Aloeemodin

CAS# 481-72-1

Aloeemodin

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Chemical structure

Aloeemodin

3D structure

Chemical Properties of Aloeemodin

Cas No. 481-72-1 SDF Download SDF
PubChem ID 10207 Appearance Orange powder
Formula C15H10O5 M.Wt 270.2
Type of Compound Anthraquinones Storage Desiccate at -20°C
Synonyms Rhabarberone; 3-Hydroxymethylchrysazine
Solubility DMSO : 41.67 mg/mL (154.20 mM; Need ultrasonic)
Ethanol : 1 mg/mL (3.70 mM; Need ultrasonic and warming)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 1,8-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione
SMILES C1=CC2=C(C(=C1)O)C(=O)C3=C(C=C(C=C3C2=O)CO)O
Standard InChIKey YDQWDHRMZQUTBA-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Aloeemodin

1 Asphodelus sp. 2 Cassia sp. 3 Polygonum sp. 4 Rhamnus sp. 5 Rheum sp.

Biological Activity of Aloeemodin

DescriptionAloeemodin is an interferon-inducing agent with IC50 of about 1 μg/mL for JEV and of about 0.33 μg/mL for EV71. Aloeemodin has antitumor, neuroprotective, and anti-fibrosis effects, it inhibited β-amyloid aggregation, downregulated the expression of Smad2 mRNA and TGF-β1,TIMP1,and type Ⅰ and Ⅲ collagen proteins,and upregulated the expression of Smad7 mRNA.
TargetsCalcium Channel | ROS | Beta Amyloid | TGF-β/Smad | MMP(e.g.TIMP) | FAK | VEGFR
In vitro

Genotoxicity of aloeemodin in vitro and in vivo.[Pubmed: 8600368]

Mutat Res. 1996 Mar 1;367(3):123-33.

The present in vitro and in vivo experiments were undertaken to clarify the genotoxic potential of the hydroxyanthrachinone Aloeemodin which can be found in different plant derived products for therapy of constipation.
METHODS AND RESULTS:
The results demonstrate that Aloeemodin is able to induce mutagenic effects in vitro. Positive results were obtained in the chromosomal aberration assay with CHO cells, as well as in the Salmonella reverse mutation assay (frameshift mutations in strains TA 1537, TA 1538 and TA 98). No mutagenic potential of Aloeemodin, however, was observed in the gene mutation assay with mammalian cells in vitro (HPRT assay in V79 cells). Each assay was performed in the presence and absence of an extrinsic metabolic activation system (S9-mix). In in vivo studies (micronucleus assay in bone marrow cells of NMRI mice; chromosome aberration assay in bone marrow cells of Wistar rats; mouse spot text [DBA/2JxNMRI]) no indication of a mutagenic activity of Aloeemodin was found. Information about a possible reaction of Aloeemodin with DNA was derived from an in vivo UDS assay. Hepatocytes of Aloeemodin-treated male Wistar rats did not show DNA damage via repair synthesis.
CONCLUSIONS:
All these data suggest that Aloeemodin is able to interact with DNA under certain in vitro conditions. However, in vivo the results that were negative did not indicate a genotoxic potential. Therefore, it may be assumed that a genotoxic risk for man might be unlikely.

Inhibition of β-Amyloid Aggregation by Albiflorin, Aloeemodin and Neohesperidin and their Neuroprotective Effect on Primary Hippocampal Cells Against β-Amyloid Induced Toxicity.[Pubmed: 25938872]

Curr Alzheimer Res. 2015;12(5):424-33.

Being one of the hallmarks of Alzheimer's disease, β-amyloid (Aβ) aggregates induce complicated neurotoxicity. Evidences show that the underlying mechanism of neurotoxicity involves a glutamate receptor subtype, N-methyl-D-aspartate (NMDA) receptor, an increase in intracellular calcium(II) ion loading as well as an elevation in oxidation stress.
METHODS AND RESULTS:
In this work, among the 35 chemical components of Chinese herbal medicines (CHMs) being screened for inhibitors of Aβ aggregation, four of them, namely albiflorin, Aloeemodin, neohesperidin and physcion, were found for the first time to exhibit a potent inhibitory effect on Aβ(1-40) and Aβ(1-42) aggregation. Their neuroprotective capability on primary hippocampal neuronal cells was also investigated by MTT assay, ROS assay and intracellular calcium(II) ion concentration measurement.
CONCLUSIONS:
It was interesting to find that physcion was rather toxic to neuronal cells while albiflorin, Aloeemodin and neohesperidin reduced the toxicity and ROS induced by both monomeric and oligomeric Aβ species. In addition, albiflorin was particularly powerful in maintaining the intracellular Ca(2+) concentration.

In vivo

Effects of combined use of aloeemodin and praziquantel on the transforming growth factor-β/Smad pathway in mice with schistosomiasis-induced liver fibrosis.[Reference: WebLink]

World Chinese Journal of Digestology, 2009, 17(27):2778-83.

To investigate the effects of combined use of Aloeemodin and praziquantel on the transforming growth factor-β (TGF-β)/Smad pathway in mice with schistosomiasis-induced liver fibrosis.
METHODS AND RESULTS:
Eighty mice were randomly divided into four groups: normal control group, infection group, praziquantel treatment group, and praziquantel and Aloeemodin treatment group. Mice in the infection group and the two treatment groups were infected with 25 Schistosoma japonicum cercariae. Eight weeks after infection, mice in the praziquantel treatment group were treated with praziquantel at a dose of 500 mg/(kg·d) for two days, while those in the praziquantel and Aloeemodin treatment group were treated with praziquantel at the same dose for the same duration followed by treatment with Aloeemodin at a dose of 0.3 mg/(kg·d) for 8 weeks. At week 16, all mice were sacrificed to take liver tissue samples. Hematoxylin and eosin staining was performed to observe changes in hepatic histopathology. Reverse transcription-polymerase chain reaction (RT-PCR) was used to detect the expression of Smad2 and Smad7 mRNAs in the liver. Immunohistochemical staining was performed to detect the expression of TGF-β1, TIMP-1, and type I and III collagen in liver tissue. Aloeemodin treatment relieved the degree of hepatic fibrosis. The expression levels of Smad2 mRNA and TGF-β1, tissue inhibitor of metalloproteinases-1 (TIMP1), and type I and III collagen proteins in liver tissue were significantly lower in the praziquantel and Aloeemodin treatment group than in the infection group and the praziquantel treatment group (q = 6.20 and 4.38, 6.22 and 4.41, 6.30 and 4.52, 6.25 and 4.44. and 6.29 and 4.48, respectively; all P < 0.01 or 0.05). In contrast, the expression level of Smad7 mRNA was significantly higher in the praziquantel and Aloeemodin treatment group than in the infection group and the praziquantel treatment group (q = 6.32 and 4.62, respectively; P < 0.01 and 0.05, respectively).
CONCLUSIONS:
Aloeemodin exerts anti-fibrotic effects perhaps through downregulation of the expression of Smad2 mRNA and TGF-β1, TIMP1, and type I and III collagen proteins, and upregulation of the expression of Smad7 mRNA.

Protocol of Aloeemodin

Cell Research

Effects of aloeemodin on proliferation cycle and apoptotic of human stomach cancer cell line HGC-27.[Reference: WebLink]

J. Modern Oncol., 2008, 16(06):919-21.

To study the suppressive role of Aloeemodin on the growth and its effect on the proliferation cycle and apoptosis of human stomach cancer cell line HGC-27.
METHODS AND RESULTS:
The survival rate and the inhibitory rate of HGC-27 cell in vitro were detected by MTT colorimetrie assay and cell growth curve assay at different time points under different concentration of Aloeemodin;the cell proliferation cycle and the apoptotic rate were examined with flow cytometry analysis.Aloeemodin inhibited the proliferation of HGC-27 cell at G0/G1 phase,decreased the cell ratio at S phase.It suppressed the growth of tumor cells and raised the apoptotic rate in a concentration and time depending manner in a certain extent.
CONCLUSIONS:
Aloeemodin could suppress the proliferation of HGC-27 cell to induce apoptosis and block cell cycle.

Animal Research

Effect of aloeemodin on liver fibrosis induced by Schistosoma Japonicum infections in mice.[Reference: WebLink]

Chinese Journal of Integrated Traditional & Western Medicine on Liver Diseases, 2012, 22(02):107-9.

To observe the effect of Aloeemodin on liver fibrosis mice in duced by Schistosoma Japonicum.
METHODS AND RESULTS:
Mice' liver fibrosis model was induced by Schistosoma Japonicum infection for 8 weeks.Suspension of Aloeemodin prepared with normal saline was given orally to the mice,0.3 mg per mouse every day for 8 weeks.The level of malondialdehyde(MDA) in liver homogenate was detected.The level of transforming growth factor beta 1(TGF-β1),vascular endothelial growth factor(VEGF),Focal adhesion kinase(FAK) and type Ⅰ,Ⅲ collagen in liver tissue were detected by immuno-histochemistry.The pathological changes of liver tissue was inpreved by Aloeemodin.The level of type Ⅰand Ⅲ collagen in schistosomiasis liver fibrosis mice were decreased.TGF-β1,VEGF and FAK expression levels were increased in liver fibrosis induced by Schistosoma Japonicum.However,TGF-β1,VEGF and FAK expression were inhibited after administration of Aloeemodin.
CONCLUSIONS:
Aloeemodin might have therapeutic effects on liver fibrosis induced by Schistosoma of liver through the effects of TGF-β1,VEGF and FAK expression.

Aloeemodin Dilution Calculator

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Preparing Stock Solutions of Aloeemodin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.701 mL 18.5048 mL 37.0096 mL 74.0192 mL 92.5241 mL
5 mM 0.7402 mL 3.701 mL 7.4019 mL 14.8038 mL 18.5048 mL
10 mM 0.3701 mL 1.8505 mL 3.701 mL 7.4019 mL 9.2524 mL
50 mM 0.074 mL 0.3701 mL 0.7402 mL 1.4804 mL 1.8505 mL
100 mM 0.037 mL 0.185 mL 0.3701 mL 0.7402 mL 0.9252 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Aloeemodin

Aloe emodin is a hydroxyanthraquinone present in Aloe vera leaves, has a specific in vitro and in vivo antitumor activity. IC50 value: Target: in vitro: aloe-emodin treatment led to the dissociation of heat shock protein 90 (HSP90) and ER α and increased ER α ubiquitination. Protein fractionation results suggest that aloe-emodin tended to induce cytosolic ER α degradation [1]. Aloe-emodin, a natural compound found in aloe, inhibited both proliferation and anchorage-independent growth of PC3 cells. Protein content analysis suggested that activation of the downstream substrates of mTORC2, Akt and PKCα, was inhibited by aloe-emodin treatment. Pull-down assay and in vitro kinase assay results indicated that aloe-emodin could bind with mTORC2 in cells and inhibit its kinase activity [2]. Of three anthraquinone derivatives, aloe-emodin, with a lower cytotoxicity showed concentration-dependently reducing virus-induced cytopathic effect and inhibiting replication of influenza A in MDCK cells. Galectin-3 also inhibited influenza A virus replication. Proteomic analysis of treated cells indicated galectin-3 up-regulation as one anti-influenza A virus action by aloe-emodin. Since galectin-3 exhibited cytokine-like regulatory actions via JAK/STAT pathways, aloe-emodin also restored NS1-inhibited STAT1-mediated antiviral responses in transfected cells: e.g., STAT1 phosphorylation of interferon (IFN) stimulation response element (ISRE)-driven promoter, RNA-dependent protein kinase (PKR) and 2'5',-oligoadenylate synthetase (2'5',-OAS) expression [3]. AE downregulated mRNA expression and promoter/gelatinolytic activity of Matrix Metalloproteinase (MMP)-2/9, as well as the RhoB expression at gene and protein level. AE suppressed the nuclear translocation and DNA binding of NF-κB [4]. in vivo: Aloe-emodin also exhibited tumor suppression effects in vivo in an athymic nude mouse model [2].

References:
[1]. Huang PH, et al. Emodin and Aloe-Emodin Suppress Breast Cancer Cell Proliferation through ER α Inhibition. Evid Based Complement Alternat Med. 2013;2013:376123. [2]. Liu K, et al. Aloe-emodin suppresses prostate cancer by targeting the mTOR complex 2. Carcinogenesis. 2012 Jul;33(7):1406-11. [3]. Li SW, et al. Antiviral activity of aloe-emodin against influenza A virus via galectin-3 up-regulation. Eur J Pharmacol. 2014 Sep 5;738:125-32. [4]. Suboj P, et al. Aloe emodin inhibits colon cancer cell migration/angiogenesis by downregulating MMP-2/9, RhoB and VEGF via reduced DNA binding activity of NF-κB. Eur J Pharm Sci. 2012 Apr 11;45(5):581-91.

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References on Aloeemodin

Inhibition of beta-amyloid Aggregation By Albiflorin, Aloeemodin And Neohesperidin And Their Neuroprotective Effect On Primary Hippocampal Cells Against beta-amyloid Induced Toxicity.[Pubmed:25938872]

Curr Alzheimer Res. 2015;12(5):424-33.

Being one of the hallmarks of Alzheimer's disease, beta-amyloid (Abeta) aggregates induce complicated neurotoxicity. Evidences show that the underlying mechanism of neurotoxicity involves a glutamate receptor subtype, N-methyl-D-aspartate (NMDA) receptor, an increase in intracellular calcium(II) ion loading as well as an elevation in oxidation stress. In this work, among the 35 chemical components of Chinese herbal medicines (CHMs) being screened for inhibitors of Abeta aggregation, four of them, namely albiflorin, Aloeemodin, neohesperidin and physcion, were found for the first time to exhibit a potent inhibitory effect on Abeta(1-40) and Abeta(1-42) aggregation. Their neuroprotective capability on primary hippocampal neuronal cells was also investigated by MTT assay, ROS assay and intracellular calcium(II) ion concentration measurement. It was interesting to find that physcion was rather toxic to neuronal cells while albiflorin, Aloeemodin and neohesperidin reduced the toxicity and ROS induced by both monomeric and oligomeric Abeta species. In addition, albiflorin was particularly powerful in maintaining the intracellular Ca(2+) concentration.

Genotoxicity of aloeemodin in vitro and in vivo.[Pubmed:8600368]

Mutat Res. 1996 Mar 1;367(3):123-33.

The present in vitro and in vivo experiments were undertaken to clarify the genotoxic potential of the hydroxyanthrachinone Aloeemodin which can be found in different plant derived products for therapy of constipation. The results demonstrate that Aloeemodin is able to induce mutagenic effects in vitro. Positive results were obtained in the chromosomal aberration assay with CHO cells, as well as in the Salmonella reverse mutation assay (frameshift mutations in strains TA 1537, TA 1538 and TA 98). No mutagenic potential of Aloeemodin, however, was observed in the gene mutation assay with mammalian cells in vitro (HPRT assay in V79 cells). Each assay was performed in the presence and absence of an extrinsic metabolic activation system (S9-mix). In in vivo studies (micronucleus assay in bone marrow cells of NMRI mice; chromosome aberration assay in bone marrow cells of Wistar rats; mouse spot text [DBA/2JxNMRI]) no indication of a mutagenic activity of Aloeemodin was found. Information about a possible reaction of Aloeemodin with DNA was derived from an in vivo UDS assay. Hepatocytes of Aloeemodin-treated male Wistar rats did not show DNA damage via repair synthesis. All these data suggest that Aloeemodin is able to interact with DNA under certain in vitro conditions. However, in vivo the results that were negative did not indicate a genotoxic potential. Therefore, it may be assumed that a genotoxic risk for man might be unlikely.

Description

Aloe emodin is a hydroxyanthraquinone present in Aloe vera leaves, has a specific in vitro and in vivo antitumor activity.

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