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  3. Naringenin

Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

For research use only. We do not sell to patients.

Naringenin Chemical Structure

Naringenin Chemical Structure

CAS No. : 480-41-1

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Customer Review

Based on 8 publication(s) in Google Scholar

Other Forms of Naringenin:

Top Publications Citing Use of Products

    Naringenin purchased from MedChemExpress. Usage Cited in: J Funct Foods. 2020 Jun.

    Naringenin decreases the number of Iba-1-positive microglia and fully-activated microglia. Schematic diagram of the selected region of brain section for immunochemistry and Representative Iba-1 staining.

    Naringenin purchased from MedChemExpress. Usage Cited in: J Funct Foods. 2020 Jun.

    Naringenin prevents the neuroinflammation. Representative Western blot bands of TNF-α, IL-1β, IL-6, IL-10, and iNOS.

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    • Biological Activity

    • Protocol

    • Purity & Documentation

    • References

    • Customer Review

    Description

    Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

    In Vitro

    Naringenin is shown to inhibit the proliferation of HepG2 cells resulted partly from an accumulation of cells in the G0/G1 and G2/M phase of the cell cycle. Naringenin has been shown to induce apoptosis as evidenced by nuclei damage and increased proportion of apoptotic cells. Naringenin triggers the mitochondrial-mediated apoptosis pathway as shown by an increased ratio of Bax/Bcl-2, subsequent release of cytochrome C, and sequential activation of caspase-3[1]. Naringenin exposure significantly reduces the cell viability of A431 cells with a concomitant increase in nuclear condensation and DNA fragmentation in a dose dependent manner. Cell cycle study shows that naringenin induced cell cycle arrest in G0/G1 phase of cell cycle and caspase-3 analysis reveal a dose dependent increment in caspase-3 activity which leads to cell apoptosis[2].

    MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

    In Vivo

    Naringenin supplementation causes a significant reduction in the amount of total triglyceride and cholesterol in plasma and liver. In addition, naringenin supplementation lowers adiposity and triglyceride contents in parametrial adipose tissue. Naringenin-fed animals show a significant increase in PPARα protein expression in the liver. The expression of CPT-1 and UCP2, known to be regulated by PPARα, is markedly enhanced by naringenin treatment[3]. Naringenin increases hepatic fatty acid oxidation through a PPARγ coactivator 1α/PPARα-mediated transcription program. It prevents sterol regulatory element-binding protein 1c–mediated lipogenesis in both liver and muscle by reducing fasting hyperinsulinemia. Naringenin decreases hepatic cholesterol and cholesterol ester synthesis[4]. Naringenin inhibits TNF-α-induced VSMC proliferation and migration in a dose-dependent manner. Mechanistic study demonstrates that naringenin prevents ERK/MAPK and Akt phosphorylation while left p38 MAPK and JNK unchanged. Naringenin also blocks the increase of ROS generation induced by TNF-α[5].

    MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

    Molecular Weight

    272.25

    Formula

    C15H12O5

    CAS No.
    Appearance

    Solid

    Color

    White to light yellow

    SMILES

    O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(O)=CC(O)=C13

    Structure Classification
    Initial Source
    Shipping

    Room temperature in continental US; may vary elsewhere.

    Storage
    Powder -20°C 3 years
    4°C 2 years
    In solvent -80°C 6 months
    -20°C 1 month
    Solvent & Solubility
    In Vitro: 

    DMSO : 66.67 mg/mL (244.89 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

    Preparing
    Stock Solutions
    Concentration Solvent Mass 1 mg 5 mg 10 mg
    1 mM 3.6731 mL 18.3655 mL 36.7309 mL
    5 mM 0.7346 mL 3.6731 mL 7.3462 mL
    View the Complete Stock Solution Preparation Table

    * Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
    Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

    • Molarity Calculator

    • Dilution Calculator

    Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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    Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

    This equation is commonly abbreviated as: C1V1 = C2V2

    Concentration (start)

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    In Vivo:

    Select the appropriate dissolution method based on your experimental animal and administration route.

    For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
    To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
    The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

    • Protocol 1

      Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

      Solubility: ≥ 3 mg/mL (11.02 mM); Clear solution

      This protocol yields a clear solution of ≥ 3 mg/mL (saturation unknown).

      Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (30.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

      Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
    • Protocol 2

      Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

      Solubility: ≥ 3 mg/mL (11.02 mM); Clear solution

      This protocol yields a clear solution of ≥ 3 mg/mL (saturation unknown).

      Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (30.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

      Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.

    For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
    The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

    • Protocol 1

      Add each solvent one by one:  50% PEG300    50% Saline

      Solubility: 33.33 mg/mL (122.42 mM); Clear solution; Need ultrasonic

    • Protocol 2

      Add each solvent one by one:  0.5% CMC/saline water

      Solubility: 30.3 mg/mL (111.29 mM); Suspended solution; Need ultrasonic

    In Vivo Dissolution Calculator
    Please enter the basic information of animal experiments:

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    Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
    Please enter your animal formula composition:
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    Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
    The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
    Calculation results:
    Working solution concentration: mg/mL
    Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
    The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
    Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
     If the continuous dosing period exceeds half a month, please choose this protocol carefully.
    Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
    Purity & Documentation

    Purity: 99.27%

    References
    Cell Assay
    [1]

    Naringenin is dissolved in DMSO and diluted in cell culture medium. The cells are rinsed with PBS and grown in a medium containing various concentrations of naringenin (50, 100, 150, 200, 250, 300 μM). The solvent DMSO treated cells are served as control. After 24 hrs of treatment, the medium is removed and replaced by another medium containing MTT. Cell viability is measured using the MTT assay[1].

    MCE has not independently confirmed the accuracy of these methods. They are for reference only.

    Animal Administration
    [3][4]

    Rats: Semi-purified, powdered diets are prepared for concentrations of naringenin: 0, 0.003, 0.006, and 0.012% of diet. After 7 days of acclimatization, rats are assigned to one of four groups, with six animals per group, and fed semi-purified experimental diets for 6 weeks. The experimental diets contain 16% fat, 45.5% sucrose, and different naringenin concentration (0, 0.003, 0.006, or 0.012%) (Table 1). Rats have ad libitum access to food and water during the study period. Food intake and body weight are measured throughout the experiment[3].

    Mouse: Eight- to 12-week-old mice are fed ad libitum a rodent standard diet or a high-fat diet containing 42% of calories from fat plus cholesterol (0.05% wt/wt). Naringenin is added to the Western diet at 1 or 3% (wt/wt). Ldlr−/− mice are fed for 4 weeks and C57BL/6J mice for 30 weeks. Food intake is measured daily, and body weight is measured biweekly. Mice are fasted for 6 h before intervention[4].

    MCE has not independently confirmed the accuracy of these methods. They are for reference only.

    References

    Complete Stock Solution Preparation Table

    * Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
    Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

    Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
    DMSO 1 mM 3.6731 mL 18.3655 mL 36.7309 mL 91.8274 mL
    5 mM 0.7346 mL 3.6731 mL 7.3462 mL 18.3655 mL
    10 mM 0.3673 mL 1.8365 mL 3.6731 mL 9.1827 mL
    15 mM 0.2449 mL 1.2244 mL 2.4487 mL 6.1218 mL
    20 mM 0.1837 mL 0.9183 mL 1.8365 mL 4.5914 mL
    25 mM 0.1469 mL 0.7346 mL 1.4692 mL 3.6731 mL
    30 mM 0.1224 mL 0.6122 mL 1.2244 mL 3.0609 mL
    40 mM 0.0918 mL 0.4591 mL 0.9183 mL 2.2957 mL
    50 mM 0.0735 mL 0.3673 mL 0.7346 mL 1.8365 mL
    60 mM 0.0612 mL 0.3061 mL 0.6122 mL 1.5305 mL
    80 mM 0.0459 mL 0.2296 mL 0.4591 mL 1.1478 mL
    100 mM 0.0367 mL 0.1837 mL 0.3673 mL 0.9183 mL
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    • Do most proteins show cross-species activity?

      Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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