NARINGIN

Investigational

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

[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

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 2678
Caspase-8 2 Target ID: CHEMBL3776 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Agonist 2678
Caspase-9 5 Target ID: CHEMBL2273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27509965	Agonist 2678

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

PubMed

Title	Date	PubMed
[Effect of grapefruit pulp on the pharmacokinetics of the dihydropyridine calcium antagonists nifedipine and nisoldipine].	2002 May	12040751
[Grapefruit juice and drugs: a hazardous combination?].	2002 Sep-Oct	12611197
Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis.	2003 Aug	12900888
Effects of flavonoids on the susceptibility of low-density lipoprotein to oxidative modification.	2003 Jul	12878454
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	15612784
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 chromatographic method for simultaneous quantification of eight major biologically active ingredients in 'Da-Chai-Hu-Tang' preparation.	2006 Apr	16161181
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
CaM-kinaseII-dependent commitment to microcystin-induced apoptosis is coupled to cell budding, but not to shrinkage or chromatin hypercondensation.	2006 Jul	16311514
Stimulative activity of Drynaria fortunei (Kunze) J. Sm. extracts and two of its flavonoids on the proliferation of osteoblastic like cells.	2006 Nov	17152991
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
Evaluation of the radioprotective effects of propolis and flavonoids in gamma-irradiated mice: the alkaline comet assay study.	2008 Jan	18175964
Multiple compounds determination and fingerprint analysis of Lidanpaishi tablet and keli by high-performance liquid chromatography.	2009 Feb 2	19110127
An updated review of tyrosinase inhibitors.	2009 May 26	19582213
[Simultaneous determination of chlorogenic acid, cryptochlorogenic acid, caffeic acid, naringin, hesperidin and linarin in xiao'erjinning oral liquid by an HPLC method].	2010 Jul	20862961
[UPLC-Q-TOF/MS analysis of naringin and naringenin and its metabolites in rat urine and feces after intragastric administration of alcohol extract of Exocarpium Citri grandis].	2010 Jun	20939187
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.	2010 Mar 2	20479987
Alleviation of iron induced oxidative stress by the grape fruit flavanone naringin in vitro.	2011 Apr 25	21345335
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.

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)