Aloeemodin

Modify Date: 2024-01-02 18:39:50

Aloeemodin Structure
Aloeemodin structure
 Common Name Aloeemodin
CAS Number 481-72-1 Molecular Weight 270.237
Density 1.6±0.1 g/cm3 Boiling Point 568.8±50.0 °C at 760 mmHg
Molecular Formula C15H10O5 Melting Point 223-224°C
MSDS Chinese USA Flash Point 311.9±26.6 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of 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].

 Names

Name Aloe emodin
Synonym More Synonyms

 Aloeemodin Biological Activity

Description 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].
Related Catalog
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.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 568.8±50.0 °C at 760 mmHg
Melting Point 223-224°C
Molecular Formula C15H10O5
Molecular Weight 270.237
Flash Point 311.9±26.6 °C
Exact Mass 270.052826
PSA 94.83000
LogP 3.38
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.746
Storage condition 2-8°C
Stability Hygroscopic

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CB6712200
CHEMICAL NAME :
Anthraquinone, 1,8-dihydroxy-3-hydroxymethyl-
CAS REGISTRY NUMBER :
481-72-1
BEILSTEIN REFERENCE NO. :
2059062
LAST UPDATED :
199612
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C15-H10-O5
MOLECULAR WEIGHT :
270.25
WISWESSER LINE NOTATION :
L C666 BV IVJ DQ F1Q NQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
10 mg/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 240,1,1990

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi
Risk Phrases R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS CB6712200

 Synthetic Route

 Articles10

More Articles
Correlation between reduction potentials and inhibitions of Epstein-Barr virus activation by anthraquinone derivatives.

Bioorg. Med. Chem. Lett. 18 , 4106-9, (2008)

As a continuation of studies using natural and synthetic products as cancer chemopreventive agents, we used cyclic voltammetry to examine the reduction-oxidation potentials of methylated emodin deriva...
In vitro inhibition of Streptococcus mutans biofilm formation on hydroxyapatite by subinhibitory concentrations of anthraquinones.

Antimicrob. Agents Chemother. 51 , 1541-4, (2007)

We report that certain anthraquinones (AQs) reduce Streptococcus mutans biofilm formation on hydroxyapatite at concentrations below the MIC. Although AQs are known to generate reactive oxygen species,...
High-affinity, non-nucleotide-derived competitive antagonists of platelet P2Y12 receptors.

J. Med. Chem. 52 , 3784-93, (2009)

Anthraquinone derivatives related to the moderately potent, nonselective P2Y(12) receptor antagonist reactive blue 2 (6) have been synthesized and optimized with respect to P2Y(12) receptor affinity. ...

 Synonyms

EINECS 207-571-7
Aloe emodin
MFCD00017373
1,8-Dihydroxy-3-(hydroxymethyl)anthracen-9,10-dion
1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone
ALOE-EMODIN
Aloeemodin:9,10-Anthracenedione,1,8-dihydroxy-3-(hydroxymethyl)-,
Aloeemodin
1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone,3-Hydroxymethylchrysazine,Aloe-emodin
3-Hydroxymethylchrysazine
EMODINE
1,8-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione
Rhabarberone
1,8-Dihydroxy-3-(hydroxymethyl)anthra-9,10-quinone
3-Hydroxymethylchrysazin
1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone,3-Hydroxymethylchrysazine
1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthraquinone
Diacerein impurity B
9,10-Anthracenedione, 1,8-dihydroxy-3-(hydroxymethyl)-
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Related Compounds: More...
Aloeemodin-triacetat
25395-11-3
ALOEEMODIN,7-HYDROXY
156547-97-6
Aloeemodin-8-monoglucoside
33037-46-6
Aloeemodin-emodin-dianthron
17062-55-4
Chrysophanol-aloeemodin-dianthron
17062-56-5
Aloeemodin-ω-O-β-D-glucopyranoside
29010-56-8
Aloeemodin-9-anthron-10-D-glucosyl-11-mono-α-L-rhamnosid (Aloinosid B)
11006-91-0
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