Naringin

Names

[ Name ]:
Naringin

[Synonym ]:
2,6-Dimethylpyrimidin-4(1H)-one
2,6-Dimethylpyrimidin-4-ol
Naringenin 7-neohesperidoside
MFCD00148888
2,6-Dimethyl-4(1H)-pyrimidinone
T6N CNJ B1 DQ F1
T6VM DNJ C1 E1
EINECS 233-566-4
2,6-Dimethyl-4(3H)-pyrimidinone
Naringenin 7-Rhamnoglucoside Hydrate
Naringenoside
Nobiletin
Naringin Hydrate
2,6-Dimethylpyrimidin-4(3H)-one
4(3H)-Pyrimidinone, 2,6-dimethyl-
4-pyrimidinol, 2,6-dimethyl-

Biological Activity

[Description]:

Naringin is a major flavanone glycoside obtained from tomatoes, grapefruits, and many other citrus fruits. Naringin exhibits biological properties such as antioxidant, anti-inflammatory, and antiapoptotic activities.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Signaling Pathways >> Autophagy >> Mitophagy

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

[In Vitro]

Naringin suppresses NF-κ B signaling pathway activation. Naringenin inhibits high glucose-induced proliferation, inflammatory reaction and oxidative stress injury in HBZY-1 cells[1]. Naringin inhibits AGS cancer cell proliferation in a dose- and time-dependent manner. Phosphorylation of PI3K and its activated downstream targets p-Akt and p-mTOR are significantly decreased at 2 mM in Naringin-treated AGS cells. Naringin induces autophagic cell death in AGS cells. Naringin activated the autophagy related protein in AGS cells[2]. Naringin protects PC12 cells from 3-NP neurotoxicity. The lactate dehydrogenase release is decreased upon naringin treatment in 3-NP-induced PC12 cells. Naringin treatment enhances the antioxidant defense by increasing the activities of enzymatic antioxidants and the level of reduced glutathione[3].

[In Vivo]

Treatment with naringin significantly alleviates renal injury in diabetic rats and increases diabetic rats body weight significantly. Administration of naringin effectively alleviates the collagen deposition and renal interstitial fibrosis in diabetic rats. Treatment with naringin could result in decreased levels of ROS and MDA and increased activities of SOD and GSH-Px[1]. Oral administration of naringin significantly improves the learning and memory abilities. Naringin significantly enhances insulin signaling pathway[3].

[Cell Assay]

HBZY-1 cells are plated into 96-well plates and pretreated with various concentrations(1, 5, 10, 25, 50, 100 μM) of naringin for 2 h. Then cells are treated with 30 mM glucose for 24 h. The control group is added sterile normal saline in the same volume. After treatment, all the wells are incubated with 20 μL of 5 mg/ml MTT for 4 h at 37°C. Subsequently, 100 μL of DMSO are used to dissolve the formed formazan crystals after removal of the supernatant. The result is recorded at 490 nm on a microplate reader[1].

[Animal admin]

Rats: The rats are randomly divided into six groups: control, naringin (80 mg/kg), STZ, STZ+naringin (20 mg/kg), STZ+naringin (40 mg/kg), STZ+naringin(80 mg/kg). The rats in the STZ and STZ+naringin groups are intraperitoneally injected with STZ (65 mg/kg). The control and naringin groups are intraperitoneally injected with 0.1 M citrate buffer of same volume. After injection of STZ for 3 and 5 days, blood glucose levels are measured by tail vein puncture blood sampling[1]. Mice: Sixty 4-week-old male mice are randomized into four groups and fed for 20 weeks with either control diet or high-fat diet chow. Mice are dosed with 100 mg/kg of naringin daily. Mice body weight and food intake are weekly measured. Following behavioral assessment, animals are deeply anesthetized with isoflurane and sacrificed by decapitation after fasting for at least 5 h. Their plasma is collected for further analysis[4].

[References]

[1]. Chen F, et al. Naringin Alleviates Diabetic Kidney Disease through Inhibiting Oxidative Stress and Inflammatory Reaction. PLoS One. 2015 Nov 30;10(11):e0143868.

[2]. Raha S, et al. Naringin induces autophagy-mediated growth inhibition by downregulating the PI3K/Akt/mTOR cascade via activation of MAPK pathways in AGS cancer cells. Int J Oncol. 2015 Sep;47(3):1061-9.

[3]. Kulasekaran G, et al. Neuroprotective efficacy of naringin on 3-nitropropionic acid-induced mitochondrial dysfunction through the modulation of Nrf2 signaling pathway in PC12 cells. Mol Cell Biochem. 2015 Nov;409(1-2):199-211.

[4]. Wang D, et al. Naringin Improves Neuronal Insulin Signaling, Brain Mitochondrial Function, and Cognitive Function in High-Fat Diet-Induced Obese Mice. Cell Mol Neurobiol. 2015 Oct;35(7):1061-71.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
928.1±65.0 °C at 760 mmHg

[ Melting Point ]:
166 °C

[ Molecular Formula ]:
C₂₇H₃₂O₁₄

[ Molecular Weight ]:
580.53

[ Flash Point ]:
308.5±27.8 °C

[ PSA ]:
225.06000

[ LogP ]:
-0.18

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.564

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QN6340000

CHEMICAL NAME :: Naringin

CAS REGISTRY NUMBER :: 10236-47-2

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C27-H32-O14

MOLECULAR WEIGHT :: 580.59

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EKMMA8 Eksperimentalna Meditsina i Morfologiya. (Hemus, Blvd. Russki 6, Sofia, Bulgaria) V.1- 1962- Volume(issue)/page/year: 19,207,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EKMMA8 Eksperimentalna Meditsina i Morfologiya. (Hemus, Blvd. Russki 6, Sofia, Bulgaria) V.1- 1962- Volume(issue)/page/year: 19,207,1980

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
QN6340000

Precursor & DownStream

Precursor

DownStream

Articles

Preconditioning L6 Muscle Cells with Naringin Ameliorates Oxidative Stress and Increases Glucose Uptake.

PLoS ONE 10 , e0132429, (2015)

Enhanced oxidative stress contributes to pathological changes in diabetes and its complications. Thus, strategies to reduce oxidative stress may alleviate these pathogenic processes. Herein, we have i...

Pseudomonas aeruginosa Biofilm Formation and Persistence, along with the Production of Quorum Sensing-Dependent Virulence Factors, Are Disrupted by a Triterpenoid Coumarate Ester Isolated from Dalbergia trichocarpa, a Tropical Legume.

PLoS ONE 10 , e0132791, (2015)

Recently, extracts of Dalbergia trichocarpa bark have been shown to disrupt P. aeruginosa PAO1 quorum sensing (QS) mechanisms, which are key regulators of virulence factor expression and implicated in...

The antioxidant and antigenotoxic properties of citrus phenolics limonene and naringin.

Food Chem. Toxicol. 81 , 160-70, (2015)

Phenolic compounds not only contribute to the sensory qualities of fruits and vegetables but also exhibit several health protective properties. Limonene and naringin are the most popular phenolics fou...