Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H32O14 |
| Molecular Weight | 580.5346 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC3=CC(O)=C4C(=O)C[C@H](OC4=C3)C5=CC=C(O)C=C5)[C@H](O)[C@H](O)[C@H]1O
InChI
InChIKey=DFPMSGMNTNDNHN-ZPHOTFPESA-N
InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
| Molecular Formula | C27H32O14 |
| Molecular Weight | 580.5346 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Naringin is a flavanone plant metabolite which found in citrus fruits and in quantitatively significant amounts from grapefruit in particular. Naringin has attracted attention as a dietary supplement purported to aid in fat and weight loss. Ingestion of naringin and related flavonoids can interfere with the absorption and metabolism of certain drugs, and therefore consumption of grapefruit juice with medication is advised against. Naringin possesses numerous biological properties such as antioxidant, anti-inflammatory, and anti-apoptotic activity. It has been extensively studied in pre-clinical models of atherosclerosis, cardiovascular disorders, diabetes mellitus, neurodegenerative disorders, osteoporosis, and rheumatological disorders, and several different cancer models.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Naringin suppresses cell metastasis and the expression of matrix metalloproteinases (MMP-2 and MMP-9) via the inhibition of ERK-P38-JNK signaling pathway in human glioblastoma. | 2016-01-25 |
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| Naringin suppress chondrosarcoma migration through inhibition vascular adhesion molecule-1 expression by modulating miR-126. | 2014-09 |
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| Naringin induces death receptor and mitochondria-mediated apoptosis in human cervical cancer (SiHa) cells. | 2013-01 |
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| Beneficial role of naringin, a flavanoid on nickel induced nephrotoxicity in rats. | 2011-08-15 |
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| Alleviation of iron induced oxidative stress by the grape fruit flavanone naringin in vitro. | 2011-04-25 |
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| Transcellular movement of hydroxyurea is mediated by specific solute carrier transporters. | 2011-04 |
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| Simvastatin impairs murine melanoma growth. | 2010-12-16 |
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| Study of the polyphenolic composition and antioxidant activity of new sherry vinegar-derived products by maceration with fruits. | 2010-11-24 |
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| Glycine tomentella Hayata inhibits IL-1β and IL-6 production, inhibits MMP-9 activity, and enhances RAW264.7 macrophage clearance of apoptotic cells. | 2010-11-05 |
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| [Naringin inhibits monocyte adhesion to high glucose-induced human umbilical vein endothelial cells]. | 2010-02 |
|
| Effect of severe acute pancreatitis on pharmacokinetics of Da-Cheng-Qi Decoction components. | 2009-12-21 |
|
| Determination of sophoricoside in rat plasma by HPLC and its application to pharmacokinetic studies. | 2009-12 |
|
| Fast analysis of prominent flavonoids in tomato using a monolithic column and isocratic HPLC. | 2009-08 |
|
| Quasi-MSn identification of flavanone 7-glycoside isomers in Da Chengqi Tang by high performance liquid chromatography-tandem mass spectrometry. | 2009-07-24 |
|
| Discrimination of three medicinal materials from the Citrus genus by HPLC fingerprint coupled with two complementary software. | 2009-05-09 |
|
| Multiple compounds determination and fingerprint analysis of Lidanpaishi tablet and keli by high-performance liquid chromatography. | 2009-02-02 |
|
| Hydrolysis of flavanone glycosides and degradation of the corresponding aglycones from dried immature Citrus fruit by human fecal flora in vitro. | 2008-11 |
|
| Cupric ion reducing antioxidant capacity assay for food antioxidants: vitamins, polyphenolics, and flavonoids in food extracts. | 2008 |
|
| Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3. | 2007-12 |
|
| Antimicrobial activity of flavonoids extracted from bergamot (Citrus bergamia Risso) peel, a byproduct of the essential oil industry. | 2007-12 |
|
| Isolation of flavonoids from aspen knotwood by pressurized hot water extraction and comparison with other extraction techniques. | 2007-11-15 |
|
| Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells. | 2007-10 |
|
| Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction. | 2007-07 |
|
| Constituents of the leaves of Holarrhena pubescens. | 2007-04 |
|
| [Identification of jizhi syrup using HPLC fingerprint]. | 2007-04 |
|
| Anti-osteoporosis activity of naringin in the retinoic acid-induced osteoporosis model. | 2007 |
|
| Stimulative activity of Drynaria fortunei (Kunze) J. Sm. extracts and two of its flavonoids on the proliferation of osteoblastic like cells. | 2006-11 |
|
| Effect of naringin on bone cells. | 2006-11 |
|
| Effect of naringin collagen graft on bone formation. | 2006-03 |
|
| A rapid LC/MS/MS quantitation assay for naringin and its two metabolites in rats plasma. | 2006-02-13 |
|
| [Study on HPLC fingerprint of different growing areas on fructus aurantii fried with bran]. | 2006-02 |
|
| Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies. | 2006-01-11 |
|
| Inhibitory effect of naringin on lipopolysaccharide (LPS)-induced endotoxin shock in mice and nitric oxide production in RAW 264.7 macrophages. | 2006-01-11 |
|
| Flavonoid composition of fruit tissues of citrus species. | 2006-01 |
|
| Inhibition of intestinal and renal Na+-glucose cotransporter by naringenin. | 2006 |
|
| Variations in content of active ingredients causing drug interactions in grapefruit juice products sold in California. | 2006 |
|
| Stimulation of hepatocytic AMP-activated protein kinase by okadaic acid and other autophagy-suppressive toxins. | 2005-03-01 |
|
| Inhibitory effects of naringenin on tumor growth in human cancer cell lines and sarcoma S-180-implanted mice. | 2005-03 |
|
| Separation of flavanone-7-O-glycoside diastereomers and analysis in citrus juices by multidimensional liquid chromatography coupled with mass spectrometry. | 2004-08-25 |
|
| Effect of Lovastatin on lipid peroxidation and total antioxidant concentrations in hemodialysis patients. | 2004-04-22 |
|
| LC-MS/MS determination of naringin, hesperidin and neohesperidin in rat serum after orally administrating the decoction of Bulpleurum falcatum L. and Fractus aurantii. | 2004-01-27 |
|
| Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. | 2004-01-15 |
|
| Naringin and naringenin inhibit nitrite-induced methemoglobin formation. | 2003-08 |
|
| Modulation by flavonoids of PAF and related phospholipids in endothelial cells during oxidative stress. | 2003-02 |
|
| Synergistic effect of deoxyanthocyanins from symbiotic fern Azolla spp. on hrmA gene induction in the cyanobacterium Nostoc punctiforme. | 2002-09 |
|
| Quantification of the production of dihydrokaempferol by flavanone 3-hydroxytransferase using capillary electrophoresis. | 2002-05-23 |
|
| [Effect of grapefruit pulp on the pharmacokinetics of the dihydropyridine calcium antagonists nifedipine and nisoldipine]. | 2002-05 |
|
| The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. | 2001-12 |
|
| Phenols in citrus peel byproducts. Concentrations of hydroxycinnamates and polymethoxylated flavones in citrus peel molasses. | 2001-07 |
|
| Genetic taste markers and food preferences. | 2001-04 |
Sample Use Guides
In a double-blind placebo-controlled study patients were provided an oral dose of 600 mg naringin in combination with 50 mg p-synephrine, and 100 mg hesperidin. The primary outcome monitored was changes in body composition as measured by Dual Energy X-ray Absorptiometry.
Route of Administration:
Oral
Human hepatocellular carcinoma HepG2 cell line was cultured in Dulbecco's Modified Eagle Media (DMEM) supplemented with 10% fetal bovine serum, 25 mM sodium bicarbonate, 20 mM HEPES, 100 ug/mL streptomycin, and 100 units/mL penicillin G and incubated at 37 deg-C in a 5% CO2 atmosphere. Cells were treated with various concentrations of naringin for 24 hours. Cytotoxicity was monitored using an MTT assay. Naringin was found to have an IC50 of 172 uM. The cytotoxic effect of naringin was due to apoptosis and occurred in a dose-dependent fashion. Furthermore, naringin induced the loss of Mitochondrial Transmembrane Potential which was observed by fluorochrome DiOC6 fluorescence intensity in the mitochondria of HepG2 cells. The mediator of apoptosis was found to be dependant on the enhancement of caspase-9, -8, and -3 activity as well as Bcl-2 family protein expressions.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:46:19 GMT 2025
by
admin
on
Mon Mar 31 17:46:19 GMT 2025
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| Record UNII |
N7TD9J649B
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| Record Status |
Validated (UNII)
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| Record Version |
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DSLD |
2517 (Number of products:1851)
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C68463
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3115 (Number of products:28)
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| Code System | Code | Type | Description | ||
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NARINGIN
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28819
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1457550
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233-566-4
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C68462
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N7TD9J649B
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10236-47-2
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100000088536
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SUB22707
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DTXSID6022478
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31538
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m7777
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442428
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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TRANSPORTER -> INHIBITOR |
