PrunetinCAS# 552-59-0 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 552-59-0 | SDF | Download SDF |
| PubChem ID | 5281804 | Appearance | Powder |
| Formula | C16H12O5 | M.Wt | 284.26 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one | ||
| SMILES | COC1=CC(=C2C(=C1)OC=C(C2=O)C3=CC=C(C=C3)O)O | ||
| Standard InChIKey | KQMVAGISDHMXJJ-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Prunetin mediates anti-obesity/adipogenesis effects by suppressing obesity-related transcription through a feedback mechanism that regulates the expression of adiponectin, adipoR1, adipoR2, and AMPK. Prunetin and biochanin A are potent reducers of NF-κB and ERK activation, zonula occludens 1 tyrosine phosphorylation, and metalloproteinase-mediated shedding activity, which may account for the barrier-improving ability of these isoflavones. |
| Targets | NOS | COX | TNF-α | IL Receptor | NF-kB | PGE | IkB | p65 | ERK | PPAR | HMG-CoA Reductase | AMPK | EGFR | IKK |
| In vitro | Effect of Prunetin on TNF-α-Induced MUC5AC Mucin Gene Expression, Production, Degradation of IκB and Translocation of NF-κB p65 in Human Airway Epithelial Cells.[Pubmed: 24348668]Tuberc Respir Dis (Seoul). 2013 Nov;75(5):205-9.We investigated whether Prunetin significantly affects tumor necrosis factor-α (TNF-α)-induced MUC5AC mucin gene expression, production, inhibitory kappa B (IκB) degradation and nuclear factor kappa B (NF-κB) p65 translocation in human airway epithelial cells.
Biochanin A and prunetin improve epithelial barrier function in intestinal CaCo-2 cells via downregulation of ERK, NF-κB, and tyrosine phosphorylation.[Pubmed: 24631489]Free Radic Biol Med. 2014 May;70:255-64.The single-layered gut epithelium represents the primary line of defense against environmental stressors; thereby monolayer integrity and tightness are essentially required to maintain gut health and function. To date only a few plant-derived phytochemicals have been described as affecting intestinal barrier function.
|
| Kinase Assay | Anti-inflammatory effect of prunetin via the suppression of NF-κB pathway.[Pubmed: 23597450]Food Chem Toxicol. 2013 Aug;58:124-32.Prunetin is an O-methylated isoflavone, which is found in Prunus yedoensis. To date no report has been published on anti-inflammatory activities of Prunetin. |
| Cell Research | Inhibition of secretion, production and gene expression of mucin from cultured airway epithelial cells by prunetin.[Pubmed: 21305630]Phytother Res. 2011 Aug;25(8):1196-200.This study investigated whether Prunetin significantly affects the secretion, production and gene expression of mucin from cultured airway epithelial cells.
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| Animal Research | Molecular mechanisms underlying the anti-obesity potential of prunetin, an O-methylated isoflavone.[Pubmed: 23438470]Biochem Pharmacol. 2013 May 15;85(10):1525-33.Prunetin is an O-methylated isoflavone, which is a type of flavonoid. There are a limited number of reports detailing the biological activities of Prunetin. Although an anti-inflammatory effect of Prunetin has been reported in vitro, to our knowledge, there have been no reports on anti-adipogenic effects of Prunetin in obese animals.
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Prunetin Dilution Calculator
Prunetin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.5179 mL | 17.5895 mL | 35.1791 mL | 70.3581 mL | 87.9477 mL |
| 5 mM | 0.7036 mL | 3.5179 mL | 7.0358 mL | 14.0716 mL | 17.5895 mL |
| 10 mM | 0.3518 mL | 1.759 mL | 3.5179 mL | 7.0358 mL | 8.7948 mL |
| 50 mM | 0.0704 mL | 0.3518 mL | 0.7036 mL | 1.4072 mL | 1.759 mL |
| 100 mM | 0.0352 mL | 0.1759 mL | 0.3518 mL | 0.7036 mL | 0.8795 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Molecular mechanisms underlying the anti-obesity potential of prunetin, an O-methylated isoflavone.[Pubmed:23438470]
Biochem Pharmacol. 2013 May 15;85(10):1525-33.
Prunetin is an O-methylated isoflavone, which is a type of flavonoid. There are a limited number of reports detailing the biological activities of Prunetin. Although an anti-inflammatory effect of Prunetin has been reported in vitro, to our knowledge, there have been no reports on anti-adipogenic effects of Prunetin in obese animals. The aims of this study were to determine whether Prunetin suppresses high-fat diet (HFD)-induced adipogenesis in the liver and visceral adipose tissues of mice, and to explore the underlying mechanisms mediating the actions of Prunetin. To this end, mice were fed a HFD for 10 weeks to induce obesity, and Prunetin (10 mug/kg or 20 mug/kg) was administered in the last 3 weeks. Compared to saline-treated mice, mice treated with Prunetin showed significantly reduced body weight gain, visceral fat pad weights, and plasma glucose levels. We found that Prunetin significantly inhibited the HFD-induced upregulation of the expression of important adipogenic genes (PPARgamma, C/EBPalpha, SREBP, aP2, LPL adiponectin, and leptin), and suppressed HFD-mediated increase in expression of lipid metabolism-related genes (SREBP, PPARgamma, LXR, and HMG-CoA) in the liver tissues. Furthermore, Prunetin induced expression of adiponectin receptors 1 and 2 (adipoR1, adipoR2), as well as that of AMP-activated protein kinase (AMPK) in the liver and adipose tissue. These results suggest that Prunetin mediates anti-obesity/adipogenesis effects by suppressing obesity-related transcription through a feedback mechanism that regulates the expression of adiponectin, adipoR1, adipoR2, and AMPK.
Inhibition of secretion, production and gene expression of mucin from cultured airway epithelial cells by prunetin.[Pubmed:21305630]
Phytother Res. 2011 Aug;25(8):1196-200.
This study investigated whether Prunetin significantly affects the secretion, production and gene expression of mucin from cultured airway epithelial cells. Confluent primary rat tracheal surface epithelial (RTSE) cells were pretreated with adenosine triphosphate (ATP) for 5 min and then chased for 30 min in the presence of Prunetin to assess the effect on mucin secretion using enzyme-linked immunosorbent assay (ELISA). At the same time, confluent NCI-H292 cells were pretreated with Prunetin for 30 min and then stimulated with epidermal growth factor (EGF) or phorbol 12-myristate 13-acetate (PMA) for 24 h, respectively. The MUC5AC mucin gene expression and mucin protein production were measured by reverse transcription-polymerase chain reaction (RT-PCR) and ELISA. The results were as follows: (1) Prunetin significantly suppressed ATP-induced mucin secretion from cultured RTSE cells; (2) Prunetin inhibited the production of MUC5AC mucin protein induced by EGF or PMA from NCI-H292 cells; (3) Prunetin also inhibited the expression of MUC5AC mucin gene induced by EGF or PMA from NCI-H292 cells. This result suggests that Prunetin can regulate the secretion, production and gene expression of mucin, by directly acting on airway epithelial cells.
Anti-inflammatory effect of prunetin via the suppression of NF-kappaB pathway.[Pubmed:23597450]
Food Chem Toxicol. 2013 Aug;58:124-32.
Prunetin is an O-methylated isoflavone, which is found in Prunus yedoensis. To date no report has been published on anti-inflammatory activities of Prunetin. In the present study, the anti-inflammatory effect of Prunetin on LPS-stimulated RAW 264.7 macrophage and LPS-induced septic shock model were investigated. Inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), tumor necrosis factor-alpha (TNF-alpha), interleukin-6 (IL-6), and interleukin-1beta (IL-1beta) expressions were determined by western blot and or realtime-PCR (RT-PCR). To elucidate its underlying mechanism, nuclear factor-kappa B (NF-kappab) activation and its downstream pathways were investigated by NF-kappaB transcription factor assay, reporter gene expression, and western blot. In vivo anti-inflammatory effects of Prunetin were evaluated in LPS-induced endotoxemia. Promoter assay revealed that Prunetin inhibits LPS-induced nitric oxide and prostaglandin E2 production through the suppression of iNOS and COX-2 at the transcriptional level. In addition, Prunetin inhibits NF-kappaB-dependent inflammatory responses by modulating IkappaB kinase (IKK)-inhibitor kappaBalpha (IkappaBalpha)-NF-kappaB signaling. Consistent with these results, Prunetin significantly reduced serum levels of inflammatory cytokines and mortality in mice challenged with lipopolysaccharide. These findings offer a potential mechanism for the anti-inflammatory activity of Prunetin.
Effect of Prunetin on TNF-alpha-Induced MUC5AC Mucin Gene Expression, Production, Degradation of IkappaB and Translocation of NF-kappaB p65 in Human Airway Epithelial Cells.[Pubmed:24348668]
Tuberc Respir Dis (Seoul). 2013 Nov;75(5):205-9.
BACKGROUND: We investigated whether Prunetin significantly affects tumor necrosis factor-alpha (TNF-alpha)-induced MUC5AC mucin gene expression, production, inhibitory kappa B (IkappaB) degradation and nuclear factor kappa B (NF-kappaB) p65 translocation in human airway epithelial cells. METHODS: Confluent NCI-H292 cells were pretreated with Prunetin for 30 minutes and then stimulated with TNF-alpha for 24 hours or the indicated periods. MUC5AC mucin gene expression and mucin protein production were measured by reverse transcription polymerase chain reaction and enzyme-linked immunosorbent assay, respectively. The effect of Prunetin on TNF-alpha-induced degradation of IkappaB and translocation of NF-kappaB p65 was investigated by western blot analysis. RESULTS: We found that incubation of NCI-H292 cells with Prunetin significantly inhibited mucin production and down-regulated the MUC5AC gene expression induced by TNF-alpha. Prunetin inhibited TNF-alpha-induced degradation of IkappaB and translocation of NF-kappaB p65. CONCLUSION: This result suggests that Prunetin inhibits the NF-kappaB signaling pathway, which may explain its role in the inhibition of MUC5AC mucin gene expression and production regulated by the NF-kappaB signaling pathway.
Biochanin A and prunetin improve epithelial barrier function in intestinal CaCo-2 cells via downregulation of ERK, NF-kappaB, and tyrosine phosphorylation.[Pubmed:24631489]
Free Radic Biol Med. 2014 May;70:255-64.
The single-layered gut epithelium represents the primary line of defense against environmental stressors; thereby monolayer integrity and tightness are essentially required to maintain gut health and function. To date only a few plant-derived phytochemicals have been described as affecting intestinal barrier function. We investigated the impact of 28 secondary plant compounds on the barrier function of intestinal epithelial CaCo-2/TC-7 cells via transepithelial electrical resistance (TEER) measurements. Apart from genistein, the compounds that had the biggest effect in the TEER measurements were biochanin A and Prunetin. These isoflavones improved barrier tightness by 36 and 60%, respectively, compared to the untreated control. Furthermore, both isoflavones significantly attenuated TNFalpha-dependent barrier disruption, thereby maintaining a high barrier resistance comparable to nonstressed cells. In docking analyses exploring the putative interaction with the tyrosine kinase EGFR, these novel modulators of barrier tightness showed very similar values compared to the known tyrosine kinase inhibitor genistein. Both biochanin A and Prunetin were also identified as potent reducers of NF-kappaB and ERK activation, zonula occludens 1 tyrosine phosphorylation, and metalloproteinase-mediated shedding activity, which may account for the barrier-improving ability of these isoflavones.
