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
[H][C@@]5(O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC2=CC3=C(C(=O)C[C@H](O3)C4=CC=C(O)C=C4)C(O)=C2)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O
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
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 |
|---|---|---|
| Flavonoids with epidermal growth factor-receptor tyrosine kinase inhibitory activity stimulate PEPT1-mediated cefixime uptake into human intestinal epithelial cells. | 2001 Oct |
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| Quantification of the production of dihydrokaempferol by flavanone 3-hydroxytransferase using capillary electrophoresis. | 2002 Mar-Apr |
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| [Grapefruit juice and drugs: a hazardous combination?]. | 2002 Sep-Oct |
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| Modulation by flavonoids of PAF and related phospholipids in endothelial cells during oxidative stress. | 2003 Feb |
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| Anti-Sindbis activity of flavanones hesperetin and naringenin. | 2003 Jan |
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| Effects of flavonoids on the susceptibility of low-density lipoprotein to oxidative modification. | 2003 Jul |
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| Toxin-induced tail phosphorylation of hepatocellular S6 kinase: evidence for a dual involvement of the AMP-activated protein kinase in S6 kinase regulation. | 2004 Dec |
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| High-performance liquid chromatographic method for simultaneous quantification of eight major biologically active ingredients in 'Da-Chai-Hu-Tang' preparation. | 2006 Apr |
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| Flavonoid composition of fruit tissues of citrus species. | 2006 Jan |
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| Inhibitory effect of naringin on lipopolysaccharide (LPS)-induced endotoxin shock in mice and nitric oxide production in RAW 264.7 macrophages. | 2006 Jan 11 |
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| CaM-kinaseII-dependent commitment to microcystin-induced apoptosis is coupled to cell budding, but not to shrinkage or chromatin hypercondensation. | 2006 Jul |
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| Effect of naringin collagen graft on bone formation. | 2006 Mar |
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| [Specific depletion of naringin from Si-Ni-San, a traditional Chinese prescription, by an immunoaffinity chromatography]. | 2006 May |
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| [Identification of jizhi syrup using HPLC fingerprint]. | 2007 Apr |
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| Hypolipidemic effects of Citrus bergamia Risso et Poiteau juice in rats fed a hypercholesterolemic diet. | 2007 Dec 26 |
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| The tumor-growth inhibitory activity of flavanone and 2'-OH flavanone in vitro and in vivo through induction of cell cycle arrest and suppression of cyclins and CDKs. | 2007 Jan |
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| Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction. | 2007 Jul |
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| Enhanced antitumor activity of irinotecan combined with propolis and its polyphenolic compounds on Ehrlich ascites tumor in mice. | 2007 Jun |
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| Potential and utilization of thermophiles and thermostable enzymes in biorefining. | 2007 Mar 15 |
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| Isolation of flavonoids from aspen knotwood by pressurized hot water extraction and comparison with other extraction techniques. | 2007 Nov 15 |
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| Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells. | 2007 Oct |
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| Role of cytochrome P450 in drug interactions. | 2008 Oct 18 |
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| Classification and prediction of free-radical scavenging activities of dangyuja (Citrus grandis Osbeck) fruit extracts using (1)H NMR spectroscopy and multivariate statistical analysis. | 2009 Feb 20 |
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| An updated review of tyrosinase inhibitors. | 2009 May 26 |
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| Sweetness and bitterness taste of meals per se does not mediate gastric emptying in humans. | 2009 Sep |
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| Promotion of bone formation by naringin in a titanium particle-induced diabetic murine calvarial osteolysis model. | 2010 Apr |
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| Estrogens of multiple classes and their role in mental health disease mechanisms. | 2010 Aug 9 |
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| Simvastatin impairs murine melanoma growth. | 2010 Dec 16 |
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| Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. | 2010 Dec 20 |
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| [Naringin inhibits monocyte adhesion to high glucose-induced human umbilical vein endothelial cells]. | 2010 Feb |
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| The diagnostic value of endothelial function as a potential sensor of fatigue in health. | 2010 Mar 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 Nov 5 |
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| Alleviation of iron induced oxidative stress by the grape fruit flavanone naringin in vitro. | 2011 Apr 25 |
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| Beneficial role of naringin, a flavanoid on nickel induced nephrotoxicity in rats. | 2011 Aug 15 |
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| Naringin induces death receptor and mitochondria-mediated apoptosis in human cervical cancer (SiHa) cells. | 2013 Jan |
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| Effects of naringin on the proliferation and osteogenic differentiation of human amniotic fluid-derived stem cells. | 2017 Jan |
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.
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DSLD |
2517 (Number of products:1851)
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NCI_THESAURUS |
C68463
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DSLD |
3115 (Number of products:28)
Created by
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| Code System | Code | Type | Description | ||
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NARINGIN
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28819
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N7TD9J649B
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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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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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SUBSTANCE RECORD
