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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24316474
Curator's Comment: referenced study was conducted in mice.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P21439 Gene ID: 5244.0 Gene Symbol: ABCB4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10734174 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | 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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The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. | 2001 Dec |
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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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Immunotoxicity of a standardized citrus polymethoxylated flavone extract. | 2001 Nov |
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Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease. | 2002 Jan 15 |
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Nobiletin as a tyrosinase inhibitor from the peel of Citrus fruit. | 2002 Jun |
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Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels. | 2002 May 8 |
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Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells. | 2002 Oct |
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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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Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. | 2003 Jun 15 |
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Effects of selected food factors with chemopreventive properties on combined lipopolysaccharide- and interferon-gamma-induced IkappaB degradation in RAW264.7 macrophages. | 2003 May 30 |
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Citrus nobiletin inhibits azoxymethane-induced large bowel carcinogenesis in rats. | 2004 |
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Cancer prevention by antioxidants. | 2004 |
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Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro. | 2004 Aug 1 |
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Rapid analysis of gene expression changes caused by liver carcinogens and chemopreventive agents using a newly developed three-dimensional microarray system. | 2004 Feb |
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Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities. | 2005 Dec 2 |
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Nobiletin, a citrus flavonoid, down-regulates matrix metalloproteinase-7 (matrilysin) expression in HT-29 human colorectal cancer cells. | 2005 Feb |
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Mechanism of neurotrophic action of nobiletin in PC12D cells. | 2005 Oct 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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Suppressive effects of demethylated metabolites of nobiletin on phorbol ester-induced expression of scavenger receptor genes in THP-1 human monocytic cells. | 2007 |
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Citrus nobiletin suppresses bone loss in ovariectomized ddY mice and collagen-induced arthritis in DBA/1J mice: possible involvement of receptor activator of NF-kappaB ligand (RANKL)-induced osteoclastogenesis regulation. | 2007 |
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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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Comparative study on nobiletin metabolism with liver microsomes from rats, Guinea pigs and hamsters and rat cytochrome p450. | 2007 Dec |
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Efficient and scalable method in isolation of polymethoxyflavones from orange peel extract by supercritical fluid chromatography. | 2007 Feb 1 |
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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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Effects of TNF-alpha on leukocyte adhesion molecule expressions in cultured human lymphatic endothelium. | 2007 Jul |
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[Characteristics of nobiletin-loaded nanoemulsion and its in vivo distribution in mice]. | 2007 Jun |
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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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Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques. | 2007 May 9 |
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Preparation of nobiletin in self-microemulsifying systems and its intestinal permeability in rats. | 2008 |
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Inhibition of oral carcinogenesis by citrus flavonoids. | 2008 |
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Sp1 is an essential transcription factor for LPS-induced tissue factor expression in THP-1 monocytic cells, and nobiletin represses the expression through inhibition of NF-kappaB, AP-1, and Sp1 activation. | 2008 Apr 1 |
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Nobiletin, a citrus polymethoxy flavonoid, suppresses gene expression and production of aggrecanases-1 and -2 in collagen-induced arthritic mice. | 2008 Aug 22 |
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A citrus polymethoxyflavonoid, nobiletin, is a novel MEK inhibitor that exhibits antitumor metastasis in human fibrosarcoma HT-1080 cells. | 2008 Feb 1 |
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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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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 |
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Apoptotic effect of citrus fruit extract nobiletin on lung cancer cell line A549 in vitro and in vivo. | 2008 Jun |
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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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Suppressive effects of nobiletin on hyperleptinemia and colitis-related colon carcinogenesis in male ICR mice. | 2008 May |
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Anti-inflammatory effects of Radix Gentianae Macrophyllae (Qinjiao), Rhizoma Coptidis (Huanglian) and Citri Unshiu Pericarpium (Wenzhou migan) in animal models. | 2008 Sep 2 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24316474
Curator's Comment: referenced study was conducted in mice
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17391969
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
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Edited
Sat Dec 16 19:04:07 GMT 2023
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Record UNII |
D65ILJ7WLY
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Record Status |
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
ABCB1, overexpressing A2780/T and A549/T cells.
IC50
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