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Synonym name: 4'-Methoxypuerarin
Catalogue No.: BP0079
Cas No.: 92117-94-7
Formula: C22H22O9
Mol Weight: 430.409
Botanical Source:
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
HPLC of 4'-O-Methylpuerarin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
165.7000
1.0200
Low
No
No
No
Unknown
No
Unknown
4'-O-Methylpuerarin (CAS No.: 92117-94-7) is an important isoflavone natural product, belonging to puerarin and its derivatives family. These compounds are mainly found in the leguminous plant Pueraria lobata, and due to their unique chemical structure and diverse biological activities, they have gained widespread attention in the field of natural product pharmacology in recent years. 4'-O-methylpuerarin, as a methylated derivative of puerarin, exhibits pharmacological properties similar to or even superior to the parent compound, especially showing potential therapeutic value in cardiovascular and cerebrovascular diseases, metabolic syndrome, and neurodegenerative diseases.
This paper aims to systematically review the chemical structure and physicochemical properties of 4'-O-methylpuerarine, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. Combined with current research progress, it explores its clinical application prospects and future research directions, providing references for researchers in related fields.
The molecular formula of 4'-O-methylpuerarin is C22H22O9, with a molecular weight of 430.40. Its structure is based on an isoflavone backbone, with the 4'-hydroxyl group being methylated to form a 4'-O-methyl substituent. This structural modification not only affects lipophilicity and water solubility, but may also alter its binding affinity and metabolic stability with biological targets.
In terms of physicochemical properties, the compound has a LogP value of 1.02, indicating moderate lipophilicity, which facilitates penetration of cell membranes without being overly hydrophobic, balancing bioavailability and solubility. The polar surface area (TPSA) is 165.7 Ų, and a higher TPSA indicates that the molecule contains more polar groups, especially hydroxyl and ester groups, enhancing its water solubility and ability to bond with the receptor. With 9 hydrogen bond receptors, it further supports its potential for multi-point binding.
The blood-brain barrier (BBB) permeability is predicted to be low, suggesting that the compound has difficulty entering the central nervous system via BBB, which may limit its direct role in neurological diseases but also reduces the risk of CNS toxicity. Assessments of hepatotoxicity, cardiotoxicity, and hERG channel inhibition were all negative, indicating high safety and suitability for further development.
4'-O-methylpuerarin is mainly found in the leguminous plant Pueraria lobata and its related species. As a traditional Chinese medicinal herb, kudzu root is widely distributed in China, Japan, South Korea, and parts of Southeast Asia. Its roots are rich in various isoflavone compounds, including puerarin and its methylated derivatives.
The extraction of 4'-O-methylpuerarin is usually done by the following steps:
Raw material preparation: Select dried kudzu root and crush it into fine powder to increase extraction efficiency.
Solvent extraction: Ethanol or methanol aqueous solution (50%-70%) is commonly used as the extractant, extracted by reflux or ultrasound-assisted extraction, with extraction time generally lasting 1-3 hours.
Crude extract concentration: The extract is concentrated under reduced pressure to remove the solvent to obtain a crude extract rich in isoflavones.
Separation and purification: Separation is performed using column chromatography techniques (such as silica gel columns and C18 reversed-phase columns), combined with high-performance liquid chromatography (HPLC) monitoring, to further purify and obtain high-purity 4'-O-methylpuerargin.
Structural identification: Confirm compound structure using mass spectrometry (MS), nuclear magnetic resonance (NMR), and infrared spectroscopy (IR) techniques.
In recent years, supercritical fluid extraction and membrane separation technologies have also been attempted for efficient extraction and purification of this compound, improving yield and purity, reducing solvent usage, and environmental pollution.
Pharmacological studies of 4'-O-methylpuerarin cover cardiovascular and cerebrovascular protection, anti-inflammatory, antioxidant, antidiabetic, and neuroprotective aspects, reflecting its multi-target, multi-pathway pharmacological characteristics.
Multiple in vivo and in vivo experiments have shown that 4'-O-methylpuerarin can significantly improve myocardial ischemia-reperfusion injury, reduce myocardial cell apoptosis, and alleviate myocardial fibrosis. Its mechanism involves antioxidant stress, inhibition of inflammatory factor release, and regulation of vasodilatory function. In animal models, this compound can lower blood pressure, improve dyslipidemia, and inhibit the progression of atherosclerosis.
4'-O-methylpuerarin exerts anti-inflammatory effects by inhibiting the NF-κB signaling pathway, reducing the expression of pro-inflammatory factors such as TNF-α and IL-6. At the same time, the phenolic hydroxyl groups in its structure endow it with excellent free radical scavenging ability, significantly reducing oxidative stress levels and protecting cells from oxidative damage.
Research shows that 4'-O-methylpuerarin can improve insulin resistance, promote glucose metabolism, and lower blood sugar levels. Its mechanism of action includes activating the AMPK signaling pathway, enhancing glucose uptake and lipid metabolism, and alleviating pathological changes related to fatty liver and metabolic syndrome.
Although this compound has low blood-brain barrier permeability, it still exhibits certain neuroprotective activity in some neurodegenerative disease models, possibly indirectly improving neural function and slowing pathological progression through peripheral anti-inflammatory and antioxidant effects.
The multiple pharmacological effects of 4'-O-methylpuerarin are attributed to its interactions with various molecular targets, involving signal transduction, gene expression regulation, and enzyme activity regulation.
Inhibition of the NF-κB signaling pathway: By blocking the phosphorylation and degradation of IκBα, it suppresses NF-κB nuclear translocation, reduces inflammatory factor expression, and alleviates inflammatory responses.
AMPK Activation: Promotes AMPK phosphorylation, enhances cellular energy metabolism, improves insulin sensitivity and lipid metabolism, and exerts anti-diabetic effects.
Enhanced antioxidant defenses: Induces Nrf2 nuclear translocation, activating antioxidant enzymes such as superoxide dismutase (SOD) and glutathione peroxidase (GPx), thereby enhancing cellular antioxidant capacity.
Calcium regulation: Some studies indicate that 4'-O-methylpuerarin can regulate intracellular calcium ion concentration, protect myocardial cell function, and prevent apoptosis.
Vasodilation factor regulation: promotes nitric oxide (NO) synthesis, improves vascular endothelial function, and lowers blood pressure.
The synergistic effect of these mechanisms enables 4'-O-methylpuerarin to demonstrate significant therapeutic potential across various disease models.
The drug-to-drug evaluation of 4'-O-methyl puerarin is based on its physicochemical properties, safety, and in vivo pharmacokinetic characteristics.
This compound has no significant hepatotoxicity or cardiotoxicity, does not inhibit hERG channels, and reduces the risk of arrhythmias. Ames-induced mutagenic test results are not yet clear, and further research is needed to confirm its genotoxicity.
Due to moderate LogP and high TPSA, oral absorption of 4'-O-methylpuerarin is relatively stable, but the low permeability of the blood-brain barrier limits direct action by the central nervous system. Animal experiments show that its oral bioavailability is moderate, mainly metabolized and excreted through the liver, with metabolic pathways involving methylation and glucuronic acid binding.
It has a moderate half-life in the body and supports a daily dosing regimen. Most of its metabolites are water-soluble conjugates, which are easily excreted by the kidneys and reduce the risk of accumulation in the body.
Based on existing pharmacological research, 4'-O-methylpuerarin has broad clinical application potential in cardiovascular and cerebrovascular diseases, metabolic syndrome, and inflammation-related diseases. Especially in adjunctive treatment for coronary heart disease, hypertension, diabetes, and their complications, 4'-O-methylpuerarin can serve as an important component of natural medicines or drug combinations.
Future research should focus on:
Preclinical safety and toxicology systematic reviews, including studies on long-term toxicity, mutagenicity, and reproductive toxicity.
Pharmacokinetics optimization improves bioavailability and targeting through structural modification or formulation technology.
Clinical trial design to verify efficacy and safety in specific diseases, clarifying dosage ranges and administration regimens.
In-depth analysis of the mechanism of action, revealing its multi-target synergistic network through multi-omics techniques.
Combination drug strategies, exploring synergistic effects with existing drugs to enhance treatment outcomes.
4'-O-methylpuerargin, as a natural isoflavone compound with unique structural modifications, demonstrates broad drug development value due to its diverse pharmacological activities and good safety. Although clinical applications are still in the early stages, with the development of modern pharmacology and medicinal chemistry technologies, their future potential in treating cardiovascular and metabolic diseases cannot be ignored. Systematic pharmacokinetic research and clinical validation will be key to driving its translational application. We look forward to more basic and clinical research in the future, laying a solid foundation for the drug development of 4'-O-methylpuerarin and benefiting a wide range of patients.
Shenshuai
Wenjing
Hedandan
