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 |
|---|---|---|
| Investigation of heat treating conditions for enhancing the anti-inflammatory activity of citrus fruit (Citrus reticulata) peels. | 2008-09-10 |
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| Anti-inflammatory effects of Radix Gentianae Macrophyllae (Qinjiao), Rhizoma Coptidis (Huanglian) and Citri Unshiu Pericarpium (Wenzhou migan) in animal models. | 2008-09-02 |
|
| Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells. | 2008-09 |
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| Pharmacological action of nobiletin, a component of AURANTII NOBILIS PERICARPIUM with anti-dementia activity, and its application for development of functional foods. | 2008-09 |
|
| Nobiletin, a citrus flavonoid, improves memory impairment and Abeta pathology in a transgenic mouse model of Alzheimer's disease. | 2008-09 |
|
| Nobiletin, a citrus polymethoxy flavonoid, suppresses gene expression and production of aggrecanases-1 and -2 in collagen-induced arthritic mice. | 2008-08-22 |
|
| Apoptotic effect of citrus fruit extract nobiletin on lung cancer cell line A549 in vitro and in vivo. | 2008-06 |
|
| Suppressive effects of nobiletin on hyperleptinemia and colitis-related colon carcinogenesis in male ICR mice. | 2008-05 |
|
| 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. | 2008-04-01 |
|
| Distribution of nobiletin chitosan-based microemulsions in brain following i.v. injection in mice. | 2008-03-20 |
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| Interactive effects of polymethoxy flavones from Citrus on cell growth inhibition in human neuroblastoma SH-SY5Y cells. | 2008-03-15 |
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| A citrus polymethoxyflavonoid, nobiletin, is a novel MEK inhibitor that exhibits antitumor metastasis in human fibrosarcoma HT-1080 cells. | 2008-02-01 |
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| LPS-induced IL-6, IL-8, VCAM-1, and ICAM-1 expression in human lymphatic endothelium. | 2008-02 |
|
| 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. | 2008-01-14 |
|
| Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water. | 2008-01 |
|
| Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts. | 2008-01 |
|
| Preparation of nobiletin in self-microemulsifying systems and its intestinal permeability in rats. | 2008 |
|
| Inhibition of oral carcinogenesis by citrus flavonoids. | 2008 |
|
| Comparative study on nobiletin metabolism with liver microsomes from rats, Guinea pigs and hamsters and rat cytochrome p450. | 2007-12 |
|
| Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3. | 2007-12 |
|
| A citrus polymethoxy flavonoid, nobiletin inhibits sebum production and sebocyte proliferation, and augments sebum excretion in hamsters. | 2007-12 |
|
| Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? | 2007-10 |
|
| Effects of various methoxyflavones on vincristine uptake and multidrug resistance to vincristine in P-gp-overexpressing K562/ADM cells. | 2007-10 |
|
| Comparison of two sample preconcentration strategies for the sensitivity enhancement of flavonoids found in Chinese herbal medicine in micellar electrokinetic chromatography with UV detection. | 2007-09-28 |
|
| Anti-inflammatory property of the urinary metabolites of nobiletin in mouse. | 2007-09-15 |
|
| Antimicrobial activity of wax and hexane extracts from Citrus spp. peels. | 2007-09 |
|
| Nobiletin, a citrus flavonoid that improves memory impairment, rescues bulbectomy-induced cholinergic neurodegeneration in mice. | 2007-09 |
|
| Nobiletin from citrus fruit peel inhibits the DNA-binding activity of NF-kappaB and ROS production in LPS-activated RAW 264.7 cells. | 2007-08-15 |
|
| Involvement of extracellular signal-regulated kinase in nobiletin-induced melanogenesis in murine B16/F10 melanoma cells. | 2007-07 |
|
| Effects of TNF-alpha on leukocyte adhesion molecule expressions in cultured human lymphatic endothelium. | 2007-07 |
|
| Tangeretin and nobiletin induce G1 cell cycle arrest but not apoptosis in human breast and colon cancer cells. | 2007-06-18 |
|
| Nobiletin enhances differentiation and lipolysis of 3T3-L1 adipocytes. | 2007-06-01 |
|
| [Characteristics of nobiletin-loaded nanoemulsion and its in vivo distribution in mice]. | 2007-06 |
|
| Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques. | 2007-05-09 |
|
| Nobiletin, a citrus flavonoid, reverses learning impairment associated with N-methyl-D-aspartate receptor antagonism by activation of extracellular signal-regulated kinase signaling. | 2007-05 |
|
| Quality control and discrimination of pericarpium citri reticulatae and pericarpium citri reticulatae viride based on high-performance liquid chromatographic fingerprints and multivariate statistical analysis. | 2007-04-11 |
|
| Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells. | 2007-04-04 |
|
| Correlation between flavonoid content and the NO production inhibitory activity of peel extracts from various citrus fruits. | 2007-04 |
|
| Protective effects of citrus nobiletin and auraptene in transgenic rats developing adenocarcinoma of the prostate (TRAP) and human prostate carcinoma cells. | 2007-04 |
|
| Chemopreventive effects of orange peel extract (OPE). II: OPE inhibits atypical hyperplastic lesions in rodent mammary gland. | 2007-03 |
|
| Chemopreventive effects of orange peel extract (OPE). I: OPE inhibits intestinal tumor growth in ApcMin/+ mice. | 2007-03 |
|
| Simultaneous analysis of eight bioactive compounds in Danning tablet by HPLC-ESI-MS and HPLC-UV. | 2007-02-19 |
|
| Efficient and scalable method in isolation of polymethoxyflavones from orange peel extract by supercritical fluid chromatography. | 2007-02-01 |
|
| Tyrosinase inhibitory effects and inhibition mechanisms of nobiletin and hesperidin from citrus peel crude extracts. | 2007-02 |
|
| Tyrosinase inhibitory effects and inhibition mechanisms of nobiletin and hesperidin from citrus peel crude extracts. | 2007-02 |
|
| Tangeretin suppresses IL-1beta-induced cyclooxygenase (COX)-2 expression through inhibition of p38 MAPK, JNK, and AKT activation in human lung carcinoma cells. | 2007-01-15 |
|
| Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography. | 2007-01 |
|
| Suppressive effects of demethylated metabolites of nobiletin on phorbol ester-induced expression of scavenger receptor genes in THP-1 human monocytic cells. | 2007 |
|
| 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 |
|
| [Antitumor effects of nobiletin on Heps and its mechanism]. | 2006-08 |
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
by
admin
on
Edited
Wed Apr 02 13:29:57 GMT 2025
by
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on
Wed Apr 02 13:29:57 GMT 2025
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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
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IC50
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