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
SMILES
OC1=CC=C(C=C1)[C@@H]2CC(=O)C3=C(O2)C=C(O)C=C3O
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
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q16555 Gene ID: 1808.0 Gene Symbol: DPYSL2 Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL2093866 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibitory activity of flavonoids and tannins against HIV-1 protease. | 2000 Sep |
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| The use of a high-volume screening procedure to assess the effects of dietary flavonoids on human cyp1a1 expression. | 2001 Aug |
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| Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1. | 2001 Jan 12 |
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| Differential activation of wild-type and variant forms of estrogen receptor alpha by synthetic and natural estrogenic compounds using a promoter containing three estrogen-responsive elements. | 2001 Jul |
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| Effect of P-glycoprotein modulators on the pharmacokinetics of camptothecin using microdialysis. | 2001 Nov |
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| Characterization of peroxidase-mediated chlorophyll bleaching in strawberry fruit. | 2001 Oct |
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| No evidence for the in vivo activity of aromatase-inhibiting flavonoids. | 2001 Sep |
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| Cloning of parsley flavone synthase I. | 2001 Sep |
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| Effect of exogenous flavonoids on nodulation of pea (Pisum sativum L.). | 2002 Aug |
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| Enantiomer separation of flavour and fragrance compounds by liquid chromatography using novel urea-covalent bonded methylated beta-cyclodextrins on silica. | 2002 Aug 30 |
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| Reaction mechanism of chalcone isomerase. pH dependence, diffusion control, and product binding differences. | 2002 Jan 11 |
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| Phenolic glycosides from Viscum angulatum. | 2002 May |
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| Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. | 2002 Sep 25 |
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| Muscanone: a 3-O-(1", 8", 14"-trimethylhexadecanyl)naringenin from Commiphora wightii. | 2003 Apr |
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| O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans. | 2003 Feb |
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| Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. | 2003 Feb |
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| New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit. | 2003 Jul |
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| Glycosyl flavonoids from the roots and rhizomes of Asarum longerhizomatosum. | 2003 Mar |
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| Flavanone 3-hydroxylase expression in Citrus paradisi and Petunia hybrida seedlings. | 2003 Sep |
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| Paclitaxel metabolism in rat and human liver microsomes is inhibited by phenolic antioxidants. | 2003 Sep |
Patents
Sample Use Guides
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
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.
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529 (Number of products:113)
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C005273
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11855
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C68463
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HN5425SBF2
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1368173
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m7776
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DB03467
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207-550-2
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NARINGENIN
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17846
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SUBSTANCE RECORD
