Myricetin

Description

Myricetin is a flavonoid compound found in many fruits and vegetables, including red wine, that acts as a powerful antioxidant. Myricetin inhibits TBARS formation with an IC₅₀ value of 6.34 and at 20 μM, blocks oxLDL uptake by U937-derived macrophages, reducing CD36 expression. Myricetin demonstrates potent chemopreventative potential by binding JAK1/STAT3 to inhibit the neoplastic transformation of murine JB6 P+ cells and inhibiting MEK1 kinase activity.

Chemical properties

The substance is a brown-yellow to brown-green crystalline powder. It can dissolve in methanol, ethanol, acetone, and ethyl acetate, and has a low solubility in water. It is not soluble in chloroform and petroleum ether. This compound is derived from the fruit of Myrica rubra (Lour.) Sieb. et Zucc. and belongs to the Populus family.

The Uses of Myricetin

Myricetin is used as an antioxidant. It is a cell-permeable flavonoid used in inflammatory, diabetes, and cancer studies. It is effective in protecting neurons against oxidative stresses. Further, it inhibits yeast alfa-glucosidase,1 glyoxalase I in vitro and bovine milk xanthine oxidase.

What are the applications of Application

Myricetin is a cell-permeable, ATP-competitive inhibitor of various casein kinases and protein kinases.

Definition

ChEBI: Myricetin is a hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7. It has been isolated from the leaves of Myrica rubra and other plants. It has a role as a cyclooxygenase 1 inhibitor, an antineoplastic agent, an antioxidant, a plant metabolite, a food component, a hypoglycemic agent and a geroprotector. It is a hexahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a myricetin(1-).

General Description

Myricetin is a novel flavanoid compound useful as chemotherapeutic, chemopreventive, and antiangiogenic agent. It also acts as an antioxidant, anti-inflammatory, and anti-cancer agent, and can inhibit the activity of reverse transcriptase.

Biochem/physiol Actions

Myricetin exerts anti-oxidant effects, and anti-inflammatory effects by regulating multiple signal pathways. It also displays anti-diabetic and hepatoprotective effects. Myricetin strongly inhibits yeast α-glucosidase, glyoxalase I in vitro, and bovine milk xanthine oxidase. It also promotes complex formation between DNA and both topoisomerase I and II, an effect that may have implications in cancer chemotherapy. Myricetin also has various nutraceuticals values and therapeutic effects.

Purification Methods

Myricetin (Cannabiscetin, 3,3',4',5,5',7-hexahydroxyflavone) [529-44-2] M 318.2, m > 3 0 0o, 357o(dec) (polyphenolic pKEst~8-11). Recrystallise myricetin from aqueous EtOH (m 357o dec, as monohydrate) or Me2CO (m 350o dec, with one mol of Me2CO) as yellow crystals. It is almost insoluble in CHCl3 and AcOH. The hexaacetate has m 213o. [Hergert J Org Chem 21 534 1956, Spada & Cameroni Gazzetta 86 965, 975 1956, Kalff & Robinson J Chem Soc 127 181 1925, Beilstein 18/5 V 670.]