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Naringenin (Synonyms: SDihydrogenistein, NSC 11855, NSC 34875, Salipurol)

Catalog No.GN10276

Naringenin is a citrus flavonoid compound that can be used to treat cancer and has antioxidant and anti-inflammatory activities.

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Naringenin Chemical Structure

Cas No.: 480-41-1

Size Price Stock Qty
10mM (in 1mL DMSO)
$36.00
In stock
20mg
$45.00
In stock

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Sample solution is provided at 25 µL, 10mM.

Description of Naringenin

Naringenin is a citrus flavonoid compound that can be used to treat cancer and has antioxidant and anti-inflammatory activities[1]. Naringenin can increase glucose uptake in muscle cells[2]. Naringenin has anti-dengue virus activity[3].

In vitro, treatment of HepG2 cells with Naringenin (50-300μM) for 24h reduced cell viability in a dose-dependent manner, induced rapid accumulation of p53, increased nuclear damage and the proportion of apoptotic cells, and increased the Bax/Bcl-2 ratio[4]. Treatment of MCF-7, HT-29, and PC-12 cells with Naringenin (50-1000μM) for 24h induced the production of ROS in all cancer cells in a dose-dependent manner[5]. Treatment of A431 cells with Naringenin (50-750μM) for 12h induced the production of intracellular ROS in a dose-dependent manner, increased nuclear condensation and DNA fragmentation, induced cell cycle G0/G1 arrest, and increased caspase-3 activity[6].

In vivo, oral administration of Naringenin (50mg/kg/day; 8 weeks) to treat lead acetate-induced oxidative stress in the liver and kidneys of rats significantly attenuated lead-induced biochemical changes in serum, liver, and kidney tissues and alleviated oxidative stress[7].

References:
[1] Motallebi M, Bhia M, Rajani H F, et al. Naringenin: A potential flavonoid phytochemical for cancer therapy[J]. Life Sciences, 2022, 305: 120752.
[2] Zygmunt K, Faubert B, MacNeil J, et al. Naringenin, a citrus flavonoid, increases muscle cell glucose uptake via AMPK[J]. Biochemical and biophysical research communications, 2010, 398(2): 178-183.
[3] Frabasile S, Koishi A C, Kuczera D, et al. The citrus flavanone naringenin impairs dengue virus replication in human cells[J]. Scientific reports, 2017, 7(1): 41864.
[4] Arul D, Subramanian P. Naringenin (citrus flavonone) induces growth inhibition, cell cycle arrest and apoptosis in human hepatocellular carcinoma cells[J]. Pathology & Oncology Research, 2013, 19: 763-770.
[5] Kocyigit A, Koyuncu I, Dikilitas M, et al. Cytotoxic, genotoxic and apoptotic effects of naringenin-oxime relative to naringenin on normal and cancer cell lines[J]. Asian Pacific journal of tropical biomedicine, 2016, 6(10): 872-880.
[6] Ahamad M S, Siddiqui S, Jafri A, et al. Induction of apoptosis and antiproliferative activity of naringenin in human epidermoid carcinoma cell through ROS generation and cell cycle arrest[J]. PloS one, 2014, 9(10): e110003.
[7] Wang J, Yang Z, Lin L, et al. Protective effect of naringenin against lead-induced oxidative stress in rats[J]. Biological trace element research, 2012, 146: 354-359.

Protocol of Naringenin

Cell experiment [1]:

Cell lines

HepG2 cells

Preparation Method

Cells were plated in 96-well plates at a density of 8×103 cells per well and incubated for 24h with medium. The cells were rinsed with PBS and grown in a medium containing various concentrations of Naringenin (50, 100, 150, 200, 250, 300μM). The solvent DMSO treated cells were served as control. After 24h of treatment, the medium was removed and replaced by another medium containing MTT solution (1mg/mL), and the cells were incubated for 2h at 37°C. To assess the proportion of viable cells, formazan was solubilized with 150μL DMSO. Plates were then vortexed at room temperature for 30min, and the level of formazan was measured using a spectrophotometer at 575nm.

Reaction Conditions

50, 100, 150, 200, 250, 300μM; 24h

Applications

Naringenin treatment significantly inhibited the proliferation of cells in dose-dependent manner (50-300μM) after 24h of incubation.

Animal experiment [2]:

Animal models

Sprague–Dawley rats

Preparation Method

Animals were randomly divided into four groups, six rats in each. (1) In the control group, the rats received lead-free distilled water and physiological saline by oral gavage daily during the course of the experiment; (2) In Naringenin treated group, the animals received Naringenin at a dose of 50mg/kg/day dissolved in 0.1% Tween-80 and distilled water daily by oral gavage; (3) In lead-treated group, the rats received an aqueous solution of lead acetate (Pb(CH3COO)2) at a concentration of 500mg Pb/L as the only drinking fluid and physiological saline by oral gavage daily during the course of the experiment; (4) In lead+Naringenin-treated group, animals received an aqueous solution of lead acetate (500mg Pb/L in drinking water) and received Naringenin at a dose of 50mg/kg/day dissolved in 0.1% Tween-80 and distilled water daily by oral gavage. The experiments lasted for 8 weeks. At the end of the experimental period, blood samples were collected from all animals from the retro-orbital venous plexus under light ether anesthesia. Following the collection of blood samples, all animals were sacrificed; the liver and kidney from each rat were removed, weighed, and washed using chilled saline solution.

Dosage form

50mg/kg/day for 8 weeks; p.o.

Applications

Naringenin markedly attenuated lead-induced biochemical alterations in serum, liver, and kidney tissue.

References:
[1]Arul D, Subramanian P. Naringenin (citrus flavonone) induces growth inhibition, cell cycle arrest and apoptosis in human hepatocellular carcinoma cells[J]. Pathology & Oncology Research, 2013, 19: 763-770.
[2]Wang J, Yang Z, Lin L, et al. Protective effect of naringenin against lead-induced oxidative stress in rats[J]. Biological trace element research, 2012, 146: 354-359.

Chemical Properties of Naringenin

Cas No. 480-41-1 SDF
Synonyms SDihydrogenistein, NSC 11855, NSC 34875, Salipurol
Chemical Name (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Canonical SMILES C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
Formula C15H12O5 M.Wt 272.25
Solubility ≥ 13.15mg/mL in DMSO Storage Store at-20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Naringenin

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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
10 mM 0.3673 mL 1.8365 mL 3.6731 mL
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