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Purity: ≥98%
Nobiletin (Hexamethoxyflavone; NOB) is a naturally occurring flavonoid compound with anti-inflammatory and anti-tumor properties that was isolated from citrus peels, such as those found in tangerines and the Chinese medicine chen-pi. Both in vitro and in animal experiments, nobiletin has the ability to inhibit the growth, invasion, proliferation, and metastasis of tumors. It was also discovered that nobiletin might prevent cartilage deterioration. By preventing ERK1/2 phosphorylation, nobiletin treatment dramatically reduced cell invasion in human nasopharyngeal carcinoma cell lines (HONE-1 and NPC-BM). Nobiletin was demonstrated to inhibit cell proliferation by suppressing ERK activity in tests conducted on rat C6 glioma cells.
| Targets |
MMP
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| ln Vitro |
Nobiletin, a citrus flavonoid with anti-inflammatory and anti-tumor properties, was extracted from citrus peels, such as those found in tangerines. It has been determined that the polymethoxyflavonoid nobiletin inhibits the production of both NO and O2-. When two TPA applications are made to the skin, nobiletin dramatically reduces the inflammation. Moreover, it inhibits prostaglandin E2 release, cyclooxygenase-2, and inducible NO synthase protein expression.[1] In the Matrigel model, nobiletin inhibits the tumor-invasive activity of human fibrosarcoma HT-1080 cells by inhibiting the phosphatidylinositol 3-kinase pathway (PI3-K), which increases the production of TIMP-1 while also suppressing the expression of MMPs.[2] Nobiletin also inhibits the formation of macrophage foam-cells, which may prevent atherosclerosis at the vascular wall level.[3]
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| ln Vivo |
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| Enzyme Assay |
Nobiletin is a citrus flavonoid that has anti-inflammatory and anti-tumor properties. It is extracted from citrus peels, such as tangerines. Research conducted on animals and in vitro has shown that nobiletin can inhibit the growth, invasion, proliferation, and metastasis of tumors. Another finding suggested that nobiletin might prevent cartilage deterioration. Through phosphorylation of ERK1/2 inhibition, nobiletin treatment significantly reduced cell invasion in human nasopharyngeal carcinoma cell lines (HONE-1 and NPC-BM). Bobinetin was demonstrated to impede cell division by downregulating ERK activity in rat C6 glioma cells.
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| Cell Assay |
Nobiletin has been demonstrated to possess the capacity to inhibit tumor growth and metastasis. By preventing ERK1/2 phosphorylation, nobiletin treatment dramatically reduced cell invasion in human nasopharyngeal carcinoma cell lines (HONE-1 and NPC-BM) [2]. Nobiletin was demonstrated to inhibit cell proliferation by suppressing ERK activity in tests conducted on rat C6 glioma cells.
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| Animal Protocol |
20- to 22-month-old male C57BL/6 mice
0.1% of regular diet Oral administration; daily; for 20 weeks |
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| References | ||
| Additional Infomation |
Nobiletin is a methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively. It has a role as a plant metabolite and an antineoplastic agent. It is functionally related to a flavone.
Nobiletin has been reported in Citrus leiocarpa, Plenodomus tracheiphilus, and other organisms with data available. See also: Tangerine peel (part of); Citrus aurantium fruit rind (part of). |
| Molecular Formula |
C21H22O8
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|---|---|---|
| Molecular Weight |
402.39
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| Exact Mass |
402.131
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| Elemental Analysis |
C, 62.68; H, 5.51; O, 31.81
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| CAS # |
478-01-3
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| Related CAS # |
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| PubChem CID |
72344
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
587.9±50.0 °C at 760 mmHg
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| Melting Point |
138 °C
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| Flash Point |
256.5±30.2 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.558
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| LogP |
2.48
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
29
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| Complexity |
593
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O1C(=C([H])C(C2C(=C(C(=C(C1=2)OC([H])([H])[H])OC([H])([H])[H])OC([H])([H])[H])OC([H])([H])[H])=O)C1C([H])=C([H])C(=C(C=1[H])OC([H])([H])[H])OC([H])([H])[H]
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| InChi Key |
MRIAQLRQZPPODS-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
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| Synonyms |
Nobiletin; NOB; Hexamethoxyflavone
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.17 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (5.17 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4852 mL | 12.4258 mL | 24.8515 mL | |
| 5 mM | 0.4970 mL | 2.4852 mL | 4.9703 mL | |
| 10 mM | 0.2485 mL | 1.2426 mL | 2.4852 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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