Product name: Puerarin-4'-O-β-D-glucopyranoside
Synonym name: Puerarin-4'-O-D-glycoside
Catalogue No.: BP2091
Cas No.: 117047-08-2
Formula: C₂₇H₃₀O₁₄
Mol Weight: 578.523
Botanical Source: Puerariae lobatae radix
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  Puerarin-4'-O-β-D-glucopyranoside

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Puerarin-4 β'-β-D-glucoside, hereinafter referred to as "Puerarin-4'-glucoside") is an important isoflavone natural product, mainly found in the traditional Chinese medicine Pueraria lobata. As a glycosidic derivative of puerarin, puerarin-4'-glucoside has a unique glycoside modification, giving it physicochemical properties and biological activity distinct from parent nuclear compounds. In recent years, with the development of natural product pharmacology and molecular biology technologies, the pharmacological effects and potential clinical application value of puerarin-4'-glucoside have gradually attracted attention. This paper aims to systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of puerarin-4'-glucoside, aiming to provide a theoretical foundation and reference for related research.

Chemical structure and physicochemical properties

Puerarin-4'-glucoside has the molecular formula C27H30O14 and a molecular weight of 578.5230, belonging to the glycoside form of isoflavone compounds. Its structural feature is that the puerarin molecule is linked to a glucose residue at the 4' hydroxyl group via a β-D-glucosidic bond. This glycosylation modification significantly affects its water solubility and bioavailability.

In terms of physicochemical properties, the LogP value of puerarin-4'-glucoside was -0.6621, indicating strong hydrophilicity but lower hydrophobicity compared to the puerarin parent kernel. Its topological polar surface area (TPSA) reaches as high as 239.9700, further confirming that its high polarity may affect its cell membrane permeability. The water solubility index is 3.8981, indicating good water solubility and facilitating dissolution and absorption after oral administration. The blood-brain barrier has a relatively low penetration capacity, suggesting that its role in the central nervous system may be limited. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.0, indicating no significant genotoxicity.

Overall, the physicochemical properties of puerarin-4'-glucoside are suitable for water-soluble drug delivery systems and have good safety, laying a solid foundation for drug development.

Plant Origins and Extraction Methods

Puerarin-4'-glucoside is mainly found in the leguminous plant Pueraria lobata, especially in high concentrations in the roots. As a traditional Chinese medicinal herb, kudzu root is widely used in the field of traditional Chinese medicine. Its active ingredients are mainly isoflavones, while puerarin and its glycoside compounds are the main active ingredients.

The extraction method typically uses alcohol solvents (such as ethanol or methanol) to extract dried kudzu root powder by reflux, followed by separation and purification through liquid-liquid partitioning, column chromatography, and other techniques. High-performance liquid chromatography (HPLC) and mass spectrometry (LC-MS) are widely used for qualitative and quantitative analysis of puerarin-4'-glucoside. In recent years, to improve extraction efficiency and purity, green extraction technologies such as ultrasound-assisted extraction and microwave-assisted extraction have gradually been applied to the preparation of puerarin-4'-glucoside.

In addition, research on biosynthetic pathways also provides theoretical support for artificial biosynthesis and metabolic engineering modification, with the potential to achieve large-scale production of puerarin-4'-glucoside.

Pharmacological activity research

Puerarin-4'-glucoside exhibits significant pharmacological activity across various disease models, covering cardiovascular diseases, metabolic syndromes, inflammatory responses, and neurodegenerative diseases.

1. Cardiovascular protective effects
   Puerarin-4'-glucoside can dilate blood vessels, lower blood pressure, and improve myocardial ischemia-reperfusion injury. Its mechanism involves antioxidant stress, inhibition of inflammatory factor release, and regulation of vascular endothelial function. Both in vitro and in vivo experiments have shown that this compound can significantly reduce the proliferation of vascular smooth muscle cells and prevent atherosclerosis.

2. Anti-inflammatory and immunomodulatory
   This compound exerts anti-inflammatory effects by inhibiting the NF-κB signaling pathway, reducing the expression of pro-inflammatory cytokines such as TNF-α and IL-6. In addition, puerarin-4'-glucoside can regulate immune cell function and enhance the body's immune defense capabilities.

3. Antioxidant effects
   Puerarin-4'-glucoside has the ability to scavenge free radicals and reduce lipid peroxidation, protecting cells from oxidative damage. Its antioxidant activity helps slow cellular aging and prevent oxidative stress-related diseases.

4. Neuroprotective effects
   Despite its low blood-brain barrier permeability, some neuronal models still show anti-neuroinflammatory and anti-apoptotic potential, suggesting it may exert neuroprotective effects through indirect mechanisms.

5. Metabolic regulation
   Puerarin-4'-glucoside can improve insulin resistance, regulate blood sugar and lipid metabolism, and show potential anti-diabetes and anti-obesity effects.

Mechanism of action and molecular targets

The pharmacological effects of puerarin-4'-glucoside involve multiple signaling pathways and molecular targets, mainly including:

• NF-κB signaling pathway: By inhibiting the degradation of IκBα, it prevents NF-κB transcription factors from entering the nucleus and reduces the expression of inflammatory factors.
• PI3K/Akt signaling pathway: Activates this pathway to promote cell survival and anti-apoptosis, protecting cardiomyocytes and nerve cells from damage.
• Nrf2/ARE antioxidant pathway: promotes Nrf2 nuclear translocation, enhances antioxidant enzyme expression, and enhances cellular antioxidant capacity.
• Regulation of calcium channels: Affects intracellular calcium homeostasis, regulates vascular smooth muscle contraction, and exerts vasodilatory effects.
• AMPK signaling pathway: regulates energy metabolism, promotes fatty acid oxidation, and improves metabolic abnormalities.

Additionally, puerarin-4'-glucoside regulates cell cycle, apoptosis, and autophagy processes through interactions with various enzymes and receptors, demonstrating multi-target and multi-mechanism pharmacological properties.

Druggability evaluation and pharmacokinetics

The druggability parameters of puerarin-4'-glucoside indicate good safety and suitable pharmacokinetic characteristics. Its LogP value and TPSA suggest better water solubility, but lower cell membrane permeability, which may affect oral absorption efficiency. The blood-brain barrier has a low penetration capacity, limiting the direct action of the central nervous system.

Pharmacokinetic studies show that puerarin-4'-glucoside remains stable in the gastrointestinal tract after oral administration, mainly absorbed through the small intestine, and subsequently metabolized in the liver. Its metabolites include deglycated puerarin, which has strong biological activity, suggesting that puerarin-4'-glucoside may act as a prodrug. The half-life in the body is moderate, and the main excretion routes are urine and bile.

In terms of safety, the hERG channel inhibition test was negative and the Ames test showed no mutagenicity, indicating low cardiotoxicity and genotoxicity risks, making it suitable for further clinical development.

Prospects and outlooks for clinical applications

Puerarin-4'-glucoside, as a natural isoflavone glycoside, shows broad application prospects in cardiovascular diseases, metabolic syndrome, inflammatory diseases, and neuroprotection due to its multi-target and multi-mechanism pharmacological effects.

Future clinical research should focus on:

• Dosage Form Optimization: Improving bioavailability and targeting through novel delivery systems such as nanocarriers and liposomes.
• Combination medication: works synergistically with other drugs to enhance treatment effects and reduce side effects.
• Clinical trial design: Conduct systematic Phase I-III clinical trials to verify safety and efficacy, and promote drug adaptation.
• In-depth Mechanism Research: Using multi-omics and systems biology approaches, further revealing its network of action and molecular mechanisms.
• Metabolic engineering and synthetic biology: Efficient production of puerarin-4'-glucoside through genetic engineering to ensure raw material supply.

In summary, puerarin-4'-glucoside has promising potential for drug development and is expected to become an important candidate molecule for natural product drug development in the future.

Conclusion

Puerarin-4'-β-D-glucoside, an important isoflavone glycoside in kudzu root, has become a hot topic in natural product pharmacology research due to its unique chemical structure and diverse biological activities. Its excellent safety profile and multi-target pharmacological action offer new ideas for the treatment of cardiovascular diseases, metabolic disorders, and inflammation-related diseases. Although its blood-brain barrier permeability is currently limited, improvements in formulation and metabolic regulation may expand its clinical indications. In the future, by integrating multidisciplinary research combining modern medicinal chemistry, molecular biology, and clinical pharmacology, Puerarin-4'-glucoside will move from the laboratory to clinical practice, benefiting a wide range of patients.