Current Pharmacological Trends on Myricetin

Gudiya Gupta; Mohd Aftab Siddiqui; Mohd Muazzam Khan; Mohd Ajmal; Rabiya Ahsan; Md Azizur Rahaman; Md Afroz Ahmad; Md Arshad; Mohammad Khushtar

doi:10.1055/a-1224-3625

Drug Research, Table of Contents

Drug Res (Stuttg) 2020; 70(10): 448-454
DOI: 10.1055/a-1224-3625

Review

Current Pharmacological Trends on Myricetin

Gudiya Gupta

¹Department of Pharmacology, Faculty of Pharmacy, Integral University, Lucknow, India

,

Mohd Aftab Siddiqui

¹Department of Pharmacology, Faculty of Pharmacy, Integral University, Lucknow, India

,

Mohd Muazzam Khan

¹Department of Pharmacology, Faculty of Pharmacy, Integral University, Lucknow, India

,

Mohd Ajmal

¹Department of Pharmacology, Faculty of Pharmacy, Integral University, Lucknow, India

,

Rabiya Ahsan

¹Department of Pharmacology, Faculty of Pharmacy, Integral University, Lucknow, India

,

Md Azizur Rahaman

²Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Integral University, Lucknow, India

,

Md Afroz Ahmad

¹Department of Pharmacology, Faculty of Pharmacy, Integral University, Lucknow, India

,

Md Arshad

³Department of Zoology, Aligarh Muslim University, Aligarh, India

,

Mohammad Khushtar

¹Department of Pharmacology, Faculty of Pharmacy, Integral University, Lucknow, India

› Author Affiliations

Abstract

Myricetin is a member of the group of ﬂavonoids called ﬂavonols. Myricetin is obtained from various fruit, vegetables, tea, berries and red wine. Myricetin is characterized by the pysrogallol B-ring, and the more hydroxylated structure is known to be capable for its increased biological properties compared with other ﬂavonols. Myricetin is produced by the Myricaceae, Anacardiaceae, Polygonaceae, Pinaceae and Primulacea families. It is soluble in organic solvent such as ethanol, DMSO (dimethyl sulfoxide), and dimethyl formamide (DMF). It is sparingly soluble in aqueous buffers. Myricetin shows its various pharmacological activities including antioxidant, anti-amyloidogenic, antibacterial, antiviral, antidiabetic, anticancer, anti-inﬂammatory, anti-epileptic and anti-ulcer. This review article focuses on pharmacological effects of Myricetin on different diseases such as osteoporotic disorder, anti-inflammatory disorder, alzheimer’s disease, anti-epileptic, cancer, cardiac disorder, diabetic metabolic disorder, hepatoprotective disorder and gastro protective disorder.

Key words

antioxidants/NO pathways drugs - behavioural pharmacology - toxicology - cardiovascular pharmacology - cancer pharmacology - cancer

Full Text

References

References
1 Agrawal AD. Pharmacological activities of flavonoids: A review. International Journal of Pharmaceutical Sciences and Nanotechnology 2011; 1394-1398
2 Semwal DK, Semwal RB, Combrinck S. et al. Myricetin: A dietary molecule with diverse biological activities. Nutrients 2016; 8: 90
3 Ong KC, Khoo HE. Biological effects of myricetin. Gen Pharmacol: Vascul Pharmacol 1997; 121-126
4 Sato M, Murakami K, Uno M. et al. Site-specific inhibitory mechanism for amyloid β42 aggregation by catechol-type flavonoids targeting the Lys residues. J Biol Chem 2013; 288: 23212-23224
5 Xu HX, Lee SF. Activity of plant flavonoids against antibiotic-resistant bacteria. Phytother Res 2001; 15: 39-43
6 Pasetto S, Pardi V, Murata RM. Anti-HIV-1 activity of flavonoid myricetin on HIV-1 infection in a dual-chamber in vitro model. PLoS One 2014; 9 (12): e115323
7 Li Y, Ding Y. Minireview: Therapeutic potential of myricetin in diabetes mellitus. Food Science and Human Wellness 2012; 1: 19-25
8 Ding Y, Zhang ZF, Dai XQ. et al. Myricetin protects against cytokine-induced cell death in RIN-m5f β cells. J Med Food 2012; 15: 733-740
9 Holder S, Zemskova M, Zhang C. et al. Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase. Molecular Cancer Therapeutics 2007; 6: 163-172
10 Phillips PA, Sangwan V, Borja-Cacho D. et al. Myricetin induces pancreatic cancer cell death via the induction of apoptosis and inhibition of the phosphatidyl inositol 3-kinase (PI3K) signaling pathway. Cancer Letters 2011; 308: 181-188
11 Tsai SH, Liang YC, Lin-Shiau SY. et al. Suppression of TNF α-mediated NF κ b activity by myricetin and other flavonoids through downregulating the activity of IKK in ECV304 cells. J Cell Biochem Suppl 1999; 74: 606-615
12 Wang SJ, Tong Y, Lu S. et al. Anti-inflammatory activity of myricetin isolated from Myrica rubra Sieb. et Zucc. Leaves. Planta Med 2010; 76: 1492-1496
13 Lau-Cam CA, Chan HH. Flavonoids from Comptoniaperegrina. Phytochemistry 1973; 12 (7): 1829
14 Umadevi I, Daniel M, Sabnis SD. Chemotaxonomic studies on some members of Anacardiaceae. Proceedings: Plant Sci 1988; 98: 205-208
15 Semwal DK, Semwal RB, Combrinck S. et al. Myricetin: A dietary molecule with diverse biological activities. Nutrients 2016; 8: 90
16 Department of Agriculture. USDA database for the ﬂavonoid content of selected foods. Beltsville (MD): US Department of Agriculture 2003
17 Bhagwat S, Haytowitz DB, Holden JM USDA database for the flavonoid content of selected foods, release 3. US Department of Agriculture 2011
18 Bhagwat S, Haytowitz DB, Holden JM USDA database for the flavonoid content of selected foods, Release 3.1. US Department of Agriculture 2014
19 Park KS, Chong Y, Kim MK. Myricetin: biological activity related to human health. Applied Biological Chemistry 2016; 59: 259-269
20 Yao Y, Lin G, Xie Y. et al. Preformulation studies of myricetin: a natural antioxidant flavonoid. Die Pharmazie-An International. Journal of Pharmaceutical Sciences 2014; 69: 19-26
21 Dang Y, Lin G, Xie Y. et al. Quantitative determination of myricetin in rat plasma by ultra performance liquid chromatography tandem mass spectrometry and its absolute bioavailability. Drug Research 2014; 64: 516-522
22 Li C, Lim SC, Kim J. et al. Effects of myricetin, an anticancer compound, on the bioavailability and pharmacokinetics of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats. Eur J Drug Metab Pharmacokinet 2011; 36: 175-182
23 Robak J, Gryglewski RJ. Flavonoids are scavengers of superoxide anions. Biochemical Pharmacology 1988; 37: 837-841
24 Ratty AK, Das NP. Effects of flavonoids on nonenzymatic lipid peroxidation: structure-activity relationship. Biochem Med Metab Biol 1988; 39: 69-79
25 Ratty AK, Sunamoto J, Das NP. Interaction of flavonoids with 1, 1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1. Biochemical Pharmacology 1988; 37: 989-995
26 Elliott AJ, Scheiber SA, Thomas C. et al. Inhibition of glutathione reductase by flavonoids: A structure-activity study. Biochemical Pharmacology 1992; 44: 1603-1608
27 Robak J, Duniec Z, Rzadkowska-Bodalska H. et al. The effect of some flavonoids on non-enzymatic lipid oxidation and enzymatic oxidation of arachidonic acid. Pol J Pharmacol Pharm 1986; 38: 483-491
28 Robak J, Shridi F, Wolbis M. et al. Screening of the influence of flavonoids on lipoxygenase and cyclooxygenase activity, as well as on nonenzymic lipid oxidation. Pol J Pharmacol Pharm 1988; 40: 451-458
29 Pereira TA, Das NP. Assay of liver cytosol lipoxygenase by differential pulse polarography. Analytical Biochemistry 1991; 197: 96-100
30 Smith C, Halliwell B, Aruoma OI. Protection by albumin against the pro-oxidant actions of phenolic dietary components. Food Chem Toxicol 1992; 30: 483-489
31 Canada AT, Giannella E, Nguyen TD. et al. The production of reactive oxygen species by dietary flavonols. Free Radical Biology and Medicine 1990; 9: 441-449
32 Ying X, Chen X, Wang T. et al. Possible osteoprotective effects of myricetin in STZ induced diabetic osteoporosis in rats. Eur J Pharmacol 2020; 866: 172805
33 Pan X, Chen T, Zhang Z. et al. Activation of Nrf2/HO-1 signal with Myricetin for attenuating ECM degradation in human chondrocytes and ameliorating the murine osteoarthritis. Int Immunopharmacol 2019; 75: 105742
34 Huang J, Wu C, Tian B. et al. Myricetin prevents alveolar bone loss in an experimental ovariectomized mouse model of periodontitis. Int J Mol Sci 2016; 17: 422
35 Fan S, Gao X, Chen P. et al. Myricetin ameliorates glucocorticoid-induced osteoporosis through the ERK signaling pathway. Life Sciences 2018; 207: 205-211
36 Aminzadeh A, Bashiri H. Myricetin ameliorates high glucose-induced endothelial dysfunction in human umbilical vein endothelial cells. Cell Biochem Funct 2020; 38: 12-20
37 Yao Z, Li C, Gu Y. et al. Dietary myricetin intake is inversely associated with the prevalence of type 2 diabetes mellitus in a Chinese population. Nutrition Research 2019; 68: 82-91
38 Yang ZJ, Wang HR, Wang YI. et al. Myricetin Attenuated Diabetes-Associated Kidney Injuries and Dysfunction via Regulating Nuclear Factor (Erythroid Derived 2)-Like 2 and Nuclear Factor-κB Signaling. Front Pharmacol 2019; 10: 647
39 Karunakaran U, Elumalai S, Moon JS. et al. Park et al. Myricetin protects against high glucose-induced β-cell apoptosis by attenuating endoplasmic reticulum stress via inactivation of cyclin-dependent kinase 5. Diabetes Metab J 2019; 43: 192-205
40 Rehman MU, Rather IA. Myricetin Abrogates Cisplatin-Induced Oxidative Stress, Inflammatory Response, and Goblet Cell Disintegration in Colon of Wistar Rats. Plants 2020; 9: 28
41 Grenier D, Chen H, Lagha AB. et al. Dual action of myricetin on Porphyromonas gingivalis and the inflammatory response of host cells: A promising therapeutic molecule for periodontal diseases. PLoS One 2015; 10
42 Chang Y, Chang CY, Wang SJ. et al. Myricetin inhibits the release of glutamate in rat cerebrocortical nerve terminals. J Med Food 2015; 18 (5): 516-523
43 Sun ZQ, Meng FH, Tu LX. et al. Myricetin attenuates the severity of seizures and neuroapoptosis in pentylenetetrazole kindled mice by regulating the of BDNF TrkB signaling pathway and modulating matrix metalloproteinase 9 and GABAA. Exp Ther Med 2019; 17: 3083-3091
44 Ramezani M, Darbandi N, Khodagholi F. et al. Myricetin protects hippocampal CA3 pyramidal neurons and improves learning and memory impairments in rats with Alzheimer’s disease. Neural Regen Res 2016; 11: 1976
45 Wang B, Zhong Y, Gao C. et al. Myricetin ameliorates scopolamine-induced memory impairment in mice via inhibiting acetylcholinesterase and down-regulating brain iron. Biochem Biophys Res Commun 2017; 490: 336-342
46 Gargari SA, Barzegar A, Tarinejad A. The role of phenolic OH groups of flavonoid compounds with H-bond formation ability to suppress amyloid mature fibrils by destabilizing β-sheet conformation of monomeric Aβ17-42. PLoS One 2018; 13 (6): e0199541
47 Tuponchai P, Kukongviriyapan V, Prawan A. et al. Myricetin ameliorates cytokine-induced migration and invasion of cholangiocarcinoma cells via suppression of STAT3 pathway. J Cancer Res Ther 2019; 15: 157
48 Wang G, Wang JJ, Wang YZ. et al. Myricetin nanoliposomes induced SIRT3-mediated glycolytic metabolism leading to glioblastoma cell death. Artif Cells Nanomed Biotechnol 2018; 46: S180-S191
49 Sun J, Zhou X. Protective functions of myricetin in LPS-induced cardiomyocytes H9c2 cells injury by regulation of MALAT1. Eur J Med Res 2019; 24: 20
50 Li M, Chen J, Yu X. et al. Myricetin Suppresses the Propagation of Hepatocellular Carcinoma via Down-Regulating Expression of YAP. Cells 2019; 8: 358
51 Lv H, An B, Yu Q, et al. The hepatoprotective effect of myricetin against lipopolysaccharide and D-galactosamine-induced fulminant hepatitis. Int J Biol Macromol 2020 155. 1092-1104
52 Liao HH, Zhang N, Meng YY, et al. Myricetin Alleviates Pathological Cardiac Hypertrophy via TRAF6/TAK1/MAPK and Nrf2 Signaling Pathway. Oxid Med Cell Longev 2019; 2019: 6304058
53 Tiwari R, Mohan M, Kasture S. et al. Cardioprotective potential of myricetin in isoproterenol-induced myocardial infarction in Wistar rats. Phytother Res 2009; 23: 1361-1366
54 Sun Y, Lian M, Lin Y. et al. Role of p-MKK7 in myricetin-induced protection against intestinal ischemia/reperfusion injury. Pharmacological Research 2018; 129: 432-442
55 Zhang N, Feng H, Liao HH. et al. Myricetin attenuated LPS induced cardiac injury in vivo and in vitro. Phytother Res 2018; 32: 459-470
56 Qiu Y, Cong N, Liang M. et al. Systems pharmacology dissection of the protective effect of myricetin against acute ischemia/reperfusion-induced myocardial injury in isolated rat heart. Cardiovascular Toxicology 2017; 17: 277-286
57 Qu X, Li Q, Song Y. et al. Potential of myricetin to restore the immune balance in dextran sulfate sodium-induced acute murine ulcerative colitis. J Pharm Pharmacol 2020; 72: 92-100