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Synonym name: Puerariaglycoside 1
Catalogue No.: BP0064
Cas No.: 117060-54-5
Formula: C21H20O10
Mol Weight: 432.381
Botanical Source: Root of 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.
HPLC of 3'-hydroxyPuerarin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
194.2600
-1.0000
-1.5000
Low
No
No
No
No
No
No
3'-hydroxypuerarin (CAS No. 117060-54-5), as an important natural isoflavone compound, has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse biological activity. This compound is mainly found in the traditional Chinese medicine Pueraria lobata, a hydroxyl derivative of puerarin with high water solubility and biological activity. With further research into its pharmacological mechanisms, 3'-hydroxypuerarin shows potential therapeutic value in cardiovascular and cerebrovascular diseases, metabolic syndrome, neurodegenerative diseases, and other fields.
This paper aims to systematically review the chemical structure and physicochemical properties, plant origin, and extraction methods of 3'-hydroxypuarrin, with a focus on evaluating its pharmacological activity and mechanism of action. By combining druggability parameters and pharmacokinetic characteristics, it explores its clinical application prospects and future research directions, providing theoretical basis and reference for related research and drug development.
3'-Hydroxypuerarin is an isoflavone compound with the molecular formula C21H20O10 and a molecular weight of 432.38. Its structural feature is the introduction of a hydroxyl group at the 3' position on the flavonoid backbone, one more hydroxyl group than puerarin, giving it stronger polarity and water solubility. Its LogP value is -1.0, indicating low lipid solubility and good water solubility, which is beneficial for absorption and distribution in the body.
The molecular surface area (TPSA) is 194.26 Ų, and the number of hydrogen bond acceptors is 10, indicating that the molecule has strong hydrogen bond formation ability, which is of great significance for binding to biological macromolecule targets and exerting biological activity. Its physicochemical properties determine its pharmacokinetic behavior and druggability in vivo; its low lipid solubility and high polarity make it difficult for it to cross the blood-brain barrier (BBB), which should be considered in applications of neurological diseases.
3'-Hydroxypuarin is mainly found in the leguminous plant Pueraria lobata, especially in high concentrations in the roots. As a traditional Chinese medicinal herb, kudzu root has a long history and is widely used in TCM to treat cardiovascular and cerebrovascular diseases and metabolic abnormalities. As one of the active components in kudzu root, optimizing the extraction and separation purification technologies of 3'-hydroxypuarin is of great significance for in-depth research on its pharmacological effects and the development of new drugs.
Traditional extraction methods mostly use ethanol or methanol aqueous solutions for extraction extraction, combined with ultrasound-assisted extraction or microwave-assisted extraction technologies to improve extraction efficiency and purity. Subsequently, separation and purification are carried out using liquid-liquid partitioning and column chromatography (silica gel, C18 reversed phase column). High-performance liquid chromatography (HPLC) and mass spectrometry (LC-MS) techniques are widely used for qualitative and quantitative analysis of 3'-hydroxypuerarin to ensure quality control of extracts.
In recent years, green extraction technologies such as supercritical CO2 extraction and enzyme-assisted extraction have gradually been applied to the extraction of this compound, aiming to increase yield, reduce solvent usage and environmental impact, and provide technical support for industrial production.
3'-Hydroxypuerarin has multiple pharmacological activities, covering cardiovascular and cerebrovascular protection, antioxidant, anti-inflammatory, antidiabetic, and neuroprotective aspects.
Numerous in vivo and in vitro experiments have shown that 3'-hydroxypuerarin exerts significant cardiovascular and cerebrovascular protective effects by improving vascular endothelial function, inhibiting platelet aggregation, and regulating blood lipid levels. It can lower blood pressure, improve coronary artery blood flow, reduce ischemia-reperfusion injury, decrease myocardial cell apoptosis, and demonstrate potential anti-myocardial and cerebral ischemic effects.
3'-Hydroxypuerar has a potent free radical scavenging ability, significantly enhancing intracellular antioxidant enzyme activity (such as superoxide dismutase and glutathione peroxidase), and reducing oxidative stress damage. At the same time, this compound exerts anti-inflammatory effects by inhibiting the nuclear factor κB (NF-κB) signaling pathway, reducing the expression of pro-inflammatory cytokines (such as TNF-α, IL-6), and helping to alleviate chronic inflammation-related diseases.
3'-Hydroxypuerin can improve insulin resistance, promote glucose metabolism, and lower blood sugar levels. By activating the AMPK signaling pathway, it regulates lipid metabolism, alleviates metabolic abnormalities related to fatty liver and obesity, and demonstrates potential for treating type 2 diabetes and metabolic syndrome.
Although 3'-hydroxypuarin has low blood-brain barrier permeability, it exhibits anti-apoptotic and antioxidant effects in neuronal models, can reduce neuroinflammation, protect neurons from oxidative damage and excitotoxicity, and suggest its potential in neurodegenerative diseases such as Alzheimer's and Parkinson's.
The multi-target mechanism of 3'-hydroxypuerarin forms the basis of its broad pharmacological activity. The main targets and signaling pathways involved are as follows:
By inducing the Nrf2-ARE signaling pathway, it enhances the intracellular antioxidant defense system, promotes glutathione synthesis and antioxidant enzyme expression, reduces the production of reactive oxygen species (ROS), and protects cells from oxidative damage.
Inhibits activation of the NF-κB signaling pathway, blocks the transcription of pro-inflammatory factors, reduces the release of inflammatory mediators, and alleviates inflammatory responses. Additionally, by inhibiting the MAPK pathway, it regulates cytokine expression and exerts anti-inflammatory effects.
Regulates nitric oxide (NO) synthesis and improves vasodilatory function; Prevents thrombosis by inhibiting platelet activating factors and thrombosis-related enzymes; Regulates calcium channels and protects myocardial cell function.
Activates the AMPK signaling pathway, promotes fatty acid oxidation and glucose uptake, inhibits the expression of lipogenesis-related genes, improves insulin sensitivity, and regulates energy metabolism balance.
By inhibiting the expression of neuronal apoptosis-related proteins (such as Caspase-3), it reduces the excitotoxicity of glutamate; Regulates neurotransmitter levels in the brain and maintains stable neuronal function.
From the perspective of druggability parameters, 3'-hydroxypuerarin has a moderate molecular weight (432.38), but its LogP is -1.0, indicating strong hydrophilicity and low lipid solubility, which limits its ability for oral absorption and penetration of biological membranes. High TPSA (194.26) and hydrogen bond receptor count (10) are beneficial for target binding but not for blood-brain barrier penetration, explaining their neurological limitations.
In terms of safety, 3'-hydroxypuerarin showed no hepatotoxicity, cardiotoxicity, or hERG channel inhibition. Ames-induced mutagenic tests were negative, demonstrating good safety and low toxicity, laying a foundation for clinical application.
Pharmacokinetic studies show that this compound has low oral bioavailability, is mainly absorbed through the intestines, is widely distributed in the body, but is difficult to enter the central nervous system. Metabolic pathways mainly involve phase II metabolism in the liver (such as glucuronic acid binding and sulfation), and the metabolites have certain activity. Excretion mainly occurs via the kidneys and bile pathways.
To improve bioavailability and targeting, modern formulation technologies such as nanocarriers, liposomes, and drug eutectics have been proposed, with some studies already making preliminary progress.
As a natural active ingredient, 3'-hydroxypuerarin shows broad clinical application prospects thanks to its multi-target and multi-mechanism pharmacological effects. Its potential in the prevention and treatment of cardiovascular and cerebrovascular diseases is particularly outstanding, particularly in conditions such as hypertension, coronary heart disease, and cerebral ischemia, where it has good therapeutic and adjunctive therapeutic value.
In addition, research on diabetes and metabolic syndrome provides new ideas for its application in the field of chronic metabolic diseases. Although its blood-brain barrier penetration is limited, improvements in drug carrier technology are expected to expand its application in neurodegenerative diseases.
Future research should focus on the following areas:
In-depth mechanism research: Using multi-omics techniques to analyze its action network, identify key targets and signaling pathways, and guide precise medication.
Pharmacokinetics optimization: Develop novel delivery systems to enhance oral bioavailability and tissue targeting, especially for central nervous system delivery.
Safety and toxicology evaluation: Conduct systematic long-term toxicological and preclinical safety studies to ensure safety in clinical applications.
Clinical trial design: Based on existing pharmacological evidence, design reasonable clinical trials to verify efficacy and safety, and promote clinical translation.
Combination drug research: Exploring synergistic effects with other drugs or natural products to enhance therapeutic effects and reduce side effects.
3'-Hydroxypuerin, as a hydroxyl derivative of puerarin, holds significant research value in the field of natural product pharmacology due to its unique chemical structure and diverse biological activities. Its multiple pharmacological effects—including cardiovascular and cerebrovascular protection, antioxidant and anti-inflammatory, metabolic regulation, and neuroprotection—provide new ideas and potential drug candidates for the treatment of various diseases.
Although its druggability faces certain challenges, such as insufficient bioavailability and blood-brain barrier penetration, with the development of modern drug formulation technologies and deeper mechanistic research, 3'-hydroxypuerarin is expected to become an important direction for natural product drug development. Future systematic research and clinical validation will be key to moving it from the laboratory to clinical applications.
In summary, 3'-hydroxypuerar not only enriches the pharmacological knowledge system of isoflavone natural products but also provides a solid scientific foundation and broad prospects for the application of natural products in modern medicine.
Shenshuai
Wenjing
Hedandan
