478-45-5

Usage

InChI:InChI=1/C15H8O7/c16-5-3-7-10(9(18)4-5)14(20)12-8(17)2-1-6(15(21)22)11(12)13(7)19/h1-4,16-18H,(H,21,22)

Upstream product

• 61350-19-4 4,5,7-triacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 202974-82-1 4,5,7-trimethoxy-9,10-dicarbonyl-9,10-dihydroanthracene-2-carboxylic acid 
• 132319-49-4 4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 
• 121210-61-5 3-(dibromomethyl)-1,6,8-trimethoxyanthracene-9,10-dione 
• 6414-42-2 1,3,8-trimethoxy-6-methyl-9,10-anthraquinone 
• 152039-21-9 Ethyl 9,10-dihydro-4-hydroxy-5,7-dimethoxy-9,10-dioxo-2-anthracenecarboxylate 
• 152039-22-0 Ethyl 9,10-dihydro-4,5-dihydroxy-7-methoxy-9,10-dioxo-2-anthracenecarboxylate 
• 152039-11-7 Ethyl 6-chloro-5,8-dihydro-4-hydroxy-5,8-dioxo-2-naphthalenecarboxylate 
• 6030-60-0 1,6,8-triacetoxy-3-methyl-9,10-anthraquinone 
• 17636-18-9 parietinic acid 

Relevant academic research and scientific papers

A biocatalytic approach towards the preparation of natural deoxyanthraquinones and their impact on cellular viability

Herein, a two-step chemoenzymatic process for the synthesis of medicinally important 3-deoxygenated anthra-9,10-quinones is developed. It involves a regio- and stereoselective reduction of hydroanthraquinones to (R)-configured dihydroanthracenones using an anthrol reductase of T. islandicus, followed by oxidation and dehydration to obtain deoxyanthraquinones in 65-80% yield. Comparison of the cell viability of normal human kidney HEK293 cells between anthraquinones and their deoxy derivatives revealed less toxicity for the latter.

Identification and characterization of an anthrol reductase from: Talaromyces islandicus (Penicillium islandicum) WF-38-12

An NADPH-dependent oxidoreductase from Talaromyces islandicus WF-38-12 has been identified through genome analysis. It has been shown to catalyze a regio- and stereoselective reduction of anthrols (formed in situ by the reduction of anthraquinones in the presence of Na2S2O4) to (R)-dihydroanthracenones, with high enantiomeric excess (>99%). The implications of results on the biosynthesis of deoxygenated (bis)anthraquinones and modified (bis)anthraquinones are discussed.

Synthesis and antibacterial activity of emodin and its derivatives against methicillin-resistant Staphylococcus aureus

Synthesis of the antibacterial emodin was improved using Friedel-Crafts acylation as a key step leading to 37% overall yield. In addition, 21 analogues were synthesized by structural modification of the hydroxyl and methyl groups, as well as the aromatic ring of emodin. Antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxicity against noncancerous Vero cells were evaluated. A structure-activity relationship (SAR) study indicated that the hydroxyl groups and the methyl group in the emodin skeleton were crucial for anti-MRSA activity. Furthermore, the presence of an iodine atom or ethylamino group on the aromatic ring enhanced the anti-MRSA activity with higher selectivity indices, while derivatives containing bromine, chlorine atoms or quaternary ammonium salt were as active as emodin. The quaternary ammonium group on the aromatic ring also led to non-cytotoxicity against Vero cells.

RHEIN CONJUGATES, PREPARATION METHOD THEREOF AND THEIR USES IN PRODUCING MEDICINES FOR TREATING DIABETIC NEPHROSIS, INTESTINAL ADHESION AND OSTEOARTHRITIS

The conjugates of present invention are formed by the combination of rhein or their analogues with the organic bases or amino acids in molecular force between them. The methods for preparing the conjugates and their uses for manufacturing medicines in the treatment of diabetic nephrosis, recovery of gastrointestinal function and prevention of intestinal adhesion, as well as treatment of osteoarthritis, rheumatic arthritis and rheumatoid arthritis are also described. Rhein or their analogues as the left part of general formula (I) is selected from (1) the compounds of rhein or their analogues, in which one or two substituents of R2~R3 and R6~R7 are COOH at least two substituents of R1~8 are -H; or (2) the rhein-containing extract derived from plants. In general formula (I), M represents nitrogen-containing organic bases or basic amino acids.

Rhein Conjugates, Preparation Method Thereof and Their Uses in Producing Medicines for Treating Diabetic Nephrosis, Intestinal Adhesion and Osteoarthritis

The conjugates of present invention are formed by the combination of rhein or their analogues with the organic bases or amino acids in molecular force between them. The methods for preparing the conjugates and their uses for manufacturing medicines in the treatment of diabetic nephrosis, recovery of gastrointestinal function and prevention of intestinal adhesion, as well as treatment of osteoarthritis, rheumatic arthritis and rheumatoid arthritis are also described. Rhein or their analogues as the left part of general formula (I) is selected from (1) the compounds of rhein or their analogues, in which one or two substituents of R2?R3 and R6?R7 are COOH at least two substituents of R1?8 are —H; or (2) the rhein-containing extract derived from plants. In general formula (I), M represents nitrogen-containing organic bases or basic amino acids.

Long-acting gonadotropin-releasing hormone analogs and methods of use thereof

The present invention relates to the design, synthesis and biological evaluation of potent long-acting gonadotropin-releasing hormone (GnRH) analogs including agonists and antagonists comprising a GnRH peptide conjugated to emodic acid or an emodic acid derivative. These long acting analogs bind to GnRH receptors with high affinity and are devoid of any toxicity or antiproliferative effects. The present invention further relates to therapeutic uses of these GnRII analogs as contraceptives, in controlling fertility and in treating and/or preventing sex-hormone dependent diseases or conditions.

Generation of free radicals by emodic acid and its [D-Lys6]GnRH-conjugate

In an attempt to develop an efficient chemotherapeutic agent targeted at malignant cells that express receptors to gonadotropin releasing hormone (GnRH) we coupled [D-Lys6]GnRH covalently to an emodin derivative, i.e. emodic acid (Emo) to yield

The Chemical Structure and the Mutagenicity of Emodin Metabolites

Emodin (1,3,8-trihydroxy-6-methyl-9,10-anthraquinone) is a natural occuring anthraquinone formed in rhubarb and fungal metabolites.Emodin was transformed into 6 major metabolites by rat hepatic microsomes.The metabolites were identified as 2-hydroxyemodin, 4-hydroxyemodin, 5-hydroxyemodin, 7-hydroxyemodin, ω-hydroxyemodin, and emodic acid by comparison with the synthetic compounds using thin-layer chromatography.It was clear that 2-hydroxyemodin is a proximate mutagen as a synthetic compound by the Salmonella assay.Other metabolites, such as 5-hydroxyemodin and ω-hydroxyemodin, became active after metabolic activation, but 4-hydroxyemodin and emodic acid were inactive either in the presence or in the absence of the metabolic activation system.