Product name: Cyperenone
Synonym name: Cyperotundone；(+)-Cyperotundone；Isopatchoulenone
Catalogue No.: BP4184
Cas No.: 3466-15-7
Formula: C₁₅H₂₂O
Mol Weight: 218.34
Botanical Source: Cyperus rotundus L.
Physical Description:
Type of Compound: Sesquiterpenoids

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 Cyperenone

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

Introduction/Overview

Cyperenone (CAS No.: 3466-15-7) is a natural compound classified as a sesquiterpene compound, first isolated from cyperus rotundus and other plants in the Cyperus family. As one of the main active ingredients in traditional Chinese medicine, Cyperus (Cyperus) has attracted widespread attention due to its diverse bioactivity, especially its potential role in anti-inflammatory fields. In recent years, with the deepening of natural product pharmacology, the chemical structure, pharmacological activity, mechanism of action, and druggability evaluation of Xiangfu enone have been systematically elucidated, providing a theoretical foundation for its clinical development.

This paper aims to systematically review the chemical structure and physicochemical properties of Cyperus enone, plant origin and extraction methods, pharmacological activity studies, mechanisms of action and molecular targets, druggability evaluation and pharmacokinetic characteristics, as well as its clinical application prospects and development trends, aiming to provide comprehensive reference materials for researchers in related fields.

Chemical structure and physicochemical properties

The molecular formula of Xiangfu Enone is C15H26O, with a molecular weight of 218.34. Its structure belongs to the sesquiterpene ketone compound, featuring a typical terpene backbone and containing a ketone functional group. According to existing structural analysis, Cyperus enone exhibits high hydrophobicity, with a LogP value of 3.8872, indicating strong lipid solubility that facilitates penetration of lipid bilayer membranes.

Its topological pole surface area (TPSA) is 17.07 Ų, indicating low molecular polarity and poor water solubility (0.0231 mg/mL), which matches its hydrophobicity. Xiangfu enone can effectively cross the blood-brain barrier, suggesting its potential value in central nervous system diseases. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity; The Ames test result was 0.0, indicating no significant mutagenicity and good safety.

In summary, the physicochemical properties of Xiangfu enone are suitable for further pharmacokinetic optimization and clinical development as a drug molecule.

Plant Origins and Extraction Methods

Cyperus rotundus l. Cyperus is mainly found in the volatile oil of Cyperus rotundus L., a perennial herbaceous plant of the Cyperaceae family, widely distributed across Asia, Africa, and parts of Europe. Cyperus is widely used in traditional Chinese medicine to regulate qi and blood, soothe the liver and relieve depression, and relieve pain.

Common methods for extracting Xiangfu enone include steam distillation and organic solvent extraction. Steam distillation is mainly used to extract plant essential oils, with Cyperus enone, one of the main components of volatile oils, in relatively high content. To improve purity, separation and purification techniques such as liquid-liquid extraction and column chromatography (such as silica gel column chromatography and reversed-phase high-performance liquid chromatography) are often combined.

In recent years, supercritical CO2 extraction technology has also been applied to extract Cyperus volatile oil, offering advantages such as high extraction efficiency, good selectivity, and no solvent residue, which helps obtain high-purity Cyperus enone. In addition, modern separation technologies such as preparative HPLC and medium-pressure liquid chromatography are also used for the purification of Cyperus eneone.

Pharmacological activity research

Research on the pharmacological activity of Xiangfu enone mainly focuses on its anti-inflammatory effects and related disease models. In vitro experiments have shown that Xiangfu enone can significantly inhibit the release of various inflammatory mediators, such as tumor necrosis factor α (TNF-α) and interleukin-6 (IL-6), demonstrating good anti-inflammatory effects.

In vivo experiments, Xiangfu enone demonstrated significant anti-inflammatory activity in various inflammation models (such as mouse plantar edema and arthritis models), reducing tissue inflammatory responses and lowering inflammatory factor expression levels. In addition, Xiangfu enone also exhibits auxiliary pharmacological effects such as analgesic and antioxidant effects, further enhancing its therapeutic potential.

In recent years, studies have also found that Xiangfu Enone has inhibitory effects on neuroinflammation, possibly by modulating neuroinflammation-related signaling pathways to alleviate inflammatory damage in neurological diseases. This provides a theoretical basis for its application in the treatment of neurodegenerative diseases and chronic pain.

Mechanism of action and molecular targets

The anti-inflammatory mechanism of xiangfu enone involves multiple molecular targets and signaling pathways. Research shows that its main targets include:

• IL-6 (interleukin 6): Cyperus enone can inhibit the expression and secretion of IL-6, reducing inflammatory responses.
• STAT3 (Signal Transduction and Transcription Activator 3): Blocks the expression of downstream pro-inflammatory genes by inhibiting STAT3 activation.
• CASP1 (caspase 1): Inhibits CASP1 activity, reduces activation of inflammasomes, and lowers the release of pro-inflammatory cytokines.
• TRPV1 and TRPA1 (transient receptor potential channels): regulate these two ion channels to reduce inflammation-related pain signaling.
• PTGS1 and PTGS2 (cyclooxygenases 1 and 2): Inhibit the activity of these two enzymes, reduce prostaglandin synthesis, and relieve inflammation.
• TNF (tumor necrosis factor): Reduces the expression of TNF-α, alleviating inflammatory cascade reactions.
• NOS2 (induced nitric oxide synthase): inhibits NOS2 expression, reduces nitric oxide production, and alleviates oxidative stress.
• NFKB1 (nuclear factor κB subunit 1): blocks the NF-κB signaling pathway and inhibits transcription of inflammatory genes.

Through the synergistic action of multiple targets, Cyperus enone can effectively regulate multiple stages of the inflammatory response, demonstrating broad-spectrum anti-inflammatory effects. Additionally, its regulatory effects on TRPV1 and TRPA1 also give it potential value in pain management.

Druggability evaluation and pharmacokinetics

Druggability evaluation of Xiangfu enone shows it has promising potential for drug development. Its molecular weight is moderate (218.34 Da), meeting the Lipinski rule. A LogP value of 3.8872 indicates good membrane permeability, effectively crossing cell membranes and the blood-brain barrier (BBB has high permeability), making it suitable for drug development for central nervous system diseases.

Lower water solubility (0.0231 mg/mL) may limit its oral bioavailability, but pharmaceutical improvements (such as nanocarriers, solid dispersions, etc.) are expected to enhance its solubility and absorption properties. The hERG channel inhibition test was negative, indicating low cardiotoxicity risk and good safety. The Ames test result was 0, indicating no mutagenicity and meeting safety requirements.

Currently, pharmacokinetic research on Cyperus enone is limited, but preliminary data indicate rapid oral absorption, moderate plasma half-life, and widespread distribution in the body, especially high concentrations in brain tissue. Metabolic pathways may involve the hepatic CYP450 enzyme system, and the metabolites and their activity require further research.

Prospects and outlooks for clinical applications

As a natural compound with significant anti-inflammatory activity, Xiangfu enone has broad clinical application potential. Its therapeutic value in inflammatory diseases (such as rheumatoid arthritis, inflammatory bowel disease, neuroinflammation, etc.) deserves further exploration. Due to its excellent blood-brain barrier penetration, Xiangfu enone has broad application prospects in central nervous system diseases such as Alzheimer's disease, multiple sclerosis, and chronic pain syndrome.

Future research should focus on the preclinical pharmacokinetics and toxicological evaluation of Xianglu Enone, optimizing its formulation to enhance oral bioavailability and targeting. At the same time, by integrating modern molecular biology techniques, the mechanisms of multi-target action are further elucidated, providing theoretical support for precision therapy.

In addition, structural modification and derivative development of Xiangfu enone are also important directions for expanding its pharmaceutical applications. By optimizing its structure, its water solubility, stability, and selectivity for targeting are improved, promising the development of novel anti-inflammatory drugs with greater clinical value.

Conclusion

Xiangfu enone, a natural sesquiterpene ketone compound derived from the traditional Chinese medicine Cyperus, has become a research hotspot in the field of natural product pharmacology due to its remarkable anti-inflammatory activity and good medicinal properties. Its multi-target and multi-pathway mechanism of action provides new ideas and strategies for anti-inflammatory treatment. Although research on its pharmacokinetics and clinical applications is still in its early stages, as research progresses, Xiangfu Enone is expected to become an important candidate for anti-inflammatory and related disease treatment.

In the future, by integrating modern medicinal chemistry, pharmacology, and pharmaceutical technologies, systematic preclinical research and clinical trials of Cyperus enone will be carried out, promoting its transition from the laboratory to clinical practice and benefiting a wide range of patients. The unique advantages of natural products and the potential of Xiangfu enone give it an irreplaceable and important position in the field of natural drug development.