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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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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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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
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Atmosphere · 2022 ·Vol. 13 ·期 4 ·543 · IF 3.11

Preparation Methods and Performance Analysis of Polyanthra-Quinone/Carbon Nanotube Composites for Capturing Carbon Dioxide

Zhongcheng Wang,Jingsong Feng,Xiaoyu Liu,Hao Guo

Carbon capture is one of the important methods to achieve carbon neutrality. In this paper, a simple and reliable method for the preparation of poly(anthraquinone)/multi-walled carbon nanotube composites (PAQ/MWCNTs) for capturing carbon dioxide is proposed. Using constant magnetic stirring, 1,4-anthraquinone (1,4-AQ) was allowed to accumulate on multi-walled carbon nanotube (MWCNTs) substrates via π–π. The poly(anthraquinone)/multi-walled carbon nanotube composites were produced by this continuous process. Besides, the carbon cloth electrode prepared from PAQ/MWCNTs composites was subjected to redox potentials for carbon dioxide capture. Results showed that PAQ/MWCNTs composites had good redox reversibility, their carbon dioxide capture capacity was 7.80 mmol·g−1while the material utilization rate reaches reached 73.4%.Keywords:1,4-anthraquinone;multi-walled carbon nanotubes;magnetic stirring;poly(anthraquinone)/multi-walled carbon nanotube composites;carboxylation;carbon dioxide capture

CAS / MDL: 635-12-1 308068-56-6
研究领域: 材料科学 · 环境工程 · 化学工程
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ACS Omega · 2019 · IF 2.584

Electrocatalytic Activity of Modified Graphite Felt in Five Anthraquinone Derivative Solutions for Redox Flow Batteries

Fanfan Gao,Xinyu Li,Yue Zhang,Chengde Huang,Wen Zhang

Redox flow batteries have received wide attention because of their unique advantages such as high efficiency, long cycle life, low operating cost, and independent adjustment of energy power. In this study, five types of anthraquinone derivative organic redox couple were selected, and the surfaces of graphite felt were modified. When the number of functional groups is increased or the substitution position is closer to the carbonyl (C═O) groups, a more pronounced hindrance for the C═O reaction on the benzene ring is observed; thus, the electrochemical performance and reversibility decreases. Sodium 9,10-anthraquinone-2-sulfonate solution is the best organic redox couple in terms of both reversibility and electrochemical performance. It was also found that all the surface treatment methods of graphite felt are beneficial for improving their electrochemical performances. All these superior results demonstrate that the graphite felt treated under air exposure at 550 °C for 3 h exhibited the best electrochemical performance, which might be attributed to the increase in the content of C–OH functional groups.

研究领域: 储能技术 · 电化学 · 材料科学
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Molecular Catalysis · 2020 · IF 3.687

Enhanced catalytic oxidation of anthracene by deposition of MoO3 and WO3 nanoparticles on MCM-41

Yangyang Fang,Jun Li,Na Sheng,Xiaozhong Wang,Di Chen,Menglu Cai,Yu An,Yingqi Chen,Liyan Dai

A series of MoW-doped MCM-41 catalysts were prepared for the selective oxidation of anthracene to high value-added anthraquinone. Although anthraquinone production has been progressively industrialized, the anthracene oxidation still faces the problems of poor solubility of reactants and low anthracene conversion, particularly when employing supported catalysts in solution media. We herein reported a challenging but crucial method for anthraquinone production by using anthracene, H 2 O 2 and Mo 1 W 2 -MCM-41 catalyst in HOAc under mild reaction conditions. In addition, experimental and theoretical results revealed that the synergistic effect between Mo, W and MCM-41 species contributes to an enchanced cataltic activity with conversion up to 97.6 %. The highly active H 2 O 2 -MCM-41 catalyst can be used for several cycles without obvious activity loss and serve as a promising candidate for anthraquinone as well as its derivatives production, making it a good alternative for various oxidation reactions.

研究领域: 化学工程 · 催化材料科学
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Molecular Catalysis · 2023 · IF 4.6

Visible-light-driven efficient photocatalytic oxidation of 5-hydroxymethylfurfural over a metal-free recyclable anthraquinone derivative

Ming Zhan,Yue Wang,Huai Liu,Rui Zhang,Lincai Peng,Junhua Zhang

Visible-light-driven upgrading of biomass and its derivatives into value-added chemicals under mild reaction conditions is an economical and sustainable strategy for biomass valorization. In this contribution, industrially-accessible anthraquinone and its derivatives (AQs) have been developed as efficient metal-free photocatalysts for the photo-oxidation of 5-hydroxymethylfurfural (HMF). Especially, a quantitative furans selectivity containing 86.0 % of 2,5-diformylfuran (DFF) and 13.6 % of 5-formyl-2-furancarboxylic acid (FFCA) was implemented at HMF conversion of 88.8 % over 2,6-dibromoanthraquinone (2,6-DB-AQ) catalyst under visible light illumination. In addition, the homogeneous 2,6-DB-AQ catalyst can be readily separated and recycled from the reaction mixture by a “water-assisted” precipitate method. Photophysical characterizations indicated that the introduction of bromine substituents on AQ enhances its visible light absorption ability, decrease its band gap energy and enables the catalyst with a more stable photoexcitation state. It has also been demonstrated that the lower photoexcitation energy of O 2 over 2,6-DB-AQ endowed the catalyst with better capacity for the activation of O 2 than that of AQ. These contributions should be in charge of the excellent catalytic activity of 2,6-DB-AQ for the photo-oxidation of HMF. This work demonstrates an efficient and recyclable organo-photocatalyst for the visible-light-mediated valorization of biomass-derived alcohols and aldehydes to value-added chemicals.

研究领域: 化学工程 · 催化 · 可持续化学 · 光化学
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INORGANICA CHIMICA ACTA · 2021 · IF 2.545

Anthraquinone functionalized pseudocalixarene for high lithium loading and chromogenic ion-pair recognition in DMSO

Yiwen Yao,Feifei Xing,Shourong Zhu

The [2 + 2] condensation between 1,8-dihydroxyanthraquinone diester and 1,3-diamino-2-propanol in ethanol affords pseudocalixarene macrocyclic L2 in high yield. Heating L2 to 200 °C in DMSO can generate much smaller [1 + 1] macrocycle L1 . Crystal structure of L1 shows that all non-hydrogen atoms are coplanar except one carbon from 1,3-diamino-2-propanol. L1 is quite inert, but L2 can interact with alkaline, alkaline-earth, as well as Zn 2+ , Cu 2+ , Fe 3+ and Al 3+ cation (chloride) evidenced by their CV and 1 H NMR. With a L2 :M (1:2), there are discernable UV–vis spectrum/ 1 H NMR changes in the presence Cu 2+ , Fe 3+ , Al 3+ . Anion plays a key role in the cation binding process as the chromogenic response to Li + , Na + , K + , Ba 2+ and TBA + hydroxide. L2 forms 1:1 complex with TBAOH and 2:3 complex with NaOH, KOH, Ba(OH) 2 in DMSO. L2 reacts with LiOH in 1:4 stoichiometric and is one of the highest lithium loading ligand. The reaction is second-order with t 1/2  ~ 30 min for 0.25 mM L2 in the presence of 4.0 eq. LiOH. Besides hydroxide, L2 can interact with TBAF to form 1:1 host–guest complexes evidenced by their color and NMR change. With bulky cation, TBAOH shifts E p(II) more negative, while other cations shift E p(II) to positive. L2 is an ion pair acceptor that binds hydroxide and fluoride salt chromogenic.

CAS / MDL: 616-29-5 105-36-2
研究领域: 化学 · 材料科学
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Water · 2021 ·Vol. 13 ·期 17 ·2315 · IF 3.103

Fabrication of rGO/Fe3O4 Magnetic Composite for the Adsorption of Anthraquinone-2-Sulfonate in Water Phase

Shuangyang Zhao,Meixi Li,Jie Ding,Shanshan Yang,Yani Zang,Yan Zhao,Xinlei Gao,Nanqi Ren

In the last few decades, anthraquinone and its derivatives (AQs) have been intensively applied to electrochemical, textile and dye, and photovoltaic industries. This has increased the levels of AQs in the natural environment and threatens human health. To remove AQs from the aqueous phase and recover these multi-functional molecules, a binary magnetic adsorbent, reduced graphene/Fe3O4(rGO/Fe3O4), was synthesized via a hydrothermal method. Transmission electron microscopy (TEM), X-ray diffraction (XRD), Fourier transform infrared (FTIR), Raman spectra, and thermogravimetric analysis (TGA) were then used to characterize the samples. The adsorption capacities of rGO/Fe3O4to AQs were investigated by selecting anthraquinone-2-sulfonate (AQ2S) as a model molecule. The adsorption process followed the Langmuir adsorption isotherm and the second-order kinetics. The regeneration of adsorbents and the recycling of AQ2S and solvent were simultaneously achieved by Soxhlet extraction and rotary evaporation. These results confirm the high adsorption efficiency of rGO/Fe3O4for removing AQs from water and provide a promising approach to recover the valuable molecules from the aqueous phase.Keywords:adsorption;magnetic composite;anthraquinone-2-sulfonate;regeneration

CAS / MDL: 131-08-8
研究领域: 环境科学 · 材料科学
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RSC Advances · 2023 ·Vol. 13 ·期 17 ·11720-11727 · IF 3.9

H2O2 activated moxa ash via ball milling for ultrafast removal of mitoxantrone

Wanqian Cai,Chongbiao Zhang,Yourong Wu,Wei Wang,Mei Lin,Tengfei Lin,Cong Lin,Min Gao,Chunlin Zhao,Xiao Wu

As emerging contaminants, antineoplastic drugs are widely used, but their residues in water may cause long-term genotoxicity to aquatic organisms and human beings. Here, waste moxa ash was selected as biomass raw material and modified by ball milling to obtain carbon-based materials with excellent adsorption performance, which were used to remove the antineoplastic drug mitoxantrone (MTX) from water. The experimental results indicate that moxa ash modified by ball milling in hydrogen peroxide exhibits ultrafast removal of MTX (the removal efficiency reaches 97.66% in 1 min and 99.72% in 30 min). The pseudo-second-order kinetics and Freundlich isotherm models accurately describe the MTX adsorption process, and the mechanism of adsorption probably involves pore filling, hydrogen bond, π–π interaction and electrostatic attraction. Not only that, moxa ash also has the ability to remove dyes such as malachite green (97.81%) and methylene blue (99.97%). In this study, a simple and environmentally friendly process was used to convert waste moxa ash into an effective MTX adsorbent, providing a feasible solution for controlling MTX pollution and identifying a circular and economic way to reuse the waste.

研究领域: 环境科学 · 材料科学 · 药学
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Journal of Pharmaceutical Analysis · 2021 · IF 4.769

Long-chain alkanol–alkyl carboxylic acid-based low-viscosity hydrophobic deep eutectic solvents for one-pot extraction of anthraquinones from Rhei Radix et Rhizoma

Anqi Huang,Wenwen Deng,Xiao Li,Qutong Zheng,Xuanxuan Wang,Yuxiu Xiao

Natural long-chain alkanol and alkyl carboxylic acid were used to prepare novel hydrophobic deep eutectic solvents (HDESs). These HDESs are liquid at room temperature and have low viscosity (<12.26 mPa‧s), low polarity (lower than that of methanol, ChCl-based deep eutectic solvents and other reported HDESs), and low density (<0.928 g/mL). A simple one-pot method based on a novel HDES–water two-phase extraction system was constructed for the extraction of weak-polarity bioactive components, anthraquinones, from Rhei Radix et Rhizoma. This HDES-based new extraction method does not consume hazardous organic solvents and can obtain a total anthraquinone yield of 21.52 mg/g, which is close to that obtained by the Chinese pharmacopoeia method (21.22 mg/g) and considerably higher than those by other reported HDESs-based extraction methods (14.20–20.09 mg/g, p  < 0.01). The high extraction yield can be mainly attributed to the severe destruction of the RRR cell walls by the extraction system and the excellent dissolving ability of novel HDESs for anthraquinones.

研究领域: 药学 · 天然产物化学
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JOURNAL OF FOOD PROCESSING AND PRESERVATION · 2016 ·Vol. 41 ·期 5 ·e13160 · IF 0.894

Main anthraquinone components in Aloe vera and their inhibitory effects on the formation of advanced glycation end-products

Shimo Kang,Xin Zhao,Lu Yue,Ling Liu

Food heating process causes increased protein glycation and the formation of advanced glycation endproducts (AGEs) which related with diabetes and ageing. Aloe vera ( A. vera ) extract is a potent antioxidant with established effects attributed largely to a key ingredient anthraquinone. This study investigated the inhibitory ability of the three anthraquinones from A. vera on the formation of AGEs in a heated model system at 70°C. Anthraquinones, including aloe-emodin (AED), emodin (ED), and chrysophanol (CSN), were extracted from A. vera and analyzed by ultra-high performance liquid chromatography-tandem mass spectrometry. Under optimal extraction conditions, the extraction yield of the anthraquinones was 4.377 mg/g. Anthraquinones showed good inhibition toward the formation of glycation products; the inhibition rates of AED, ED, and CSN on crosslinked AGEs were 46.48%, 66.38%, and 57.32% at 10 μM concentrations. Sodium dodecyl sulfate–polyacrylamide gel electrophoresis images also proved that the anthraquinones could significantly inhibit crosslinked AGE formation in a time-dependent manner. ED showed higher inhibitory ability than AED and CSN on the formation of N ɛ -(carboxymethyl)lysine and crosslinked AGEs. The results indicate that the antiglycation properties of these anthraquinones are likely related to the phenolic hydroxyl groups in their structures, but this ability is not related to their antioxidant activity, which probably depends on the whole structure of the quinone. Generally, the anthraquinones in A. vera , especially ED, can effectively inhibit AGE formation and reduce protein crosslinking during food processing, even at low concentration. Practical applications The inhibitory effects of three anthraquinones extracted from Aloe vera on the formation of AGEs were investigated in a heated model system. The results indicate Aloe can be used as an effective inhibitor of glycation products in food processing, moreover, this research can be useful for finding suitable nature inhibitors of AGEs for food processing.

研究领域: 食品科学 · 生物化学
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