(±)-Naringenin
Based on 4 publication(s) in Google Scholar
(±)-Naringenin is an orally available anti-inflammatory agent that can regulate both acute and chronic inflammation responses, while also showing antioxidant, neuroprotective, liver-protective, and anti-cancer effects. (±)-Naringenin promotes vasodilation in endothelial cells by activating BKCa channels in muscle cells. It also exerts protective effects against experimental colitis by inhibiting Toll-like receptor 4/NF-κB signaling, making it useful in studies related to sepsis, fulminant hepatitis, fibrosis, and cancer research.
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- Pureté : 99.83%
- CAS No.: 67604-48-2
- Formule: C15H12O5
- Masse moléculaire:272.26
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Stockage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Protocole
- Pureté et documentation
- Références
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Help & FAQs
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Publications Citing Use of MedChemExpress (MCE) (±)-Naringenin
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Activité biologique
Description
IC50 & Target
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NF-κB |
Caspase 9 |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HCT-116 | IC50 |
36.75 μM
Compound: (+/-)-Naringenin
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Cytotoxicity against human HCT116 cells after 7 days by crystal violet staining based clonogenic assay
Cytotoxicity against human HCT116 cells after 7 days by crystal violet staining based clonogenic assay
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[PMID: 23177257] |
| Neutrophil | IC50 |
31 μM
Compound: 5a
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Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as inhibition of superoxide anion radical-induced lucigenin oxidation incubated for 5 mins prior to PMA challenge by chemiluminescence assay
Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as inhibition of superoxide anion radical-induced lucigenin oxidation incubated for 5 mins prior to PMA challenge by chemiluminescence assay
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[PMID: 23871908] |
| Neutrophil | IC50 |
51.4 μM
Compound: 5a
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Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as inhibition of ROS-induced luminol oxidation incubated for 5 mins prior to PMA challenge by chemiluminescence assay
Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as inhibition of ROS-induced luminol oxidation incubated for 5 mins prior to PMA challenge by chemiluminescence assay
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[PMID: 23871908] |
In Vitro
(±)-Naringenin induces concentration-dependent relaxation in endothelium-denuded aortic rings from rats pre-contracted with 20 mM KCl or norepinephrine, with pIC50 values of 4.74 and 4.68 respectively[1].
(±)-Naringenin increases large conductance calcium-activated potassium (BKCa) current in rat tail artery smooth muscle cells in a concentration-dependent manner[1].
(±)-Naringenin (1-25 μmol/L, 2 h) significantly inhibits TNF-α induced NF-κB luciferase expression in HT29 cells[2].
(±)-Naringenin (25 μmol/L, 2 h) blocks LPS-induced NF-κB p65 nuclear translocation in mouse macrophage RAW264.7 cells[2].
(±)-Naringenin induces apoptosis through both intrinsic (mitochondrial) and extrinsic pathways, upregulating pro-apoptotic genes such as P18, P21, p38, and Bcl-2-associated X protein (Bax), which stimulates mitochondrial cytochrome c release and forms apoptosomes including pro-caspase-9 and apoptosis protease-activating factor 1 (Apaf-1), thereby enhancing caspase-9 expression[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
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Cell Line:RAW264.7
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Concentration:25 μmol/L
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Incubation Time:2 h
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Result:Inhibited NF-κB p65 nuclear translocation.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6[2]
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Dosage:50 mg/kg
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Administration:Oral; daily; 10 days
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Result:Reduced the severity of DSS-induced colitis in mice, downregulated pro-inflammatory mediators (iNOS, ICAM-1, MCP-1, Cox2, TNF-α, and IL-6 mRNA) in the colonic mucosa, inhibited the increase in TLR4 mRNA and protein levels, and reduced the phosphorylated NF-κB p65 protein level.
Chemical Information
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CAS No. 67604-48-2
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Appearance Solid
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Masse moléculaire 272.26
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Formule C15H12O5
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Color Off-white to light yellow
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SMILES
O=C1CC(C2=CC=C(O)C=C2)OC3=CC(O)=CC(O)=C13
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Structure Classification
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Initial Source
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Publications (4)
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Journal Impact Factor
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Most Recent
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J Ethnopharmacol
The neuroprotective mechanisms of naringenin: Inhibition of apoptosis through the PI3K/AKT pathway after hypoxic-ischemic brain damage. [Abstract]2024 Jan 10;318(Pt A):116941. PMID: 37480970 -
Foods
2022 Nov 22;11(23):3755. PMID: 36496566 -
Mol Med Rep
Tea seed saponin‑reduced extract ameliorates palmitic acid‑induced insulin resistance in HepG2 cells. [Abstract]2024 Feb;29(2):26. PMID: 38099345 -
Cytotechnology
Naringin regulates the cGAS-STING pathway to improve mitochondrial dysfunction and ferroptosis after myocardial ischemia-reperfusion injury. [Abstract]2025 Jun;77(3):103. PMID: 40384845
Solvant et solubilité
In Vitro:
DMSO : 120 mg/mL (440.76 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
H2O : < 0.1 mg/mL (insoluble)
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.
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.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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.
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.
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.
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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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
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).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
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.
Protocole
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Fibrosis/Collagen Morphometry
Fibrosis and collagen morphometry is based on the quantitative visualization of fibrillar collagen deposition in tissue sections using histochemical stains such as Sirius Red (Picrosirius Red) or Masson's trichrome, followed by image-based or polarization-enhanced analysis to estimate collagen proportional area as a surrogate of extracellular matrix accumulation during fibrotic remodeling. Sirius Red combined with polarized light microscopy enhances detection of collagen fibers due to birefringence properties, enabling more specific visualization of collagen type I and III fibrils compared to conventional bright-field histology, while whole-section or region-restricted digital morphometry reduces field-selection bias in fibrosis assessment. Alternative quantitative approaches include second harmonic generation (SHG) and two-photon excited fluorescence microscopy, which enable label-free detection of fibrillar collagen and have been validated against histological staining and biochemica
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Collagen: Sirius Red Staining
Sirius Red or picrosirius red staining is a histochemical method for visualizing collagen-rich extracellular matrix in tissue sections, and collagen fibers are detected as red-stained structures under bright-field microscopy with enhanced birefringence under polarized light. Picrosirius red is useful for assessing total collagen organization, distribution, and fibrosis burden, but polarized color should not be interpreted as a definitive collagen type I versus type III readout because color is affected by fiber orientation, thickness, and packing.
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LPS-Induced Endotoxemia/Systemic Inflammation
Lipopolysaccharide (LPS)-induced endotoxemia is a widely used in vivo model of acute systemic inflammation in which LPS, a Gram-negative bacterial endotoxin, activates innate immune signaling primarily through TLR4, leading to rapid and transient induction of pro-inflammatory cytokines such as TNF-α, IL-6, and IL-1β in circulation and tissues. This cytokine surge is commonly used as a measurable readout of systemic inflammatory activation and immune dysregulation, and is typically assessed within hours after intraperitoneal LPS administration in mouse models of endotoxemia. The model captures key features of systemic inflammatory response syndrome, including cytokine release, immune cell activation, and downstream tissue responses, and has been used to evaluate anti-inflammatory interventions such as cytokine modulation, lipid mediators, and immune cell-targeting therapies.
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Cotton Pellet Granuloma
Cotton pellet granuloma is a classical in vivo chronic inflammation model used to evaluate the anti-inflammatory potential of test substances by measuring their ability to inhibit granuloma tissue formation around an implanted foreign body (cotton pellet) in rodents. The method is based on the biological response to a sterile implanted material, which induces proliferative phase inflammation characterized by fibroblast proliferation and collagen-rich granuloma formation, and the final readout reflects the extent of chronic inflammatory tissue growth surrounding the pellet. In multiple preclinical pharmacological evaluations, inhibition of cotton pellet-induced granuloma formation has been used as an indicator of anti-inflammatory activity in both synthetic and natural product screening contexts.
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DSS-Induced Colitis
Dextran sulfate sodium (DSS)-induced colitis is generated by administering DSS in mouse drinking water, producing epithelial injury, barrier disruption, weight loss, diarrhea, fecal blood, colon shortening, histologic mucosal damage, and inflammatory mediator changes; the model is mainly used to study acute or chronic intestinal inflammation resembling selected features of ulcerative colitis. DSS injury is interpreted through clinical and tissue readouts rather than a single molecular endpoint: daily body weight, stool consistency, and bleeding are combined into a disease activity index, while colon length, histology, cytokines, myeloperoxidase activity, intestinal permeability, and tight-junction markers provide complementary measures of inflammation and barrier damage.
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TNBS-Induced Colitis
TNBS-induced colitis is produced by intrarectal delivery of 2,4,6-trinitrobenzene sulfonic acid in ethanol, where ethanol disrupts the mucosal barrier and TNBS haptenates colonic proteins, generating immune-mediated colonic inflammation with weight loss, diarrhea, ulceration, transmural injury, inflammatory-cell infiltration, and cytokine responses. The model is used as an experimental intestinal inflammation model with Crohn’s disease–like features, especially when Th1-type responses, IL-12–dependent inflammation, chronic relapsing inflammation, or fibrosis-related endpoints are studied.
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Connective Tissue: Masson's Trichrome/Collagen Trichrome Staining
Masson’s Trichrome (collagen/trichrome staining) is a histological technique that differentially stains tissue compartments using sequential acidic dyes to distinguish collagen from muscle and cytoplasmic components based on dye affinity and tissue permeability differences, enabling visualization of fibrosis and connective tissue architecture in histological sections. The classical formulation typically uses Weigert's iron hematoxylin for nuclear staining, Biebrich scarlet-acid fuchsin for cytoplasm and muscle, and aniline blue (or light green variants) for collagen, producing a characteristic blue/green collagen signal contrasted against red cytoplasm and dark nuclei. The staining principle relies on selective displacement of smaller dye molecules by larger anionic dyes in collagen-rich regions under controlled acidified conditions, which enhances collagen-specific dye retention. This property makes the method widely used for fibrosis assessment in organs such as heart, liver, lung, a
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Endothelial Tube Formation Assay
Endothelial tube formation assay evaluates the ability of endothelial cells to attach, migrate, align, and organize into capillary-like networks when cultured on gelled basement membrane extract or Matrigel; the readout is the morphology and quantity of tube-like networks, which reflects an in vitro endothelial morphogenesis step related to angiogenesis. Basement membrane extract/Matrigel provides laminin-rich extracellular matrix cues that support endothelial differentiation into capillary-like structures, but it can contain biologically active growth factors, so growth-factor-reduced matrix is preferred when testing defined angiogenic stimulators or inhibitors.
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Research Protocol for Inflammation-related Diseases
The NLRP3 inflammasome is a cytosolic innate immune signaling platform that integrates priming signals and danger-signal activation to promote caspase-1 activation, maturation of IL-1β and IL-18, and gasdermin D-mediated pyroptotic cell death. The core experimental logic is to determine whether inflammatory disease phenotypes are driven by increased NLRP3 expression, ASC-containing inflammasome assembly, caspase-1 cleavage, GSDMD cleavage, and extracellular release of IL-1β/IL-18 rather than by nonspecific cell injury alone. The pathway is strongly linked to inflammation-related disease phenotypes because monosodium urate crystals activate NALP3/NLRP3 inflammasome signaling in gout-like crystal inflammation, cholesterol crystals activate NLRP3 inflammasomes in atherogenesis models, and DSS-induced intestinal inflammation has been reported to involve NLRP3 inflammasome activity. However, experimental colitis studies also show context-dependent protective effects of NLRP3 inflammasome co
Pureté et documentation
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Fiche technique (279 KB)
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SDS (393 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. Saponara S, et al. (+/-)-Naringenin as large conductance Ca(2+)-activated K+ (BKCa) channel opener in vascular smooth muscle cells. Br J Pharmacol. 2006 Dec;149(8):1013-21. [Content Brief]
[2]. Wei Dou, et al. Protective effect of naringenin against experimental colitis via suppression of Toll-like receptor 4/NF-κB signalling. Br J Nutr. 2013 Aug;110(4):599-608. [Content Brief]
[3]. Mahzad Motallebi, et al. Naringenin: A potential flavonoid phytochemical for cancer therapy. Life Sci. 2022 Sep 15:305:120752. [Content Brief]
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 | 3.6730 mL | 18.3648 mL | 36.7296 mL | 91.8240 mL |
| 5 mM | 0.7346 mL | 3.6730 mL | 7.3459 mL | 18.3648 mL | |
| 10 mM | 0.3673 mL | 1.8365 mL | 3.6730 mL | 9.1824 mL | |
| 15 mM | 0.2449 mL | 1.2243 mL | 2.4486 mL | 6.1216 mL | |
| 20 mM | 0.1836 mL | 0.9182 mL | 1.8365 mL | 4.5912 mL | |
| 25 mM | 0.1469 mL | 0.7346 mL | 1.4692 mL | 3.6730 mL | |
| 30 mM | 0.1224 mL | 0.6122 mL | 1.2243 mL | 3.0608 mL | |
| 40 mM | 0.0918 mL | 0.4591 mL | 0.9182 mL | 2.2956 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 | 1.5304 mL | |
| 80 mM | 0.0459 mL | 0.2296 mL | 0.4591 mL | 1.1478 mL | |
| 100 mM | 0.0367 mL | 0.1836 mL | 0.3673 mL | 0.9182 mL |
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