480-70-6

Usage

InChI:InChI=1/C15H10O6/c16-8-5-11(19)14-12(6-8)21-13(15(14)20)4-7-1-2-9(17)10(18)3-7/h1-6,16-19H/b13-4-

Upstream product

• 3260-49-9 4,6-dihydroxybenzofuran-3(2H)-one 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 23053-69-2 (Z)-2-(3,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1202495-48-4 (2Z)-2-[3,4-bis(methoxymethoxy)benzylidene]-4,6-bis(methoxymethoxy)-1-benzofuran-3(2H)-one 
• 73692-51-0 2',3,4,4',6'-pentahydroxychalcone 
• 112772-60-8 3-(3,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 118075-12-0 2'-hydroxy-4,4',6'-trimethoxymethoxylchalcone 
• 23053-69-2 4,6,3',4'-tetramethoxyaurone 
• 10496-67-0 3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 

Downstream Products

• 57765-66-9 eriodictoyl dihydrochalcone 
• 65370-64-1 4,6-diacetoxy-2-((Z)-3,4-diacetoxy-benzylidene)-benzofuran-3-one 

Relevant academic research and scientific papers

Design, synthesis and biological activities of dihydroaurones

To widen aurones applicability in achromatic food and cosmetic applications, a series of dihydroaurones were designed to mimic natural aurones as well as synthetic aurones. Dihydroaurones have been synthesized from the corresponding aurones by hydrogenation. These dihydroaurones and their corresponding aurones were screened for antioxidant, anti-inflammatory and tyrosinase enzyme inhibitory activity. Synthesized dihydroaurones (3b-f) displayed superior antioxidant activity in superoxide free radical scavenging assay than the standard gallic acid. Dihydroaurones (3b-f) also exhibited significant tyrosinase enzyme inhibitory activity and two dihydroaurones (3h, 3j) showed promising 5-lipoxygenase inhibitory activity.

Hydroxyaurone derivative as well as preparation method and application thereof

The invention relates to a hydroxyaurone derivative as well as a preparation method and application thereof. A monomeric compound aurone separated from Kunlun chrysanthemum in Xinjiang is used as a mother nucleus compound, hydroxyl is introduced into auro

Aurones as new porcine pancreatic α-amylase inhibitors

Background: Aurones, (Z)-2-benzylidenebenzofuran-3-one derivatives, are naturally-occurring structural isomers of flavones, with promising pharmacological potential. Methods: In this study, the structural requirements for the inhibition of porcine pancreatic α-amylase by hydroxylated or methoxylated aurone derivatives were investigated by assessing their in vitro biological activities against porcine pancreatic α-amylase. Results: The structure-activity relationship of these inhibitors based on both in vitro and in silico findings showed that the hydrogen bonds between the OH groups of the A or B ring of (Z)-benzylidenebenzofuran-3-one derivatives and the catalytic residues of the binding site are crucial for their inhibitory activities. Conclusion: It seems that the OH groups in aurones inhibit α-amylase in a manner similar to that of OH groups in flavones and flavonols.

COMPOSITIONS AND METHODS FOR INHIBITING GROUP II INTRON RNA

The present invention provides compositions and methods for inhibiting group II intron splicing for treating or preventing a disease or disorder associated with an organism harboring an active group II intron. The present invention also provides compositi

Investigation of binding-site homology between mushroom and bacterial tyrosinases by using aurones as effectors

Tyrosinase is a copper-containing enzyme found in plants and bacteria, as well as in humans, where it is involved in the biosynthesis of melanin-type pigments. Tyrosinase inhibitors have attracted remarkable research interest as whitening agents in cosmetology, antibrowning agents in food chemistry, and as therapeutics. In this context, commercially available tyrosinase from mushroom (TyM) is frequently used for the identification of inhibitors. This and bacterial tyrosinase (TyB) have been the subjects of intense biochemical and structural studies, including X-ray diffraction analysis, and this has led to the identification of structural homology and divergence among enzymes from different sources. To better understand the behavior of potential inhibitors of TyM and TyB, we selected the aurone family - previously identified as potential inhibitors of melanin biosynthesis in human melanocytes. In this study, a series of 24 aurones with different hydroxylation patterns at the A- and B-rings were evaluated on TyM and TyB. The results show that, depending on the hydroxylation pattern of A- and B-rings, aurones can behave as inhibitors, substrates, and activators of both enzymes. Computational analysis was performed to identify residues surrounding the aurones in the active sites of both enzymes and to rationalize the interactions. Our results highlight similarities and divergence in the behavior of TyM and TyB toward the same set of molecules. A lighter future: Aurones have been identified as inhibitors of melanin biosynthesis. In this study, 24 aurones were evaluated on mushroom and bacterial tyrosinases (TyM and TyB). The compounds behaved as inhibitors, substrates, or activators of both enzymes. Our results highlight similarities and differences in behavior between TyM and TyB with the same set of molecules.

Aurones as histone deacetylase inhibitors: Identification of key features

In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET-based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 μM in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation.

A one-pot synthesis of aurones from substituted acetophenones and benzaldehydes: A concise synthesis of aureusidin

A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations. Georg Thieme Verlag Stuttgart New York.

Discovery of naturally occurring aurones that are potent allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase

We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC50 below 5 μM and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indol-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC50 of 2.2 μM. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

Crude peroxidase from onion solid waste as a tool for organic synthesis. Part I: Cyclization of 2′,3,4,4′,6′-pentahydroxy-chalcone into aureusidin

The potential of a crude peroxidase (POD) from onion solid waste as a biocatalyst for the synthesis of a naturally occurring aurone is described. The crude enzyme preparation effectively promotes the cyclization of 2′,3,4,4′,6′-pentahydroxy-chalcone (which is not a natural substrate of onion POD) into aureusidin.

Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

A series of 2′-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition.