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Details

Stereochemistry ACHIRAL
Molecular Formula C20H20O7
Molecular Weight 372.3686
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TANGERETIN

SMILES

COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(OC)=C(OC)C(OC)=C3OC

InChI

InChIKey=ULSUXBXHSYSGDT-UHFFFAOYSA-N
InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3

HIDE SMILES / InChI

Molecular Formula C20H20O7
Molecular Weight 372.3686
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tangeretin is an O-polymethoxylated flavone that is found in tangerine and other citrus peels. Its natural role is to strengthen the cell wall and act as a plant's defensive mechanism against disease-causing pathogens. Animal studies have shown the potential fo tangeretin as a therapeutic in a number of conditions including cancers, asthma, CKD, hypercholesterolemia, and Parkinson's disease.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P42574
Gene ID: 836.0
Gene Symbol: CASP3
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cytotoxicity and antiproliferative activities of several phenolic compounds against three melanocytes cell lines: relationship between structure and activity.
2004
Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux.
2004 Dec
Phytochemical analysis of anti-atherogenic constituents of Xue-Fu-Zhu-Yu-Tang using HPLC-DAD-ESI-MS.
2004 Nov
Nobiletin, a citrus flavonoid isolated from tangerines, selectively inhibits class A scavenger receptor-mediated metabolism of acetylated LDL by mouse macrophages.
2005 Jan
A safety study of oral tangeretin and xanthohumol administration to laboratory mice.
2005 Jan-Feb
Tangeretin inhibits extracellular-signal-regulated kinase (ERK) phosphorylation.
2005 Mar 14
Apigenin inhibits pancreatic cancer cell proliferation through G2/M cell cycle arrest.
2006 Dec 29
[Chemical constituents from roots of Ficus hirta].
2006 Jan
TCDD-induced CYP1A1 expression, an index of dioxin toxicity, is suppressed by flavonoids permeating the human intestinal Caco-2 cell monolayers.
2006 Nov 15
[6]-Gingerol induces cell cycle arrest and cell death of mutant p53-expressing pancreatic cancer cells.
2006 Oct 31
Correlation between flavonoid content and the NO production inhibitory activity of peel extracts from various citrus fruits.
2007 Apr
Quality control and discrimination of pericarpium citri reticulatae and pericarpium citri reticulatae viride based on high-performance liquid chromatographic fingerprints and multivariate statistical analysis.
2007 Apr 11
Characterization of polymethoxylated flavones in Fructus aurantii by liquid chromatography with atmospheric pressure chemical ionization combined with tandem mass spectrometry.
2007 Apr 11
Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.
2007 Apr 4
Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3.
2007 Dec
Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography.
2007 Jan
Inhibitors of stress-activated protein/mitogen-activated protein kinase pathways.
2007 Jun
Tangeretin and nobiletin induce G1 cell cycle arrest but not apoptosis in human breast and colon cancer cells.
2007 Jun 18
Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques.
2007 May 9
Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.
2007 Nov
Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass?
2007 Oct
Inhibition of oral carcinogenesis by citrus flavonoids.
2008
Plant polyphenolics as anti-invasive cancer agents.
2008 Feb
Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water.
2008 Jan
Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts.
2008 Jan
Activation of pregnane X receptor and induction of MDR1 by dietary phytochemicals.
2008 Jul 9
Interactive effects of polymethoxy flavones from Citrus on cell growth inhibition in human neuroblastoma SH-SY5Y cells.
2008 Mar 15
Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.
2008 Mar 15
Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells.
2008 Sep
Investigation of heat treating conditions for enhancing the anti-inflammatory activity of citrus fruit (Citrus reticulata) peels.
2008 Sep 10
Simultaneous determination of five bioactive flavonoids in pericarpium Citri reticulatae from china by high-performance liquid chromatography with dual wavelength detection.
2009 Aug 12
UPLC/Q-TOFMS/MS as a powerful technique for rapid identification of polymethoxylated flavones in Fructus aurantii.
2009 Aug 15
Synthesis and biological evaluation of a series of tangeretin-derived chalcones.
2009 Jan 1
Semisynthesis and antiproliferative evaluation of a series of 3'-aminoflavones.
2009 Jul 1
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.
2009 Jun 16
Hepatoprotective effects of flavonoids from shekwasha (Citrus depressa) against D-galactosamine-induced liver injury in rats.
2010
Semisynthesis of natural flavones inhibiting tubulin polymerization, from hesperidin.
2010 Apr 23
Simultaneous determination of flavonoids in different parts of Citrus reticulata 'Chachi' fruit by high performance liquid chromatography-photodiode array detection.
2010 Aug 5
[Study on the contents of flavonoids in Citrus reticulata 'Chachi' from various habitats and different collecting periods].
2010 Feb
Evaluation of the effect of lime fruit juice on the anticoagulant effect of warfarin.
2010 Jul
Inhibitory effects of 5-hydroxy polymethoxyflavones on colon cancer cells.
2010 Jul
Use of silkworms for identification of drug candidates having appropriate pharmacokinetics from plant sources.
2010 Jun 11
Drug-target interaction prediction from chemical, genomic and pharmacological data in an integrated framework.
2010 Jun 15
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.
2010 Mar 2
Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines ( Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand.
2010 May 26
Polyphenols and human health: prevention of disease and mechanisms of action.
2010 Nov
Antioxidant enrichment and antimicrobial protection of fresh-cut fruits using their own byproducts: looking for integral exploitation.
2010 Oct
Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong.
2010 Sep 8
Tangeretin ameliorates oxidative stress in the renal tissues of rats with experimental breast cancer induced by 7,12-dimethylbenz[a]anthracene.
2014 Sep 2
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.
2015 Mar
Patents

Sample Use Guides

CKD was induced in Sprague-Dawley rats by 5/6 nephrectomy (Nx). Separated groups of 5/6 Nx rats were treated intragastrically with tangeretin (50, 100 or 200 mg/kg bw) or enalapril for 30 days, starting 5 days after the surgery. Elevated TNF-α, nitric oxide (NO) and cytokines-IL-6 and IL-1β with upregulated NF-κB/TNF-α/iNOS signaling pathways were effectively down-regulated by tangeretin. Cognitive disturbances and memory impairments observed in Nx rats were substantially improved by tangeretin. Collectively, the experimental data indicate that the anti-oxidant and anti-inflammatory effects of tangeretin effectively improved renal function and reduced the cognitive and memory impairments in CKD-induced animals.
Route of Administration: Intragastric
Human colorectal adenocarcinoma cell line, LoVo, and its resistant subline, LoVo/Dx, obtained by prolonged exposure to doxorubicin were cultivated in Ham's F12 medium at 37 deg-C and an atmosphere of 5% CO2 (with addition of 10% fetal bovine serum, L-glutamine, antibiotics, and in the case of loVo/Dx cells, doxorubicin at 100 ng/mL). Cells were seeded in 96-well plates in 75 micro-L of medium and allowed to attach for 60 min at 37 deg-C. An equal volume of medium containing Tangeretin was added, and the incubation was continued for 72 hours. Cytotoxicity was monitored using a sulforhodamine B assay. Tangeretin demonstrated the greatest cytotoxicity among studied compounds in both LoVo, and LoVo/Dx cells with an IC50 range between 20 - 40 microM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:00:53 GMT 2023
Edited
by admin
on Fri Dec 15 16:00:53 GMT 2023
Record UNII
I4TLA1DLX6
Record Status Validated (UNII)
Record Version
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Name Type Language
TANGERETIN
WHO-DD  
Common Name English
NSC-618905
Code English
Tangeretin [WHO-DD]
Common Name English
TANGERITIN [INCI]
Common Name English
FLAVONE, 4',5,6,7,8-PENTAMETHOXY-
Systematic Name English
4H-1-BENZOPYRAN-4-ONE, 5,6,7,8-TETRAMETHOXY-2-(4-METHOXYPHENYL)-
Systematic Name English
5,6,7,8-TETRAMETHOXY-2-(4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
NSC-53909
Code English
PONKANETIN
Common Name English
4',5,6,7,8-PENTAMETHOXYFLAVONE
Systematic Name English
5,6,7,8,4'-PENTAMETHOXYFLAVONE
Systematic Name English
TANGERITIN
INCI  
INCI  
Official Name English
Classification Tree Code System Code
NCI_THESAURUS C68464
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID30197417
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
FDA UNII
I4TLA1DLX6
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
NSC
53909
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
PUBCHEM
68077
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
NCI_THESAURUS
C68468
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-570-1
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
SMS_ID
300000037347
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
CHEBI
9400
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
MESH
C059006
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
WIKIPEDIA
TANGERITIN
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
CAS
481-53-8
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
NSC
618905
Created by admin on Fri Dec 15 16:00:53 GMT 2023 , Edited by admin on Fri Dec 15 16:00:53 GMT 2023
PRIMARY
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TRANSPORTER -> INHIBITOR