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℃
Cimigenol (CAS number: 3779-59-7), as an important active ingredient in plants of the Cimicium genus, has attracted much attention in recent years due to its significant anti-tumor activity. The plants of the Cistanche genus are widely used in traditional Chinese medicine for the treatment of surface heat dissipation, clearing heat and detoxifying. Modern pharmacological research has revealed their rich chemical composition and diverse biological activities. As a key triterpenoid compound, coumarin has shown inhibitory effects on various tumor cells, especially in the field of liver cancer, demonstrating great potential. As one of the malignant tumors with high incidence rate and mortality worldwide, liver cancer urgently needs to develop new effective and low toxic therapeutic drugs. This article provides a systematic review of the chemical structure, sources, pharmacological activity, and mechanism of action of coumarin, aiming to provide theoretical basis and research direction for its clinical development and application.
Shengma alcohol is a typical triterpenoid compound with a molecular formula of C30H48O5 and a molecular weight of 488.6900. Its structural characteristics include a multi ring skeleton and modifications with multiple hydroxyl and ester groups, endowing it with high biological activity. The LogP value of coumarin is 4.5, indicating that it has good lipid solubility, which is beneficial for cell membrane penetration. However, it also suggests that its water solubility is poor, which may affect its bioavailability. Its topological polar surface area (TPSA) is 92.83 Å ², indicating moderate polarity that facilitates binding with biomolecules such as proteins. Shengma alcohol has 5 hydrogen bond receptor sites, enhancing its binding ability with target proteins. The low permeability of the blood-brain barrier suggests its limited role in the central nervous system. Hepatotoxicity is not yet clear, and cardiac toxicity and hERG channel inhibition experiments are negative, indicating preliminary good safety.
Cimicifuga alcohol mainly exists in plants of the Cimicifuga genus, such as the rhizomes of Cimicifuga spp. The plants of the Cistanche genus are widely distributed in temperate regions of the Northern Hemisphere, especially in China, Japan, and North America where they have abundant resources. Traditionally, the roots and stems of Cistanche have been used as traditional Chinese medicine, while modern research has extracted coumarin 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 techniques such as silica gel column chromatography, reverse phase high performance liquid chromatography (RP-HPLC), etc., to obtain high-purity coumarin. In recent years, green extraction techniques such as supercritical CO2 extraction have also been attempted to be applied to the extraction of coumarin to improve extraction efficiency and environmental friendliness.
The pharmacological activity research of coumarin mainly focuses on its anti-tumor effect, especially its proliferation inhibition and apoptosis induction effect on liver cancer cells. In vitro cell experiments have shown that coumarin can significantly inhibit the proliferation of liver cancer cell lines (such as HepG2, Huh7, etc.), induce cell cycle arrest, and promote cell apoptosis. In addition, coumarin also exhibits auxiliary effects such as anti-inflammatory and antioxidant properties, which help improve the tumor microenvironment.
Animal model studies further confirmed the anti-tumor activity of coumarin. In the mouse liver cancer transplantation model, the tumor volume of the group treated with coumarin was significantly reduced, the survival period was prolonged, and no obvious toxic side effects were observed. Related mechanism studies have shown that coumarin exerts its anti-tumor effect by regulating multiple cellular signaling pathways.
The anti-tumor mechanism of coumarin involves multiple molecular targets and signaling pathways, especially targeting key proteins and genes related to liver cancer. The main targets include:
Through multi-target synergistic regulation, coumarin can effectively inhibit the growth, invasion, and metastasis of liver cancer cells, demonstrating broad-spectrum and comprehensive anti-tumor potential.
The pharmacological parameters of coumarin indicate its potential for development. Although the molecular weight of 488.69 is slightly higher than the recommended range of 500 by Lipinski's rule, it is still within an acceptable range. A LogP value of 4.5 suggests good lipid solubility, which facilitates cell membrane penetration, but insufficient water solubility, which may affect oral bioavailability. The TPSA is 92.83 Å ², indicating moderate polarity that facilitates binding to biological targets.
In terms of safety, coumarin did not show cardiac toxicity or hERG channel inhibition, reducing the risk of cardiovascular side effects. There is no clear data on hepatotoxicity and genotoxicity (Ames test), further systematic evaluation is needed. The low permeability of the blood-brain barrier suggests that it mainly acts on peripheral tissues to reduce adverse reactions in the central nervous system.
Pharmacokinetic studies are still in the preliminary stage, and in vivo metabolic pathways may involve redox reactions of liver enzymes. In the future, it is necessary to conduct in-depth research on its absorption, distribution, metabolism, and excretion (ADME) characteristics, optimize the dosing regimen and formulation design.
As a natural product with multi-target anti-tumor activity, coumarin has shown promising application prospects, especially in the field of liver cancer treatment. Its multiple mechanisms not only inhibit tumor cell proliferation, but also block pro cancer signals in the tumor microenvironment, which has potential synergistic therapeutic advantages. Combining modern drug design with nanocarrier technology is expected to enhance its bioavailability and targeting, and reduce side effects.
Future clinical translational research should focus on pharmacokinetic optimization, toxicological safety assessment, and combination therapy strategies of coumarin. By combining with existing liver cancer treatment drugs such as targeted drugs and immune checkpoint inhibitors, it is possible to enhance efficacy and overcome drug resistance. In addition, the potential role of coumarin in other types of tumors and inflammation related diseases is also worth further exploration.
As an important triterpenoid compound in plants of the Cistanche genus, coumarin exhibits significant therapeutic potential for liver cancer due to its unique chemical structure and multi-target anti-tumor mechanism. The current research has preliminarily revealed its target and signaling pathway, and the drug evaluation shows good safety and development prospects. In the future, through systematic pharmacokinetic studies, toxicological evaluations, and clinical trials, coumarin is expected to become an important candidate molecule for the development of natural anti-tumor drugs, bringing new treatment options for liver cancer patients. Continuous basic and applied research will drive it from the laboratory to clinical practice, promoting the widespread use of natural products in modern cancer treatment.
