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Synonym name:
Catalogue No.: BP0357
Cas No.: 3779-59-7
Formula: C30H48O5
Mol Weight: 488.709
Botanical Source:
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:
Cimigenol is a potential antitumor compound, combination of it with an autophagy inhibitor may be a valuable strategy for the chemoprevention or treatment of colon cancer. It exerted potent cytotoxic activity against SMMC-7721 (7.87 µM) and A-549 (12.16 µM).
References:
Cancer Manag Res. 2018 Dec 6;10:6715-6729.
Anticancer efficiency of cycloartane triterpenoid derivatives isolated from Cimicifuga yunnanensis Hsiao on triple-negative breast cancer cells.
The roots and rhizomes of Cimicifuga yunnanensis Hsiao are commonly used as anti-inflammatory, antipyretic, and analgesic remedies and detoxification agents in traditional Chinese medicine (TCM). Although C. yunnanensis has been considered as supplementary medicine for several disorders, the antitumor effect of this herb and its key components has not been explored.
METHODS AND RESULTS:
The rhizomes of C. yunnanensis were isolated by chromatographic techniques. Structures of isolated compounds were identified based on spectroscopic methods and comparison with published data. The in vitro anticancer activities of purified components were also performed by MTT experiments. The in vivo anticancer activities were examined by subcutaneous tumor model or a breast cancer liver metastasis model. In this study, we aimed to identify and characterize the effective antitumor components from the rhizomes of C. yunnanensis. By bioassay-guided fractionation techniques and chemical characterization, 12 cycloartane triterpenes and four chromones were isolated, among them, 11 compounds were identified in this genus at first. The identified two compounds showed dramatic inhibitory activities against breast cancer cells: compound 4 (23-epi-26-deoxyactein) and compound 13 (Cimigenol). Then, we examined the antitumor effect of these two selective candidate chemicals on triple-negative breast cancer (TNBC) cells in vivo and found that they could reduce tumor growth in subcutaneous tumor model or breast cancer liver metastasis model.
CONCLUSIONS:
These results suggested that the selective compounds isolated from C. yunnanensis Hsiao could be the promising new agents for TNBC treatment.
Chem Pharm Bull (Tokyo). 2012;60(5):571-7.
Studies on the constituents of Cimicifuga foetida collected in Guizhou Province and their cytotoxic activities.
METHODS AND RESULTS:
Two new triterpenoids and a chromone glycoside, namely, 24-epi-Cimigenol-3-one (1), foetinoside (2), cimifugin-4'-O-[6″-feruloyl]-β-D-glucopyranoside (3), together with 18 known compounds, were isolated from the rhizomes of Cimicifuga foetida L. collected in Guizhou Province, China. All of the compounds were identified by spectroscopic methods, as well as chemical methods.
CONCLUSIONS:
In the in vitro cytotoxicity evaluation of these compounds against 5 human cancer cell lines, Cimigenol (8) exerted the most potent cytotoxic activity against SMMC-7721 (7.87 µM) and A-549 (12.16 µM), while cimiacerin B (9) also showed obvious cytotoxicity against the A-549 cell line, with an IC(50) value of 16.77 µM.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
92.8300
4.5000
3.5000
Low
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No
No
No
Unknown
No
Unknown
No
Cimigenol (CAS No.: 3779-59-7), an important active ingredient in plants of the genus Cimicifuga genus, has attracted significant attention in recent years due to its remarkable antitumor activity. Cimicifuga plants are widely used in traditional Chinese medicine for releasing exterior heat and clearing heat and detoxifying, while modern pharmacological research reveals their rich chemical composition and diverse biological activities. Cimicmarthenol, as a key triterpenoid compound, has shown inhibitory effects on various tumor cells, showing particular potential in the field of liver cancer. As one of the malignant tumors with high incidence and mortality worldwide, liver cancer urgently needs to develop new, highly effective, and low-toxicity treatments. This article provides a systematic review of the chemical structure, origins, pharmacological activity, and mechanism of action of cimicifulol, aiming to provide theoretical basis and research directions for its clinical development and application.
Cimicifalin alcohol is a typical triterpene compound, with a molecular formula of C30H48O5 and a molecular weight of 488.6900. Its structural features include a multicyclic framework and modifications of multiple hydroxyl and ester groups, giving it high biological activity. The LogP value of cimicifalol is 4.5, indicating good lipid solubility and facilitating cell membrane penetration, but also suggesting poor water solubility, which may affect bioavailability. Its topological pole surface area (TPSA) is 92.83 Ų, showing moderate polarity that facilitates binding with biological macromolecules such as proteins. Cimicifulol has five hydrogen bond receptor sites, enhancing its binding ability to target proteins. The blood-brain barrier has low permeability, suggesting its limited role in the central nervous system. Hepatotoxicity remains unclear; cardiotoxicity and hERG channel inhibition tests are negative, indicating preliminary good safety.
Cimicifuga is mainly found in plants of the genus Cimicifuga, such as the rhizome part of Cimicifuga spp.. Cimicifuga plants are widely distributed in temperate regions of the Northern Hemisphere, especially abundant in China, Japan, and North America. Traditionally, the rhizomes of the cimicifuga have been used as medicinal herbs, but modern research extracts cimicificing alcohol through modern separation and purification techniques.
Common extraction methods include solvent extraction, ultrasound-assisted extraction, and liquid chromatography separation. Generally, ethanol or methanol is used as the extraction solvent, combined with multi-stage separation and purification technologies such as silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC), enabling the acquisition of high-purity cimarinol. In recent years, green extraction technologies such as supercritical CO2 extraction have also been attempted to extract cimicifalized alcohol to improve extraction efficiency and environmental friendliness.
Research on the pharmacological activity of cimicifolol mainly focuses on its antitumor effects, particularly its proliferation inhibition and apoptosis induction effects on liver cancer cells. In vitro cell experiments have shown that cimicifol can significantly inhibit the proliferation of liver cancer cell lines (such as HepG2, Huh7, etc.), induce cell cycle arrest, and promote apoptosis. In addition, cimicifol exhibits anti-inflammatory and antioxidant auxiliary effects, helping to improve the tumor microenvironment.
Animal model studies further confirmed the anti-tumor activity of cimicmarinol. In mouse liver cancer transplantation models, the cimicalinol treatment group showed significantly reduced tumor volume, prolonged survival, and no obvious toxic side effects. Relevant mechanistic studies have shown that cimicifoliol exerts its anti-tumor effects by regulating multiple cellular signaling pathways.
The antitumor mechanism of cimicifoliol involves multiple molecular targets and signaling pathways, especially targeting key proteins and genes related to liver cancer. The main targets include:
Through multi-target coordinated regulation, cimicifoliol can effectively inhibit the growth, invasion, and metastasis of liver cancer cells, demonstrating broad-spectrum and comprehensive anti-tumor potential.
The druggability parameters of cimicifulol indicate that it has certain development potential. The molecular weight of 488.69, although slightly above the Lipinski rule recommended below 500, is still within an acceptable range. A LogP value of 4.5 indicates good lipid solubility, which facilitates cell membrane penetration, but insufficient water solubility may affect oral bioavailability. TPSA is 92.83 Ų, indicating moderate polarity, which helps bind to biological targets.
In terms of safety, cimicmarinol showed no cardiotoxicity or hERG channel inhibition, reducing the risk of cardiovascular side effects. Hepatotoxicity and genotoxicity (Ames test) do not have clear data and require further systematic evaluation. The low permeability of the blood-brain barrier suggests it mainly acts on peripheral tissues and reduces adverse reactions in the central nervous system.
Pharmacokinetic research is still in its early stages, and metabolic pathways in vivo may involve redox reactions in liver enzyme systems. In the future, further research is needed on its absorption, distribution, metabolism, and excretion (ADME) characteristics to optimize administration regimens and formulation design.
Cimicifal, as a natural compound with multi-target anti-tumor activity, shows promising application prospects, especially in the field of liver cancer treatment. Its multi-mechanism action not only inhibits tumor cell proliferation but also blocks pro-cancer signals in the tumor microenvironment, offering potential synergistic therapeutic advantages. By combining modern drug design with nanocarrier technology, it is expected to enhance bioavailability and targeting, reducing side effects.
Future clinical translational research should focus on optimizing the pharmacokinetics, toxicological safety assessment, and combination therapy strategies for cimicifinol. By combining with existing liver cancer treatments (such as targeted drugs and immune checkpoint inhibitors), it is possible to enhance efficacy and overcome resistance. In addition, the potential role of cimicifalinol in other tumor types and inflammation-related diseases is also worth further exploration.
As an important triterpene compound in the genus Cimicifuga species, Cimicifalxol demonstrates significant therapeutic potential for liver cancer thanks to its unique chemical structure and multi-target anti-tumor mechanism. Current research has preliminarily revealed its target of action and signaling pathway, and druggability evaluations have shown good safety and development prospects. In the future, through systematic pharmacokinetic studies, toxicological evaluations, and clinical trials, cimicifolol is expected to become an important candidate molecule for the development of natural anti-tumor drugs, offering new treatment options for liver cancer patients. Ongoing basic and applied research will drive it from the laboratory to clinical practice, promoting the widespread use of natural products in modern cancer treatment.
Shenshuai
Wenjing
Hedandan
