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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
Structure of NARINGIN

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

HIDE SMILES / InChI

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.

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
The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice.
2001 Dec
[Effect of grapefruit pulp on the pharmacokinetics of the dihydropyridine calcium antagonists nifedipine and nisoldipine].
2002 May
Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis.
2003 Aug
Anti-Sindbis activity of flavanones hesperetin and naringenin.
2003 Jan
Okadaic acid-induced, naringin-sensitive phosphorylation of glycine N-methyltransferase in isolated rat hepatocytes.
2003 Jul 15
Effect of Lovastatin on lipid peroxidation and total antioxidant concentrations in hemodialysis patients.
2004 Apr 22
Separation of flavanone-7-O-glycoside diastereomers and analysis in citrus juices by multidimensional liquid chromatography coupled with mass spectrometry.
2004 Aug 25
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
Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method.
2004 Dec 29
Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products.
2004 Jan 15
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
Variations in content of active ingredients causing drug interactions in grapefruit juice products sold in California.
2006
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
CaM-kinaseII-dependent commitment to microcystin-induced apoptosis is coupled to cell budding, but not to shrinkage or chromatin hypercondensation.
2006 Jul
Effect of naringin collagen graft on bone formation.
2006 Mar
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
Anti-osteoporosis activity of naringin in the retinoic acid-induced osteoporosis model.
2007
The effects of Rhizoma Curculiginis and Rhizoma Drynariae extracts on bones.
2007 Dec 19
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
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
Cupric ion reducing antioxidant capacity assay for food antioxidants: vitamins, polyphenolics, and flavonoids in food extracts.
2008
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
Hydrolysis of flavanone glycosides and degradation of the corresponding aglycones from dried immature Citrus fruit by human fecal flora in vitro.
2008 Nov
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
Protective effect of naringin against ischemic reperfusion cerebral injury: possible neurobehavioral, biochemical and cellular alterations in rat brain.
2009 Aug 15
Determination of sophoricoside in rat plasma by HPLC and its application to pharmacokinetic studies.
2009 Dec
Multiple compounds determination and fingerprint analysis of Lidanpaishi tablet and keli by high-performance liquid chromatography.
2009 Feb 2
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
Discrimination of three medicinal materials from the Citrus genus by HPLC fingerprint coupled with two complementary software.
2009 Jul-Aug
An updated review of tyrosinase inhibitors.
2009 May 26
The role of transporters in the pharmacokinetics of orally administered drugs.
2009 Sep
Effect of naringin on the DNA damage induced by daunorubicin in mouse hepatocytes and cardiocytes.
2010
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
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 suppress chondrosarcoma migration through inhibition vascular adhesion molecule-1 expression by modulating miR-126.
2014 Sep
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 Wed Jul 05 22:37:48 UTC 2023
Edited
by admin
on Wed Jul 05 22:37:48 UTC 2023
Record UNII
N7TD9J649B
Record Status Validated (UNII)
Record Version
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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 Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
NCI_THESAURUS C68463
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
DSLD 3115 (Number of products:28)
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
Code System Code Type Description
WIKIPEDIA
NARINGIN
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
CHEBI
28819
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
RS_ITEM_NUM
1457550
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
233-566-4
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
NCI_THESAURUS
C68462
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
FDA UNII
N7TD9J649B
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
CAS
10236-47-2
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
SMS_ID
100000088536
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
EVMPD
SUB22707
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID6022478
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
RXCUI
31538
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M7777
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY Merck Index
PUBCHEM
442428
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (HPLC)
TRANSPORTER -> INHIBITOR