6030-60-0

Upstream product

• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 481-70-9 endocrocin 
• 84993-87-3 6-bromomethyl-1,3,8-triacetoxyanthracene-9,10-dione 
• 500357-04-0 1,3,8,9-tetraacetoxy-6-methyl-anthracene 

Downstream Products

• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 478-45-5 emodic acid 
• 481-72-1 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione 
• 491-60-1 emodinanthrone 
• 481-73-2 citreorosein 

Relevant academic research and scientific papers

Synthesis and preliminary evaluation of mono-[123I]iodohypericin monocarboxylic acid as a necrosis avid imaging agent

Hypericin monocarboxylic acid was synthesized in an overall yield of 25% in four steps and radiolabelled with iodine-123 in good yield (>75%). The resulting mono-[123I]iodohypericin monocarboxylic acid was evaluated in normal mice and in rats with ethanol induced liver necrosis. In this model, tracer concentration in necrotic liver tissue was 14 times higher than in the viable liver tissue as quantified by autoradiography at 24 h post injection. The results indicate the feasibility of visualization of necrotic tissue with the novel tracer.

Apoptosis and DNA intercalating activities of novel emodin derivatives

Emodin belongs to the anthraquinone class of compounds and is the major bioactive compound of several herb species. A library of novel emodin derivatives was synthesized and their antiproliferative activities were evaluated against HepG2, PC-3, DU-145, MC

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.

Chemoenzymatic, biomimetic total synthesis of (-)-rugulosin B, C and rugulin analogues and their biosynthetic implications

Herein, we report the chemoenzymatic synthesis of a heterodimeric (-)-rugulosin B, homodimeric (-)-rugulosin C, and several rugulin analogues in three to four steps starting from anthraquinones. This work supports dimerization between variously substituted putative monomeric intermediates during the biosynthesis of naturally occurring (+)-rugulosin B and C.

Chemoenzymatic reduction of citreorosein and its implications on aloe-emodin and rugulosin C (bio)synthesis

A chemoenzymatic reduction of citreorosein by the NADPH-dependent polyhydroxyanthracene reductase from Cochliobolus lunatus or MdpC from Aspergillus nidulans in the presence of Na2S2O4 gave access to putative biosynthetic intermediates, (R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracene-1(2H)-one and its oxidized form, (R)-3,4-dihydrocitreorosein. Herein, we discuss the implications of these results towards the (bio)synthesis of aloe-emodin and (+)-rugulosin C in fungi.

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.

Chemical Reactivity of Emodin and Its Oxidative Metabolites to Thiols

Polygonum multiflorum is an herbal medicine widely employed in China. Hepatotoxicity of the herbal medicine has been well documented, but the mechanisms of the toxicity remain unknown. Emodin (EM) is a major constituent of the herb and has been reported to be hepatotoxic. The main purpose of this study was to define the metabolic pathways of EM in order to characterize the potential reactive intermediates. EM was incubated with rat liver microsomes or human liver microsomes, followed by LC-MS/MS analysis to investigate the in vitro and in vivo metabolism of EM. As a result, three monohydroxylation metabolites (M1-M3) were detected after exposure to EM: -hydroxyemodin, 2-hydroxyemodin, and 5-hydroxyemodin. Urinary M1 and M2 were detected in rats administered EM. Three mercapturic acids (M4-M6) were found in microsomal incubations containing EM, NADPH, and N-acetylcysteine. It appears that M4 originated from parent compound EM, and M5 and M6 originated from M1 and M2, respectively. Two biliary EM-derived GSH conjugates were found in EM-treated rats. One arose from direct adduction of EM with GSH, and the other was derived from M1. Cytochrome P450's 1A2, 2C19, and 3A4 were the predominant P450 enzymes to oxidize EM. The findings helped us to understand the mechanisms of EM-induced hepatotoxicity.

Preparation of novel antiproliferative emodin derivatives and studies on their cell cycle arrest, caspase dependent apoptosis and DNA binding interaction

Emodin (1) is the major bioactive compound of several herb species, which belongs to anthraquinone class of compound. As a part of our drug discovery program, large quantities of emodin (1) was isolated from the roots of Rheum emodi and a library of novel

A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain

A new procedure for the preparation of emodin carbaldehyde and citreorosein was described, in which, ω,ω'-dibromomethylemodin triacetate was prepared as a key intermediate by NBSmediated bromination of 1,3,8-triacetylemodin. Reduction of emodin and citreorosein with SnCl 2 in a 1:1 mixture of HOAc and HCl afforded the corresponding anthrones in 90% and 92% yield, respectively, while the corresponding 10-desoxyemodin carbaldehyde was prepared by MnO2 oxidation of 10-desoxycitreorosein. 10-Desoxycitreorosein and emodin carbaldehyde showed feasible μ-calpain inhibitory activities with IC50 values of 20.15 and 25.77 M, respectively.

Characterization of emodin metabolites in Raji cells by LC-APCI-MS/MS

A rapid, simple, and sensitive liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS) method was developed for the identification and quantification of emodin metabolites in Raji cells, using aloe-emodin as an internal standard. Analyses were performed on an LC system employing a Cosmosil 5C18 AR-II column and a stepwise gradient elution with methanol-20 mM ammonium formate at a flow rate of 1.0 mL/min operating in the negative ion mode. As a result, the starting material emodin and its five metabolites were detected by analyzing extracts of Raji cells that had been cultivated in the presence of emodin. The identification of the metabolites and elucidation of their structures were performed by comparing their retention times and spectral patterns with those of synthetic samples. In addition to the major metabolite 8-O-methylemodin, four other metabolites were assigned as ω-hydroxyemodin, 3-O-methyl-ω-hydroxyemodin, 3-O-methylemodin (physcion), and chrysophanol.