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Myricetin
"Descrizione"
by admin (19362 pt)
2024-Sep-30 16:57

Myricetin is a natural flavonoid found in various fruits, vegetables, tea, berries, red wine and plants, grapes, onions.  It is known for its potent antioxidant, anti-inflammatory, and potential anticancer properties. In cosmetic formulations, Myricetin is valued for its ability to protect the skin from oxidative stress, reduce inflammation, and improve overall skin health. Its incorporation into skincare products helps promote a brighter and more youthful complexion.

Chemical Composition and Structure

Myricetin is characterized by:

  • Chemical Formula: C15H10O7
  • Structure: A flavonol with a complex structure consisting of a flavone backbone with multiple hydroxyl (-OH) groups, contributing to its antioxidant activity.

The unique structure of Myricetin enables it to effectively scavenge free radicals and provide various health benefits.

Physical Properties

  • Appearance: Typically a yellow to orange crystalline powder.

  • Solubility: Soluble in organic solvents; slightly soluble in water.

  • Melting Point: Generally melts at around 305–308°C (581–586°F).

  • Odor: Odorless.

  • Stability: Stable under normal storage conditions; should be protected from excessive heat and light.

Production Process

  1. Extraction: Myricetin is extracted from plant sources using methods such as solvent extraction or steam distillation to obtain the flavonoid in concentrated form.

  2. Purification: The extract is purified to remove impurities and ensure a high-quality product.

  3. Formulation: Purified Myricetin is incorporated into various cosmetic products to enhance their antioxidant and protective properties.

Applications

  • Medical: Explored for its potential therapeutic effects in various health-related applications (1), including its role in the treatment of cancer, breast cancer (2), as an anti-inflammatory (3), cardioprotective (4), as a contrast to the progression of prostate cancer cells (5) and as a neuroprotective agent (6)
  • Cosmetics: Commonly used in creams, serums, and lotions for its antioxidant and anti-inflammatory benefits. It helps calm irritated skin, reduce redness, and improve overall skin health.

  • Dietary Supplements: Sometimes included in supplements for its antioxidant properties.

Environmental and Safety Considerations

Myricetin is generally regarded as safe for use in cosmetics when applied according to recommended guidelines. It is well-tolerated by most skin types, including sensitive skin. 

Responsible sourcing and formulation practices are essential to ensure that the ingredient is free from harmful contaminants and produced sustainably.


Molecular Formula  C15H10O8

Molecular Weight  318.23 g/mol

CAS     529-44-2

UNII    76XC01FTOJ

EC Number  208-463-2

DTXSID8022400

Synonyms:

Myricitin

Myricetol

References__________________________________________________________________________

(1) Felice MR, Maugeri A, De Sarro G, Navarra M, Barreca D. Molecular Pathways Involved in the Anti-Cancer Activity of Flavonols: A Focus on Myricetin and Kaempferol. Int J Mol Sci. 2022 Apr 16;23(8):4411. doi: 10.3390/ijms23084411. 

Abstract. Natural compounds have always represented valuable allies in the battle against several illnesses, particularly cancer. In this field, flavonoids are known to modulate a wide panel of mechanisms involved in tumorigenesis, thus rendering them worthy candidates for both cancer prevention and treatment. In particular, it was reported that flavonoids regulate apoptosis, as well as hamper migration and proliferation, crucial events for the progression of cancer. In this review, we collect recent evidence concerning the anti-cancer properties of the flavonols myricetin and kaempferol, discussing their mechanisms of action to give a thorough overview of their noteworthy capabilities, which are comparable to those of their most famous analogue, namely quercetin. On the whole, these flavonols possess great potential, and hence further study is highly advised to allow a proper definition of their pharmaco-toxicological profile and assess their potential use in protocols of chemoprevention and adjuvant therapies.

(2) Lu Y, Sun J, Yang M, Xing Y, Zhu W, Zhu J, Ma X, Wang Y, Wang L, Jia Y. Myricetin Induces Ferroptosis and Inhibits Gastric Cancer Progression by Targeting NOX4. J Agric Food Chem. 2024 Mar 27;72(12):6178-6188. doi: 10.1021/acs.jafc.3c05243. 

Abstract. Ferroptosis holds great potential as a therapeutic approach for gastric cancer (GC), a prevalent and deadly malignant tumor associated with high rates of incidence and mortality. Myricetin, well-known for its multifaceted biomedical attributes, particularly its anticancer properties, has yet to be thoroughly investigated regarding its involvement in ferroptosis. The aim of this research was to elucidate the impact of myricetin on ferroptosis in GC progression. The present study observed that myricetin could trigger ferroptosis in GC cells by enhancing malondialdehyde production and Fe2+ accumulation while suppressing glutathione levels. Mechanistically, myricetin directly interacted with NADPH oxidase 4 (NOX4), influencing its stability by inhibiting its ubiquitin degradation. Moreover, myricetin regulated the inhibition of ferroptosis induced by Helicobacter pylori cytotoxin-associated gene A (CagA) through the NOX4/NRF2/GPX4 pathway. In vivo experiments demonstrated that myricetin treatment significantly inhibited the growth of subcutaneous tumors in BALB/c nude mice. It was accompanied by increased NOX4 expression in tumor tissue and suppression of the NRF2/GPX4 antioxidant pathway. Therefore, this research underscores myricetin as a novel inducer of ferroptosis in GC cells through its interaction with NOX4. It is a promising candidate for GC treatment.

Soleimani M, Sajedi N. Myricetin Apoptotic Effects on T47D Breast Cancer Cells is a P53-Independent Approach. Asian Pac J Cancer Prev. 2020 Dec 1;21(12):3697-3704. doi: 10.31557/APJCP.2020.21.12.3697. 

Abstract. Objective: Using nutraceuticals in cancer therapy is a strategy contributing with other approaches to promote apoptosis in cancer cells. Myricetin is a polyphenol flavonoid that forms main ingredients of various type of foods and beverages. The inducing properties of myricetin in apoptosis is reported by several investigations. The present study aimed to assess apoptotic effects of myricetin on T47D breast cancer cells and to evaluate part of the mechanisms of action.....Conclusion: Myricetin enhances apoptosis in T47D breast cancer cells by evoking both extrinsic and intrinsic apoptotic pathways. myricetin may practices its apoptotic properties on T47D cells through inducing BRCA1- GADD45 pathway.

(3) Sun WL, Li XY, Dou HY, Wang XD, Li JD, Shen L, Ji HF. Myricetin supplementation decreases hepatic lipid synthesis and inflammation by modulating gut microbiota. Cell Rep. 2021 Aug 31;36(9):109641. doi: 10.1016/j.celrep.2021.109641. 

(4) Wang L, Wu H, Yang F, Dong W. The Protective Effects of Myricetin against Cardiovascular Disease. J Nutr Sci Vitaminol (Tokyo). 2019;65(6):470-476. doi: 10.3177/jnsv.65.470. 

Abstract. Cardiovascular disease (CVD) is the leading cause of death globally, except Africa, and poses a severe health burden worldwide. Both in vitro and in vivo studies have demonstrated the protective effects of myricetin for preventing CVD. For this review, we have assessed the literature from 2009 to 2019 at home and abroad to uncover the protective roles of myricetin for preventing CVD. Myricetin exhibits cardioprotective, anti-hypertensive, anti-atherosclerotic, anti-hyperglycemic, and anti-hyperlipidemic effects. In addition, myricetin may alleviate some of the complications caused by adult-onset diabetes. The combined functions of myricetin allow for the prevention of CVD. This review describes the possible therapeutic benefits of myricetin, along with its potential mechanisms of action, to support the clinical use of the myricetin for the prevention of CVD.

(5) Crocetto F, di Zazzo E, Buonerba C, Aveta A, Pandolfo SD, Barone B, Trama F, Caputo VF, Scafuri L, Ferro M, Cosimato V, Fusco F, Imbimbo C, Di Lorenzo G. Kaempferol, Myricetin and Fisetin in Prostate and Bladder Cancer: A Systematic Review of the Literature. Nutrients. 2021 Oct 23;13(11):3750. doi: 10.3390/nu13113750. 

Abstract. Prostate and bladder cancer represent the two most frequently diagnosed genito-urinary malignancies. Diet has been implicated in both prostate and bladder cancer. Given their prolonged latency and high prevalence rates, both prostate and bladder cancer represent attractive candidates for dietary preventive measures, including the use of nutritional supplements. Flavonols, a class of flavonoids, are commonly found in fruit and vegetables and are known for their protective effect against diabetes and cardiovascular diseases. Furthermore, a higher dietary intake of flavonols was associated with a lower risk of both bladder and prostate cancer in epidemiological studies. In this systematic review, we gathered all available evidence supporting the anti-cancer potential of selected flavonols (kaempferol, fisetin and myricetin) against bladder and prostate cancer. A total of 21, 15 and 7 pre-clinical articles on bladder or prostate cancer reporting on kaempferol, fisetin and myricetin, respectively, were found, while more limited evidence was available from animal models and epidemiological studies or clinical trials. In conclusion, the available evidence supports the potential use of these flavonols in prostate and bladder cancer, with a low expected toxicity, thus providing the rationale for clinical trials that explore dosing, settings for clinical use as well as their use in combination with other pharmacological and non-pharmacological interventions.

(6) Gupta G, Siddiqui MA, Khan MM, Ajmal M, Ahsan R, Rahaman MA, Ahmad MA, Arshad M, Khushtar M. Current Pharmacological Trends on Myricetin. Drug Res (Stuttg). 2020 Oct;70(10):448-454. doi: 10.1055/a-1224-3625. 

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. Thieme. All rights reserved.

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