100433-06-5Relevant articles and documents
The comparison of neuroprotective effects of isoliquiritigenin and its Phase I metabolites against glutamate-induced HT22 cell death
Yang, Eun-Ju,Kim, Minjun,Woo, Ji Eun,Lee, Taeho,Jung, Jong-Wha,Song, Kyung-Sik
, p. 5639 - 5643 (2016)
It is becoming increasingly important to investigate drug metabolites to evaluate their toxic or preventive effects after administration of the parent compound. In our previous study, isoliquiritigenin isolated from Glycyrrhizae Radix effectively protected mouse-derived hippocampal neuronal cells (HT22) against 5 mM glutamate-induced oxidative stress. However, there is little information on the protective effects of the metabolites of isoliquiritigenin on HT22 cells. In this study, isoliquiritigenin and its Phase I metabolites were prepared and their neuroprotective activities on glutamate-treated HT22 cells were compared. The prepared metabolites were liquiritigenin (1), 2′,4,4′,5′-tetrahydroxychalcone (2), sulfuretin (3), butein (4), davidigenin (5), and cis-6,4′-dihydroxyaurone (6). Among the six metabolites, 4 showed better neuroprotective effects than the parent compound, isoliquiritigenin. Our study suggests that the neuroprotective effect of isoliquiritigenin could be elevated by its active metabolite 4, which is a chalcone containing a catechol group in the B ring.
Aurone synthase is a catechol oxidase with hydroxylase activity and provides insights into the mechanism of plant polyphenol oxidases
Molitor, Christian,Mauracher, Stephan Gerhard,Rompel, Annette
, p. E1806 - E1815 (2016)
Tyrosinases and catechol oxidases belong to the family of polyphenol oxidases (PPOs). Tyrosinases catalyze the o-hydroxylation and oxidation of phenolic compounds, whereas catechol oxidases were so far defined to lack the hydroxylation activity and catalyze solely the oxidation of o-diphenolic compounds. Aurone synthase from Coreopsis grandiflora (AUS1) is a specialized plant PPO involved in the anabolic pathway of aurones. We present, to our knowledge, the first crystal structures of a latent plant PPO, its mature active and inactive form, caused by a sulfation of a copper binding histidine. Analysis of the latent proenzyme's interface between the shielding C-terminal domain and the main core provides insights into its activation mechanisms. As AUS1 did not accept common tyrosinase substrates (tyrosine and tyramine), the enzyme is classified as a catechol oxidase. However, AUS1 showed hydroxylase activity toward its natural substrate (isoliquiritigenin), revealing that the hydroxylase activity is not correlated with the acceptance of common tyrosinase substrates. Therefore, we propose that the hydroxylase reaction is a general functionality of PPOs. Molecular dynamics simulations of docked substrate-enzyme complexes were performed, and a key residue was identified that influences the plant PPO's acceptance or rejection of tyramine. Based on the evidenced hydroxylase activity and the interactions of specific residues with the substrates during the molecular dynamics simulations, a novel catalytic reaction mechanism for plant PPOs is proposed. The presented results strongly suggest that the physiological role of plant catechol oxidases were previously underestimated, as they might hydroxylate their - so far unknown - natural substrates in vivo.
Biflavonoids from flowers of Butea monosperma (Lam.) Taub.
Ahmed, Fakhruddin Ali,Kim, Sang-Yong,Kurimoto, Shin-Ichiro,Sasaki, Hisako,Shibata, Hirofumi,Kashiwada, Yoshiki,Takaishi, Yoshihisa
, p. 2079 - 2089 (2011)
A new aurone glucoside (1) and three new biflavonoids (12 - 14), together with fourteen known compounds, were isolated from the flowers of Butea monosperma (Lam.) Taub. The structures of the new compounds were established by 1D, 2D NMR, MS and CD analyses. The isolated compounds were evaluated for their influenza A neuraminidase inhibitory activity and DPPH free-radical scavenging activity.
Fabrication, characterisation and in vitro biological activities of a sulfuretin-supplemented nanofibrous composite scaffold for tissue engineering
Koo, Youngwon,Lee, Hyeongjin,Kim, Suji,Song, No-Joon,Ku, Jin-Mo,Lee, Jaehwan,Choi, Chang Hyun,Park, Kye Won,Kim, Geunhyung
, p. 44943 - 44952 (2015)
Electrospun micro/nanofibrous scaffolds are widely used in various tissue regeneration applications because they have a similar structure to the extracellular matrix and can induce high attachment, proliferation and even differentiation of cultured cells. Here, we designed a new composite scaffold consisting of poly(ε-caprolactone) (PCL), bone morphogenetic protein (BMP-2) and sulfuretin fabricated using a combined process, i.e. electrospinning/plasma-treatment/coating. In the composite, we introduced a new bioactive component, sulfuretin, which was used as a cell stimulant to regenerate bone tissue. Sulfuretin release from the composite was controlled by coating of a fixed concentration of alginate. The in vitro biocompatibilities of the fibrous composites were examined using preosteoblasts (MC3T3-E1s), and the composite showed high cell adhesion and differentiation for a limited range of sulfuretin compared to the control, which lacked sulfuretin. These results suggest sulfuretin to be an effective supplemental bioactive agent for enhancing bone tissue growth on fibrous composite scaffolds.
Hydroxyaurone derivative as well as preparation method and application thereof
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Paragraph 0138-0139; 0143-0144, (2021/07/14)
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
Roshanzamir, Khashayar,Kashani-Amin, Elaheh,Ebrahim-Habibi, Azadeh,Navidpour, Latifeh
, p. 333 - 340 (2019/06/20)
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.
