piceatannol (20 mg/kg/d, 9 days, oral) inhibits lung metastasis of MAT-Ly-Lu (MLL) cells in nude mice [12].

References:
[1]. Piotrowska H, Kucinska M, Murias M. Biological activity of piceatannol: leaving the shadow of resveratrol[J]. Mutation Research/Reviews in Mutation Research, 2012, 750(1): 60-82.
[2]. Yokozawa T, Kim Y J. Piceatannol inhibits melanogenesis by its antioxidative actions[J]. Biological and Pharmaceutical Bulletin, 2007, 30(11).
[3]. Pavanetto M, Zarpellon A, Borgo C, et al. Regulation of serotonin transport in human platelets by tyrosine kinase Syk[J]. Cellular Physiology and Biochemistry, 2011, 27(2): 139-148.
[4]. Beckmann S, Buro C, Dissous C, et al. The Syk kinase SmTK4 of Schistosoma mansoni is involved in the regulation of spermatogenesis and oogenesis[J]. PLoS Pathogens, 2010, 6(2): e1000769.
[5]. Hayes M J, Cambridge G. An IgM class anti-neutrophil cytoplasm antibody inhibits neutrophil adhesion and apoptosis via a Syk dependent signaling cascade[J]. Molecular immunology, 2004, 41(4): 457-468.
[6]. Ortiz‐Stern A, Rosales C. FcγRIIIB stimulation promotes β1 integrin activation in human neutrophils[J]. Journal of leukocyte biology, 2005, 77(5): 787-799.
[7]. Luo Y, Pollard J W, Casadevall A. Fcγ receptor cross-linking stimulates cell proliferation of macrophages via the ERK pathway[J]. Journal of Biological Chemistry, 2010, 285(6): 4232-4242.
[8]. Gevrey J C, Isaac B M, Cox D. Syk is required for monocyte/macrophage chemotaxis to CX3CL1 (Fractalkine)[J]. The Journal of Immunology, 2005, 175(6): 3737-3745.
[9]. Lau H K F, Ho J. Regulation of plasminogen activator inhibitor‿ secretion by urokinase and tissue plasminogen activator in rat epithelioid‐type smooth muscle cells[J]. British journal of haematology, 2002, 117(1): 151-158.
[10]. Lee H M, Lee C K, Lee S H, et al. p38 mitogen-activated protein kinase contributes to angiotensin II-stimulated migration of rat aortic smooth muscle cells[J]. Journal of pharmacological sciences, 2007, 105(1): 74-81.
[11]. Song H, Jung J I, Cho H J, et al. Inhibition of tumor progression by oral piceatannol in mouse 4T1 mammary cancer is associated with decreased angiogenesis and macrophage infiltration[J]. The Journal of nutritional biochemistry, 2015, 26(11): 1368-1378.
[12]. Kwon G T, Jung J I, Song H R, et al. Piceatannol inhibits migration and invasion of prostate cancer cells: possible mediation by decreased interleukin-6 signaling[J]. The Journal of nutritional biochemistry, 2012, 23(3): 228-238.

Chemical Properties

Cas No. 10083-24-6 SDF
别名 白皮杉醇; Astringenin; trans-Piceatannol
化学名 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
Canonical SMILES C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O
分子式 C14H12O4 分子量 244.24
溶解度 ≥ 12.2mg/mL in DMSO 储存条件 Store at 2-8°C
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1 mM 4.0943 mL 20.4717 mL 40.9433 mL
5 mM 0.8189 mL 4.0943 mL 8.1887 mL
10 mM 0.4094 mL 2.0472 mL 4.0943 mL
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Research Update

Piceatannol: A natural stilbene for the prevention and treatment of cancer

Pharmacol Res2020 Mar;153:104635.PMID: 31926274DOI: 10.1016/j.phrs.2020.104635

The World Health Organization (WHO) has documented that cancer is the second foremost reason for death worldwide. Various factors are responsible for cancer, for instance, exposure to different physical, chemical and biological carcinogens, infections, hereditary, poor dietary habits and lifestyle etc. Cancer is a preventable disease if detected at an early stage; however, most of the cases of cancer are diagnosed at an incurable advanced or metastatic stage. According to WHO about 70 % of deaths due to cancer occur in countries with low- or middle-income. The major problems associated with the conventional therapies are cancer recurrence, development of chemoresistance, affordability, late-stage diagnosis, adverse side effects and inaccessible treatment. Thus, there is an urgent need to find alternative treatment modalities, which have easy accessibility and are affordable with minimum side effects. In this article, we reviewed the natural stilbene known as "Piceatannol" for its anticancer properties. Numerous preclinical studies have reported the potential of Piceatannol to prevent or impede the growth of various cancers originating from different organs such as brain, breast, cervical, colon, liver, lung, prostate, skin, etc. The current review primarily emphasises on the insights of Piceatannol source, chemistry, and the molecular mechanisms involved in the regression of the tumor. This review supports Piceatannol as a potential anticancer and chemopreventive agent and suggests that it can be effectively employed as a capable anti-cancer drug.

Benefits of skin application of piceatannol-A minireview

Australas J Dermatol2022 Oct 20.PMID: 36264002DOI: 10.1111/ajd.13937

The skin is the largest organ of the human body and has several functions such as barrier against external agents, the maintenance of temperature and homeostatic functions. Skin ageing is a natural process that can be influenced by environmental factors, intrinsic skin factors and lifestyle. UV light plays an important role in skin ageing and can cause spots, requiring the use of depigmenting agents. Nowadays, there is a great demand for ingredients that prevent skin ageing, with natural agents occupying a promising position. Among the natural agents, polyphenols, such as resveratrol and piceatannol, found in grapes, passion fruits and other fruits, have a huge relevance. Great benefits of piceatannol have been reported, so thus, this work focuses specifically on a review of the literature regarding the application of this polyphenol in skin care products. This polyphenol can be used in a wound-healing, or as anti-ageing, antioxidant, anti-acne and skin whitening, among other effects.

Piceatannol, a metabolite of resveratrol, attenuates atopic dermatitis by targeting Janus kinase 1

Phytomedicine2022 Feb 12;99:153981.PMID: 35235887DOI: 10.1016/j.phymed.2022.153981

Background: Piceatannol is a resveratrol metabolite commonly found in red wine, grapes. Several studies have investigated the immune-modulating effects of piceatannol on processes related to allergic reactions. However, the relationship between piceatannol and atopic dermatitis (AD) has not yet been reported. This study sought to investigate the effects of piceatannol in animal and cell line models.
Methods: AD-like symptoms and skin lesions were triggered by repeated topical treatment of Dermatophagoides farinae extract (DFE) on the skin of NC/Nga mice. The molecular mechanism of piceatannol was studied in the TNFα/IFNγ-induced HaCaT cell line.
Results: Piceatannol attenuated DFE-induced AD-like symptoms, as shown by skin thickness, dermatitis score, scratching time, and skin water loss. Histopathological analysis showed that piceatannol suppressed DFE-induced immune cell infiltration into the skin. These results occurred concomitantly with the downregulation of inflammatory markers, including serum and skin TARC and MDC. Piceatannol decreased phosphorylation of JAK-STAT protein in the TNFα/IFNγ-induced HaCaT cell line. A molecular docking study showed that piceatannol strongly interacts with JAK1, suggesting a possible mode of action.
Conclusion: The study results showed that piceatannol, a metabolite of resveratrol, attenuates atopic dermatitis and provide important implication of development of piceatannol as functional ingredients or therapeutic agents.

Piceatannol Protects Brain Endothelial Cell Line (bEnd.3) against Lipopolysaccharide-Induced Inflammation and Oxidative Stress

Molecules2022 Feb 11;27(4):1206.PMID: 35208996DOI: 10.3390/molecules27041206

Dysfunction of the blood-brain barrier (BBB) is involved in the pathogenesis of many cerebral diseases. Oxidative stress and inflammation are contributing factors for BBB injury. Piceatannol, a natural ingredient found in various plants, such as grapes, white tea, and passion fruit, plays an important role in antioxidant and anti-inflammatory responses. In this study, we examined the protective effects of piceatannol on lipopolysaccharide (LPS) insult in mouse brain endothelial cell line (bEnd.3) cells and the underlying mechanisms. The results showed that piceatannol mitigated the upregulated expression of adhesion molecules (ICAM-1 and VCAM-1) and iNOS in LPS-treated bEnd.3 cells. Moreover, piceatannol prevented the generation of reactive oxygen species in bEnd.3 cells stimulated with LPS. Mechanism investigations suggested that piceatannol inhibited NF-κB and MAPK activation. Taken together, these observations suggest that piceatannol reduces inflammation and oxidative stress through inactivating the NF-κB and MAPK signaling pathways on cerebral endothelial cells in vitro.

Piceatannol alleviate ROS-mediated PC-12 cells damage and mitochondrial dysfunction through SIRT3/FOXO3a signaling pathway

J Food Biochem2022 Mar;46(3):e13820.PMID: 34132394DOI: 10.1111/jfbc.13820

Oxidative stress-associated mitochondrial dysfunction has been identified as a major mechanism in multiple neurodegenerative diseases. This study aims to investigate the cytoprotective effects of piceatannol on ROS-mediated PC-12 cells damage and related mitochondrial dysfunction. Piceatannol treatment could significantly attenuate PC-12 cells oxidative damage and ROS-mediated cells apoptosis. Moreover, pretreatment with piceatannol effectively decreased mitochondrial membrane depolarization, cleaved-caspase 3, and increased Bcl-2 and Bcl-2/Bax compared with control H2 O2 group. Meanwhile, piceatannol treatment improved mitochondrial respiration function which led to an enhancement in the maximal respiration and spare respiratory capacity. Further mechanisms analysis showed that the protein expression of SIRT3 and its downstream protein FOXO3a were significantly increased after piceatannol addition in a dose-dependent manner. Whereas the cytoprotective role of piceatannol was markedly abolished by the SIRT3 inhibitor 3-TYP, suggesting that SIRT3/FOXO3a signaling pathway played a vital role in mediating the neuronal cytoprotective effects of piceatannol. PRACTICAL APPLICATIONS: The results of our study provide a novel insight that piceatannol could be potentially used as a promising bioactive component against oxidative damage and neurocyte apoptosis. The findings may provide theoretical basis for brain health of piceatannol consumption in some extent.