Product name: Alpha Cyperone
Synonym name: (+)-Alpha Cyperone; 4,11-Selinadien-3-one; (-)-Alpha Cyperone, 23665-61-4
Catalogue No.: BP0152
Cas No.: 473-08-5
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.




Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.

HPLCof Alpha Cyperone

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

Introduction/Overview

α-Cyperone (CAS No.: 473-08-5) is a natural sesquiterpene compound isolated from the traditional Chinese medicine Cyperus rotundus L. As one of the main active ingredients of Cyperus luteus, α-Cyperus ketone has attracted attention for its remarkable pharmacological activity, especially showing potential therapeutic value in anti-inflammatory, antioxidant, and metabolic regulation fields. In recent years, with in-depth research into the mechanisms of chronic inflammation-related diseases, α-Xiangfu ketone has demonstrated good anti-inflammatory effects by regulating the expression of inflammation-related molecules such as Cox-2, IL-6, and cytoskeleton-regulating proteins Nck-2, Cdc42, and Rac1. In addition, α-Xiangfu ketone also shows certain potential in the treatment of metabolic diseases such as hyperglycemia, involving multiple key targets such as EHMT2, AMPK, and SGLT2.

This paper provides a systematic review of the chemical structure and physicochemical properties of α-Cyperus, plant origin, and extraction methods, with a focus on its pharmacological activity and molecular mechanisms. Combined with druggability evaluation and pharmacokinetic data, it explores its clinical application prospects and development directions, aiming to provide researchers in the field of natural product pharmacology with comprehensive and in-depth reference materials.

Chemical structure and physicochemical properties

α-Xiangfu ketone is a sesquiterpene ketone compound with a molecular formula of C15H22O and a molecular weight of 218.34. Its structural features include a sesquiterpene skeleton containing a circular framework and a ketone group, which imparts certain polarity and reactivity. In terms of physicochemical properties, the LogP value of α-Cyperus ketone is 3.5, indicating moderate lipid solubility, which facilitates penetration of cell membranes and the blood-brain barrier (BBB has high permeability). Its topological polar surface area (TPSA) is 17.07 Ų, with only one hydrogen bond acceptor, indicating low molecular polarity and beneficial for enhancing bioavailability in vivo.

Additionally, α-Xiangfu ketone is neither hepatotoxic nor cardiotoxic, and does not inhibit hERG channels. Ames mutagenic assay results were negative, indicating high safety and a solid foundation for druggability. These physicochemical and toxicological characteristics lay a solid foundation for its potential drug molecules.

Plant Origins and Extraction Methods

α-Cyperus ketone is mainly found in the volatile oil of Cyperus rotundus L., a plant of the Cyperaceae family, widely distributed in Asia, Africa, and parts of Europe. It is an important herb in traditional Chinese medicine for regulating qi and blood, relieving pain, and fighting inflammation. Cyperus volatile oil is rich in sesquiterpene components, with α-Cyperus ketone being relatively high, which is one of its main active components.

Common methods for extracting α-Cyperus ketone include steam distillation and solvent extraction. Steam distillation is suitable for extracting Cyperus volatile oil, followed by chromatographic separation techniques (such as column chromatography and preparative high-performance liquid chromatography) to purify α-Cyperus ketone. Solvent extraction usually uses ethanol or ethyl acetate as extractors, combined with ultrasound-assisted extraction or reflux extraction to improve extraction efficiency. During purification, technologies such as silica gel column chromatography and reversed-phase HPLC can be used to obtain high-purity α-Xiangfu ketone, which facilitates subsequent pharmacological research.

In recent years, with the development of extraction technology, supercritical CO2 extraction technology has also been applied to the extraction of Cyperus volatile oil, offering advantages of environmental friendliness and high extraction efficiency, providing new ideas for the industrial production of α-Cyperus ketone.

Pharmacological activity research

Pharmacological activity studies of α-Cyperus ketone mainly focus on its anti-inflammatory, antioxidant, and metabolic regulatory effects.

Anti-inflammatory effects

Numerous in vivo and in vitro experiments have shown that α-Xiangfu ketone can significantly suppress inflammatory responses. Its mechanism involves downregulating the expression of inflammation-related enzymes and cytokines, such as cyclooxygenase-2 (Cox-2) and interleukin-6 (IL-6). Cox-2, as a key enzyme in inflammatory mediator synthesis, has reduced expression that directly reduces prostaglandin production and alleviates inflammatory responses. As a multifunctional pro-inflammatory cytokine, IL-6 plays a key role in various inflammatory diseases. α-Xiangfu ketone regulates immune responses and alleviates inflammatory symptoms by inhibiting IL-6 expression.

In addition, α-Xiangfu ketone also affects the expression of cytoskeleton-related proteins Nck-2, Cdc42, and Rac1. These proteins are involved in cell migration, morphological changes, and signal transduction, regulating the activation and chemotaxis of inflammatory cells, and further exerting anti-inflammatory effects.

Antioxidant effects

Oxidative stress is an important mechanism for the occurrence and development of various chronic diseases. α-Xiangfu ketone has the ability to scavenge free radicals and reduce oxidative damage, enhancing intracellular antioxidant enzyme activity, reducing cell damage caused by oxidative stress, and protecting tissue function.

Metabolic regulation

In research on hyperglycemia and related metabolic diseases, α-Xiangfufen has shown potential in regulating blood sugar and improving metabolic disorders. Although its direct target is not yet fully understood, related studies suggest that it may participate in glucose metabolism, insulin signaling, and energy homeostasis regulation by regulating the expression and function of key proteins such as EHMT2, UBP2, PAI1, AMPK, SGLT2, GCK, APP, BACE1, CES1, and PTPN1.

Among them, AMPK acts as a central regulator of energy metabolism, and α-Cyperus activates the AMPK pathway, helping to improve insulin resistance and promote glucose uptake. Inhibition of SGLT2 helps reduce renal glucose reabsorption and alleviate hyperglycemic levels.

Mechanism of action and molecular targets

The mechanisms of action of α-Xiangfu ketone are complex and diverse, covering multiple signaling pathways and molecular targets, mainly reflected in the following aspects:

Anti-inflammatory mechanism

• Inhibition of Cox-2 expression: By blocking the NF-κB signaling pathway, it reduces Cox-2 gene transcription, lowers prostaglandin E2 (PGE2) production, and alleviates inflammatory responses.
• Downregulate IL-6 levels: inhibits the release of pro-inflammatory cytokine IL-6, modulates immune cell activity, and alleviates chronic inflammation.
• Regulating cytoskeletal proteins: Nck-2, Cdc42, and Rac1 are Rho family small GTPase-related proteins involved in cell migration and inflammatory cell activation. α-Xiangfu ketone intervenes in the chemotaxis and adhesion processes of inflammatory cells by inhibiting the expression of these proteins, thereby reducing infiltration of inflammatory cells.

Metabolic regulatory mechanisms

• EHMT2 (histone methyltransferase 2): involved in epigenetic regulation, affecting the expression of genes related to glucose metabolism. α-Xiangfu ketone may improve metabolic abnormalities by modulating EHMT2 activity.
• AMPK activation: promotes glucose uptake and fatty acid oxidation, improving insulin sensitivity.
• SGLT2 inhibition: reduces renal glucose reabsorption and lowers blood sugar levels.
• GCK (glucokinase) regulation: promotes glucose metabolism in the liver and pancreas.
• PTPN1 (protein tyrosine phosphatase 1B) inhibition: enhances insulin signaling and improves insulin resistance.

Additionally, the regulation of APP and BACE1 by α-Xiangfu ketone suggests potential protective effects in neurodegenerative diseases, warranting further study.

Druggability evaluation and pharmacokinetics

The druggability evaluation of α-Xiangfu ketone shows it has promising drug development potential:

• Molecular weight 218.34, conforming to the Lipinski rule, facilitating oral absorption.
• LogP 3.5, moderate lipid solubility, facilitates cell membrane penetration and blood-brain barrier penetration, supporting its potential application in central nervous system diseases.
• TPSA 17.07, with extremely low polarity, helps improve bioavailability.
• The number of hydrogen bond receptors is 1, which helps with molecular binding affinity and pharmacokinetic properties between the molecule and the target.
• The blood-brain barrier has high penetration, offering possibilities for treating neurological diseases.
• Good safety: No hepatotoxicity or cardiotoxicity, no hERG channel inhibition, negative Ames test indicates low risk of toxic side effects.

Pharmacokinetics, although there are few current literature reports, based on its physicochemical properties, α-Cyperus ketone is well absorbed orally and widely distributed, especially possibly enriched in the central nervous system. Its metabolic pathway may involve liver enzymes, with excretion mainly via the kidneys. In the future, systematic ADME (Absorption, Distribution, Metabolism, Excretion) studies are needed to clarify its behavior in vivo.

Prospects and outlooks for clinical applications

Based on the multi-target regulatory capability and good safety profile of α-Xiangfu ketone, its clinical application prospects in various diseases are broad:

• Chronic inflammatory diseases: such as rheumatoid arthritis and inflammatory bowel disease, α-Xiangfu ketone has potential anti-inflammatory therapeutic value by inhibiting inflammatory factors like Cox-2 and IL-6.
• Metabolic diseases: In the treatment of hyperglycemia and diabetes-related complications, α-Xiangfu ketone is expected to improve blood sugar control and metabolic disorders by regulating targets such as AMPK and SGLT2.
• Neurodegenerative diseases: Regulating APP and BACE1 expression suggests that it may play a neuroprotective role in neurodegenerative diseases such as Alzheimer's disease.
• Central nervous system diseases: The high blood-brain barrier penetration gives it potential for research on neuropsychiatric disorders such as depression and anxiety.

Future research should focus on the preclinical pharmacokinetics and toxicology evaluation of α-Cyperus, systematic in vivo disease model validation, and optimization of dosage forms and administration regimens. Additionally, based on its multi-target mechanism of action and combined with modern drug design technologies, developing α-Xiangfu ketone derivatives or combination therapy strategies will help enhance their clinical translational value.

Conclusion

As a natural sesquiterpene ketone derived from the traditional Chinese medicine Cyperus, α-Xiangfu ketone has become an important research subject in the field of natural product pharmacology due to its remarkable anti-inflammatory and metabolic regulatory activities, as well as its excellent medicinal properties. By regulating inflammatory and metabolic molecules through multiple targets and pathways, it demonstrates broad pharmacological potential and promising clinical applications. In the future, by combining modern pharmacology and medicinal chemistry techniques, the mechanism of action and in vivo behavior of α-Cyperus ketone will provide a solid foundation for its development into a novel natural drug and promote its application in the treatment of chronic inflammatory and metabolic diseases.