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Chrysophanol
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Product Name Chrysophanol
Price: $30 / 20mg
CAS No.: 481-74-3
Catalog No.: CFN98751
Molecular Formula: C15H10O4
Molecular Weight: 254.2 g/mol
Purity: >=98%
Type of Compound: Anthraquinones
Physical Desc.: Yellow powder
Source: The roots and rhizomes of Rheum palmatum L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
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Similar structural: Comparison (Web)  (SDF)
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries
Biological Activity
Description: Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. Chrysophanol has anti-inflammatory, cytotoxicity and anti-diabetic properties, it can play metabolic roles in the insulin-stimulated glucose transport pathway; it can inhibit NALP3 inflammasome activation and ameliorate cerebral ischemia/reperfusion in mice; it also is active against plant powdery mildew.
Targets: ROS | NF-kB | Caspase | Calcium Channel | GLUT | TNF-α | COX | IL Receptor | EGFR | mTOR
In vitro:
Environ Toxicol. 2014 May;29(7):740-9.
Chrysophanol-induced cell death (necrosis) in human lung cancer A549 cells is mediated through increasing reactive oxygen species and decreasing the level of mitochondrial membrane potential.[Pubmed: 22848001]
Chrysophanol (1,8-dihydroxy-3-methylanthraquinone) is one of the anthraquinone compounds, and it has been shown to induce cell death in different types of cancer cells. The effects of Chrysophanol on human lung cancer cell death have not been well studied.
METHODS AND RESULTS:
The purpose of this study is to examine Chrysophanol-induced cytotoxic effects and also to investigate such influences that involved apoptosis or necrosis in A549 human lung cancer cells in vitro. Our results indicated that Chrysophanol decreased the viable A549 cells in a dose- and time-dependent manner. Chrysophanol also promoted the release of reactive oxygen species (ROS) and Ca(2+) and decreased the levels of mitochondria membrane potential (ΔΨm ) and adenosine triphosphate in A549 cells. Furthermore, Chrysophanol triggered DNA damage by using Comet assay and DAPI staining. Importantly, Chrysophanol only stimulated the cytocheome c release, but it did not activate other apoptosis-associated protein levels including caspase-3, caspase-8, Apaf-1, and AIF.
CONCLUSIONS:
In conclusion, human lung cancer A549 cells treated with Chrysophanol exhibited a cellular pattern associated with necrotic cell death and not apoptosis in vitro.
Pest Manag Sci. 2007 May;63(5):511-5.
Synergistic interaction of physcion and chrysophanol on plant powdery mildew.[Pubmed: 17397111]
The extract of the plant Rheum officinale Baill, mainly containing the anthraquinones physcion and Chrysophanol, is highly active against plant powdery mildew.
METHODS AND RESULTS:
Experiments were conducted in the laboratory and greenhouse to determine the interaction of the two compounds on cucumber powdery mildew [Sphaerotheca fuliginea (Schlecht.) Poll] and on wheat powdery mildew [Blumeria graminis (DC.) Speer f. sp. tritici Marchal]. Physcion was much more bioactive than Chrysophanol against these powdery mildews. There was a significant synergistic interaction between the two compounds on the diseases when the ratios of physcion to Chrysophanol ranged from 1:9 to 5:5. The synergistic degree increased with increase in the Chrysophanol proportion in the combination.
CONCLUSIONS:
The findings indicate that, in order to ensure constant efficacy of the extract on the disease, both the contents and the proportion of the main active ingredients physcion and Chrysophanol have to be determined.
Biol Pharm Bull. 2008 Nov;31(11):2154-7.
Anti-diabetic properties of chrysophanol and its glucoside from rhubarb rhizome.[Pubmed: 18981591]
An ethanol extract of rhubarb rhizome exhibited marked glucose transport activity in differentiated L6 rat myotubes. Activity-guided fractionation resulted in the isolation of two anthraquinones, Chrysophanol-8-O-beta-D-glucopyranoside (1) and Chrysophanol (2).
METHODS AND RESULTS:
The anti-diabetic effect was examined by glucose transport activity, glucose transporter 4 (Glut4) expression in myotubes, and the level of insulin receptor (IR) tyrosine phosphorylation as influenced by tyrosine phosphatase 1B, each of which is a major target of diabetes treatment. Chrysophanol-8-O-beta-D-glucopyranoside up to 25 microM dose-dependently activated glucose transport in insulin-stimulated myotubes. Increased tyrosine phosphorylation of IR due to tyrosine phosphatase 1B inhibitory activity with an IC50 value of 18.34+/-0.29 microM and unchanged Glut4 mRNA levels was observed following Chrysophanol-8-O-beta-D-glucopyranoside treatment. Chrysophanol up to 100 microM exerted mild glucose transport activity and elevated the tyrosine phosphorylation of IR via tyrosine phosphatase 1B inhibition (IC50=79.86+/-0.12 microM); Glut4 mRNA expression was also significantly increased by 100 microM. The ED50 values of the two compounds were 59.38+/-0.66 and 79.69+/-0.03 microM, respectively.
CONCLUSIONS:
Therefore, these two anthraquinones from rhubarb rhizome, Chrysophanol-8-O-beta-D-glucopyranoside and Chrysophanol, have mild cytotoxicity and anti-diabetic properties and could play metabolic roles in the insulin-stimulated glucose transport pathway.
2016 Dec 8;7:476.
Chrysophanic Acid Suppresses Adipogenesis and Induces Thermogenesis by Activating AMP-Activated Protein Kinase Alpha In vivo and In vitro[Pubmed: 28008317]
Chrysophanic acid (CA) is a member of the anthraquinone family abundant in rhubarb, a widely used herb for obesity treatment in Traditional Korean Medicine. Though several studies have indicated numerous features of CA, no study has yet reported the effect of CA on obesity. In this study, we tried to identify the anti-obesity effects of CA. By using 3T3-L1 adipocytes and primary cultured brown adipocytes as in vitro models, high-fat diet (HFD)-induced obese mice, and zebrafish as in vivo models, we determined the anti-obesity effects of CA. CA reduced weight gain in HFD-induced obese mice. They also decreased lipid accumulation and the expressions of adipogenesis factors including peroxisome proliferator-activated receptor gamma (PPARγ) and CCAAT/enhancer-binding protein alpha (C/EBPα) in 3T3-L1 adipocytes. In addition, uncoupling protein 1 (UCP1) and peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PGC1α), the brown fat specific thermogenic genes, were up-regulated in brown adipocytes by CA treatment. Furthermore, when co-treated with Compound C, the AMP-activated protein kinase (AMPK) inhibitor, the action of CA on AMPKα was nullified in both types of adipocytes, indicating the multi-controlling effect of CA was partially via the AMPKα pathway. Given all together, these results indicate that CA can ameliorate obesity by controlling the adipogenic and thermogenic pathway at the same time. On these bases, we suggest the new potential of CA as an anti-obese pharmacotherapy. Keywords: AMP-activated protein kinase alpha; adipogenesis; chrysophanic acid; obesity; thermogenesis.
In vivo:
Neural Regen Res. 2014 May 1;9(9):924-30.
Chrysophanol attenuates lead exposure-induced injury to hippocampal neurons in neonatal mice.[Pubmed: 25206913]
Previous studies have shown that Chrysophanol protects against learning and memory impairments in lead-exposed adult mice.
METHODS AND RESULTS:
In the present study, we investigated whether Chrysophanol can alleviate learning and memory dysfunction and hippocampal neuronal injury in lead-exposed neonatal mice. At the end of lactation, Chrysophanol (0.1, 1.0, 10.0 mg/kg) was administered to the neonatal mice by intraperitoneal injection for 15 days. Chrysophanol significantly alleviated injury to hippocampal neurons and improved learning and memory abilities in the lead-poisoned neonatal mice. Chrysophanol also significantly decreased lead content in blood, brain, heart, spleen, liver and kidney in the lead-exposed neonatal mice. The levels of malondialdehyde in the brain, liver and kidney were significantly reduced, and superoxide dismutase and glutathione peroxidase activities were significantly increased after Chrysophanol treatment.
CONCLUSIONS:
Collectively, these findings indicate that Chrysophanol can significantly reduce damage to hippocampal neurons in lead-exposed neonatal mice.
Chrysophanol Description
Source: The roots and rhizomes of Rheum palmatum L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever 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 -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.9339 mL 19.6696 mL 39.3391 mL 78.6782 mL 98.3478 mL
5 mM 0.7868 mL 3.9339 mL 7.8678 mL 15.7356 mL 19.6696 mL
10 mM 0.3934 mL 1.967 mL 3.9339 mL 7.8678 mL 9.8348 mL
50 mM 0.0787 mL 0.3934 mL 0.7868 mL 1.5736 mL 1.967 mL
100 mM 0.0393 mL 0.1967 mL 0.3934 mL 0.7868 mL 0.9835 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Cell Research:
Mol Nutr Food Res. 2010 Jul;54(7):967-76.
Chrysophanol induces necrosis through the production of ROS and alteration of ATP levels in J5 human liver cancer cells.[Pubmed: 20169580 ]
Anthraquinone compounds have been shown to induce apoptosis in different cancer cell types. Effects of Chrysophanol, an anthraquinone compound, on cancer cell death have not been well studied.
METHODS AND RESULTS:
The goal of this study was to examine if Chrysophanol had cytotoxic effects and if such effects involved apoptosis or necrosis in J5 human liver cancer cells. Chrysophanol induced necrosis in J5 cells in a dose- and time-dependent manner. Non-apoptotic cell death was induced by Chrysophanol in J5 cells and was characterized by caspase independence, delayed externalization of phosphatidylserine and plasma membrane disruption. Blockage of apoptotic induction by a general caspase inhibitor (z-VAD-fmk) failed to protect cells against Chrysophanol-induced cell death. The levels of reactive oxygen species production and loss of mitochondrial membrane potential (DeltaPsi(m)) were also determined to assess the effects of Chrysophanol. However, reductions in adenosine triphosphate levels and increases in lactate dehydrogenase activity indicated that Chrysophanol stimulated necrotic cell death.
CONCLUSIONS:
In summary, human liver cancer cells treated with Chrysophanol exhibited a cellular pattern associated with necrosis and not apoptosis.
Molecules. 2010 Sep 16;15(9):6436-51.
Anti-Inflammatory activity of chrysophanol through the suppression of NF-kappaB/caspase-1 activation in vitro and in vivo.[Pubmed: 20877234 ]
Chrysophanol is a member of the anthraquinone family and has multiple pharmacological effects, but the exact mechanism of the anti-inflammatory effects of Chrysophanol has yet to be thoroughly elucidated. In this study, we attempted to determine the effects of Chrysophanol on dextran sulfate sodium (DSS)-induced colitis and lipopolysaccharide (LPS)-induced inflammatory responses in mouse peritoneal macrophages. The findings of this study demonstrated that Chrysophanol effectively attenuated overall clinical scores as well as various pathological markers of colitis. Additionally, Chrysophanol inhibited the production of tumor necrosis factor (TNF)-alpha, interleukin (IL)-6 and the expression of cyclooxygenase (COX)-2 levels induced by LPS. We showed that this anti-inflammatory effect of Chrysophanol is through suppression of the activation of NF-kappaB and caspase-1 in LPS-stimulated macrophages. These results provide novel insights into the pharmacological actions of Chrysophanol as a potential molecule for use in the treatment of inflammatory diseases.
Animal Research:
Mediators Inflamm. 2014;2014:370530.
Chrysophanol inhibits NALP3 inflammasome activation and ameliorates cerebral ischemia/reperfusion in mice.[Pubmed: 24876671]
The most effective way to contain cerebral ischemic injury is reperfusion; however, reperfusion itself may result in tissue injury, for which inflammatory damage is one of the main causative factors. NALP3 inflammasome is a multiprotein complex. It consists of NALP3, ASC, and caspase-1, whose function is to switch on the inflammatory process. Chrysophanol is an extract from plants of Rheum genus and it possesses many pharmacological effects including its anti-inflammation activity.
METHODS AND RESULTS:
In this study, the effects of Chrysophanol in cerebral ischemia/reperfusion and the potential mechanisms were investigated. Male CD1 mice were subject to transient middle cerebral artery occlusion (tMCAO). The NALP3 inflammasome activation status and its dynamic expression during the natural inflammatory response induced by tMCAO were first profiled. The neuroprotective effects of Chrysophanol were then assessed and the potential mechanisms mediating the observed neuroprotection were then explored. Physical parameters including neurological deficit, infarct size, brain edema, and BBB permeability were measured at 24 h after tMCAO. Confocal microscopy, Western blotting, immunohistochemistry, and qRT-PCR techniques were utilized to analyze the expression of NALP3 inflammasome and IL-1 β .
CONCLUSIONS:
Our results indicated that the brain tissue damage during cerebral ischemia/reperfusion is accompanied by NALP3 inflammasome activation. Chrysophanol could inhibit the activation of NALP3 inflammasome and protect cerebral ischemic stroke.
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