478-01-3 Usage
Description
Different sources of media describe the Description of 478-01-3 differently. You can refer to the following data:
1. Nobiletin (NOB) chemically known as 5,6,7,8,3′,4′-hexamethoxyflavone is a dietary polymethoxylated flavonoid found in Citrus fruits. Nobiletin is a flavonoid isolated from citrus peels. It is an O-methylated flavone that has the activity to rescue bulbectomy-induced memory impairment.
2. Nobiletin (478-01-3) is a natural product isolated from citrus peels.? It has recently been shown to possess circadian clock amplitude-enhancing properties and was able to prevent metabolic syndrome in mice?via?a?Clock?gene-dependent mechanism.1? Nobiletin directly bound to and activated RORα/γ.? Nobiletin has previously been shown to attenuate the effects of metabolic syndrome2, have anti-neuroinflammatory effects3, possess neurotrophic activity4, and be a cancer chemopreventative agent5.
Source
Nobiletin is a nonpolar polymethoxylated flavone (PMFs) found in the citrus peel of various fruits, such as tangerine. Its chemical structure is similar to tangeretin, containing the typical flavonoid structure and six methoxyl groups (one more than tangeretin).
Uses
Different sources of media describe the Uses of 478-01-3 differently. You can refer to the following data:
1. NOB is a multifunctional pharmaceutical agent. The various pharmacological activities of NOB include neuroprotection, cardiovascular protection, antimetabolic disorder, anticancer, anti-inflammation, and antioxidation.
2. matrix metaloproteinase inhibitor; antineoplastic
3. Nobiletin is an O-methylated flavone, a flavonoid isolated from citrus peels like in tangerine. It is a potent antioxidant with good bioavailability. Nobiletin directly inhibits the ATP-binding cassette proteins P-glycoprotein and breast cancer resistance protein.
structure and hydrogen bonding
The crystal structure study on NOB shows that the chromene and the arene rings are almost in the same plane. The C atoms of the two methoxy groups in the arene ring are also in the same plane, while the C atoms of four methoxy groups linking to the chromene ring are not in parallel. This conformational characteristic of chiral structure is indicated by the covalent bond rotation between the arene and the chromene rings and the conformational alternations of methoxy groups.
Application
Nobiletin has been shown to exhibit antioxidant, anti-inflammatory, antitumor/cancer, and antiangiogenic activity in vitro and in vivo. Animal and in vitro data also demonstrate nobiletin's potential ability to suppress bone loss, lower cholesterol and atherosclerosis, and improve hyperglycemia and insulin resistance.
Chemical Properties
White powder
Definition
ChEBI: A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.
benefits
Nobiletin improved cognitive deficits and the pathological features of AD, such as Aβ pathology, hyperphosphorylation of tau, and oxidative stress, in animal models of AD. In addition, nobiletin improved motor and cognitive deficits in PD animal models. These observations suggest that nobiletin has the potential to become a novel drug for the treatment and prevention of neurodegenerative diseases such as AD and PD.
References
1) He?et al.?(2016),?The Small Molecule Nobiletin Targets the Molecular Oscillator to Enhance Circadian Rhythms and Protect against Metabolic Syndrome; Cell Metabolism,?23?610
2) Mulvihill?et al.?(2011),?Nobiletin attenuates VLDL overproduction, dyslipidemia, and atherosclerosis in mice with diet-induced insulin resistance; Diabetes?60?1446
3) Cui?et al.?(2010),?Anti-neuroinflammatory activity of nobiletin on suppression of microglial activation; Biol. Pharm. Bull.,?33?1814
4) Nagase?et al.?(2005),?Mechanism of neurotrophic action of nobiletin in PC12D cells; Biochemistry?44?13683
5) Walle (2007),?Methoxylated flavones, a superior cancer chemopreventative flavonoid subclass?;?Semin. Cancer Biol.?17?354
Check Digit Verification of cas no
The CAS Registry Mumber 478-01-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 8 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 478-01:
(5*4)+(4*7)+(3*8)+(2*0)+(1*1)=73
73 % 10 = 3
So 478-01-3 is a valid CAS Registry Number.
InChI:InChI=1/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
478-01-3Relevant articles and documents
Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity
Su, Liang,Jin, Zhizhong,Liu, Kexiong,Wang, Qiuan
, p. 100 - 105 (2022/03/27)
[Figure not available: see fulltext.] A series of polymethoxyflavonoids were synthesized via cleavage of the glycosidic bond, dehydrogenation, selective methylation, bromination, nucleophilic aromatic substitution, O-prenylation, Claisen–Schmidt aldol condensation, cyclization, and oxidation from very abundant and inexpensive natural flavonoids hesperidin and naringin. The in vitro antiproliferative activity of the synthesized compounds was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2, and SUN-5) by the CellTiter-Glo assay. The results showed that some of synthesized compounds exhibited moderate to high antiproliferative activity. Among them, (2E)-1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-en-1-one was revealed to be the most active with IC50 values ranging from 10.35 to 13.89 μM against all four cancer cell lines, the IC50 value (10.35 μM) being below positive control cisplatin (12.36 μM) against HepG-2 cells.
Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives
Asakawa, Tomohiro,Sagara, Hiroto,Kanakogi, Masaki,Hiza, Aiki,Tsukaguchi, Yuta,Ogawa, Takahiro,Nakayama, Miho,Ouchi, Hitoshi,Inai, Makoto,Kan, Toshiyuki
, p. 595 - 602 (2019/04/01)
We present a practical synthesis of the polymethoxylated citrus flavone nobiletin that is suitable for use on a hundred gram scale. Ready availability of this compound and its derivatives will aid detailed chemical-biological investigations of their biological activities, including activation of signaling via the cAMP-dependent protein kinase A/extracellular signal-related protein kinase/cAMP response element-binding protein pathway.
Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs
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Page/Page column 48; 49; 50; 52, (2017/07/01)
Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.
