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CHEMOSPHERE · 2019 · IF 5.108

Effects of acetylacetone on the thermal and photochemical conversion of benzoquinone in aqueous solution

Jiyuan Jin,Zhihao Chen,Xiaojie Song,Bingdang Wu,Guoyang Zhang,Shujuan Zhang

Quinones are components of electron transport chains in photosynthesis and respiration. Acetylacetone (AA), structurally similar to benzoquinone (BQ) for the presence of two identical carbonyl groups, has been reported as a quinone-like electron shuttle. Both BQ and AA are important chemicals in the aquatic environment. However, little information is known about their interactions if co-existed. We found here that AA significantly enhanced the conversion of BQ. By analyzing the evolution of chemical concentration, solution pH, dissolved oxygen, and the final products, the interactions between AA and BQ were elucidated. The reactions between BQ and AA generated oxygen but ultimately led to the reduction of solution pH and dissolved oxygen. The reactions proceeded faster under indoor lighting condition than in the dark. The formation of semiquinone radicals is believed as the primary step. The secondary AA-derived radicals might be strongly oxidative or reductive, depending on the concentration of dissolved oxygen. Insoluble humus was generated in the mixture of BQ and AA. These results suggest that the presence of AA might interfere with photosynthesis and respiration through the interactions with quinones.

CAS / MDL: 7778-77-0
研究领域: 环境科学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ChemistrySelect · 2023 ·Vol. 8 ·期 15 ·e202300287 · IF 2.1

A New Method for the Rapid Polymerization of Hydroquinone Catalyzed by Copper-ammonia Complexes

Mengyu Liu,Xiang Yu,Lanting Yang,Guangzai Nong

Graphical In this study, copper-ammonia complexes were utilized as catalysts for the polymerization of hydroquinone. These complexes not only acted as catalysts, but also bound to the poly(hydroquinone) during the polymerization process. With acid hydrolysis to remove the complexes, a thermally stable poly(hydroquinone was obtained with a degree of polymerization of 2–9 and yield of 63.2 %. The copper-ammonia complexes also accelerated the polymerization rate by three times compared to using only ammonia solution, offering potential for improving hydroquinone polymerization efficiency. Poly(hydroquinone) (PHQ) is a class of polymers with a leading chain composed entirely of quinone-phenol structures, which possess both the heat resistance of polymers and the redox activity of the monomer quinone-phenol and have promising applications in sensors, anti-corrosion and antioxidants. However, the current synthesis efficiency is low, and the product solubility is poor, which hinders its wide application. In this paper, the copper-ammonia complex was used to catalyze the polymerization of hydroquinone. The product‘s structure was verified by FTIR, UV-Vis, XPS, SSNMR and EDS. The degree of PHQ obtained by GPC was 2–9, and the reaction mechanism of the polymerization process was demonstrated in detail. The experiments showed that the copper-ammonia complex not only acted as a catalyst but also participated in the reaction, firstly generating the PHQ copper-ammonia complex, which is almost insoluble in water and common organic solvents. Then by further acid washing to dislodge the copper-amino groups, the resulting PHQ was able to dissolve in solvents such as DMSO and methanol. In addition, the method is three times faster than the catalytic rate using an equivalent amount of ammonia.

研究领域: 材料科学 · 化学工程
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APPLIED SURFACE SCIENCE · 2023 · IF 6.7

All-organic aqueous batteries consisting of quinone-hydroquinone derivatives with proton/aluminum-ion co-insertion mechanism

Yitian Su,Hongmin Jiang,Qiaoling Kang,Xianhe Meng,Xiaomei Zheng,Jianfei Lu,Xingkun Mei,Xiangdong Sun,Lijing Yan,Tingli Ma

All-organic aqueous batteries are deemed attractive energy storage systems for some application scenarios demanding recyclability or wearability. The efficient redox activity of quinone/hydroquinone-derived couples in biosystems inspires us to develop advanced batteries based on them. However, designing such an all-organic aqueous battery is challenging in selecting suitable electrolytes and active materials. A possible battery configuration consisting of the 9, 10-anthraquinone (AQ) anode, hydroquinone derivatives cathode, and weak acid metal-ion aqueous electrolyte is demonstrated herein. The molecular configuration of quinones and ionic type of electrolytes affect the redox behaviors of electrodes. Gratifyingly, a combination of AQ-tetrachlorohydroquinone-Al 2 (SO 4 ) 3 exhibits optimal performance. The underlying work mechanism of this full-battery configuration is disclosed by electrochemical and structural characterizations, finding that H + and Al 3+ are jointly involved in the redox reaction of quinone electrodes, and Al 3+ plays a crucial role. This work inaugurates a new framework for designing an all-organic aqueous battery.

研究领域: 能量存储系统 · 电化学 · 材料科学
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TOXICOLOGY · 2017 · IF 3.582

The electrophilic character of quinones is essential for the suppression of Bach1

Chuanyang Su,Zixuan Liu,Yawen Wang,Yuxin Wang,Erqun Song,Yang Song

The activation of nuclear factor erythroid 2-related factor 2 (Nrf2) is the most important cellular defense mechanisms against oxidative attack. BTB and CNC homology-1 (Bach1), like Kelch-like ECH-associated protein 1 (Keap1), is one of a negative regulator of Nrf2 that control antioxidant response elements (ARE)-dependent gene expressions. In the current study, we found that quinones show greater capacity than hydroquinones in nuclear Bach1 export, as well as ubiquitin-dependent Bach1 degradation in our experimental time frame. Consistently, quinones are easier than hydroquinones in Nrf2 activation and ARE-driven antioxidant protein expressions. Considering the redox cycling potential of quinone-hydroquinone couple, we investigated the effect of transit metal oxidation on the regulation of Nrf2 activity. As shown, Fe 3+ enhanced hydroquinone-induced Nrf2 activation and ARE-driven gene expressions, suggesting quinones rather than hydroquinone activate Nrf2 through Bach1 arylation. Taking together, our investigation illustrated that the electrophilic character of quinones ensure their conjugation with Bach1, which is important for the downregulation of Bach1 and the upregulation of Nrf2 signaling.

CAS / MDL: 1948-33-0 123-31-9
研究领域: 生物化学 · 分子生物学 · 细胞信号传导 · 氧化应激
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POLYMER · 2021 · IF 4.43

Polysulfone grafted with anthraquinone-hydroanthraquinone redox as a flexible membrane electrode for aqueous batteries

Xiaojiao Li,Hong-bin Sun,Xudong Sun

Polymeric membranes obtained much attention for decades owing to low cost, ease of process, and operation for battery separators, water purification , medical, etc., especially for the preparation of portable device materials. In this paper, we designed a membrane with polysulfone (PSF) grafted anthraquinone-hydroanthraquinone, namely the PSFAQ membrane. Various characterization (such as field emission scanning electron microscopy , transmission electron microscopy , etc.) and battery performance (such as galvanostatic charge/discharge test, cyclic voltammetry , etc.) indicated that the PSFAQ polymer membrane as an electrode can improve its electrochemical performance through pores and exposed anthraquinone-hydroanthraquinone redox couple. Zinc ion battery (ZIB) was assembled with PSFAQ membrane and metallic zinc as the electrode pair. This research proposes a new, safe, and inexpensive material that can be used for water system energy storage.

研究领域: 材料科学 · 电化学 · 能源存储
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JOURNAL OF SEPARATION SCIENCE · 2015 ·Vol. 38 ·期 8 ·1263-1270 · IF 2.737

Synthesis and evaluation of dummy molecularly imprinted microspheres for the specific solid-phase extraction of six anthraquinones from slimming tea

Xingqiang Wu,Shuxuan Liang,Xusheng Ge,Yunkai Lv,Hanwen Sun

Dummy molecularly imprinted microspheres with danthron as template were synthesized and their performance was evaluated. Accelerated solvent extraction can rapidly and effectively remove template molecules from the microspheres. The microspheres were applied as a specific sorbent for solid-phase extraction of six anthraquinones from slimming tea, showing excellent affinity and high selectivity to danthron and the target analytes. The molecular recognition mechanisms were discussed by the experimental validation with IR spectroscopy. The sample was treated using accelerated solvent extraction followed by dummy molecularly imprinted microspheres solid-phase extraction. Under the optimized ultra high performance liquid chromatographic conditions, the six target analytes can be baseline separated in 8 min, and good linearity was obtained in a range of 0.1–40 μg/mL with the correlation coefficient ( r 2 ) of ≥0.9998. The method limit of quantification was in a range of 1–2 mg/kg, it can ensure analysis of anthraquinones at mg/kg level. The intra- and interday precision (RSD, n = 6) for the analysis of the six analytes in a slimming tea was less than 4.5 and 5.4%, respectively. The developed method can be applied for the selective extraction, effective separation, and rapid determination of six anthraquinones in slimming tea.

研究领域: 分析化学 · 药物分析
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ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH · 2020 ·Vol. 27 ·期 25 ·31289-31299 · IF 3.056

Photochemical reactions between 1,4-benzoquinone and O2•−

Zhu Mengyu,Lu Jun,Hu Yadong,Liu Ying,Hu Shuheng,Zhu Chengzhu

The superoxide anion radical (O 2 •− ) is one of the most predominant reactive oxygen species (ROS), which is also involved in diverse chemical and biological processes. In this study, O 2 •− was generated by irradiating riboflavin in an O 2 -saturated solution using an ultraviolet lamp ( λ em = 365 nm) as the light source. The photochemical reduction of 1,4-benzoquinone ( p -BQ) by O 2 •− was explored by 355-nm laser flash photolysis (LFP) and 365-nm UV light steady irradiation. The results showed that the photodecomposition efficiency of p -BQ was influenced by the riboflavin concentration, p -BQ initial concentration, and pH values. The superoxide anion radical originating from riboflavin photolysis served as a reductant to react with p -BQ, forming reduced BQ radicals (BQ •− ) with a second-order rate constant of 1.1 × 10 9 L mol −1 s −1 . The main product of the photochemical reaction between p -BQ and O 2 •− was hydroquinone (H 2 Q). The present work suggests that the reaction with O 2 •− is a potential transformation pathway of 1, 4-benzoquinone in atmospheric aqueous environments.

CAS / MDL: 123-31-9
研究领域: 环境科学 · 化学 · 生物学
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HIGH PERFORMANCE POLYMERS · 2016 · IF 1.045

Synthesis and characterization of three different structures of polyacene quinone radical polymers

Wenfeng Guo,Xin Mao,Chengzhang Li,Jie Yang,Lirong Du,Xianzhong Tang

Three types of polyacene quinone radical (PAQR) polymers were synthesized by the step-growth polymerization of naphthalene, anthracene, or anthraquinone reacting with pyromellitic dianhydride via solution polymerization under a temperature gradient. Zinc chloride was used as the catalyst, and nitrobenzene was the solvent. The different structures of PAQR polymers were analyzed by infrared, X-ray diffraction, and scanning electron microscopy. The thermal properties of PAQR polymers were described by thermal gravimetric analysis, and the electrical performances were investigated by a precision LCR meter and a digital high insulation meter.

研究领域: 材料科学 · 化学
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JOURNAL OF ETHNOPHARMACOLOGY · 2017 · IF 2.981

Anti-thrombotic and pro-angiogenic effects of Rubia cordifolia extract in zebrafish

Yi Chen,Pei-Dong Chen,Bei-Hua Bao,Ming-Qiu Shan,Kai-Cheng Zhang,Fang-Fang Cheng,Yu-Dan Cao,Li Zhang,An-Wei Ding

Ethnopharmacological relevance Rubia cordifolia is a common traditional Chinese medicine that promotes blood circulation and eliminates blood stasis , and has been used to cure diseases related to blood stasis syndrome (BSS) clinically for many years. It has been previously demonstrated that anti-thrombosis and pro-angiogenesis can improve BSS. However, the anti-thrombotic and pro-angiogenic activities of Rubia cordifolia have not been well investigated. Aim of study To determine the potential anti-thrombotic and pro-angiogenic activities of Rubia cordifolia and to elucidate the underlying mechanisms. In addition, the major chemical constituents of Rubia cordifolia extract (QC) were qualitatively analysed by UPLC-Q-TOF/MS to explore the association between pharmacological activity and chemical constituents. Material and methods The QC samples were composed of a 95% ethanol extract and an aqueous extract following extraction using 95% ethanol. UPLC-Q-TOF/MS was used to analyse the major chemical constituents of QC. For the anti-thrombotic experiment of QC, a phenylhydrazine (PHZ)-induced AB strain zebrafish thrombosis model was used. The zebrafish larvae were stained using O-dianisidine, and the heart and caudal vein of the zebrafish were observed and imaged with a fluorescence microscope. The staining intensity of erythrocytes in the heart (SI) of each group and the morphology of thrombus in the caudal vein were used to assess the anti-thrombotic effect of QC. For the pro-angiogenic assay of QC, the intersegmental blood vessel (ISV) insufficiency model of Tg(fli-1: EGFP)y1 transgenic zebrafish (Flik zebrafish), which was induced by the VEGF receptor tyrosine kinase inhibitor II (VRI), was used. The morphology of the intact ISVs and defective ISVs was observed to evaluate the pro-angiogenic activity of QC. The mechanism involved in promoting angiogenesis was studied with real-time PCR. Results A total of 12 components in QC were identified based on standard compounds and references, including nine anthraquinones and three naphthoquinones . After treatment with QC, the PHZ-induced thrombosis in AB strain zebrafish larvae decreased to a certain degree, which we believe was related to its dosages, and the therapeutic effect within the 50–200 µg/mL QC treatment groups was especially prominent (P < 0.01, P < 0.001) compared to that in the PHZ model group. Similarly, QC also recovered the loss of the ISVs, which was induced by VRI in Flik zebrafish larvae, which have a certain dose-effect relationship. The pro-angiogenic activity of QC was also conspicuous (P < 0.01, P < 0.001) compared to that of the VRI model group. The following real-time PCR assay proved that QC significantly restored the VRI-induced downregulation of vWF, VEGF-A, kdrl, and flt-1 in Flik zebrafish (P < 0.05, P < 0.01, P < 0.001). Conclusions A total of 12 compounds from QC were analysed by UPLC-Q-TOF/MS. The data of the pharmacological experiments demonstrated that QC presented anti-thrombotic and pro-angiogenic activities in zebrafish, and the principal active components were likely anthraquinones and naphthoquinones. Thus, the current study provided a theoretical basis for the clinical use of Rubia cordifolia as a traditional Chinese medicine in promoting blood circulation and eliminating stasis.

CAS / MDL: 50-78-2
研究领域: 药理学 · 民族药理学 · 斑马鱼生物学 · 传统中药 · 化学分析
✓ 已验证 产品关联 DOI PubMed 高影响因子
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TOXICOLOGY AND INDUSTRIAL HEALTH · 2024 · IF 1.7

Evaluation on purine metabolism in human skin fibroblast cells exposed to oxygenated polycyclic aromatic hydrocarbons

Junqi Liu,Saijin Wang,Meng Wang,Zan Li,Shi Zhou,Jinlian Li,Dongmei Wu

A rapid and sensitive assessment of the toxicity of oxygenated polycyclic aromatic hydrocarbons (OPAHs), widely distributed persistent organic pollutants in the environment, is crucial for human health. In this study, using high-performance liquid chromatography, the separation and detection of four purines, xanthine (X), guanine (G), adenine (A), and hypoxanthine (HX) in cells were performed. The aim was to evaluate the cytotoxicity of three OPAHs, namely 1,4-benzoquinone (1,4-BQ), 1,2-naphthoquinone (1,2-NQ) and 9,10-phenanthrenequinone (9,10-PQ), with higher environmental concentrations, from the perspective of purine nucleotide metabolism in human skin fibroblast cells (HFF-1). The results revealed that the levels of G and A were low in HFF-1 cells, while the levels of HX and X showed a dose-response relationship with persistent organic pollutants concentration. With increased concentration of the three persistent organic pollutants, the purine metabolism in HFF-1 cells weakened, and the impact of the three persistent organic pollutants on purine metabolism in cells was in the order of 9,10-PQ > 1,4-BQ > 1,2-NQ. This study provided valuable insights into the toxic mechanisms of 1,4-BQ, 1,2-NQ and 9,10-PQ, contributing to the formulation of relevant protective measures and the safeguarding of human health.

研究领域: 环境毒理学 · 细胞生物学 · 分析化学
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RESEARCH IN MICROBIOLOGY · 2022 · IF 3.946

2-Alkyl-anthraquinones inhibit Candida albicans biofilm via inhibiting the formation of matrix and hyphae

Yuanyuan Song,Ziqi Wang,Yijing Long,Yang Mao,Feng Jiang,Yuanyuan Lu

Candida albicans can form biofilm on biotic and abiotic surfaces of medical implants to cause superficial and systemic infections under specific condition. The formation of hyphae and matrix of C. albicans are considered as probable virulence factors . We assessed the inhibitory activities of 26 anthraquinones against C. albicans biofilm formation, which were substituted by different functional groups including hydroxyl groups, amino groups, carboxyl groups, alkyl groups, and glycoside groups at C1- or C2-position. Among them, anthraquinones without substituents at other positions but only an alkyl group attached to C2-position, namely 2-alkyl-anthraquinones were determined to have significant anti-biofilm activities. Furthermore, 2-ethylanthraquinone can significantly affect genes related to extracellular matrix ( PMT6 and IFD6 ), and hyphal formation ( HWP1 , ECE1 and EFG1 ), leading to the disrupted formation of biofilm, by detail transcriptomics analysis. We believed that 2-ethylanthraquinone could inspire more discoveries of anti-biofilm agents against C. albicans .

研究领域: 微生物学 · 药理学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF HAZARDOUS MATERIALS · 2025 · IF 11.3

Monoterpenes amplify the oxidative potential of biomass burning secondary aerosols

Xiaowen Chen,Kun Li,Haizhen Bian,Shan Zhang,Xueqi Ma,Li Fang,Wei Jiang,Caiqing Yan,Lin Du

The interactions between different emission sources have significant impacts on secondary organic aerosol (SOA) formation and related environmental effects. Biomass burning and biogenic emissions could interact with each other; however, the formation, composition, and health effects of SOA from such mixtures remain poorly understood. Here, we investigated the interactions and atmospheric evolution of mixed biomass burning-derived guaiacol and biogenic α -pinene using an oxidation flow reactor (OFR), coupled with aerosol size distribution, offline iodometry-mass spectrometry, and dithiothreitol (DTT) assays. The results show that the mixed SOA yield shifted from suppression (at low hydroxyl radicals (OH) exposure) to enhancement (at high OH exposure), driven by low-volatility organics and subsequent enhanced gas-particle partitioning of intermediates. Fresh guaiacol SOA exhibited higher oxidative potential (OP) due to redox-active C 7 quinones and methoxy-hydroquinones, whereas the declining total peroxide of α -pinene SOA was attributed to the oxidative degradation. The OP of aged mixed SOA surpassed predicted values, which may be linked to the C 15 -C 17 quinone-terpenoid adducts and C 7 toxic products stabilizing semiquinone radicals, thereby facilitating sustained reactive oxygen species (ROS) generation. This study revealed that biogenic emissions amplify the health risks of biomass-burning emissions.

CAS / MDL: 80-56-8 90-05-1
研究领域: 环境健康学 · 大气化学 · 气溶胶科学 · 氧化应激 · 呼吸毒理学
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