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Synonym name:
Catalogue No.: BP0420
Cas No.: 19431-84-6
Formula: C15H22O2
Mol Weight: 234.339
Botanical Source: Curcuma zedoaria (zedoary) and Curcuma longa (turmeric)
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Description:
Curcumenol possesses a variety of health and medicinal values which includes neuroprotection, anti-inflammatory, anti-tumor and hepatoprotective activities. It inhibits NF-κB activation by suppressing the nuclear translocation of the NF-κB p65 subunit and blocking IκBα phosphorylation and degradation.
References:
Phytother Res. 2010 Aug;24(8):1213-6.
Inhibitory effects of curcumenol on human liver cytochrome P450 enzymes.
Curcumenol, one of the major components of Zedoary turmeric oil, has been widely used to treat cancer and inflammation. As an antibiotic or anticancer drug, Curcumenol is highly likely to be used in combination with various synthetic drugs in most cases, thus it is necessary to evaluate potential pharmacokinetic drug-drug interactions induced by Curcumenol.
METHODS AND RESULTS:
In this study, the inhibitory effects of Curcumenol on seven CYP isoforms were investigated, and the results demonstrated that only CYP3A4 was strongly inhibited (IC(50) = 12.6 +/- 1.3 microM). Kinetic analysis showed the inhibition type was competitive with K(i) value of 10.8 microM. Time- and NADPH-dependent inhibitions were also investigated to show Curcumenol is not a mechanism-based inhibitor. Employing these in vitro data and maximum plasma concentration of Curcumenol in human predicted from beagle dog's in vivo pharmacokinetic data, the change in AUC of victim drugs was predicted to be 0.4%, which suggested that Curcumenol may be safely used without inducing metabolic drug-drug interaction through P450 inhibition. Nevertheless, due to the limited pharmacokinetic data available for Curcumenol in humans, it is still not possible to evaluate its potential clinical effects on human patients from in vitro data.
CONCLUSIONS:
Thus, the magnitude of drug-drug interaction (DDI) induced by Curcumenol warrants further investigation.
HPLC of Curcumenol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
38.6900
2.6100
2.6100
High
null
No
No
No
Unknown
No
Unknown
null
Curcumenol, CAS number 19431-84-6, is an important natural active ingredient isolated from the ginger family plant Curcuma zedoaria. As a sesquiterpene compound, curcuma enol has attracted attention for its diverse pharmacological activities, especially showing significant biological effects in neuroprotection, anti-inflammation, anti-tumor, and liver protection. In recent years, with deepening pharmacological research on natural products, the molecular mechanisms of curcuma enol have gradually been revealed, especially showing unique advantages in regulating inflammatory responses and tumor cell signaling pathways.
Curcuma enol, as a highly effective CYP3A4 enzyme inhibitor (IC50=12.6 μM), not only affects drug metabolism kinetics but may also exert multiple biological effects by modulating intracellular signaling pathways. Its role in inhibiting Akt-mediated NF-κB activation and the p38 MAPK signaling pathway in LPS-stimulated BV-2 microglia suggests its potential application value in neuroinflammation and immune regulation. At the same time, curcuma enol has regulatory effects on molecular targets related to liver cancer such as BCL2, STAT3, MMP9, EGFR, TP53, and AKT1, demonstrating its potential as an antitumor drug candidate.
This paper will systematically review the chemical structure and physicochemical properties of curcuma enol, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and explore its clinical application prospects and future research directions, aiming to provide scientific basis and theoretical support for drug development of this natural product.
Curcuma enol is a sesquiterpene compound with the molecular formula C15H26O2 and a molecular weight of 234.34. Its structural features include a ring-shaped framework containing hydroxyl groups, with a certain balance of hydrophobicity and polar groups. Its LogP value is 2.61, indicating that the molecule has moderate lipid solubility, which is beneficial for cell membrane penetration and distribution in vivo. TPSA (topological pole surface area) is 38.69 Ų, with 2 hydrogen bond receptors. These physicochemical parameters meet good drug compatibility, which is beneficial for oral absorption and blood-brain barrier penetration.
The presence of hydroxyl groups in the structure of curcuma enol gives it a certain degree of hydrophilicity, while its hydrophobic sesquiterpene framework ensures molecular stability and biological activity. Its high blood-brain barrier permeability suggests its potential application in central nervous system diseases. In vitro and in vivo toxicological studies showed that curcuma enol showed no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition, making it relatively safe.
Curcuma zedoaria enol mainly comes from the ginger family plant Curcuma zedoaria, which is widely distributed in tropical and subtropical Asia. In traditional Chinese medicine, its dried tubers are often used medicinally, with effects such as promoting blood circulation, removing blood stasis, reducing swelling, and relieving pain. As one of the main active components in Curcuma zedoaria, its content varies depending on the plant's growing environment, harvest period, and processing method.
Common methods for extracting curcuma enol include solvent extraction, chromatographic separation, and crystallization purification. Generally, ethanol or methanol is used as extraction solvents, followed by reflux extraction or ultrasonic-assisted extraction to obtain crude extracts, followed by separation and purification by silica gel column chromatography or high-performance liquid chromatography (HPLC). In recent years, supercritical CO2 extraction technology has gradually been applied to the extraction of curcuma enol due to its environmental friendliness and high efficiency, significantly improving extraction efficiency and purity.
Optimizing the extraction process not only improves the yield of curcuma enol but also ensures the stability of its biological activity, laying the foundation for subsequent pharmacological research and drug development.
Curcuma enol exhibits a variety of pharmacological activities, covering neuroprotection, anti-inflammation, anti-tumor, and liver protection.
Curcuma enol exhibits significant neuroprotective effects in models of neurological diseases. Studies have shown that in LPS-stimulated BV-2 microglia, curcuma enol can inhibit Akt-mediated activation of the NF-κB signaling pathway and the p38 MAPK pathway, reduce the expression of inflammatory factors such as TNF-α and IL-1β, and alleviate neuroinflammatory responses. This mechanism of action helps alleviate inflammatory damage in neurodegenerative diseases, suggesting its potential application value in neurological diseases such as Alzheimer's and Parkinson's.
Curcuma enol regulates inflammatory signaling pathways through multiple targets, demonstrating good anti-inflammatory activity. It can inhibit NF-κB nuclear translocation, reduce the release of pro-inflammatory cytokines, regulate immune cell activity, and reduce the generation of inflammatory mediators. In vivo inflammation models, curcuma enol significantly reduced edema and cellular infiltration in inflamed tissues, demonstrating good anti-inflammatory effects.
Curcuma enol exhibits proliferation inhibition and apoptosis-inducing effects on various tumor cells, with particularly in-depth research in the field of liver cancer. Its targets involve key molecules such as BCL2, STAT3, TOP1, TERT, PIK3CA, MMP9, EGFR, TP53, NFKB1, and AKT1, regulating the cell cycle, apoptosis signaling, and tumor microenvironment. Curcuma enol reduces tumor cell proliferation and invasiveness by inhibiting the STAT3 and AKT signaling pathways, while promoting the expression of apoptosis-related proteins and inhibiting tumor growth and metastasis.
Curcuma enol demonstrates significant liver-protective effects in liver injury models, reducing hepatocyte necrosis and inflammatory responses, and promoting hepatocyte repair. Its mechanism may be related to antioxidant, anti-inflammatory, and regulatory signaling pathways related to hepatocyte apoptosis, demonstrating potential for protecting liver function.
The multiple pharmacological effects of curcuma enol are mainly attributed to its ability to regulate key cellular signaling pathways. Its mechanism of action involves the following aspects:
Curcuma enol is a highly effective CYP3A4 inhibitor with an IC50 value of 12.6 μM. CYP3A4, as the main drug-metabolizing enzyme in the human body, participates in the metabolic processes of various drugs. Curcuma enol may affect drug metabolism by inhibiting this enzyme activity, suggesting that potential drug interactions should be noted when combining drugs.
In inflammation and tumor cells, curcuma enol blocks nuclear translocation and transcriptional activity of NF-κB by inhibiting the activation of Akt kinase, reducing the expression of pro-inflammatory cytokines, and suppressing inflammatory responses and tumor cell survival signals. Inhibition of this pathway is of great significance for reducing neuroinflammation and tumor progression.
Curcuma enol can inhibit phosphorylation of p38 MAPK, weaken the release of inflammatory mediators and cell stress responses, and exert anti-inflammatory and cell-protective effects.
Curcuma enol exerts antitumor effects by modulating various liver cancer-related targets, including:
The synergistic regulation of these molecular targets enables curcuma enol to demonstrate comprehensive anti-tumor effects with multiple targets and pathways in liver cancer treatment.
The druggability parameters of curcuma enol indicate that it has good potential for drug development. The molecular weight is 234.34, meeting the Lipinski rule, with a LogP of 2.61, indicating moderate lipid solubility, which is beneficial for oral absorption and internal distribution. TPSA is 38.69, with 2 hydrogen bond receptors, both of which help molecules penetrate cell membranes and the blood-brain barrier.
Its high blood-brain barrier permeability makes it possible for treating neurological diseases. In vivo and in vitro toxicological data showed that Curcuma Enol showed no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition, indicating relatively high safety. Ames-induced mutagenic test results are still unclear, and further research is needed to assess their genotoxicity risk.
In terms of pharmacokinetics, there are currently few systematic studies on curcuma enol. Preliminary data indicate good oral bioavailability, wide distribution in the body, and particularly high concentrations in liver and brain tissue. The metabolic pathway may involve the hepatic CYP450 enzyme system, especially the inhibitory effect of CYP3A4, suggesting it may affect the metabolism of the patient and other drugs, requiring further research.
As a multifunctional natural product, curcuma enol has broad clinical application prospects due to its multiple pharmacological activities—including neuroprotection, anti-inflammation, anti-tumor, and liver protection.
In neurodegenerative diseases such as Alzheimer's and Parkinson's, curcuma enol protects neuronal function by inhibiting neuroinflammation and oxidative stress, offering potential therapeutic value. In the future, combined with modern drug delivery technologies, curper enol formulations targeting the central nervous system can be developed.
In the field of liver cancer treatment, curcuma enol regulates tumor cell proliferation, apoptosis, and metastasis through multiple targets, demonstrating potential as an adjunctive therapy. Its combination with existing chemotherapy drugs may enhance efficacy and reduce side effects, making it worthwhile to conduct preclinical and clinical trial validation.
Moreover, the anti-inflammatory and hepatoprotective effects of curcuma enol give it research value for its application in chronic liver and inflammatory diseases. In the future, pharmacokinetic and toxicological research should be strengthened to clarify safe dosage ranges and long-term risks.
Although curcuma enol demonstrates good druggability and multiple biological effects, key issues such as in vivo metabolic stability, targeting, and formulation development still need to be addressed. Integrating modern medicinal chemistry, pharmacology, and pharmaceutical technologies to promote the transformation of curlotene alcohol from a natural product into a clinical drug is an important direction for future research.
As an important active ingredient in curcuma zedoaria, enol has become a hot topic in natural product pharmacology research due to its unique chemical structure and diverse pharmacological activities. Its remarkable effects in neuroprotection, anti-inflammation, anti-tumor, and liver protection, as well as its regulation of multiple key molecular targets, lay the foundation for its status as a potential drug candidate.
In the future, by deeply analyzing the mechanism of action of curcuma enol, optimizing extraction and preparation processes, and improving pharmacokinetics and safety evaluations, clinical application will be promoted. Research on curcuma enol not only enriches the theoretical framework of natural product pharmacology, but also provides valuable scientific basis and innovative ideas for developing novel multi-target natural drugs.
Shenshuai
Wenjing
Hedandan
