Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H22O8 |
| Molecular Weight | 402.3946 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1OC)C2=CC(=O)C3=C(O2)C(OC)=C(OC)C(OC)=C3OC
InChI
InChIKey=MRIAQLRQZPPODS-UHFFFAOYSA-N
InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3
| Molecular Formula | C21H22O8 |
| Molecular Weight | 402.3946 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Nobiletin is a flavanoid isolatable from citrus peels. It has demonstrated anti-cancer properties in several in vitro cell models and garnered interest as a potential treatment for the motor and cognitive symptoms of Parkinson's disease. However, investigation of this compound has not moved beyond animal studies.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P21439 Gene ID: 5244.0 Gene Symbol: ABCB4 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. | 2001 Dec |
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| Evaluation of the effects of swainsonine, captopril, tangeretin and nobiletin on the biological behaviour of brain tumour cells in vitro. | 2001 Feb |
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| Cancer chemopreventive activity of 3,5,6,7,8,3',4'-heptamethoxyflavone from the peel of citrus plants. | 2001 Feb 10 |
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| In vitro absorption and metabolism of nobiletin, a chemopreventive polymethoxyflavonoid in citrus fruits. | 2001 Jan |
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| Dietary administration of citrus nobiletin inhibits azoxymethane-induced colonic aberrant crypt foci in rats. | 2001 Jul 13 |
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| Characteristic rat tissue accumulation of nobiletin, a chemopreventive polymethoxyflavonoid, in comparison with luteolin. | 2002 |
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| Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels. | 2002 May 8 |
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| Urinary metabolites of nobiletin orally administered to rats. | 2003 Dec |
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| Effect of extraction method on the concentrations of selected bioactive compounds in mandarin juice. | 2003 Dec 3 |
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| Changes in the levels of polymethoxyflavones and flavanones as part of the defense mechanism of Citrus sinensis (cv. Valencia Late) fruits against Phytophthora citrophthora. | 2004 Apr 7 |
|
| Anti-tumour effects of nobiletin, a citrus flavonoid, on gastric cancer include: antiproliferative effects, induction of apoptosis and cell cycle deregulation. | 2004 Jul |
|
| Biotransformation of nobiletin by Aspergillus niger and the antimutagenic activity of a metabolite, 4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone. | 2004 Nov |
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| Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities. | 2005 Dec 2 |
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| Metabolite fingerprinting in transgenic Nicotiana tabacum altered by the Escherichia coli glutamate dehydrogenase gene. | 2005 Jun 30 |
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| Mechanism of neurotrophic action of nobiletin in PC12D cells. | 2005 Oct 25 |
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| Liquid chromatography/mass spectrometry and liquid chromatography/nuclear magnetic resonance as complementary analytical techniques for unambiguous identification of polymethoxylated flavones in residues from molecular distillation of orange peel oils (Citrus sinensis). | 2006 Jan 25 |
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| Nobiletin restoring beta-amyloid-impaired CREB phosphorylation rescues memory deterioration in Alzheimer's disease model rats. | 2006 Jun 12 |
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| Protective effects of citrus nobiletin and auraptene in transgenic rats developing adenocarcinoma of the prostate (TRAP) and human prostate carcinoma cells. | 2007 Apr |
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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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| Simultaneous analysis of eight bioactive compounds in Danning tablet by HPLC-ESI-MS and HPLC-UV. | 2007 Feb 19 |
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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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| Tangeretin suppresses IL-1beta-induced cyclooxygenase (COX)-2 expression through inhibition of p38 MAPK, JNK, and AKT activation in human lung carcinoma cells. | 2007 Jan 15 |
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| Nobiletin enhances differentiation and lipolysis of 3T3-L1 adipocytes. | 2007 Jun 1 |
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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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| Nobiletin, a citrus flavonoid, reverses learning impairment associated with N-methyl-D-aspartate receptor antagonism by activation of extracellular signal-regulated kinase signaling. | 2007 May |
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| Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? | 2007 Oct |
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| Nobiletin, a citrus flavonoid with neurotrophic action, augments protein kinase A-mediated phosphorylation of the AMPA receptor subunit, GluR1, and the postsynaptic receptor response to glutamate in murine hippocampus. | 2008 Jan 14 |
|
| Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells. | 2008 Sep |
Sample Use Guides
In a mouse model of Parkinson's disease mice were induced to motor and cognitive deficits by dosing with 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Intraperitoneal administration of 50 mg/kg of Nobiletin for 2 consecutive weeks improved motor and cognitive deficits and continued to improve for 2 weeks after withdrawal. However, nobiletin did not block loss of dopaminergic neurons seen in the MPTP-treated mouse midbrain, nor did it rescue decreased tyrosine hydroxylase (TH) protein levels seen in the striatum or hippocampal CA1 region of these mice.
Route of Administration:
Intraperitoneal
Human leukemia HL-60 cells were maintained in RPMI-1640 medium supplemented with 10% fetal bovine serum, 2 mM glutamine and 1% penicillin/streptomycin. Cell line was maintained at 37 deg-C and 5% CO2 atmosphere. HL60 cells were placed into 12-well plates at a density of 2 x 10^5 cells per well. Cultures were incubated overnight and then treated with different concentrations of nobiletin for 24 hours. At the end of incubation, cells were harvested and counted in a hemocytometer. Nobiletin was found to have an IC50 of 41.5 micro-M and AC50 above 100 micro-M.
| Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 19:04:07 GMT 2023
by
admin
on
Sat Dec 16 19:04:07 GMT 2023
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| Record UNII |
D65ILJ7WLY
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Validated (UNII)
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4008 (Number of products:1)
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
44% Cell growth rate of mouse myeloid leukemia M1 cells at 50 uM of compound vs control
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PARENT -> CONSTITUENT ALWAYS PRESENT |
48% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control
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TRANSPORTER -> INHIBITOR |
Decreased the IC50 value of paclitaxel by 15.92-fold. Restored the sensitivity of paclitaxel, doxorubicin, docetaxel, and daunorubicin in
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IC50
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