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

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 antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus.	1992 Jan	1310583
Antifungal activity of anthraquinone derivatives from Rheum emodi.	2000 Sep	10967452
[Effect of aloe-emodin on c-myc gene expression of cultured vascular smooth muscle cells of injured artery].	2001 Jul	12575400
Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity.	2001 Jul 23	11459643
Cytotoxic and DNA damage-inducing activities of low molecular weight phenols from rhubarb.	2001 Jul-Aug	11724365
In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus.	2001 Mar	11428243
Effects and mechanisms of aloe-emodin on cell death in human lung squamous cell carcinoma.	2001 Nov 23	11730720
Studies on the photostability and phototoxicity of aloe-emodin, emodin and rhein.	2002 Jun	12116877
[Determination of six effective components in Rheum by cyclodextrin modified micellar electrokinetic chromatography].	2002 Oct	12567865
Signaling pathway for aloe-emodin-induced apoptosis in human H460 lung nonsmall carcinoma cell.	2003 Aug 10	12794753
Combined effect of aloe-emodin and chemotherapeutic agents on the proliferation of an adherent variant cell line of Merkel cell carcinoma.	2004 Jan	14654928
Determination of active ingredients in Huangdan Yinchen Keli by CZE with amperometric detection.	2004 Jun 29	15193742
Preparative isolation and purification of hydroxyanthraquinones and cinnamic acid from the chinese medicinal herb Rheum officinale Baill. by high-speed counter-current chromatography.	2004 Oct 15	15527141
Separation and determination of four active anthraquinones in Chinese herbal preparations by flow injection-capillary electrophoresis.	2005 Aug	16007705
[Studies on the chemical constituents in herb of Mentha haplocalyx].	2005 Jul	16161444
Simultaneous determination of anthraquinones, their 8-beta-D-glucosides, and sennosides of Rhei Rhizoma by capillary electrophoresis.	2005 May	15863933
Simultaneous determination of anthraquinones in Rhubarb by pressurized liquid extraction and capillary zone electrophoresis.	2005 May	15800969
Evaluation of the anti-angiogenic effect of aloe-emodin.	2006 Dec	17131052
[Studies on chemical constituents of hairy root of Cassia obtusifolia].	2006 Feb	16573002
Aloe-emodin induces apoptosis in T24 human bladder cancer cells through the p53 dependent apoptotic pathway.	2006 Jan	16406939
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
Preparative isolation and purification of hydroxyanthraquinones from Rheum tanguticum Maxim. on normal phase silica gel: using a Flash Master Personal system.	2007	17516248
Inhibitory effect of schisandrin B on gastric cancer cells in vitro.	2007 Dec 28	18161920
Rapid separation and determination of structurally related anthraquinones in Rhubarb by pressurized capillary electrochromatography.	2007 Jan 4	16875795
Simultaneous determination of eight active components in Chinese medicine 'YIQING' capsule using high-performance liquid chromatography.	2007 Jan 4	16846714
Affinity chromatography with immobilized DNA stationary phase for biological fingerprinting analysis of traditional Chinese medicines.	2007 Jun 22	17451725
Simultaneous quantification of five anthraquinones in rat plasma by high-performance liquid chromatography with fluorescence detection.	2007 May	17294506
Anthraquinone pharmacokinetics in Xiexin decoction and the different combinations of its constituent herbs.	2008 Apr-Jun	18777942
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
Profiling the metabolic differences of anthraquinone derivatives using liquid chromatography/tandem mass spectrometry with data-dependent acquisition.	2009 Feb	19142847
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).

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