Product name: Chrysophanol
Synonym name: Chrysophanic acid; 1,8-Dihydroxy-3-methylanthraquinone
Catalogue No.: BP0348
Cas No.: 481-74-3
Formula: C₁₅H₁₀O₄
Mol Weight: 254.241
Botanical Source: Cassia, Rumex, Rheum, sphodelus, Muehlenbeckia spp., Monilinia fructicola and others. V. widely distributed in plants and also found in the marine annelid Urechis unicinctus
Physical Description: Yellow powder
Type of Compound: Anthraquinones

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, up to kilograms
Inquire for bulk scale.

Descriptions:
Chrysophanol has anti-inflammatory activity through the suppression of NF-κB/caspase-1 activation in vitro and in vivo.[1]
Chrysophanol induces necrosis through the production of ROS and alteration of ATP levels in J5 human liver cancer cells.[2]
Chrysophanol has mild cytotoxicity and anti-diabetic properties, it up to 100 microM exerts mild glucose transport activity and elevates the tyrosine phosphorylation of IR via tyrosine phosphatase 1B inhibition (IC50=79.86+/-0.12 microM), thus it could play metabolic roles in the insulin-stimulated glucose transport pathway.[3]
Chrysophanol and physcion, are main active compounds of the plant Baill, has is active against plant powdery mildew, and physcion is much more bioactive than chrysophanol against these powdery mildews.[4]
Chrysophanol can inhibit NALP3 inflammasome activation and ameliorate cerebral ischemia/reperfusion in mice.[5]

References:
[1] Sujin K, Mincheol K, Byongjoo L, et al. Molecules, 2010, 15(9):6436-51.
[2] Lu C C, Yang J S, Huang A C, et al. Mol Nutr Food Res, 2010, 54(7):967–76.
[3] Lee M S, Sohn C B. Biol Pharm Bull, 2008, 31(11):2154-7.
[4] Yang X, Yang L, Wang S, et al. Pest Manag Sci, 2007, 63(5):511-5.
[5] Zhang N, Zhang X, Liu X, et al. Mediat Inflamm, 2014, 2014(1):289-339.
[6] Tang W F, Yu Q, Wan M H, et al. Biomed Chromatogr, 2007, 21(7):701-7.

HPLC of Chrysophanol

HNMR of Chrysophanol

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

Introduction/Overview

Chrysophanol, also known as rhubarb-anthraquinone acid, is a naturally occurring anthraquinone compound widely distributed in various traditional Chinese medicinal materials, with Rheum palmatum L. being especially abundant. As an important natural product, emodol has attracted widespread attention in pharmacology and medicinal chemistry due to its diverse biological activities. In recent years, with in-depth research into tumor molecular mechanisms, the potential value of emodol in the treatment of malignant tumors such as liver cancer has gradually emerged, especially showing significant pharmacological activity in inhibiting the epidermal growth factor receptor (EGFR) signaling pathway and its key downstream molecular activity.

This paper aims to systematically review the chemical structure and physicochemical properties, plant origin, and extraction methods of rhebinol, elaborate in detail on its pharmacological activity and mechanism of action, focus on analyzing its regulatory role on molecular targets related to liver cancer, evaluate its druggability and pharmacokinetic characteristics, explore its clinical application prospects and development directions, and provide theoretical basis and practical guidance for pharmacological research of natural products and new drug development.

Chemical structure and physicochemical properties

The chemical name of rhetinol is 1,8-Dihydroxy-3-methylanthraquinone, with the molecular formula C15H10O4 and a molecular weight of 254.24. Its structural core is the anthraquinone framework, which contains two hydroxyl substituents and one methyl substituent, endowing it with unique chemical properties and biological activity. The CAS number of emodol is 481-74-3.

In terms of physicochemical properties, the LogP value of emodol is about 3.37, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and distribution in vivo. Its topological pole surface area (TPSA) is 74.6 Ų, and it has 4 hydrogen bond receptors, suggesting that it possesses certain hydrophilicity and binding ability in intermolecular interactions. Efainol has relatively low blood-brain barrier penetration ability, but no significant negative effects were observed in hepatotoxicity, cardiotoxicity, or hERG channel inhibition. Moreover, Ames-induced mutagenic tests were negative, indicating high safety.

Plant Origins and Extraction Methods

Edapill is mainly found in plants of the genus Rhubarb, such as rhubarb (Rheum palmatum L.) and Rheum officinale Baill. In traditional Chinese medicine, rhubarb is widely used for purgative and heat-clearing and detoxifying treatments, with pharmacological effects closely related to anthraquinone components.

Common methods for extracting rhebutol include solvent extraction by extraction, ultrasound-assisted extraction, and microwave-assisted extraction. Ethanol or methanol is generally used as extraction solvents. By optimizing parameters such as extraction temperature, time, and solvent concentration, the extraction rate of rhein can be effectively improved. Then, through liquid-liquid separation and column chromatography and other separation and purification techniques, high-purity rhebutol is obtained. In recent years, green extraction technologies such as supercritical CO2 extraction have also been applied to emodol extraction, further improving extraction efficiency and environmental friendliness.

Pharmacological activity research

Emodol exhibits a variety of biological activities, covering anti-inflammation, antioxidant, antibacterial, and antitumor properties. Especially in the field of tumor suppression, rhein demonstrates significant anti-cancer potential through multi-target and multi-pathway regulation.

In liver cancer models, emodol can effectively inhibit the proliferation, migration, and invasion of liver cancer cells, inducing cell cycle arrest and apoptosis. Its antitumor effects are related to regulating various signaling pathways, such as inhibiting EGF-induced EGFR phosphorylation and blocking activation of the PI3K/AKT/MTOR signaling axis, thereby affecting cell survival and proliferation. In addition, emodol regulates the expression of key molecules such as BCL2, STAT3, and MMP9, inhibiting invasion and metastasis in the tumor microenvironment.

Besides tumors, emodol also shows good activity in anti-inflammatory responses, downregulating the NF-κB signaling pathway, reducing the release of inflammatory mediators, and demonstrating potential immunomodulatory functions.

Mechanism of action and molecular targets

The pharmacological mechanism of rhein mainly involves intervening in cellular signaling pathways. Its core targets include:

1. EGFR (epidermal growth factor receptor)
   Efabinol can inhibit EGF-induced EGFR phosphorylation, blocking its active state and thereby suppressing downstream signal transduction. As an important driver of liver cancer and various other tumors, EGFR's inhibition helps suppress tumor cell proliferation and survival.

2. AKT/mTOR/p70S6K signal path
   Emodol inhibits the activation of AKT protein kinase, blocks phosphorylation of mTOR and its downstream effector p70S6K, leading to impeded cell growth and protein synthesis, thereby exerting anti-proliferative effects.

3. BCL2
   By regulating the expression of the anti-apoptotic protein BCL2, emodol promotes tumor cell apoptosis and enhances cell death signals.

4. STAT3
   Inhibiting the STAT3 signaling pathway, blocking its transcriptional activity, and reducing the expression of tumor-promoting genes.

5. MMP9
   Inhibits matrix metalloproteinase 9 (MMP9) activity, reducing tumor cell invasion and metastasis.

6. TP53, TERT, PIK3CA, NFKB1, etc
   Erectol regulates these key genes and proteins, affecting the cell cycle, apoptosis, gene stability, and inflammatory response, working synergistically to exert anti-tumor effects.

In summary, emodol forms a complex anti-tumor network through coordinated regulation of multiple targets and pathways, demonstrating its unique advantages as a potential anti-tumor drug.

Druggability evaluation and pharmacokinetics

From the perspective of druggability, emodol has promising potential for drug development. Its molecular weight is moderate, lipid solubility, and can penetrate cell membranes well, but the blood-brain barrier has relatively low permeability, which helps reduce central nervous system side effects. Toxicological evaluation showed that rhotol had no significant hepatotoxicity, cardiotoxicity, or genetic toxicity, and was relatively safe.

Pharmacokinetic studies show that emodol is well absorbed orally, but its bioavailability is limited by first-pass effects and metabolizing enzyme activity. In the body, it is mainly metabolized by the liver, with most metabolites being hydroxylated and glucuronic acid conjugates. Efanophenol has a moderate half-life, making it suitable for routine dosing regimens. In the future, structural modification or nanocarrier technology is expected to further improve its pharmacokinetic properties and enhance its clinical application value.

Prospects and outlooks for clinical applications

As a natural anthraquinone compound, emodol has broad clinical application prospects due to its multi-target anti-tumor mechanism and good safety profile. Especially in the treatment of malignant tumors such as liver cancer, rhein is expected to serve as an adjunctive therapy, enhancing the effectiveness of existing chemotherapy or targeted therapies and reducing the risk of drug resistance.

Moreover, the potential of emodol in anti-inflammatory, antioxidant, and immunomodulatory fields opens up possibilities for applications in chronic inflammation, metabolic diseases, and other fields. Future research should focus on:

• Optimizing the administration method and dosage form of emodol to enhance bioavailability and targeting;
• In-depth analysis of its molecular mechanisms of action to discover new drug targets;
• Conduct systematic preclinical and clinical trials to verify safety and efficacy;
• Explore strategies for combined use with other drugs to achieve synergistic effects.

Through multidisciplinary collaboration, promote the transformation of rhein from a natural product to clinical drugs, facilitating its application in modern medicine.

Conclusion

Dahunool, a natural anthraquinone compound with significant biological activity, demonstrates broad drug development potential thanks to its multi-target regulatory capability and good safety. Its mechanisms of antitumor action in malignant tumors such as liver cancer are becoming increasingly elucidated, providing an important theoretical foundation and practical direction for the development of novel anticancer drugs. In the future, by combining modern methods of medicinal chemistry, molecular biology, and pharmacokinetics, deeply exploring and optimizing the pharmacological properties of efainol will help promote its clinical application and benefit a wide range of patients.