Product name: Eupatoriochromene
Synonym name: De-O-methylencecalin; Demethylencecalin
Catalogue No.: SBP00156
Cas No.: 19013-03-7
Formula: C₁₃H₁₄O₃
Mol Weight: 218.252
Botanical Source:
Physical Description: Cryst.
Type of Compound: Phenols

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.

For Reference Standard and R&D, Not for Human Use Directly.

HPLC of Eupatoriochromene

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

Introduction/Overview

Eupatoriochromene (CAS No.: 19013-03-7) is a class of plant-derived benzopyran natural products. Due to its unique chemical structure and significant biological activity, it has attracted widespread attention in the field of natural product pharmacology in recent years. As a compound with inhibitory activity against xanthine oxidase (XO), Zelansenoene shows potential application value in anti-inflammatory, antioxidant, and related disease treatments. Xanthine oxidase, as a key enzyme in purine metabolism, participates in uric acid production. Its abnormal activity is closely related to gout, hyperuricemia, and various inflammatory diseases. Zelanskorenene may offer new approaches for treating these diseases by modulating XO activity.

In addition, Zelansenoene demonstrates multi-target regulatory capabilities in the anti-inflammatory field, involving important inflammatory signaling pathways and molecular targets such as IL-6, STAT3, CASP1, TRPV1, PTGS1, TNF, TRPA1, NOS2, PTGS2, and NFKB1, demonstrating its complex mechanisms in regulating immune responses and inflammatory processes. This paper will systematically review the chemical structure and physicochemical properties of Zelansenoene, plant origin and extraction methods, pharmacological activity and mechanism, druggability evaluation, and pharmacokinetic characteristics, combined with its clinical application potential, aiming to provide scientific basis and theoretical support for the in-depth research and development of this natural product.

Chemical structure and physicochemical properties

Zelansenoene belongs to the benzopyran compounds, with a basic framework of a fusion structure of benzene and pyranan rings, possessing strong chemical stability and a basis for biological activity. Its molecular formula is C14H14O3, molecular weight is 218.2520, and its structure contains functional groups such as hydroxyl and methoxy groups, which give it certain polarity and the ability to bind to biological targets.

In terms of physicochemical properties, Zelansenoene has a LogP value of 3.0322, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and distribution in vivo. Its topological pole surface area (TPSA) is 46.53 Ų, indicating moderate polarity, which may affect oral absorption and blood-brain barrier permeability. Its low water solubility (0.1478 mg/mL) somewhat limits its bioavailability, but it also provides directions for improving drug formulation design.

Notably, Zelanseroene has a high ability to cross the blood-brain barrier, which means it may play a role in treating central nervous system diseases. Additionally, the hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity, while the Ames test result was 0.0, indicating no significant genotoxicity risk. These druggability parameters provide preliminary assurance for its safety.

Plant Origins and Extraction Methods

Zelan chromoene is mainly found in Zelan species, especially abundant in the medicinal herb Zelan (Eupatorium fortunei Turcz.). Zelan is a plant in the Asteraceae family, widely distributed in southern China and Southeast Asia. It has long been used in traditional Chinese medicine, with effects such as clearing heat and detoxifying, promoting blood circulation, and removing blood stasis.

Common methods for extracting Zelansenoene include solvent extraction, column chromatography separation, and high-performance liquid chromatography (HPLC) purification. Typically, ethanol or methanol is used as extraction solvents, and crude extracts are obtained by reflux extraction. These are then separated by silica gel column chromatography, combined with thin-layer chromatography (TLC) to monitor the presence of target components. Purified Zelansproene can be identified structurally using technologies such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR).

In recent years, emerging technologies such as ultrasound-assisted extraction and microwave-assisted extraction have also been applied to the extraction of Zelansenoene, significantly improving extraction efficiency and purity, laying the foundation for large-scale production.

Pharmacological activity research

Pharmacological studies on Zelansenoene mainly focus on its anti-inflammatory and antioxidant effects. As an inhibitor of xanthine oxidase, Zelanskoene can effectively reduce XO-mediated reactive oxygen species (ROS) production, alleviate oxidative stress damage, and thereby alleviate inflammatory responses.

Multiple in vitro experiments have shown that Zelansenoene can significantly inhibit the expression of inflammatory factors IL-6 and TNF-α, reduce the release of inflammatory mediators, and exert anti-inflammatory effects. In cell models, Zelanskotene regulates immune cell activation by inhibiting the STAT3 and NF-κB signaling pathways, thereby reducing inflammatory cascade responses. Additionally, its regulatory effect on CASP1 (caspase 1) suggests it may be involved in the regulation of inflammasome activity.

Animal experiments further confirmed that Zelanskotene can reduce tissue damage and improve pathological status in models of inflammatory diseases. For example, in arthritis and enteritis models, Zelanstrytene significantly reduced inflammatory markers, improved tissue inflammation and edema, and demonstrated good anti-inflammatory effects.

In addition to its anti-inflammatory effects, Zelanstenene also modulates pain-related receptors such as TRPV1 and TRPA1, suggesting its potential value in pain management. Its inhibition of NOS2 (induced nitric oxide synthase) may further alleviate inflammation-related oxidative damage.

Mechanism of action and molecular targets

The mechanism of action involves regulation of multiple inflammatory signaling pathways and molecular targets. As an inhibitor of xanthine oxidase, it directly blocks the production of reactive oxygen species in purine metabolism, reducing oxidative stress and alleviating the inflammatory microenvironment.

At the cellular signaling level, Zelaskodene inhibits NF-κB (NFKB1) activation, blocks transcriptional expression of pro-inflammatory genes, and reduces the release of key inflammatory factors such as IL-6, TNF-α, and PTGS2 (COX-2). Additionally, Zelansenoene can regulate the STAT3 signaling pathway, inhibit the proliferation and activation of inflammatory cells, and alleviate chronic inflammatory states.

CASP1, as the core enzyme of the inflammasome, is involved in the maturation and secretion of the pro-inflammatory cytokine IL-1β. Zelansenoene's inhibitory effect on CASP1 suggests it may regulate inflammatory body activity and control the initiation and spread of inflammatory responses.

TRPV1 and TRPA1 are important ion channels for sensing pain and inflammatory signals. Zelanseroene's regulatory effect may alleviate inflammation-related pain symptoms and improve patients' quality of life.

Additionally, Zelanskotene's dual regulation of PTGS1 (COX-1) and PTGS2 (COX-2) may suppress inflammation while reducing the common gastrointestinal side effects of traditional nonsteroidal anti-inflammatory drugs (NSAIDs). This property provides the theoretical basis for it to become a safer anti-inflammatory drug.

Druggability evaluation and pharmacokinetics

Druggability evaluation of Zelanskotene indicates it has good potential for drug development. Its molecular weight is moderate (218.25 Da), conforming to the Lipinski rule, which is beneficial for oral absorption. The LogP value was 3.03, indicating moderate lipid solubility, ensuring distribution in the body while avoiding reduced bioavailability caused by excessive lipid solubility.

The TPSA value of 46.53 Ų indicates good cell membrane penetration. Combined with its high blood-brain barrier permeability, Zelanskonoene holds promise for the treatment of central nervous system-related diseases.

In terms of safety, the hERG channel inhibition test was negative, reducing the potential risk of cardiotoxicity. The Ames test showed no mutagenicity, indicating a low genotoxicity risk and meeting drug safety requirements.

Currently, pharmacokinetic (PK) data on Zelanskodonene are limited. Preliminary in vivo studies suggest its oral bioavailability is limited, possibly related to its low water solubility. The metabolic pathway is not fully understood and is presumed to mainly be metabolized through hepatic enzyme systems. Future research on in vivo pharmacokinetics and metabolic kinetics is needed to optimize dosage forms and administration regimens.

Prospects and outlooks for clinical applications

Zelanseroene, with its multi-target anti-inflammatory effects and good safety profile, shows broad clinical application prospects. As a xanthine oxidase inhibitor, it is suitable as an adjunct therapy for metabolic diseases such as gout and hyperuricemia, and may reduce the side effects of traditional XO inhibitors like allopurinol.

In chronic inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease, Zelanseroene is expected to become a novel anti-inflammatory drug by regulating multiple inflammatory signaling pathways, improving patient symptoms and slowing disease progression.

Additionally, its ability to regulate central nervous system inflammation and pain-related targets suggests potential application value in neuroinflammation, neurodegenerative diseases, and chronic pain management.

In the future, clinical translation of Zelanstrytene will focus on addressing its water solubility and bioavailability, developing efficient drug formulations, and conducting systematic toxicological and pharmacokinetic studies to ensure its safety and efficacy. Combined with modern drug design technologies such as structural optimization and nanocarrier delivery, its clinical application potential is expected to be enhanced.

Conclusion

Zelanstryten, a natural benzopyran compound with significant xanthine oxidase inhibitory activity, has become a hot topic in natural product pharmacology due to its multi-target anti-inflammatory mechanism and excellent druggability. Its potential in anti-inflammation, antioxidant, and related disease treatments provides valuable resources for the development of novel natural medicines.

Although research on Zelanskoene has made some progress, its pharmacokinetic characteristics and clinical applications still require further exploration. In the future, through multidisciplinary collaborative innovation combined with modern medicinal chemistry and pharmacological technologies, Zelanseroene is expected to successfully transition from laboratory to clinical practice, becoming an important candidate drug for treating inflammatory and metabolic diseases.