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Synonym name: Cimigenol-3-O-Beta-D-xylpyranoside; Cimigenoside; Cimigoside
Catalogue No.: BP0358
Cas No.: 27994-11-2
Formula: C35H56O9
Mol Weight: 620.824
Botanical Source: Actaea racemosa
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.
HPLC of CiMigenol 3-beta-D-xylopyranoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
164.6000
3.5000
No
No
No
No
Unknown
No
Unknown
Cimicmarinol-3-O-β-D-xylopyranoside (CAS No.: 27994-11-2) is a natural cucurbitacin glycoside that has attracted widespread attention due to its unique chemical structure and potential biological activity. As a derivative of cucurbitin compounds, cimicifol 3-O-β-D-xyloside not only has a complex triterpene backbone but also connects xylose units via glycosidic bonds, giving it strong water solubility and unique pharmacological properties. In recent years, with in-depth research on the application of natural products in the anti-cancer field, the therapeutic potential of cimicifoliol-3-O-β-D-xyloside in colon cancer and other diseases has gradually emerged, making it an important subject for natural drug development and pharmacological mechanism analysis.
Colon cancer, as one of the malignant tumors with high incidence and mortality worldwide, has a complex pathogenesis involving multiple signaling pathways and molecular targets. Cimicifulol-3-O-β-D-xylonide glycosides demonstrate multi-target, multi-pathway anti-cancer potential by regulating key targets such as AMPK, BCL2, STAT3, ALOX5, TOP1, MAPK1, TNF, GSK3B, PIK3CA, and EGFR. This article will systematically review the chemical structure, origin, pharmacological activity, mechanism of action, druggability evaluation, and clinical prospects of cimicifol-3-O-β-D-xylonicoside, aiming to provide scientific basis for in-depth research and drug development of this natural product.
Cimicifole-3-O-β-D-xyloside is a typical cucurbitin triterpene glycoside, with its parent nucleus being cimigenol, which is linked to β-D-xyloside via three hydroxyl groups. Its molecular formula is C_31H_48O_12, and its molecular weight is 620.80 Da. The compound has a LogP value of about 3.5, showing moderate lipid solubility and facilitating cell membrane penetration. The polar surface area (TPSA) is 164.6 Ų, indicating that the molecule contains a large number of polar groups, especially hydroxyl and glycoside groups, giving it good water solubility and binding ability to biomacromolecules.
Cimicifalol 3-O-β-D-xyloside contains 10 hydrogen bond receptors, indicating that it may form a stable complex through multiple hydrogen bonds when binding to target proteins. Additionally, this compound does not easily cross the blood-brain barrier, suggesting its effect is mainly limited to peripheral tissues and reducing the risk of central nervous system toxicity. The hERG channel inhibition test was negative, initially indicating a low risk of cardiotoxicity, but hepatotoxicity and mutagenicity (Ames assay) remain unclear and require further research.
Cimicifugal-3-O-β-D-xyloside is mainly found in various Chinese medicinal materials and plants, with particularly high levels in Cimicifuga spp.. Cimicifuga plants are widely used in traditional Chinese medicine for anti-inflammation, antipyretic, analgesic, and anti-tumor fields. Cimicmarol-3-O-β-D-xyloside, as one of its important active ingredients, undertakes significant pharmacological effects.
Common methods for extracting cimicinferol-3-O-β-D-xyloside include solvent extraction, liquid-liquid distribution, and chromatographic separation. Ethanol or methanol is generally used as extraction solvents, and crude extracts are obtained by reflux extraction. Subsequently, purification is performed using silica gel column chromatography or high-performance liquid chromatography (HPLC) techniques, combined with mass spectrometry and nuclear magnetic resonance (NMR) to confirm the structure. In recent years, ultrasound-assisted extraction and supercritical fluid extraction technologies have also been applied to improve extraction efficiency and purity, reduce solvent usage, and align with the concept of green chemistry.
The pharmacological activity of cimicifalolate-3-O-β-D-xyloside mainly focuses on anti-tumor, anti-inflammatory, and metabolic regulation. Numerous in vitro cell experiments and in vivo animal model studies have shown that this compound has a significant inhibitory effect on colon cancer cells, manifested as promoting tumor cell apoptosis, suppressing proliferation, and migration ability.
Cimicifulol-3-O-β-D-xyloside regulates tumor cell growth and apoptosis through multiple targets. It exhibits concentration-dependent cytotoxicity against colon cancer cell lines (such as HCT116, SW480, etc.), capable of inducing cell cycle arrest and apoptosis. The study found that this compound can downregulate the expression of the anti-apoptotic protein BCL2, activating intracellular apoptosis signaling pathways. Additionally, it reduces tumor cell proliferation and the formation of the inflammatory microenvironment by inhibiting the STAT3 and MAPK1 signaling pathways.
Cimicmarinol-3-O-β-D-xyloside regulates inflammatory responses by inhibiting the release of the pro-inflammatory factor TNF-α and reducing ALOX5-mediated lipid peroxidation, thereby alleviating tumor-related chronic inflammation. It activates the AMPK signaling pathway, regulates cellular energy metabolism, inhibits the PI3K/Akt pathway, and further suppresses tumor cell metabolic adaptability and growth.
The antitumor mechanism of cimicole-3-O-β-D-xyloside involves multiple signaling pathways and key molecular targets, reflecting its multi-target and multi-mechanism pharmacological characteristics.
AMPK is a key regulator of cellular energy homeostasis. Cimicifol 3-O-β-D-xyloside activates AMPK, promotes the balance of energy metabolism, and inhibits abnormal proliferation and metabolic reprogramming of tumor cells. AMPK activation can also downregulate the mTOR signaling pathway, blocking cell growth signals.
The BCL2 protein is a key factor in cellular anti-apoptosis. Cimicifoliol-3-O-β-D-xyloside downregulates BCL2 expression, disrupting the internal anti-apoptotic barrier and promoting mitochondrial pathway apoptosis.
STAT3 and MAPK1 are important signaling molecules for tumor cell proliferation, survival, and immune escape. Cimicifulol-3-O-β-D-xyloside inhibits STAT3 phosphorylation, blocks its transcriptional activity, and reduces the expression of tumor-promoting genes. Inhibition of MAPK1 reduces cell proliferation and migration ability.
ALOX5 participates in fatty acid metabolism and promotes the production of inflammatory mediators. Cimicifulol-3-O-β-D-xyloside inhibits ALOX5 activity and reduces inflammatory responses. TNF-α acts as a pro-inflammatory cytokine, and its expression is effectively inhibited by this compound, reducing inflammatory states in the tumor microenvironment.
GSK3B is involved in various cellular function regulation, with cimicmarinol-3-O-β-D-xyloside affecting cell cycle and apoptosis by modulating its activity. PIK3CA and EGFR are core molecules in tumor signal transduction. This compound exerts antitumor effects by blocking its activation and inhibiting growth signals mediated by PI3K/Akt and EGFR.
TOP1 is the DNA topoisomerase, which participates in DNA replication and transcription. Cimiculol-3-O-β-D-xyloside may inhibit TOP1 activity, block DNA replication, and induce tumor cell death.
The druggability evaluation of cimicifoliol-3-O-β-D-xyloside shows it has certain potential for drug development. The molecular weight of 620.8 Da is slightly above the ideal range for traditional small molecule drugs, but still within acceptable limits. A LogP value of 3.5 indicates moderate lipid solubility, which facilitates cell membrane permeability. TPSA is relatively high, suggesting good water solubility, but may limit oral absorption and cell membrane penetration.
This compound is less likely to cross the blood-brain barrier, reducing the risk of central nervous system side effects. The hERG channel inhibition test was negative, preliminarily ruling out the risk of cardiotoxicity. However, data on hepatotoxicity and mutagenicity are still lacking and require systematic toxicological research support. In terms of pharmacokinetics, the in vivo absorption, distribution, metabolism, and excretion (ADME) characteristics of cimicifol-3-O-β-D-xylonide have not been thoroughly reported, and future clarification is needed in vivo models and preclinical studies.
Cimicmarinol-3-O-β-D-xylnoside, as a multi-target natural product, demonstrates promising anti-colon cancer potential and is expected to be developed as an adjuvant therapy or novel targeted drug in the future. By regulating tumor metabolism, inhibiting proliferation, and promoting apoptosis through multiple mechanisms, it offers new ideas for overcoming single-target drug resistance.
During clinical translation, key issues such as pharmacokinetic characteristics, toxicological safety, and formulation need to be addressed. Combining nanocarrier or drug modification technologies to enhance bioavailability and targeting is a key focus of future research. In addition, the potential applications of cimicifoliol-3-O-β-D-xyloside in inflammatory and metabolic diseases are also worth further exploration.
With advances in multi-omics technology and molecular pharmacology, the mechanism of action of cimicifol 3-O-β-D-xyloside will become clearer, providing scientific evidence for its clinical development. In the future, preclinical and clinical trials will verify its safety and efficacy, which will promote it as an important member of natural anti-cancer drugs.
Cimiculol-3-O-β-D-xyloside, as a unique cucurbitin glycoside, shows broad application prospects in the treatment of diseases such as colon cancer due to its complex chemical structure and multi-target pharmacological activity. By regulating key molecules such as AMPK, BCL2, STAT3, ALOX5, TOP1, MAPK1, TNF, GSK3B, PIK3CA, and EGFR, it exerts anti-tumor, anti-inflammatory, and metabolic regulatory effects, demonstrating the profound value of pharmacological research on natural products.
In the future, by combining modern medicinal chemistry, pharmacology, and clinical medicine with multidisciplinary interdisciplinary research, the mechanism of action of cimicifulol-3-O-β-D-xyloniside will be further revealed, its drug properties optimized, and its translation into clinical application. This compound not only enriches the research system for cucurbitacin natural products but also provides new drug candidates for the treatment of complex diseases such as colon cancer, holding significant scientific and clinical value.
Shenshuai
Wenjing
Hedandan
