Aloeemodin

Names

[ CAS No. ]:
481-72-1

[ Name ]:
Aloeemodin

[Synonym ]:
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)-

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]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Quinones

[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.

[Related Small Molecules]

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

[ 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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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. ...

Related Compounds

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