Product name: 7-Prenyloxycoumarin
Synonym name:
Catalogue No.: BP4202
Cas No.: 10387-50-5
Formula: C₁₄H₁₄O₃
Mol Weight: 230.263
Botanical Source:
Type of Compound:

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.

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

Introduction/Overview

7-Prenyloxycoumarin (CAS No.: 10387-50-5), also known as 7-O-Prenylumbelliferone, is a natural secondary metabolite derived from the endophytic fungus Annulohypoxylon ilanense. As a derivative of coumarin-class compounds, 7-isoprenyl oxycoumarin, due to its unique structural modification, has attracted widespread attention in the field of natural product pharmacology. In recent years, with in-depth research into its anti-inflammatory activity and related molecular mechanisms, this compound has shown promising potential for drug development. This paper systematically reviews the chemical structure, origins, pharmacological activity, mechanism of action, druggability evaluation, and future clinical application prospects of 7-isopentenoxycoumarin, aiming to provide a theoretical basis and research direction for drug development of this class of natural products.

Chemical structure and physicochemical properties

7-isoprenyl oxycoumarin, a coumarin-type compound, is structurally based on the coumarin-based backbone, with an isopentyl group attached at the hydroxyl position of position 7 via an ether bond. Its molecular formula is C14H14O3, and its molecular weight is 230.2630. The introduction of this structure gives it high lipophilicity, with a LogP value of 3.4143, indicating moderate lipophilicity that facilitates penetration of cell membranes and biological barriers.

In terms of physicochemical properties, 7-isopentyloxycoumarin's polar surface area (TPSA) is 39.44 Ų, and a lower TPSA helps with cell membrane permeability. Its water solubility is relatively low, about 0.0141 mg/mL, showing poor water solubility, which somewhat limits its absorption in the body but may also facilitate its distribution in lipid environments. Additionally, this compound has a high blood-brain barrier penetration capability, suggesting its potential application value in the treatment of central nervous system-related diseases. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames trial scored 0.9, indicating a low genotoxicity risk and good safety.

Plant Origins and Extraction Methods

7-isoprenyl oxycoumarins were originally isolated from the endophytic fungus Annulohypoxylon ilanense. Fungi of the genus Annulohypoxylon are widely distributed in tropical and subtropical regions, and their endophytic fungal communities are a rich source of secondary metabolites. The discovery of this compound expands the range of coumarin natural products and highlights the importance of endophytic fungi as medicinal natural product resources.

Extraction methods typically include solid culture fermentation of fungi, followed by organic solvents such as ethyl acetate and methanol. After concentration, the extract was separated and purified using column chromatography (silica gel column, C18 reversed-phase column) and high-performance liquid chromatography (HPLC) technology, ultimately obtaining high-purity 7-isoprenyoxycoumarin. In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, providing technical support for large-scale preparation.

Pharmacological activity research

Pharmacological studies on 7-isoprelene oxycoumarin, mainly focusing on their anti-inflammatory effects. As the common pathological basis of multiple diseases, the development of drugs targeting inflammatory signaling pathways is of great clinical significance. Both in vitro cell and in vivo animal models have confirmed that 7-isoprenyloxycoumarins can significantly inhibit the expression and release of various inflammatory mediators.

Specifically, this compound can downregulate the expression of pro-inflammatory cytokines IL-6 and TNF-α, inhibit the activity of inflammation-related enzymes PTGS1 (COX-1) and PTGS2 (COX-2), and reduce the synthesis of inflammatory mediators. Additionally, 7-isoprelene oxycoumarins significantly inhibit the activity of key inflammatory signal transduction factor STAT3 and transcription factor NFKB1, thereby blocking the transmission of inflammatory signals. Its regulatory effect on the inflammation-related ion channels TRPV1 and TRPA1 further alleviates neuroinflammation and pain responses. Inhibition of CASP1 (caspase-1) helps reduce the activation of inflammasomes and lessens the inflammatory cascade. The inhibition of NOS2 (induced nitric oxide synthase) reduces the occurrence of oxidative stress, protecting tissues from inflammatory damage.

Additionally, some studies show that 7-isoprelene oxycoumarins have antioxidant activity, can eliminate free radicals, reduce oxidative stress, and synergistically exert anti-inflammatory effects. Its anti-inflammatory activity shows good therapeutic potential in various disease models including inflammatory bowel disease, arthritis, and neuroinflammation.

Mechanism of action and molecular targets

The anti-inflammatory mechanism of 7-isopentyloxycoumarins involves regulation of multiple signaling pathways and molecular targets. Its main targets include:

• IL-6 (interleukin-6): As a pro-inflammatory cytokine, IL-6 plays a key role in the inflammatory response. 7-isopenteneoxycoumarin, by inhibiting IL-6 expression, weakens the amplification effect of inflammatory signals.

• STAT3 (Signal Transduction and Transcription Activator 3): The IL-6-mediated STAT3 signaling pathway plays an important role in inflammation and tumorigenesis. This compound inhibits the phosphorylation and nuclear translocation of STAT3, blocking its transcriptional activity.

• CASP1 (caspase-1): CASP1 mediates inflammasome activation and promotes the maturation and release of IL-1β and IL-18. 7-isopenteneoxycoumarin, by inhibiting CASP1 activity, reduces the inflammatory cascade.

• TRPV1 and TRPA1 (Transient Receptor Potential Channels): These two ion channels play important roles in inflammatory pain and neuroinflammation. The regulation of this compound helps relieve pain and inflammation.

• PTGS1 and PTGS2 (cyclooxygenase-1 and -2): catalyze prostaglandin synthesis and are important sources of inflammatory mediators. 7-isopentenoxycoumarins inhibit their activity and reduce prostaglandin production.

• NOS2 (induced nitric oxide synthase): Excess NO is involved in inflammation and oxidative stress. This compound inhibits NOS2 expression and lowers NO levels.

• NFKB1 (nuclear factor κB subunit): As a core transcription factor for inflammatory signals, inhibition of NFKB1 is an important mechanism for anti-inflammatory drugs. 7-isopentenoxycoumarin, by blocking NFKB1 activation, reduces the expression of pro-inflammatory genes.

In summary, 7-isopentenoxycoumarin, through multi-target and multi-pathway synergistic effects, systematically regulates inflammatory responses and demonstrates a relatively comprehensive anti-inflammatory mechanism.

Druggability evaluation and pharmacokinetics

From the perspective of druggability, 7-isopentenoxycoumarins possess relatively ideal medicinal properties. Its molecular weight of 230.2630 complies with the Lipinski rule, and its LogP value of 3.4143 indicates moderate lipid solubility, which is beneficial for absorption and distribution in the body. TPSA is 39.44 Ų, and its low polarity helps with cell membrane penetration and blood-brain barrier penetration. Experimental data also confirm its high central nervous system penetration, making it suitable for treating central diseases such as neuroinflammation.

Low water solubility (0.0141 mg/mL) is a potential formulation challenge, requiring improved bioavailability through technologies such as nanocarriers, liposomes, or solid dispersions. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity and good safety. The Ames test score of 0.9 indicates a low genotoxicity risk and is suitable for further drug development.

Currently, pharmacokinetic data on it in vivo are limited, but based on structural speculation, the compound may undergo hepatic metabolism, mainly cleared through oxidative and binding reactions. In the future, systematic ADME (absorption, distribution, metabolism, excretion) and toxicology studies are needed to comprehensively assess its drug development potential.

Prospects and outlooks for clinical applications

7-isopentenoxycoumarin, as a multi-target anti-inflammatory natural product, has broad clinical application prospects. Its inhibitory effect on key inflammatory signaling pathways such as IL-6/STAT3 and NFKB1 gives it potential advantages in treating inflammatory diseases such as rheumatoid arthritis, inflammatory bowel disease, neuroinflammation, and chronic pain.

Moreover, its excellent blood-brain barrier penetration ability makes drug development possible for neurological diseases, such as multiple sclerosis and Alzheimer's-related inflammation. Combined with its low toxicity and good druggability, 7-isopentyloxycoumarins can be a candidate molecule for novel anti-inflammatory drugs.

Future research should focus on pharmacokinetic optimization, formulation development, and preclinical safety evaluation. At the same time, combining modern drug design technologies, such as structural optimization and targeted delivery system construction, is expected to enhance its clinical application value. Based on its multi-target mechanism of action, combined strategies with other drugs can also be explored to achieve synergistic therapeutic effects.

Conclusion

7-isopentyloxycoumarin, as a secondary metabolite of the endophytic fungus of Annulohypoxylon ilanense, demonstrates promising drug development potential due to its unique structure and multi-target anti-inflammatory effects. Its mechanism of action in regulating key inflammatory molecules such as IL-6, STAT3, and NFKB1 and related ion channels provides new ideas for anti-inflammatory drug development. Although its low water solubility and pharmacokinetic properties require further research, its good safety and blood-brain barrier penetration give it unique advantages in treating central nervous system diseases.

In the future, by integrating modern medicinal chemistry and pharmacological techniques, 7-isopentyloxycoumarins are expected to become an important natural drug candidate in the anti-inflammatory field, providing new drug options for the treatment of inflammation-related diseases. Systematic preclinical research and mechanism exploration will lay a solid foundation for clinical translation.