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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28501723 | https://www.ncbi.nlm.nih.gov/pubmed/11726811
Curator's Comment: referenced study was conducted in rat
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P42574 Gene ID: 836.0 Gene Symbol: CASP3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23137376 |
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Target ID: GO:0014065 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28501723 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Cytotoxicity and antiproliferative activities of several phenolic compounds against three melanocytes cell lines: relationship between structure and activity. | 2004 |
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Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux. | 2004 Dec |
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Phytochemical analysis of anti-atherogenic constituents of Xue-Fu-Zhu-Yu-Tang using HPLC-DAD-ESI-MS. | 2004 Nov |
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Nobiletin, a citrus flavonoid isolated from tangerines, selectively inhibits class A scavenger receptor-mediated metabolism of acetylated LDL by mouse macrophages. | 2005 Jan |
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A safety study of oral tangeretin and xanthohumol administration to laboratory mice. | 2005 Jan-Feb |
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Tangeretin inhibits extracellular-signal-regulated kinase (ERK) phosphorylation. | 2005 Mar 14 |
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Apigenin inhibits pancreatic cancer cell proliferation through G2/M cell cycle arrest. | 2006 Dec 29 |
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[Chemical constituents from roots of Ficus hirta]. | 2006 Jan |
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TCDD-induced CYP1A1 expression, an index of dioxin toxicity, is suppressed by flavonoids permeating the human intestinal Caco-2 cell monolayers. | 2006 Nov 15 |
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[6]-Gingerol induces cell cycle arrest and cell death of mutant p53-expressing pancreatic cancer cells. | 2006 Oct 31 |
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Correlation between flavonoid content and the NO production inhibitory activity of peel extracts from various citrus fruits. | 2007 Apr |
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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 |
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Characterization of polymethoxylated flavones in Fructus aurantii by liquid chromatography with atmospheric pressure chemical ionization combined with tandem mass spectrometry. | 2007 Apr 11 |
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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 |
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Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3. | 2007 Dec |
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Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography. | 2007 Jan |
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Inhibitors of stress-activated protein/mitogen-activated protein kinase pathways. | 2007 Jun |
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Tangeretin and nobiletin induce G1 cell cycle arrest but not apoptosis in human breast and colon cancer cells. | 2007 Jun 18 |
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Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques. | 2007 May 9 |
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Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones. | 2007 Nov |
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Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? | 2007 Oct |
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Inhibition of oral carcinogenesis by citrus flavonoids. | 2008 |
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Plant polyphenolics as anti-invasive cancer agents. | 2008 Feb |
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Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water. | 2008 Jan |
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Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts. | 2008 Jan |
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Activation of pregnane X receptor and induction of MDR1 by dietary phytochemicals. | 2008 Jul 9 |
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Interactive effects of polymethoxy flavones from Citrus on cell growth inhibition in human neuroblastoma SH-SY5Y cells. | 2008 Mar 15 |
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Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes. | 2008 Mar 15 |
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Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells. | 2008 Sep |
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Investigation of heat treating conditions for enhancing the anti-inflammatory activity of citrus fruit (Citrus reticulata) peels. | 2008 Sep 10 |
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Simultaneous determination of five bioactive flavonoids in pericarpium Citri reticulatae from china by high-performance liquid chromatography with dual wavelength detection. | 2009 Aug 12 |
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UPLC/Q-TOFMS/MS as a powerful technique for rapid identification of polymethoxylated flavones in Fructus aurantii. | 2009 Aug 15 |
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Synthesis and biological evaluation of a series of tangeretin-derived chalcones. | 2009 Jan 1 |
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Semisynthesis and antiproliferative evaluation of a series of 3'-aminoflavones. | 2009 Jul 1 |
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Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention. | 2009 Jun 16 |
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Hepatoprotective effects of flavonoids from shekwasha (Citrus depressa) against D-galactosamine-induced liver injury in rats. | 2010 |
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Semisynthesis of natural flavones inhibiting tubulin polymerization, from hesperidin. | 2010 Apr 23 |
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Simultaneous determination of flavonoids in different parts of Citrus reticulata 'Chachi' fruit by high performance liquid chromatography-photodiode array detection. | 2010 Aug 5 |
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[Study on the contents of flavonoids in Citrus reticulata 'Chachi' from various habitats and different collecting periods]. | 2010 Feb |
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Evaluation of the effect of lime fruit juice on the anticoagulant effect of warfarin. | 2010 Jul |
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Inhibitory effects of 5-hydroxy polymethoxyflavones on colon cancer cells. | 2010 Jul |
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Use of silkworms for identification of drug candidates having appropriate pharmacokinetics from plant sources. | 2010 Jun 11 |
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Drug-target interaction prediction from chemical, genomic and pharmacological data in an integrated framework. | 2010 Jun 15 |
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Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints. | 2010 Mar 2 |
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Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines ( Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand. | 2010 May 26 |
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Polyphenols and human health: prevention of disease and mechanisms of action. | 2010 Nov |
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Antioxidant enrichment and antimicrobial protection of fresh-cut fruits using their own byproducts: looking for integral exploitation. | 2010 Oct |
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Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong. | 2010 Sep 8 |
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Tangeretin ameliorates oxidative stress in the renal tissues of rats with experimental breast cancer induced by 7,12-dimethylbenz[a]anthracene. | 2014 Sep 2 |
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In vitro effects of some flavones on human pyruvate kinase isoenzyme M2. | 2015 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28871498
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23137376
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
Edited
Fri Dec 15 16:00:53 GMT 2023
by
admin
on
Fri Dec 15 16:00:53 GMT 2023
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Record UNII |
I4TLA1DLX6
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Record Status |
Validated (UNII)
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Record Version |
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C68464
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68077
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C68468
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207-570-1
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C059006
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TANGERITIN
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