NARINGIN

Investigational

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 Search

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

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT01423019 | https://clinicaltrials.gov/ct2/show/NCT01272167 | https://www.ncbi.nlm.nih.gov/pubmed/7586927 | https://www.ncbi.nlm.nih.gov/pubmed/24710903 | https://www.ncbi.nlm.nih.gov/pubmed/27509965 | https://www.ncbi.nlm.nih.gov/pubmed/25317167 | https://www.ncbi.nlm.nih.gov/pubmed/21372385

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Caspase-3 20 Target ID: CHEMBL2334 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Agonist 2470
Caspase-8 2 Target ID: CHEMBL3776 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Agonist 2470
Caspase-9 5 Target ID: CHEMBL2273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Agonist 2470

Conditions

Condition	Modality	Targets	Highest Phase	Product
Liver cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Primary		Basic research	Unknown Approved Use Unknown
Parkinson's disease 219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25317167	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds.	2001 Sep-Dec	11737987
Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity.	2002 Nov	12592672
[Grapefruit juice and drugs: a hazardous combination?].	2002 Sep-Oct	12611197
Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages.	2003 Jun 15	12787887
Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: implications of matrix metalloproteinase activity.	2004	15231453
Separation of flavanone-7-O-glycoside diastereomers and analysis in citrus juices by multidimensional liquid chromatography coupled with mass spectrometry.	2004 Aug 25	15315361
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	14738930
High-performance liquid chromatography methods for the analysis of adrenergic amines and flavanones in Citrus aurantium L. var. amara.	2004 Jul-Aug	15311840
Bound sugars in hepatic glycoproteins from male rats during dietary citrus bioflavonoid and/or ascorbic acid supplementation.	2005 Winter	16379564
Inhibition of intestinal and renal Na+-glucose cotransporter by naringenin.	2006	16289850
Variations in content of active ingredients causing drug interactions in grapefruit juice products sold in California.	2006	16841515
Preventive effect of naringin on lipid peroxides and antioxidants in isoproterenol-induced cardiotoxicity in Wistar rats: biochemical and histopathological evidences.	2006 Dec 7	17084010
[Study on HPLC fingerprint of different growing areas on fructus aurantii fried with bran].	2006 Feb	16706019
A rapid LC/MS/MS quantitation assay for naringin and its two metabolites in rats plasma.	2006 Feb 13	16406442
Flavonoid composition of fruit tissues of citrus species.	2006 Jan	16428836
Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies.	2006 Jan 11	16390207
Inhibitory effect of naringin on lipopolysaccharide (LPS)-induced endotoxin shock in mice and nitric oxide production in RAW 264.7 macrophages.	2006 Jan 11	16137700
[Flavonoids as effective protectors of urease from ultrasonic inactivation in solutions].	2006 Jul-Aug	16909863
[Specific depletion of naringin from Si-Ni-San, a traditional Chinese prescription, by an immunoaffinity chromatography].	2006 May	16929840
Effect of naringin on bone cells.	2006 Nov	16944474
Naringin time-dependently lowers hepatic cholesterol biosynthesis and plasma cholesterol in rats fed high-fat and high-cholesterol diet.	2006 Winter	17201649
Effects of isoflavones and soybeans fermented with Bacillus subtilis on lipopolysaccharide-induced production of tumor necrosis factor-alpha and fibrinolysis in vivo.	2007	17849275
Constituents of the leaves of Holarrhena pubescens.	2007 Apr	17329039
[Identification of jizhi syrup using HPLC fingerprint].	2007 Apr	17608218
Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction.	2007 Jul	17452418
Enhanced antitumor activity of irinotecan combined with propolis and its polyphenolic compounds on Ehrlich ascites tumor in mice.	2007 Jun	17412551
Potential and utilization of thermophiles and thermostable enzymes in biorefining.	2007 Mar 15	17359551
Isolation of flavonoids from aspen knotwood by pressurized hot water extraction and comparison with other extraction techniques.	2007 Nov 15	18371609
Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells.	2007 Oct	17542018
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	18951945
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	19015756
Fast analysis of prominent flavonoids in tomato using a monolithic column and isocratic HPLC.	2009 Aug	19575378
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	19147314
Gustatory responsiveness to six bitter tastants in three species of nonhuman primates.	2009 May	19399556
An updated review of tyrosinase inhibitors.	2009 May 26	19582213
Naringenin prevents dyslipidemia, apolipoprotein B overproduction, and hyperinsulinemia in LDL receptor-null mice with diet-induced insulin resistance.	2009 Oct	19592617
Sweetness and bitterness taste of meals per se does not mediate gastric emptying in humans.	2009 Sep	19535679
Promotion of bone formation by naringin in a titanium particle-induced diabetic murine calvarial osteolysis model.	2010 Apr	19824055
Estrogens of multiple classes and their role in mental health disease mechanisms.	2010 Aug 9	21072308
Simvastatin impairs murine melanoma growth.	2010 Dec 16	21162733
Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives.	2010 Dec 20	21053930
[Naringin inhibits monocyte adhesion to high glucose-induced human umbilical vein endothelial cells].	2010 Feb	20159712
Protective effects of silybin and analogues against X-ray radiation-induced damage.	2010 Jul	20705588
Study of the polyphenolic composition and antioxidant activity of new sherry vinegar-derived products by maceration with fruits.	2010 Nov 24	21080728
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	21054849
Transcellular movement of hydroxyurea is mediated by specific solute carrier transporters.	2011 Apr	21256917
Alleviation of iron induced oxidative stress by the grape fruit flavanone naringin in vitro.	2011 Apr 25	21345335
Beneficial role of naringin, a flavanoid on nickel induced nephrotoxicity in rats.	2011 Aug 15	21600195
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	26721195
Effects of naringin on the proliferation and osteogenic differentiation of human amniotic fluid-derived stem cells.	2017 Jan	24915843

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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

Common Name

English

Classification Tree Code System Code

DSLD

2517 (Number of products:1851)