Product name: Myricetin 3-glucoside
Synonym name:Myricetin 3-O-β-D-glucopyranoside Isomyricitrin
Catalogue No.: BP4684
Cas No.: 19833-12-6
Formula: C21H20O13
Mol Weight: 480.378
Botanical Source:
Type of Compound: Flavonoids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Myricetin 3-glucoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Myricetin-3-O-glucoside (CAS No.: 19833-12-6), as an important natural flavonoid glycoside, has attracted widespread attention in recent years due to its remarkable biological activity and potential medicinal value. This compound is a glycoside derivative of myricetin, exhibiting excellent antioxidant, anti-inflammatory, and hepatoprotective effects, especially showing significant protective effects in alcoholic liver injury models. With the rising incidence of alcoholic liver disease, the search for safe and effective natural liver protectants has become a research hotspot. Myorin-3-O-glucoside demonstrates promising clinical application by regulating multiple molecular targets to reduce hepatocyte damage. This paper will systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, and druggability evaluation of myricetin-3-O-glucoside, aiming to provide a theoretical foundation for subsequent research and clinical translation.
Myorin-3-O-glucoside is a flavonoid glycoside among flavonoids, with a molecular formula of C21H20O13 and a molecular weight of 480.3780. Its chemical structure consists of myrumitin forming a core structure and a glucose molecule connected by a glycosidic bond at the 3 hydroxyl positions. Myruminin itself is a trihydroxyflavonoid alcohol, with multiple hydroxyl groups in its structure, which imparts excellent antioxidant activity. The introduction of glycosyls not only improved its water solubility (1.4382) but also affected its bioavailability and metabolic stability.
In terms of physicochemical properties, Myricetin-3-O-glucoside has a LogP value of -0.2991, indicating strong hydrophilicity and high molecular polarity (TPSA 230.74 Ų), which facilitates its dissolution and biological distribution in the aqueous phase. It has good water solubility, which helps absorption after oral administration. The blood-brain barrier has low permeability, indicating that its main target is concentrated in peripheral tissues, especially the liver. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames-induced mutagenic test scored 1.2, indicating low genotoxicity risk and good safety.
Myricin-3-O-glucoside is widely found in various plants, with high levels in Myrica rubra, red grapes, blueberries, tea, and various medicinal plants. The fruit and leaves of bayberry are the main natural sources of this compound. Because the ripe fruit is rich in polyphenols, it serves as an important raw material for extracting this compound.
The extraction method typically uses water extraction or alcohol extraction combined with chromatography separation techniques. Conventional processes include:
In recent years, green extraction technologies such as supercritical CO2 extraction and microwave-assisted extraction have also been explored and applied, aiming to achieve efficient and environmentally friendly industrial production.
Pharmacological studies on myricetin-3-O-glucoside mainly focus on its antioxidant, anti-inflammatory, and hepatoprotective effects, especially in models of alcohol-induced liver injury.
Myorin-3-O-glucoside can effectively eliminate free radicals and reduce oxidative stress damage. In vitro experiments show that this compound can enhance the activity of intracellular antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase (CAT), and glutathione peroxidase (GPX1), reduce reactive oxygen species (ROS) levels, and protect cells from oxidative damage.
In the inflammation model, myricetin-3-O-glucoside reduces tissue inflammatory responses by inhibiting inflammatory factor expression. For example, it can downregulate pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6), reducing infiltration of liver inflammatory cells.
Ethanol-induced liver injury is a key focus in myricetin-3-O-glucoside research. In vivo experiments have shown that this compound can significantly reduce liver transaminase (ALT, AST) activity in HepG2 cells and animal models, alleviating hepatocyte damage. By regulating oxidative stress and inflammatory responses, it prevents steatosis and fibrosis, demonstrating potential therapeutic value for alcoholic liver disease.
In addition, myriatin-3-O-glucoside also exhibits certain anticancer, antibacterial, and neuroprotective effects, but related research is still in its early stages and requires further validation.
The biological activity of myricetin-3-O-glucoside is closely related to its multi-target regulatory mechanism. Its main mechanisms of action include:
Myricetin-3-O-glucoside activates the NFE2L2/NRF2 signaling pathway, promoting the expression of downstream antioxidant enzyme genes (such as SOD1, SOD2, CAT, GPX1, HMOX1), thereby enhancing cellular antioxidant defense capabilities. NRF2, as a key transcription factor, regulates cellular responses to oxidative stress, and its activation helps alleviate hepatocyte damage.
Myorin-3-O-glucoside can inhibit the expression and activity of MMP1 and MMP3, prevent extracellular matrix degradation, and slow down the process of liver fibrosis. MMPs play an important role in liver injury and repair, and their regulation helps maintain the integrity of liver structure.
By inhibiting the NF-κB signaling pathway, myricetin-3-O-glucoside reduces the production of pro-inflammatory cytokines (such as TNF-α, IL-6), alleviates inflammatory responses, and protects hepatocytes from inflammation-mediated damage.
Myorin-3-O-glucoside may also participate in cellular metabolism and signal transduction by regulating enzyme activities such as tyrosinase (TYR), but the specific mechanism still requires further research.
The druggability parameters of myriatin-3-O-glucoside indicate that it has certain potential for drug development. It has good water solubility, which is beneficial for formulation development and oral absorption. A lower LogP value indicates strong hydrophilicity, which may limit its transmembrane diffusion rate but contributes to stability in blood circulation.
The low permeability of the blood-brain barrier suggests it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects. hERG channel inhibition negative, reducing the risk of cardiotoxicity. Ames test results indicate that it carries a low genotoxicity risk and is relatively safe.
Pharmacokinetics, myricetin-3-O-glucoside releases myricetin in the body after water resolvation, with the latter being the active form. Its absorption, distribution, metabolism, and excretion (ADME) are influenced by glycoside modification; glycoside structures help improve stability and bioavailability, but may also lead to first-pass effects. In the future, in vivo pharmacokinetic studies are needed to clarify its half-life, biotransformation pathways, and metabolite activity.
Myrumin-3-O-glucoside shows broad application prospects in the prevention and treatment of alcoholic liver disease, non-alcoholic fatty liver, liver fibrosis, and other liver diseases due to its significant antioxidant and hepatoprotective effects. Its low toxicity and good safety provide favorable conditions for clinical translation.
Future research directions should focus on:
In addition, the potential of myricetin-3-O-glucoside in anti-inflammatory, anti-tumor, and neuroprotective fields is also worth further exploration.
Myricetin-3-O-glucoside, a natural flavonoid glycoside with multiple biological activities, has become an important research subject in natural product pharmacology due to its excellent antioxidant and liver-protective effects. By regulating the NRF2 signaling pathway and various key enzymes, it significantly alleviates ethanol-induced liver damage, demonstrating good medicinal value and development potential. In the future, by combining modern medicinal chemistry, molecular biology, and clinical research methods, in-depth exploration of its mechanisms of action and optimization of formulations will lay a solid foundation for its clinical application and promote innovative development of natural products in liver disease prevention and treatment.
