NARINGENIN

First approved in 2017

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H12O5
Molecular Weight	272.2528
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)[C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=FTVWIRXFELQLPI-ZDUSSCGKSA-N

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28674493 | https://www.ncbi.nlm.nih.gov/pubmed/29331869 |https://www.ncbi.nlm.nih.gov/pubmed/24260594

Naringenin is one of the most abundant flavonoids in natural citrus fruits and has been studied as an antioxidant and anti-inflammatory agent. Besides, it has been investigated for its ability to inhibit the growth of breast, colon, gastric and prostate cancer cells. Experiments on rodents have revealed, that naringenin is a component of Drynaria Rhizome and can enhance memory function and ameliorate Alzheimer's disease pathologies. Using the experimental autoimmune encephalomyelitis, a rodent model of human multiple sclerosis was determined that naringenin may have a potential to ameliorate autoimmune disease by favorably modulating autoimmune response. The precise mechanism of action of naringenin compound is not clear, but it is known, that it is a partial agonist of estrogen receptor that can act as a competitive antagonist in the presence of a potent (or full) agonist. In addition, it binds to collapsin response mediator protein 2 protein (CRMP2) and reduces the Aβ-induced phosphorylation of CRMP2, resulting in axonal growth facilitation.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydropyrimidinase-related protein 2 4 Target ID: Q16555 Gene ID: 1808.0 Gene Symbol: DPYSL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28674493	Binding Agent 1076
Estrogen receptor 72 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24260594	Partial Agonist 297

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28674493	Primary	Preclinical	Unknown Approved Use Unknown
Multiple sclerosis 107 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29331869	Palliative	Preclinical	Unknown Approved Use Unknown
Colorectal cancer 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26074733	Primary	Basic research	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26074733	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth.	2003-09	12943774
Flavanone 3-hydroxylase expression in Citrus paradisi and Petunia hybrida seedlings.	2003-09	12943760
Paclitaxel metabolism in rat and human liver microsomes is inhibited by phenolic antioxidants.	2003-09	12920504
Xanthones and benzophenones from the stems of Garcinia multiflora.	2003-08	12932126
Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria.	2003-08	12932124
Separation of some chiral flavanones by micellar electrokinetic chromatography.	2003-08	12900864
New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit.	2003-07	12913285
Simultaneous detection of the antioxidant and pro-oxidant activity of dietary polyphenolics in a peroxidase system.	2003-07	12911276
Cloning and expression of the isoflavone synthase gene (IFS-Tp) from Trifolium pratense.	2003-06-30	12872984
Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley.	2003-06-05	12782296
Influence of solvents on the antioxidant property of flavonoids.	2003-06	12866621
Pro-oxidative properties of flavonoids in human lymphocytes.	2003-06	12843645
Cell-specific activation of aflatoxin B1 correlates with presence of some cytochrome P450 enzymes in olfactory and respiratory tissues in horse.	2003-06	12726741
Naringenin inhibits phosphoinositide 3-kinase activity and glucose uptake in 3T3-L1 adipocytes.	2003-05-30	12745063
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.	2003-05	12736527
Phenolic extractives in Salix caprea wood and knots.	2003-05	12711137
Activation of the aryl hydrocarbon receptor by some vegetable constituents determined using in vitro reporter gene assay.	2003-04	12673038
Muscanone: a 3-O-(1", 8", 14"-trimethylhexadecanyl)naringenin from Commiphora wightii.	2003-04	12648547
Interaction between flavonoids and the blood-brain barrier: in vitro studies.	2003-04	12641740
[Grapefruit juice and drugs: a hazardous combination?].	2003-03-04	12611197
The variable effect on proliferation of a colon cancer cell line by the citrus fruit flavonoid Naringenin.	2003-03	12780904
Glycosyl flavonoids from the roots and rhizomes of Asarum longerhizomatosum.	2003-03	12608635
Comparison of in vitro hepatic models for the prediction of metabolic interaction between simvastatin and naringenin.	2003-02-18	12587952
Hepatocyte apoB-containing lipoprotein secretion is decreased by the grapefruit flavonoid, naringenin, via inhibition of MTP-mediated microsomal triglyceride accumulation.	2003-02-11	12564931
Naringenin 7-O-cetyl ether as inhibitor of HMG-CoA reductase and modulator of plasma and hepatic lipids in high cholesterol-fed rats.	2003-02-06	12517434
Bioflavonoids attenuate renal proximal tubular cell injury during cold preservation in Euro-Collins and University of Wisconsin solutions.	2003-02	12631120
Flavonol synthase from Citrus unshiu is a bifunctional dioxygenase.	2003-02	12620339
O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans.	2003-02	12576658
Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice.	2003-02	12571654
In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juice.	2003-01	12554070
Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao).	2003-01	12526004
Anti-Sindbis activity of flavanones hesperetin and naringenin.	2003-01	12520185
Bioflavonoid stimulation of glutathione transport by the 190-kDa multidrug resistance protein 1 (MRP1).	2003-01	12485947
Polyphenol pattern and antioxidant activity of different tomato lines and cultivars.	2003	12652057
Problems for risk assessment of endocrine-active estrogenic compounds.	2002-12	12634121
Flavonoids and nitric oxide synthase.	2002-12	12512693
Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity.	2002-11	12592672
Molecular characterization of root-specific chalcone synthases from Cassia alata.	2002-11	12430015
Differential modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1)-catalyzed estradiol-3-glucuronidation by the addition of UGT1A1 substrates and other compounds to human liver microsomes.	2002-11	12386134
Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9.	2002-11	12386133
Fasting plasma concentrations of selected flavonoids as markers of their ordinary dietary intake.	2002-10	12395214
High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1.	2002-10	12368501
Assessing estrogenic activity of phytochemicals using transcriptional activation and immature mouse uterotrophic responses.	2002-09-25	12270211
Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood.	2002-09-25	12270199
Inhibition of hepatocyte apoB secretion by naringenin: enhanced rapid intracellular degradation independent of reduced microsomal cholesteryl esters.	2002-09	12235187
Plasma concentrations of the flavonoids hesperetin, naringenin and quercetin in human subjects following their habitual diets, and diets high or low in fruit and vegetables.	2002-09	12209378
Enantiomer separation of flavour and fragrance compounds by liquid chromatography using novel urea-covalent bonded methylated beta-cyclodextrins on silica.	2002-08-30	12236512
Free radical scavengers from the heartwood of Juniperus chinensis.	2002-08	12214854
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.	2002-07	12224631
Preincubation of Mesorhizobium ciceri with flavonoids improves its nodule occupancy.	2002	12503401

Patents

Sample Use Guides

In Vivo Use Guide

orally administered a high dose of Drynaria Rhizome (DR) (13 g kg-1) to the 5XFAD mice. Naringenin was present at 0.27 mg g-1 in DR extract

Route of Administration: Oral

In Vitro Use Guide

Naringenin (NGN) induced anti-inflammatory effects in paraquat (PQ)-treated SH-SY5Y cells by a mechanism associated with the Nrf2/HO-1 signaling pathway. Pretreatment with NGN at 80 µM for 2 h decreased the levels of pro-inflammatory cytokines interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) in PQ-treated SH-SY5Y cells. The production of nitric oxide (NO·) and levels of cyclooxygenase-2 (COX-2) and of the inducible isoform of nitric oxide synthase (iNOS) were downregulated by NGN in the cells exposed to PQ. Moreover, NGN downregulated the activation of the nuclear factor-κB (NF-κB) in PQ-treated cells.

Name

Type

Language

NSC-11855

Preferred Name

English

NARINGENIN

Official Name

English

SALIPUROL

Common Name

English

2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

NSC-34875

Code

English

SALIPURPOL

Common Name

English

NARINGENIN, (-)-

Common Name

English

5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-CHROMAN-4-ONE

Systematic Name

English

(2S)-NARINGENIN

Common Name

English

NARINGENINE

Common Name

English

NARINGENIN [MI]

Common Name

English

(-)-NARINGENIN

Common Name

English

Classification Tree Code System Code

DSLD

529 (Number of products:113)