Description
Myricetin is a flavonoid compound found in many fruits and vegetables, including red wine, that acts as a powerful antioxidant.
1 Myricetin inhibits TBARS formation with an IC
50 value of 6.34 and at 20 μM, blocks oxLDL uptake by U937-derived macrophages, reducing CD36 expression.
2 Myricetin demonstrates potent chemopreventative potential by binding JAK1/STAT3 to inhibit the neoplastic transformation of murine JB6 P+ cells and inhibiting MEK1 kinase activity.
3,4
Chemical Properties
brown-yellow to brown-green crystalline powder
Uses
A novel flavanoid compound useful as chemotherapeutic, chemopreventive, and antiangiogenic agent.
Uses
anti-oxidant, anti-inflammatory and anti-neoplastic activity, reverse transcriptase inhibitor
Definition
ChEBI: 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.
General Description
Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.
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.]
References
[1] CHRISTOPHER J. BENNETT . Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation[J]. Bioorganic & Medicinal Chemistry, 2004, 12 9: Pages 2079-2098. DOI:
10.1016/j.bmc.2004.02.031[2] TZI-WEI LIAN . Fisetin, morin and myricetin attenuate CD36 expression and oxLDL uptake in U937-derived macrophages[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2008, 1781 10: Pages 601-609. DOI:
10.1016/j.bbalip.2008.06.009[3] TAKUMA KUMAMOTO De X H Makoto Fujii. Myricetin directly targets JAK1 to inhibit cell transformation[J]. Cancer letters, 2009, 275 1: Pages 17-26. DOI:
10.1016/j.canlet.2008.09.027[4] KI WON LEE. Myricetin is a novel natural inhibitor of neoplastic cell transformation and MEK1.[J]. Carcinogenesis, 2007, 28 9: 1918-1927. DOI:
10.1093/carcin/bgm110
