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Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
82.0400
2.2362
2.2362
.0371
1.3932
7.8590
High
80.6146
3.4017
Yes
No
No
No
Yes
Yes
0.9
Yes
No
Yes
Yes
Natural products, as important resources for drug discovery, have always played a central role in new drug development. Furancoumarin-type compounds have become one of the hot topics in natural product pharmacology research due to their extensive bioactivity and unique chemical structure. Oxypeucedanin methanolate (CAS No.: 52939-12-5) is a typical furanocoumarin-derived derivative, mainly found in the traditional Chinese medicinal herb Angelica dahurica. In recent years, with advances in molecular pharmacology and medicinal chemistry technologies, the multiple biological activities and mechanisms of oxidized prephemerol methanol ester have gradually been revealed, demonstrating its potential applications in multiple fields such as anticancer, anti-inflammation, antioxidant, antiarrhythmic, and antiviral properties.
This review aims to systematically summarize the chemical structure and physicochemical properties of oxidized prehumin methanol ester, plant origin, and extraction methods, with a focus on evaluating its pharmacological activity and mechanism of action, exploring its pharmacokinetic characteristics in combination with druggability parameters, and finally looking ahead to its clinical application prospects, providing theoretical basis and directions for subsequent basic research and drug development.
Oxidized prephemerol methanol ester belongs to the furanocoumarin-class compounds, with a molecular formula of C18H18O5 and a molecular weight of 318.3250. Its structural feature is that a furan ring is attached to the coumarin's core backbone, and methanol ester groups are introduced into the molecule, giving it strong lipophilicity and moderate polarity. The compound has a LogP value of 2.2362, indicating moderate lipid solubility, which facilitates cell membrane penetration and oral absorption. Its topological pole surface area (TPSA) is 82.0400, showing polar characteristics suitable for binding to biological macromolecules.
Oxidized prefuginol methanol ester has low water solubility (0.0371 mg/mL), but its high blood-brain barrier permeability gives it potential for central nervous system pharmacological activity. Importantly, the compound does not significantly inhibit hERG channels, suggesting a lower risk of cardiotoxicity. The Ames test result was 0.9, indicating a low genotoxicity risk and a solid safety foundation.
Oxidized algae methanol ester is mainly found in the umbellifery plant Angelica dahurica, a traditional Chinese medicinal herb widely distributed in Northeast and North China, as well as the Korean Peninsula. The root of this plant is the main medicinal part and contains abundant furanocoumarins.
Common methods for extracting oxidized prepherus methanol ester include solvent extraction, ultrasound-assisted extraction, and column chromatography separation. Ethanol or methanol is generally used as extraction solvents, combined with ultrasonic-assisted technology to improve extraction efficiency. The extract undergoes concentration, separation, and silica gel column chromatography purification, and is finally analyzed qualitatively and quantitatively by high-performance liquid chromatography (HPLC). In recent years, the introduction of supercritical fluid extraction and molecular blotting technology has further improved the extraction purity and yield of oxidized prehumin methanol esters.
Oxidized alphedrine methanol ester exhibits significant inhibitory effects across various tumor cell lines. Its anticancer mechanism mainly works by inducing cell cycle inhibition and promoting apoptosis. Related studies have shown that this compound can regulate the PI3K/AKT signaling pathway, inhibit NF-κB activity, and reduce tumor cell proliferation. Additionally, oxidized prephedrin methanol ester modulates the MAPK pathway, affecting cell survival and apoptosis-related protein expression, thereby enhancing cellular sensitivity to chemotherapy drugs.
Oxidized prehumin methanol ester has significant anti-inflammatory effects, inhibiting the expression of pro-inflammatory factors such as TNF-α and IL-6, thereby reducing inflammatory responses. Its mechanism involves inhibiting ROS (reactive oxygen species) production to reduce cellular damage caused by oxidative stress. By modulating the MAPK and NF-κB signaling pathways, oxidized alphedrin methanol esters effectively reduce the release of inflammatory mediators, demonstrating good anti-inflammatory potential.
This compound modulates cardiac electrophysiology, especially by inhibiting hKv1.5 current (IC50 of 76 nM), suggesting its potential application in arrhythmia treatment. The hKv1.5 channel is an important component of atrial-specific currents; its blocking helps regulate the action potential of the atrial muscle, preventing and treating arrhythmias such as atrial fibrillation.
Oxidized prehumin methanol ester exhibits broad-spectrum antiviral activity, targeting various virus-associated proteins including MPO, UL42, UL54, ICP27, TK, gD, CCR5, CXCR4, HIV1-PR, and INT. These targets cover viral replication, transcription, and invasion processes, suggesting that oxidized prephedrine methanol ester may inhibit viral infection through multi-target synergy, especially showing potential advantages against HIV and herpes viruses.
The pharmacological activity of oxidized prephemerine methanol ester depends on its regulation of multiple cellular signaling pathways and molecular targets. Its main mechanisms of action include:
PI3K/AKT/NF-κB signaling pathway inhibition: By inhibiting PI3K kinase activity, it blocks AKT phosphorylation, thereby suppressing nuclear translocation of NF-κB, reducing the expression of pro-inflammatory and anti-apoptotic genes, and promoting apoptosis.
MAPK pathway regulation: Oxidized prehumin methanol esters can regulate the activity of MAPK family members such as ERK, JNK, and p38, affecting cell proliferation, differentiation, and stress responses.
ROS generation inhibition: By eliminating excess reactive oxygen species, it reduces oxidative stress, protects cells from damage, and strengthens the antioxidant defense system.
hKv1.5 channel blockade: Directly acts on atri-specific potassium channels, regulates myocardial cell action potentials, and exerts antiarrhythmic effects.
Diversity of antiviral targets: Oxidized pre-alphedrine methanol ester can interfere with viral DNA polymerase (UL54), viral protein expression regulator (ICP27), viral enzyme (HIV1-PR), and viral invasion receptors (CCR5, CXCR4), blocking multiple stages of the viral lifecycle.
Oxidized prephemental methanol ester exhibits excellent druggability parameters. Its molecular weight of 318.3250 complies with the Lipinski rule, and a LogP value of 2.2362 indicates moderate lipid solubility, which is beneficial for oral absorption. TPSA is 82.0400, indicating moderate molecular polarity and possibly good membrane permeability. Its low water solubility suggests that strategies to improve solubility should be considered in drug formulation design.
The high permeability of the blood-brain barrier provides potential for the development of drugs for central nervous system-related diseases. The hERG channel showed no significant inhibition, reducing the risk of cardiotoxicity. Ames test results showed low genotoxicity risk and good safety.
Pharmacokinetics, although specific in vivo metabolic and excretion data are still insufficient, its oral activity and high blood-brain barrier permeability suggest that this compound has good bioavailability and distribution characteristics in vivo. Future research on in vivo pharmacokinetics, including systematic evaluation of absorption, distribution, metabolism, and excretion (ADME) characteristics, is needed.
Oxidized alphedrin methanol ester demonstrates broad clinical application potential due to its multi-target and multi-pathway pharmacological activity. Its anticancer activity makes it a strong candidate for adjuvant therapy in tumors, especially in regulating the tumor cell cycle and inducing apoptosis, offering unique advantages. Its anti-inflammatory and antioxidant effects offer new ideas for the treatment of chronic inflammatory diseases and neurodegenerative diseases.
Antiarrhythmic activity brings new therapeutic strategies in cardiovascular diseases, especially targeting common arrhythmias such as atrial fibrillation. Antiviral activity provides a new chemical framework and mechanism of action for drug development against HIV and other viral infections.
Future research should focus on in vivo pharmacokinetics, safety evaluation, and preclinical animal model validation of oxyprephemental methanol ester, integrating modern drug design techniques to optimize its structure and improve bioavailability and targetability. Additionally, based on its multi-target characteristics, research on combination therapy is being conducted to explore its potential in comprehensive treatment of multiple diseases.
Oxidized prehumerol methanol ester, derived from the traditional medicinal plant Angelica dahurica, is a furanocoumarin-derived derivative of natural products due to its unique chemical structure and diverse biological activities, making it a hot topic in pharmacological research of natural products. Its significant activity in anticancer, anti-inflammatory, antioxidant, antiarrhythmic, and antiviral properties, combined with favorable druggability parameters, shows broad prospects for drug development.
In the future, in-depth analysis of its molecular mechanisms is needed, improving in vivo pharmacokinetics and safety studies to promote its clinical application. Oxidized prehumin methanol ester not only enriches the pharmacological knowledge system of furanocoumarin-based natural products but also provides a valuable chemical and biological foundation for the development of novel multifunctional drugs.
Shenshuai
Wenjing
Hedandan
