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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H32O14
Molecular Weight 580.5356
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NARINGIN

SMILES

C[C@@]1([H])[C@@]([H])([C@]([H])([C@]([H])([C@@]([H])(O1)O[C@]2([H])[C@]([H])([C@@]([H])([C@@]([H])(CO)O[C@@]2([H])Oc3cc(c4C(=O)C[C@@]([H])(c5ccc(cc5)O)Oc4c3)O)O)O)O)O)O

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

HIDE SMILES / InChI

Molecular Formula C27H32O14
Molecular Weight 580.5356
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.

CNS Activity

Curator's Comment:: referenced study was conducted in rat

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds.
2001 Sep-Dec
Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity.
2002 Nov
[Grapefruit juice and drugs: a hazardous combination?].
2002 Sep-Oct
Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages.
2003 Jun 15
Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: implications of matrix metalloproteinase activity.
2004
Separation of flavanone-7-O-glycoside diastereomers and analysis in citrus juices by multidimensional liquid chromatography coupled with mass spectrometry.
2004 Aug 25
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 Jan 27
High-performance liquid chromatography methods for the analysis of adrenergic amines and flavanones in Citrus aurantium L. var. amara.
2004 Jul-Aug
Bound sugars in hepatic glycoproteins from male rats during dietary citrus bioflavonoid and/or ascorbic acid supplementation.
2005 Winter
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
Preventive effect of naringin on lipid peroxides and antioxidants in isoproterenol-induced cardiotoxicity in Wistar rats: biochemical and histopathological evidences.
2006 Dec 7
[Study on HPLC fingerprint of different growing areas on fructus aurantii fried with bran].
2006 Feb
A rapid LC/MS/MS quantitation assay for naringin and its two metabolites in rats plasma.
2006 Feb 13
Flavonoid composition of fruit tissues of citrus species.
2006 Jan
Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies.
2006 Jan 11
Inhibitory effect of naringin on lipopolysaccharide (LPS)-induced endotoxin shock in mice and nitric oxide production in RAW 264.7 macrophages.
2006 Jan 11
[Flavonoids as effective protectors of urease from ultrasonic inactivation in solutions].
2006 Jul-Aug
[Specific depletion of naringin from Si-Ni-San, a traditional Chinese prescription, by an immunoaffinity chromatography].
2006 May
Effect of naringin on bone cells.
2006 Nov
Naringin time-dependently lowers hepatic cholesterol biosynthesis and plasma cholesterol in rats fed high-fat and high-cholesterol diet.
2006 Winter
Effects of isoflavones and soybeans fermented with Bacillus subtilis on lipopolysaccharide-induced production of tumor necrosis factor-alpha and fibrinolysis in vivo.
2007
Constituents of the leaves of Holarrhena pubescens.
2007 Apr
[Identification of jizhi syrup using HPLC fingerprint].
2007 Apr
Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction.
2007 Jul
Enhanced antitumor activity of irinotecan combined with propolis and its polyphenolic compounds on Ehrlich ascites tumor in mice.
2007 Jun
Potential and utilization of thermophiles and thermostable enzymes in biorefining.
2007 Mar 15
Isolation of flavonoids from aspen knotwood by pressurized hot water extraction and comparison with other extraction techniques.
2007 Nov 15
Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells.
2007 Oct
Naringin-induced p21WAF1-mediated G(1)-phase cell cycle arrest via activation of the Ras/Raf/ERK signaling pathway in vascular smooth muscle cells.
2008 Dec
Lemon Polyphenols Suppress Diet-induced Obesity by Up-Regulation of mRNA Levels of the Enzymes Involved in beta-Oxidation in Mouse White Adipose Tissue.
2008 Nov
Fast analysis of prominent flavonoids in tomato using a monolithic column and isocratic HPLC.
2009 Aug
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
Gustatory responsiveness to six bitter tastants in three species of nonhuman primates.
2009 May
An updated review of tyrosinase inhibitors.
2009 May 26
Naringenin prevents dyslipidemia, apolipoprotein B overproduction, and hyperinsulinemia in LDL receptor-null mice with diet-induced insulin resistance.
2009 Oct
Sweetness and bitterness taste of meals per se does not mediate gastric emptying in humans.
2009 Sep
Promotion of bone formation by naringin in a titanium particle-induced diabetic murine calvarial osteolysis model.
2010 Apr
Estrogens of multiple classes and their role in mental health disease mechanisms.
2010 Aug 9
Simvastatin impairs murine melanoma growth.
2010 Dec 16
Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives.
2010 Dec 20
[Naringin inhibits monocyte adhesion to high glucose-induced human umbilical vein endothelial cells].
2010 Feb
Protective effects of silybin and analogues against X-ray radiation-induced damage.
2010 Jul
Study of the polyphenolic composition and antioxidant activity of new sherry vinegar-derived products by maceration with fruits.
2010 Nov 24
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
Transcellular movement of hydroxyurea is mediated by specific solute carrier transporters.
2011 Apr
Alleviation of iron induced oxidative stress by the grape fruit flavanone naringin in vitro.
2011 Apr 25
Beneficial role of naringin, a flavanoid on nickel induced nephrotoxicity in rats.
2011 Aug 15
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 Jan 25
Effects of naringin on the proliferation and osteogenic differentiation of human amniotic fluid-derived stem cells.
2017 Jan
Patents

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 Sat Jun 26 14:21:18 UTC 2021
Edited
by admin
on Sat Jun 26 14:21:18 UTC 2021
Record UNII
N7TD9J649B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NARINGIN
INCI   MI  
INCI  
Official Name English
4',5,7-TRIHYDROXYFLAVANONE-7-RHAMNOGLUCOSIDE
Common Name English
NARINGIN EXTRACT [FHFI]
Common Name English
NARINGIN [USP-RS]
Common Name English
7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Common Name English
NARINGIN [MI]
Common Name English
NARINGIN [INCI]
Common Name English
NARINGENIN-7-RHAMNOGLUCOSIDE
Common Name English
AURANTIIN [WHO-DD]
Common Name English
CITRUS NARINGININE [VANDF]
Common Name English
AURANTIIN
WHO-DD  
Common Name English
Classification Tree Code System Code
DSLD 2517 (Number of products:1851)
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
NCI_THESAURUS C68463
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
DSLD 3115 (Number of products:28)
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
Code System Code Type Description
WIKIPEDIA
NARINGIN
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY
ECHA (EC/EINECS)
233-566-4
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY
NCI_THESAURUS
C68462
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY
FDA UNII
N7TD9J649B
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY
CAS
10236-47-2
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY
EVMPD
SUB22707
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY
EPA CompTox
10236-47-2
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY
RXCUI
31538
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M7777
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY Merck Index
PUBCHEM
442428
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY
USP_CATALOG
1457550
Created by admin on Sat Jun 26 14:21:18 UTC 2021 , Edited by admin on Sat Jun 26 14:21:18 UTC 2021
PRIMARY USP-RS
Related Record Type Details
TRANSPORTER -> INHIBITOR
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (HPLC)