ALOE EMODIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O5
Molecular Weight	270.2369
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCC1=CC2=C(C(O)=C1)C(=O)C3=C(C=CC=C3O)C2=O

InChI

InChIKey=YDQWDHRMZQUTBA-UHFFFAOYSA-N

InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2

HIDE SMILES / InChI

Molecular Formula	C15H10O5
Molecular Weight	270.2369
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10850417 | https://www.ncbi.nlm.nih.gov/pubmed/957911 | https://www.ncbi.nlm.nih.gov/pubmed/23869465 | https://www.ncbi.nlm.nih.gov/pubmed/15747063 | https://www.ncbi.nlm.nih.gov/pubmed/29071869

Aloe emodin is a hydroxyanthraquinone found in Aloe vera leaves. It plays an important role in the regulation of cell growth and death. It has been reported to promote the anti-cancer effects in various cancer cells by inducing apoptosis. Aloe emodin selectively inhibits human neuroectodermal tumor cell growth in tissue cultures and in animal models. It has significant antileukemic activity against the P-388 lymphocytic leukemia in mice. Anti-glioma action of Aloe emodin involves ERK-independent induction of both apoptosis and autophagy, as well as ERK inhibition-mediated differentiation of glioma cells. Aloe-emodin can not pass through the blood-brain barrier.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10850417	Activator 1430
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15531293	Modulator 828
Mitogen-activated protein kinase 1 and 3 (ERK2 and ERK1) 1 Target ID: CHEMBL2111356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15747063	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Neuroblastoma 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10850417	Primary	Preclinical	Unknown Approved Use Unknown
Glioma 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23869465 https://www.ncbi.nlm.nih.gov/pubmed/15747063 https://www.ncbi.nlm.nih.gov/pubmed/15531293	Primary	Basic research	Unknown Approved Use Unknown
Lymphocytic leukemia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/957911	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of the anti-angiogenic effect of aloe-emodin.	2006 Dec	17131052
Aloe-emodin affects the levels of cytokines and functions of leukocytes from Sprague-Dawley rats.	2006 Jul-Aug	16900781
[Induction of hairy roots and anthraquinone production in Rheum palmatum].	2006 Sep	17144464
Effect of a polyphenol-rich extract from Aloe vera gel on experimentally induced insulin resistance in mice.	2007	18186589
Final report on the safety assessment of AloeAndongensis Extract, Aloe Andongensis Leaf Juice,aloe Arborescens Leaf Extract, Aloe Arborescens Leaf Juice, Aloe Arborescens Leaf Protoplasts, Aloe Barbadensis Flower Extract, Aloe Barbadensis Leaf, Aloe Barbadensis Leaf Extract, Aloe Barbadensis Leaf Juice,aloe Barbadensis Leaf Polysaccharides, Aloe Barbadensis Leaf Water, Aloe Ferox Leaf Extract, Aloe Ferox Leaf Juice, and Aloe Ferox Leaf Juice Extract.	2007	17613130
Preparative isolation and purification of hydroxyanthraquinones from Rheum tanguticum Maxim. on normal phase silica gel: using a Flash Master Personal system.	2007	17516248
Aloe-emodin metabolites protected N-methyl-d-aspartate-treated retinal ganglion cells by Cu-Zn superoxide dismutase.	2007 Apr	17444804
Application of 1-alkyl-3-methylimidazolium-based ionic liquids as background electrolyte in capillary zone electrophoresis for the simultaneous determination of five anthraquinones in Rhubarb.	2007 Apr 30	19071659
Anticancer effect of aloe-emodin on cervical cancer cells involves G2/M arrest and induction of differentiation.	2007 Dec	18031614
Inhibitory effect of schisandrin B on gastric cancer cells in vitro.	2007 Dec 28	18161920
Large-scale separation of hydroxyanthraquinones from Rheum palmatum L. by pH-zone-refining counter-current chromatography.	2007 Dec 28	18022630
Growth inhibitory effects of gastric cancer cells with an increase in S phase and alkaline phosphatase activity repression by aloe-emodin.	2007 Jan	17172820
Determination of the anthraquinones aloe-emodin and aloin-A by liquid chromatography with mass spectrometric and diode array detection.	2007 Jan-Feb	17373434
Phenolic constituents in dried flowers of aloe vera (Aloe barbadensis) and their in vitro antioxidative capacity.	2007 Jun	17520524
Affinity chromatography with immobilized DNA stationary phase for biological fingerprinting analysis of traditional Chinese medicines.	2007 Jun 22	17451725
Simultaneous determination of anthraquinones in rhubarb by high-performance liquid chromatography and capillary electrophoresis.	2007 Mar 23	17289060
Chemical constituents of cape aloe and their synergistic growth-inhibiting effect on Ehrlich ascites tumor cells.	2007 May	17485848
Simultaneous quantification of five anthraquinones in rat plasma by high-performance liquid chromatography with fluorescence detection.	2007 May	17294506
Aloe-emodin suppressed NMDA-induced apoptosis of retinal ganglion cells through regulation of ERK phosphorylation.	2007 Nov	17661329
Aloe-emodin-induced apoptosis in human gastric carcinoma cells.	2007 Nov	17637488
Chaperones are the target in aloe-emodin-induced human lung nonsmall carcinoma H460 cell apoptosis.	2007 Nov 14	17643413
Aloe-emodin induces in vitro G2/M arrest and alkaline phosphatase activation in human oral cancer KB cells.	2007 Oct	17257888
Anti-cancer properties of anthraquinones from rhubarb.	2007 Sep	17022020
Mitochondria, PPARs, and Cancer: Is Receptor-Independent Action of PPAR Agonists a Key?	2008	18645611
Preparation of 1,8-di-O-alkylaloe-emodins and 15-amino-, 15-thiocyano-, and 15-selenocyanochrysophanol derivatives from aloe-emodin and studying their cytotoxic effects.	2008 Apr	18379097
Modeling the interactions of herbal drugs to beta-ketoacyl ACP synthase of Mycobacterium tuberculosis H37Rv.	2008 Apr	18282003
Anthraquinone pharmacokinetics in Xiexin decoction and the different combinations of its constituent herbs.	2008 Apr-Jun	18777942
Development and validation of a UPLC method for quality control of rhubarb-based medicine: fast simultaneous determination of five anthraquinone derivatives.	2008 Aug 5	18440751
Purification of hydroxyanthraquinones and cinnamic acid from the roots of Rheum officinale Baill.	2008 Feb	18183553
Studies of the interaction between Aloe-emodin and DNA and preparation of DNA biosensor for detection of PML-RARalpha fusion gene in acute promyelocytic leukemia.	2008 Jan 15	18371732
Determination of pharmacologically active compounds in root extracts of Cassia alata L. by use of high performance liquid chromatography.	2008 Jan 15	18371725
Ultrasonic extraction and separation of anthraquinones from Rheum palmatum L.	2008 Jul	18280764
Rapid simultaneous quantification of five active constituents in rat plasma by high-performance liquid chromatography/tandem mass spectrometry after oral administration of Da-Cheng-Qi decoction.	2008 Jul 15	18358661
Simultaneous determination of anthraquinones in radix Polygoni multiflori by capillary gas chromatography coupled with flame ionization and mass spectrometric detection.	2008 Jul 18	18262194
Anti-proliferative effects of estrogen receptor-modulating compounds isolated from Rheum palmatum.	2008 Jun	18563353
Comment on "Aloe-emodin induces in vitro G2/M arrest and alkaline phosphatase activation in human oral cancer KB cells" [Xiao B, Guo J, Liu D, Zhang S. Oral Oncol 2007;43(9):905-10].	2008 Jun	18282787
Structure-activity models of oral clearance, cytotoxicity, and LD50: a screen for promising anticancer compounds.	2008 Jun 13	18554402
[Theoretical and experimental studies on solubility parameters of multiple components for traditional Chinese materia medica with HPLC].	2008 Mar	18590190
Aloin induces apoptosis in Jurkat cells.	2008 Mar	18068945
Suppression of C-myc expression associates with anti-proliferation of aloe-emodin on gastric cancer cells.	2008 May	18443957
Inhibitory effect of aloe-emodin on metastasis potential in HO-8910PM cell line.	2008 May-Jun	18464074
Antitumor and antimetastatic actions of anthrone-C-glucoside, cassialoin isolated from Cassia garrettiana heartwood in colon 26-bearing mice.	2008 Nov	18823377
Aloe-emodin is an interferon-inducing agent with antiviral activity against Japanese encephalitis virus and enterovirus 71.	2008 Oct	18701259
Anthraquinone-benzisochromanquinone dimers from the roots of Berchemia floribunda.	2008 Sep	18758095
Profiling the metabolic differences of anthraquinone derivatives using liquid chromatography/tandem mass spectrometry with data-dependent acquisition.	2009 Feb	19142847
Chemical constituents isolated from Polygala japonica leaves and their inhibitory effect on nitric oxide production in vitro.	2009 Feb	18825536
Anti-angiogenic effects of rhubarb and its anthraquinone derivatives.	2009 Jan 21	19061946
Quantitative HPLC determination and extraction of anthraquinones in Senna alata leaves.	2009 Mar	19298705
Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.	2009 Mar	19269596
Pharmacokinetics of anthraquinones in Xiexin decoction and in different combinations of its constituent herbs.	2009 Mar	18844291

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

The colony growth was only partially reduced at high concentrations of aloe-emodin, with ED50s of 80 and 120 uM, respectively, for bone marrow- and cord blood-derived colony forming unit granulocyte/macrophages. In contrast, the colony-forming activity of neuroblastoma cells (SJ-N-KP) was inhibited at a much lower concentration of aloe-emodin (ED50 of 7 uM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:13:42 GMT 2023` Edited by `admin` on `Fri Dec 15 19:13:42 GMT 2023`
Record UNII	C8IYT9CR7C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALOE EMODIN

Common Name

English

ALOE-EMODIN [MI]

Common Name

English

NSC-38628

Code

English

1,8-DIHYDROXY-3-(HYDROXYMETHYL)-9,10-ANTHRACENEDIONE

Systematic Name

English

DIHYDROXY-3-HYDROXYMETHYLANTHRAQUINONE, 1,8-

Systematic Name

English

3-HYDROXYMETHYLCHRYSAZIN

Common Name

English

3-HYDROXYMETHYLCHRYSAZINE

Common Name

English

ALOE-EMODIN

Common Name

English

RHABARBERONE

Common Name

English

ANTHRAQUINONE, 1,8-DIHYDROXY-3-(HYDROXYMETHYL)-

Systematic Name

English

1,8-DIHYDROXY-3-(HYDROXYMETHYL)ANTHRAQUINONE

Systematic Name

English

Code System Code Type Description

MERCK INDEX

m1570