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    Naringenin chalcone
    Information
    CAS No. 73692-50-9 Price $168 / 20mg
    Catalog No.CFN90606Purity>=98%
    Molecular Weight272.25Type of CompoundChalcones
    FormulaC15H12O5Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Naringenin chalcone has antiallergic, anti-inflammatory ,and anti-asthmatic properties, it inhibits the production of proinflammatory cytokines in the interaction between adipocytes and macrophages, and improves adipocyte metabolic functions and exerts insulin-sensitizing effects by activating an adiponectin-related pathway.
    Targets: gp120/CD4 | TNF-α | NO | MCP-1 | Th2
    In vitro:
    Mol Cell Endocrinol. 2010 Jul 29;323(2):208-14.
    Naringenin chalcone improves adipocyte functions by enhancing adiponectin production.[Pubmed: 20363289]
    Naringenin chalcone is a flavonoid contained in tomato peel.
    METHODS AND RESULTS:
    In this study, we investigated its effects on adipocyte functions related to metabolic processes, including adipocytokine production. Naringenin chalcone promoted the gene expression (8.0-fold, p<0.001) and protein secretion (2.2-fold, p<0.001) of adiponectin from 3T3-L1 adipocytes. Reporter gene assays revealed that naringenin enhanced the activity of peroxisome proliferator-activated receptor gamma. DNA microarray experiments and Gene Ontology analysis revealed that Naringenin chalcone also up-regulated the genes associated with mitochondrial energy metabolism, reflecting its insulin-sensitizing effects. Conversely, genes in categories such as those for cell adhesion were down-regulated. The expression of one adiponectin receptor, AdipoR2, was also increased (1.8-fold, p<0.01), suggesting that Naringenin chalcone could activate the adiponectin pathway through the elevation of both the ligand and its receptor.
    CONCLUSIONS:
    These results indicate that Naringenin chalcone is a potent tomato flavonoid that improves adipocyte metabolic functions and exerts insulin-sensitizing effects by activating an adiponectin-related pathway.
    Life Sci. 2007 Sep 29;81(16):1272-9.
    Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages.[Pubmed: 17915259]
    Obese adipose tissue is characterized by an enhanced infiltration of macrophages. It is considered that the paracrine loop involving monocyte chemoattractant protein (MCP)-1 and tumor necrosis factor (TNF)-alpha between adipocytes and macrophages establishes a vicious cycle that augments the inflammatory changes and insulin resistance in obese adipose tissue. Polyphenols, which are widely distributed in fruit and vegetables, can act as antioxidants and some of them are also reported to have anti-inflammatory properties. Tomato is one of the most popular and extensively consumed vegetable crops worldwide, which also contains many flavonoids, mainly Naringenin chalcone.
    METHODS AND RESULTS:
    We investigated the effect of flavonoids, including Naringenin chalcone, on the production of proinflammatory mediators in lipopolysaccharide (LPS)-stimulated macrophages and in the interaction between adipocytes and macrophages. Naringenin chalcone inhibited the production of TNF-alpha, MCP-1, and nitric oxide (NO) by LPS-stimulated RAW 264 macrophages in a dose-dependent manner. Coculture of 3T3-L1 adipocytes and RAW 264 macrophages markedly enhanced the production of TNF-alpha, MCP-1, and NO compared with the control cultures; however, treatment with Naringenin chalcone dose-dependently inhibited the production of these proinflammatory mediators.
    CONCLUSIONS:
    These results indicate that Naringenin chalcone exhibits anti-inflammatory properties by inhibiting the production of proinflammatory cytokines in the interaction between adipocytes and macrophages. Naringenin chalcone may be useful for ameliorating the inflammatory changes in obese adipose tissue.
    In vivo:
    J Agric Food Chem. 2009 Jul 22;57(14):6432-7.
    Identification and quantification of metabolites of orally administered naringenin chalcone in rats.[Pubmed: 19558184]
    Naringenin chalcone is the main active component of tomato skin extract, which has an antiallergic activity.
    METHODS AND RESULTS:
    In this study, Naringenin chalcone was orally administered to rats, and the chemical structures and levels of the major metabolites in the plasma and urine of rats were determined. HPLC analysis indicated the presence of three major metabolites in the urine. LC-MS and NMR analyses tentatively identified these as Naringenin chalcone-2'-O-beta-D-glucuronide, naringenin-7-O-beta-D-glucuronide, and naringenin-4'-O-beta-D-glucuronide. Naringenin chalcone-2'-O-beta-D-glucuronide was the only metabolite detected in the plasma, and its peak plasma level was observed 1 h after Naringenin chalcone administration. Naringenin chalcone-2'-O-beta-D-glucuronide also inhibited histamine release from rat peritoneal mast cells stimulated with compound 48/80.
    CONCLUSIONS:
    This activity might contribute to the antiallergic activity of Naringenin chalcone in vivo. To the best of the authors' knowledge, this study is the first to report determination of Naringenin chalcone metabolites in rat plasma and urine.
    Naringenin chalcone Description
    Source: The peels of Citrus maxima.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.6731 mL 18.3655 mL 36.7309 mL 73.4619 mL 91.8274 mL
    5 mM 0.7346 mL 3.6731 mL 7.3462 mL 14.6924 mL 18.3655 mL
    10 mM 0.3673 mL 1.8365 mL 3.6731 mL 7.3462 mL 9.1827 mL
    50 mM 0.0735 mL 0.3673 mL 0.7346 mL 1.4692 mL 1.8365 mL
    100 mM 0.0367 mL 0.1837 mL 0.3673 mL 0.7346 mL 0.9183 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Animal Research:
    Allergol Int. 2010 Mar;59(1):67-73.
    Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells.[Pubmed: 20035147]
    Some polyphenols possess anti-allergic activities. Naringenin chalcone is one of the polyphenols that is present in the skin of red tomatoes. In this study, we investigated the effect of Naringenin chalcone in allergic responses in vivo using an experimental mouse model system of allergic asthma.
    METHODS AND RESULTS:
    Allergic airway inflammation was induced in mice by sensitization and challenge with ovalbumin. Naringenin chalcone was orally administrated every day during the course of the experiment. Airway hyperreactivity, the eosinophilic infiltration in the bronchioalveolar lavage fluid and Th2 cytokine production from splenic CD4 T cells were assessed. Eosinophilic airway inflammation, airway hyperreactivity and Th2 cytokine production from CD4 T cells were significantly suppressed in mice that were treated with Naringenin chalcone. Hyperproduction of mucus was slightly reduced.
    CONCLUSIONS:
    The results of this study suggest that Naringenin chalcone suppresses asthmatic symptoms by inhibiting Th2 cytokine production from CD4 T cells. Thus, Naringenin chalcone may be a useful supplement for the suppression of allergic symptoms in humans.