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Synonym name: Puerariaglycoside 3
Catalogue No.: BP0067
Cas No.: 117047-07-1
Formula: C22H22O10
Mol Weight: 446.408
Botanical Source: Pueraria lobata
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.
Description:
3'-Methoxypuerarin shows neuron protection activity, it can protect hippocampal neurons against ischemia/reperfusion injury by inhibiting apoptosis. 3'-Methoxypuerarin has antioxidant activities, it shows ONOO(-) scavenging activity and weak NO· and O(2)(-) scavenging activities.
References:
Arch. Pharm. Res., 2012, 35(5):823-37.
Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots.
In order to evaluate the anti-inflammatory and antioxidant activities of Pueraria lobata roots and its active components, in vitro inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) protein expression, and tert-butylhydroperoxide (t-BHP)-induced reactive oxygen species (ROS) generation in RAW 264.7 cells, as well as in vitro scavenging activities against 1,1-diphenyl-2-picrylhydrazyl (DPPH), peroxynitrite (ONOO(-)), nitric oxide (NO·), superoxide anion (·O(2)(-)) and total ROS, and inhibitory activities against ONOO(-)-mediated tyrosine nitration, were determined.
METHODS AND RESULTS:
Repeated column chromatography was performed to isolate four known compounds from the anti-inflammatory and antioxidant EtOAc fraction: daidzein; genistein; puerarin; (+)-puerarol B-2-O-glucopyranoside; four known compounds from the anti-inflammatory n-hexane fraction: lupenone; lupeol; puerarol; coumestrol; seven known compounds from the antioxidant n-BuOH fraction: allantoin; 3'-hydroxypuerarin; daidzein 8-C-apiosyl-(1→6)-glucoside; puerarin; genistin; 3'-Methoxypuerarin; daidzin. Among these compounds, lupenone and lupeol reduced NO production, as well as iNOS and COX-2 protein levels in LPS-stimulated RAW 264.7 cells. Furthermore, lupeol showed significant inhibitory activity against intracellular ROS generation by t-BHP. Meanwhile, 3'-hydroxypuerarin showed marked ONOO(-), NO·, total ROS scavenging activities, and weak ·O(2)(-) scavenging activity, while 3'-Methoxypuerarin showed ONOO(-) scavenging activity and weak NO· and O(2)(-) scavenging activities, suggesting that existence of the 3'-hydroxyl group in puerarin plays an important role in the scavenging of ONOO(-), NO·, and total ROS, as well as inhibiting the ONOO(-)-mediated tyrosine nitration mechanism.
CONCLUSIONS:
These results indicate that P. lobata roots and its constituents may be a useful therapeutic and preventive approach to various inflammatory diseases and oxidative stress-related disease.
Chinese Journal of Physiology, 2010, 53(2):136-40.
Protection by 3'-methoxypuerarin of rat hippocampal neurons against ischemia/reperfusion injury.
3'-Methoxypuerarin (3'-MOP) is an isoflavone extracted from radix puerariae. The aim of this study was to investigate the role and the mechanism of 3'-MOP in the protection of hippocampal neurons against cerebral ischemia/reperfusion (I/R) injury in rats.
METHODS AND RESULTS:
I/R injury was induced by a modified four-vessel occlusion model. Rats were randomly divided into an I/R group, an I/R + 3'-MOP group and a control group. Histological changes in the neurons of the hippocampal CA1 region were observed with hematoxylin and eosine (H&E) staining. The apoptotic neurons in the hippocampal CA1 area were counted with the terminal deoxynucleotidyl transferase-mediated dUTP nick-end labeling (TUNEL) staining.
CONCLUSIONS:
The results showed that compared with the I/R group, 3'-MOP increased the number of surviving neurons in the hippocampal CA1 region (P < 0.001) and markedly reduced the number of apoptotic pyramidal neurons (P < 0.001) after I/R injury. In conclusion, 3'-MOP can protect hippocampal neurons against I/R injury by inhibiting apoptosis.
HPLC of 3'-MethoxyPuerarin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
189.6700
.9800
Low
Unknown
Unknown
No
Unknown
Unknown
Unknown
Unknown
3'-MethoxyPuerarin (CAS No. 117047-07-1) is an important natural isoflavone compound, belonging to the Puerarin family and its derivatives. As one of the active ingredients in the traditional Chinese medicinal herb Pueraria lobata, 3'-methoxypuerine has attracted much attention in traditional medicine due to its diverse biological activities. In recent years, with the continuous development of natural product pharmacology, this compound has shown significant potential in antioxidant, anti-inflammatory, and cardiovascular protection, becoming an important candidate for natural drug development.
This paper aims to systematically review the chemical structure and physicochemical properties of 3'-methoxypuerarine, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, explore its clinical application prospects and future research directions, and provide references for scientific research and drug development in related fields.
The molecular formula of 3'-methoxypuerine is C_21H_20O_11, with a molecular weight of 446.40. Its structure is based on an isoflavone backbone, featuring typical biphenyl ring structures (A and B rings) and oxane rings (C rings). The 3' hydroxyl group is replaced by a methoxy group, giving it unique chemical properties. The compound's topological pole surface area (TPSA) is 189.67 Ų, and the number of hydrogen bond acceptors reaches 10, indicating strong hydrophilicity and extensive hydrogen bond formation capability. The LogP value was 0.98, indicating moderate lipid solubility, with certain water and lipid solubility characteristics, which is beneficial for distribution in the body.
From a pharmacological perspective, the physicochemical properties of 3'-methoxypuerarin determine its absorption, distribution, and metabolic behavior in organisms. Higher TPSA and hydrogen bond receptor counts usually indicate limited transmembrane capacity and low blood-brain barrier permeability (Low), meaning its role in the central nervous system may be limited. Additionally, existing data indicate that this compound has no hepatotoxicity, cardiotoxicity, or hERG channel inhibitory activity, and is relatively safe, but Ames-induced mutagenic test results remain unclear.
3'-Methoxypuerarin 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, Korea, and Southeast Asia. The roots of this plant are rich in isoflavones, among which 3'-methoxypuerarin is a methoxy derivative of puerarin in relatively low amounts, but its biological activity has attracted significant attention from researchers.
The main methods for extracting 3'-methoxypuerarin include solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) separation and purification. Common solvents are ethanol, water, or their mixed solvent systems. The extraction process generally begins with rough extraction, followed by column chromatography (such as silica gel columns or reversed-phase columns) for separation and purification. Ultrasound-assisted extraction technology, due to its efficiency, energy savings, and gentle nature, has been widely used for the extraction of isoflavones from kudzu root. During purification, HPLC and LC-MS technologies are used for qualitative and quantitative analysis to ensure the purity and structural identification of 3'-methoxypuerarin.
With advances in separation technology, research into biosynthetic pathways has deepened, providing a theoretical foundation for both artificial and semi-synthesis, and promising large-scale production of this compound.
Research on the pharmacological activity of 3'-methoxypuerarin mainly focuses on its antioxidant, anti-inflammatory, cardiovascular and cerebrovascular protection, and metabolic regulation.
Oxidative stress is a key factor in the occurrence and development of various diseases. Research shows that 3'-methoxypuerarin can effectively scavenge free radicals, inhibit lipid peroxidation, and enhance the activity of intracellular antioxidant enzymes (such as superoxide dismutase SOD and glutathione peroxidase GPx). Its antioxidant effects not only protect cells from oxidative damage but also reduce inflammatory responses, providing multiple protective effects.
Inflammatory responses play an important role in various chronic diseases. 3'-Methoxypuerarin reduces inflammatory cell infiltration and regulates immune responses by inhibiting the expression of pro-inflammatory factors (such as TNF-α, IL-6, IL-1β). Both in vivo and in vitro experiments have confirmed that it can significantly reduce levels of inflammatory markers, lessen tissue damage, and demonstrate good anti-inflammatory potential.
Puerarin and its derivatives have wide applications in the prevention and treatment of cardiovascular and cerebrovascular diseases. 3'-Methoxypuerarin protects cardiovascular and cerebrovascular functions by dilating blood vessels, improving microcirculation, inhibiting platelet aggregation, and inhibiting apoptosis of vascular endothelial cells. Animal model studies have shown that this compound can reduce ischemia-reperfusion injury, lower myocardial cell necrosis rates, and improve cardiac function indicators.
Some studies have indicated that 3'-methoxypuerarin has potential in regulating blood sugar and lipid metabolism. By regulating insulin signaling pathways and the expression of lipid metabolism-related enzymes, it improves insulin resistance and lowers blood lipid levels, making it promising as a novel natural drug for adjunctive treatment of metabolic syndrome and diabetes.
The biological effects of 3'-methoxypuerine involve multiple signaling pathways and molecular targets, mainly including:
This compound can activate the Nrf2 (nuclear factor red blood cell 2-related factor 2) signaling pathway, promoting the expression of downstream antioxidant enzymes and enhancing cellular antioxidant defense capabilities. As an important intracellular transcription factor, Nrf2's activation helps resist cellular damage induced by oxidative stress.
3'-Methoxypuerarin reduces transcription of pro-inflammatory genes and release of inflammatory factors by inhibiting the NF-κB (nuclear factor κB) signaling pathway. Additionally, it can regulate the MAPK (mitogen-activated protein kinase) pathway, reduce inflammatory responses, and protect tissues from inflammatory damage.
This compound promotes NO production by modulating vascular endothelial nitric oxide synthase (eNOS) activity, dilates blood vessels, and improves hemodynamics. At the same time, by inhibiting the expression of apoptosis-related proteins (such as Caspase-3), it reduces myocardial cell apoptosis and protects myocardial function.
3'-Methoxypuerarin can activate the AMPK (5' AMP-activated protein kinase) signaling pathway, promote glucose uptake and fatty acid oxidation, and improve metabolic abnormalities. Additionally, lipid metabolism and inflammatory responses may be regulated by regulating PPARγ (peroxisome proliferator-activated receptor γ).
From the perspective of druggability, 3'-methoxypuerarin demonstrated good safety and moderate drug compatibility. Its LogP value is 0.98, indicating suitable lipophilic properties and beneficial for oral absorption. High TPSA and hydrogen bond receptor count suggest strong polarity, which may limit its ability to cross cell membranes, especially with low blood-brain barrier permeability, which restricts its application in the central nervous system.
Toxicological studies show that this compound has no significant hepatotoxicity or cardiotoxicity, and does not inhibit hERG channels, reducing the risk of arrhythmias. Ames-induced mutagenic assay data are still lacking and require further supplementation to assess their genotoxicity.
In terms of pharmacokinetics, current research is relatively limited. Preliminary in vivo experiments show that 3'-methoxypuerarin is absorbed quickly after oral administration, but its bioavailability is limited, possibly related to its polarity and first-pass effect. Metabolic pathways mainly involve the liver's phase I and II enzyme systems, generating various metabolic products. Excretion is mainly carried out through bile and urine. In the future, systematic research on pharmacokinetics and metabolic kinetics is needed to optimize dosing regimens and dosage form design.
3'-Methoxypuerarin demonstrates broad clinical application potential due to its multi-target and multi-pathway pharmacological activity. Its therapeutic value in cardiovascular and cerebrovascular diseases, metabolic syndrome, chronic inflammation, and oxidative stress-related diseases deserves further exploration.
Currently, kudzu root and puerarin compounds have established a certain clinical application basis, but clinical research on 3'-methoxypuerarin as a monomer component is still in its early stages. Future research should focus on:
In addition, by leveraging modern molecular biology and medicinal chemistry techniques, in-depth analysis of its mechanism of action and target network will provide theoretical support for the drug development of 3'-methoxypuerine.
3'-Methoxypuerarin, as a naturally occurring isoflavone compound with rich biological activity, shows significant potential in cardiovascular and cerebrovascular protection, anti-inflammatory and antioxidant properties, and metabolic regulation. Its unique chemical structure and good safety profile lay the foundation for new drug development. Although clinical research and pharmacokinetic data are still insufficient, with deeper research and technological advancements, 3'-methoxypuerarin is expected to become an important candidate drug in the field of natural product pharmacology.
Future research should focus on systematic pharmacological mechanism elucidation, optimizing drug formulations, and conducting clinical validation, promoting their transition from the laboratory to clinical application and benefiting a broad patient base. As a key resource for drug discovery, the study of 3'-methoxypuerarin not only enriches the scientific connotations of isoflavone drugs but also provides new ideas for innovation in natural medicines.
Shenshuai
Wenjing
Hedandan
