Nobiletin

Alias: Nobiletin; NOB; Hexamethoxyflavone
Cat No.:V0738 Purity: ≥98%
Nobiletin (Hexamethoxyflavone; NOB), a naturally occurring flavonoid compound isolated from citrus peels like in tangerine and the Chinese drug chen-pi, has anti-inflammatory and anti-tumor activities.
Nobiletin Chemical Structure CAS No.: 478-01-3
Product category: MMP
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

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.

Biological Activity I Assay Protocols (From Reference)
Targets
MMP
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]
ln Vivo
Nobiletin (50 mg/kg) administered intraperitoneally for seven days in a row significantly reduced delayed neuronal death in the hippocampal CA1 neurons of a mouse model of 5-min BCCAO-induced brain ischemia and enhanced contextual memory. When administered intraperitoneally for two weeks in a row, Nobiletin (50 mg/kg i.p.) ameliorated both motor and cognitive deficits in the MPTP-induced Parkinson mouse model.
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.
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.
Animal Protocol
20- to 22-month-old male C57BL/6 mice
0.1% of regular diet
Oral administration; daily; for 20 weeks
References

[1]. Cancer Res . 2000 Sep 15;60(18):5059-66.

[2]. Cancer Res . 2002 Feb 15;62(4):1025-9.

[3]. Atherosclerosis . 2005 Jan;178(1):25-32.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H22O8
Molecular Weight
402.39
Exact Mass
402.13
Elemental Analysis
C, 62.68; H, 5.51; O, 31.81
CAS #
478-01-3
Appearance
Solid powder
SMILES
COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC
InChi Key
MRIAQLRQZPPODS-UHFFFAOYSA-N
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
Chemical Name
2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
Synonyms
Nobiletin; NOB; Hexamethoxyflavone
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~81 mg/mL (~201.3 mM)
Water: <1 mg/mL
Ethanol: ~3 mg/mL (~7.5 mM)
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.

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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.
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Biological Data
  • Nobiletin

    Nobiletin suppresses tumor cell invasion in vitro.Cancer Res.2002 Feb 15;62(4):1025-9.
  • Nobiletin

    Effect of nobiletin on the production of proMMPs and TIMP-1 in HT-1080 cells.Cancer Res.2002 Feb 15;62(4):1025-9.
  • Nobiletin

    Effect of nobiletin on the gene expression of proMMPs and TIMP-1 in HT-1080 cells.Cancer Res.2002 Feb 15;62(4):1025-9.
  • Nobiletin

    Nobiletin does not modify the expression of proMMP-2, MT1-MMP, and TIMP-2 in HT-1080 cells.Cancer Res.2002 Feb 15;62(4):1025-9.
  • Nobiletin

    Nobiletin inhibits AP-1 binding activity in HT-1080 cells.Cancer Res.2002 Feb 15;62(4):1025-9.
  • Nobiletin

    PI3K inhibitor, LY-294002, mimics the effect of nobiletin on proMMP-9 and TIMP-1 production in HT-1080 cells.Cancer Res.2002 Feb 15;62(4):1025-9.
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