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Chemical Structure| 529-44-2 Chemical Structure| 529-44-2

Structure of Myricetin
CAS No.: 529-44-2

Chemical Structure| 529-44-2

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Myricetin (Standard) serves as the analytical standard of Myricetin, intended for research and analytical applications. This plant-derived flavonoid exhibits strong antioxidant, anticancer, antidiabetic, and anti-inflammatory activities.

Synonyms: Cannabiscetin; LDN-0014058; HSDB 7682

4.5 *For Research Use Only !

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Product Citations

Product Citations

Krueger, Nadine ; Kronenberger, Thales ; Xie, Hang ; Rocha, Cheila ; Poehlmann, Stefan ; Su, Haixia , et al.

Abstract: The severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has forced the development of direct-acting antiviral drugs due to the coronavirus disease 2019 (COVID-19) pandemic. The main protease of SARS-CoV-2 is a crucial enzyme that breaks down polyproteins synthesized from the viral RNA, making it a validated target for the development of SARS-CoV-2 therapeutics. New chem. phenotypes are frequently discovered in natural goods. In the current study, we used a fluorogenic assay to test a variety of natural products for their ability to inhibit SARS-CoV-2 Mpro. Several compounds were discovered to inhibit Mpro at low micromolar concentrations It was possible to crystallize robinetin together with SARS-CoV-2 Mpro, and the X-ray structure revealed covalent interaction with the protease's catalytic Cys145 site. Selected potent mols. also exhibited antiviral properties without cytotoxicity. Some of these powerful inhibitors might be utilized as lead compounds for future COVID-19 research.

Keywords: COVID-19 ; antivirals ; coronavirus ; covalent drugs ; dynamic light scattering ; inhibitors ; main protease ; natural products

Alternative Products

Product Details of Myricetin

CAS No. :529-44-2
Formula : C15H10O8
M.W : 318.24
SMILES Code : OC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C1=CC(O)=C(O)C(O)=C1
Synonyms :
Cannabiscetin; LDN-0014058; HSDB 7682
MDL No. :MFCD00006827
InChI Key :IKMDFBPHZNJCSN-UHFFFAOYSA-N
Pubchem ID :5281672

Safety of Myricetin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of Myricetin

PI3K-AKT

Isoform Comparison

Biological Activity

Target
  • MEK1

In Vitro:

Cell Line
Concentration Treated Time Description References
INS-1 cells 20 µM 24 hours Myricetin significantly inhibited HG-induced apoptosis in INS-1 cells and reduced mitochondrial dysfunction. Diabetes Metab J. 2019 Apr;43(2):192-205.
SK-BR-3 human breast cancer cells 0, 5, 10, 15, 20, 25 µM 24 hours Myricetin inhibited the viability of SK-BR-3 cells in a dose-dependent manner. A significant increase in apoptosis was observed through DAPI and Annexin V/PI staining. Western blot analysis showed that myricetin induced the expression of apoptosis-related proteins, such as increased levels of cleaved PARP and Bax proteins, and decreased levels of Bcl-2 protein. Additionally, myricetin induced autophagy by promoting autophagy-related proteins such as LC 3 and beclin 1. Int J Mol Med. 2022 Apr;49(4):54.
Schistosoma japonicum adult worms 300, 400, 500, 600, 700, 800 µM 24, 48, 72, 96 hours Myricetin exhibited a time- and dose-dependent helminthicidal effect on adult S. japonicum in vitro, with an LC50 of 600 µM (24 hours). Myricetin significantly reduced the number of eggs laid by female worms. Front Immunol. 2020 Apr 16;11:593.
Rat islets 20 µM 48 hours Myricetin significantly inhibited HG-induced apoptosis in rat islets. Diabetes Metab J. 2019 Apr;43(2):192-205.
Vero E6 cells 55.18 µM 72 hours To evaluate the effect of Myricetin on SARS-CoV-2 replication, the results showed that Myricetin significantly inhibited SARS-CoV-2 replication. Phytomedicine. 2023 Jul 25;116:154858.
THP1 macrophages 100, 200, 400 µM To evaluate the effect of Myricetin on inflammation, the results showed that Myricetin significantly inhibited RIPK1-driven inflammation and NF-κB signaling pathway. Phytomedicine. 2023 Jul 25;116:154858.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
BALB/c mice S. japonicum infection model Oral 250 mg/kg Daily for 7 days Myricetin significantly reduced the liver egg load in S. japonicum-infected mice and alleviated liver fibrosis. Myricetin attenuated liver fibrosis via modulating TGFβ1 and Akt signaling and shifting Th1/Th2 balance. Front Immunol. 2020 Apr 16;11:593.
Rats Carrageenan-induced paw edema model Oral 50, 100, 200 mg/kg Once daily for 7 days To evaluate the effect of Myricetin on inflammation, the results showed that Myricetin significantly alleviated carrageenan-induced paw edema. Phytomedicine. 2023 Jul 25;116:154858.
Nude mice Orthotopic pancreatic cancer model (MIA PaCa-2 and S2-013 cells) Intraperitoneal injection 30mg/kg and 50mg/kg Daily for 35 days (MIA PaCa-2 model) or 18 days (S2-013 model) Myricetin significantly inhibited tumor growth and loco-regional spread without toxicity Cancer Lett. 2011 Sep 28;308(2):181-8.
Balb/c nu/nu mice C4-2B xenograft model Intraperitoneal injection 20 mg/kg Three times a week for 3 weeks To evaluate the effect of PLGA-encapsulated myricetin on tumor growth in C4-2B xenograft model, results showed that PLGA-myricetin significantly inhibited tumor growth. J Biomed Sci. 2022 May 9;29(1):29.
Sprague-Dawley (SD) rats Carrageenan-induced paw edema model Oral 50, 100, 200 mg/kg Once daily for 7 days Evaluate the anti-inflammatory effect of Myricetin on carrageenan-induced inflammation, results showed Myricetin significantly reduced inflammatory responses. Phytomedicine. 2023 Jul 25;116:154858.

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.14mL

0.63mL

0.31mL

15.71mL

3.14mL

1.57mL

31.42mL

6.28mL

3.14mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

[1]Phillips PA, Sangwan V, et al. Myricetin induces pancreatic cancer cell death via the induction of apoptosis and inhibition of the phosphatidylinositol 3-kinase (PI3K) signaling pathway. Cancer Lett. 2011 Sep 28;308(2):181-8.

[2]Knekt P, Kumpulainen J, et al. Flavonoid intake and risk of chronic diseases. Am J Clin Nutr. 2002 Sep;76(3):560-8.

[3]Kaneda MM, Messer KS, Ralainirina N, Li H, Leem CJ, Gorjestani S, Woo G, Nguyen AV, Figueiredo CC, Foubert P, Schmid MC, Pink M, Winkler DG, Rausch M, Palombella VJ, Kutok J, McGovern K, Frazer KA, Wu X, Karin M, Sasik R, Cohen EE, Varner JA. PI3Kγ is a molecular switch that controls immune suppression. Nature. 2016 Nov 17;539(7629):437-442. doi: 10.1038/nature19834. Epub 2016 Sep 19. Erratum in: Nature. 2017 Feb 2;542(7639):124. PMID: 27642729; PMCID: PMC5479689.

[4]Walker EH, Pacold ME, Perisic O, Stephens L, Hawkins PT, Wymann MP, Williams RL. Structural determinants of phosphoinositide 3-kinase inhibition by wortmannin, LY294002, quercetin, myricetin, and staurosporine. Mol Cell. 2000 Oct;6(4):909-19. doi: 10.1016/s1097-2765(05)00089-4. PMID: 11090628.

[5]Lee KW, Kang NJ, Rogozin EA, Kim HG, Cho YY, Bode AM, Lee HJ, Surh YJ, Bowden GT, Dong Z. Myricetin is a novel natural inhibitor of neoplastic cell transformation and MEK1. Carcinogenesis. 2007 Sep;28(9):1918-27. doi: 10.1093/carcin/bgm110. Epub 2007 Aug 11. PMID: 17693661.

[6]Xu Y, Xie Q, Wu S, Yi D, Yu Y, Liu S, Li S, Li Z. Myricetin induces apoptosis via endoplasmic reticulum stress and DNA double-strand breaks in human ovarian cancer cells. Mol Med Rep. 2016 Mar;13(3):2094-100. doi: 10.3892/mmr.2016.4763. Epub 2016 Jan 12. PMID: 26782830; PMCID: PMC4768956.

[7]Tzeng SH, Ko WC, Ko FN, Teng CM. Inhibition of platelet aggregation by some flavonoids. Thromb Res. 1991 Oct 1;64(1):91-100. doi: 10.1016/0049-3848(91)90208-e. PMID: 1776142.

 

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