NARINGIN

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 Search

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

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

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 21 Target ID: CHEMBL2334 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Agonist 2752
Caspase-8 2 Target ID: CHEMBL3776 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Agonist 2752
Caspase-9 5 Target ID: CHEMBL2273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Agonist 2752

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 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25317167	Primary		Basic research	Unknown Approved Use Unknown

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	11561098
Anti-Sindbis activity of flavanones hesperetin and naringenin.	2003 Jan	12520185
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
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	15342961
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
Constituents of the leaves of Holarrhena pubescens.	2007 Apr	17329039
[Identification of jizhi syrup using HPLC fingerprint].	2007 Apr	17608218
Potential and utilization of thermophiles and thermostable enzymes in biorefining.	2007 Mar 15	17359551
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
Discrimination of three medicinal materials from the Citrus genus by HPLC fingerprint coupled with two complementary software.	2009 Jul-Aug	19425114
Sweetness and bitterness taste of meals per se does not mediate gastric emptying in humans.	2009 Sep	19535679
[Naringin inhibits monocyte adhesion to high glucose-induced human umbilical vein endothelial cells].	2010 Feb	20159712
Alleviation of iron induced oxidative stress by the grape fruit flavanone naringin in vitro.	2011 Apr 25	21345335
Naringin suppress chondrosarcoma migration through inhibition vascular adhesion molecule-1 expression by modulating miR-126.	2014 Sep	24975661

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 `Mon Mar 31 17:46:19 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:19 GMT 2025`
Record UNII	N7TD9J649B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NARINGIN

Official Name

English

AURANTIIN

Preferred 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

NARINGENIN-7-RHAMNOGLUCOSIDE

Common Name

English

Aurantiin [WHO-DD]

Common Name

English

CITRUS NARINGININE [VANDF]

Common Name

English

Classification Tree Code System Code

DSLD

2517 (Number of products:1851)