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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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PHYTOCHEMICAL ANALYSIS · 2022 ·Vol. 33 ·期 8 ·1246-1256 · IF 3.024

Simultaneous determination of seven anthraquinones in Cassiae semen by natural deep eutectic solvent extraction

Ying Xu,Yiqun Wan,Fan Liu,Jinping Chen,Ting Tan,Lan Guo

Introduction Anthraquinones are considered to be an important class of bioactive substances in Cassiae semen , and the content of anthraquinones is an essential indicator of the quality of Cassiae semen raw herbal materials. Objectives The present study aimed to propose a novel, efficient and effective ultra-high-performance liquid chromatography (UHPLC) method for the simultaneous determination of aurantio-obtusin, aloe-emodin, rhein, obtusin, emodin, chrysophanol and physcion, with the help of natural deep eutectic solvents (NADESs) as extraction solvents. Methodology NADESs were introduced to the simultaneous extraction of anthraquinones from Cassiae semen samples. Several NADESs were designed by menthol, choline chloride, d -glucose as hydrogen bond acceptors, with nine different acids and appropriate water as hydrogen bond donors. The parameters affecting the extraction efficiency of seven anthraquinones were demonstrated in detail. Results Among the obtained NADESs, the highest extraction efficiency was demonstrated by a solution consisting of d -glucose, lactic acid and water with a molar ratio of 1:5:4. The seven anthraquinones were separated on an ACQUITY UPLC® BEH C 18 column (2.1 mm × 100 mm, 1.8 μm) and detected within 12 min by a photodiode array (PDA) detector at 254 and 284 nm. The limits of detection and quantitation were from 1.00 to 7.26 μg/l and 3.29 to 24.22 μg/l, respectively. And Cassiae semen sample-based recoveries ranged from 81.13% to 113.78% with the relative standard deviation (RSD) ( n = 6) of 1.4% to 10.1%. Conclusion The developed method demonstrated that NADESs were applied successfully to analyse the anthraquinones in Cassiae semen samples collected from different regions in China.

研究领域: 中药学 · 分析化学
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ACS Applied Materials & Interfaces · 2024 · IF 8.3

Ion-Induced Nanoarchitectonics for Anthraquinone Single Crystals with Enhanced Fluorescence Properties

Yilin Liu,Zibo Li,Yang Xu,Xia Xu,Jie Zhao,Wei Cui,Junbai Li

Recently, bioinspired fluorescent materials have drawn ever-increasing attention due to their ecofriendliness and easy accessibility. Herein, we demonstrate that anthraquinone/metal ion coordination complexes can form well-defined crystals and possess obvious fluorescence enhancement properties. The fluorescence quantum yields of anthraquinone/metal ion assemblies are more than 2 orders of magnitude compared to those of anthraquinone assemblies. The electronic structures of the first excited singlet states of anthraquinone/metal ion molecules are obtained, and the mechanism of the fluorescence enhancement is elucidated. Such photoluminescent anthraquinone/metal ion crystals can be considered as efficient phosphors in fabricating light-emitting diodes. This work provides a simple route for the development of highly efficient natural fluorescent materials.

CAS / MDL: 9011-14-7
研究领域: 材料科学 · 光学
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JOURNAL OF ETHNOPHARMACOLOGY · 2022 · IF 5.195

Pharmacokinetic characteristics of emodin in polygoni Multiflori Radix Praeparata

Dongpeng Wang,Jufeng Duan,Xiao-Jing Chen,Kaiqi Liu,Yingying Guo,Run Shi,Sha Li,Ming Liu,Lijun Zhao,Bei Li,Hongtao Liu,Minglun Li,Yibin Feng,Hongliang Li,Xuanbin Wang

Ethnopharmacological relevance Polygoni Multiflori Radix Praeparata (Zhiheshouwu) has been a Wudang Taoist medicine for tonifying the liver and kidney, resolving turbidity and reducing lipid. Emodin is one of the active anthraquinones in Zhiheshouwu. Our previous studies showed that emodin (EM) and the other anthraquinones in Zhiheshouwu extract (HSWE) exerted similar inhibitory effects on liver cancer cells in vitro . However, it is still unknown if the other anthraquinones enhance pharmacokinetics (PK) of EM in HSWE in vivo . Aim of the study In this study, we compared the PK characteristics of EM alone with that in Zhiheshouwu aiming to explore which anthraquinones in HSWE contribute to the changed PK of EM in rats. Materials and methods Quality control of HSWE was determined using high performance liquid chromatography (HPLC). The ratios of emodin to other anthraquinones, physcion (PH), chrysophanol (CH), rhein (RH), aloe-emodin (AE), emodin-8-O- β -D-glycoside (EMG), physcion-1-O- β -D-glycoside (PHG) and chrysophanol-8-O- β -D-glycoside (CHG) in HSWE were determined and analyzed using UPLC combined with tandem mass spectrometry (UPLC/MS). The PK parameters and intestinal tissue concentration of EM alone, EM in HSWE, or with other anthraquinones in SD rats were analyzed using UPLC/MS. Results The quality of the Zhiheshouwu samples met the quality standard of the Chinese Pharmacopoeia (Version 2020). The PK results showed that compared with EM alone, C max (239.90 ± 146.71 vs . 898.46 ± 291.62, P  < 0.001), T max (0.26 ± 0.15 vs. 12.55 ± 1.33, P  < 0.001), AUC 0-t (1575.09 ± 570.46 vs. 12154.96 ± 5394.25, P  < 0.001), and AUC 0-∞ (4742.51 ± 1837.62 vs. 37131.34 ± 21647.39, P  < 0.001) of EM in HSWE were decreased due to PH and EMG, while the values of V d (380.75 ± 217.74 vs . 11.75 ± 7.35, P  < 0.001), T 1/2 (10.81 ± 1.99 vs . 6.65 ± 2.76, P  < 0.05) and CL (19.30 ± 7.82 vs . 2.78 ± 1.88, P  < 0.001) of EM in HSWE were increased due to PH and AE. In addition, the intestinal tissue concentration of emodin in HSWE was decreased compared with that of EM alone in 20 and 780 min (25.37 ± 5.98 vs . 43.29 ± 4.16 and 26.72 ± 4.03 vs . 43.40 ± 14.19, respectively. P  < 0.05) dominantly due to RH and PH. Conclusion In conclusion, compared with treatment of EM alone, the AUC 0-t value of EM in HSWE was decreased with different ways in rats. PH shortened T max , and increased V d and CL. While AE prolonged T 1/2 of EM. This indicated that the other anthraquinones in HSWE changed the PK of EM in rats and participated in the complex effects of EM on liver cancer. Besides the other anthraquinones, other components (e.g., 2,3,5,4′-tetrahydroxystilbene-2-O- β -D-glucoside) in Zhiheshouwu may contribute in the pharmacokinetic and pharmacodynamic interactions with EM for anti-liver cancer.

CAS / MDL: 9004-32-4 9085-26-1
研究领域: 中药学 · 药理学 · 生物化学
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INORGANICA CHIMICA ACTA · 2020 · IF 2.304

Synthesis of 1,8-anthraquinone functionalized aza 18/20-crown-5 macrocycles and their chromogenic ion-pair recognition of hydroxides in DMSO

Li Li,Feifei Xing,Shourong Zhu

Two N 3 O 3 macrocyclic compounds with rigid chromogenic 1,8-dihydroxylenanthraquione and flexible diethylenetriamine/dipropenetriamine (L1 and L2), were synthesized and characterized. L1/L2 can interact with alkaline, alkaline-earth, as well as Zn 2+ , Pb 2+ , and Al 3+ chloride/perchloride evidenced by their DPV change and 1 H NMR spectra. Unexpectedly, both L1 and L2 can show chromogenic response to Na + , K + , and TBA + hydroxide (but not LiOH). Large cavity L2 can show chromic response to Ca(OH) 2 and Ba(OH) 2 , but L1 can only respond to Ca(OH) 2 in DMSO. L1 and L2 form 1:1 and 2:1 (Host:Guest) complex respectively with NaCl, NaOH, TBAOH in DMF/DMSO. Both hosts bind smaller Zn 2+ and Al 3+ in 2:1 in DMSO. L2 can form L2·TBAOH greenish yellow complex that gradually transformed to red L2 2 ·TBAOH in two steps in DMSO. Different from other macrocycles, L1 and L2 are ion-pair hosts that recognize cation and OH − via carbonyl groups.

研究领域: 有机化学 · 分析化学
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SCIENCE OF THE TOTAL ENVIRONMENT · 2019 · IF 5.589

Faceted TiO2 photocatalytic degradation of anthraquinone in aquatic solution under solar irradiation

Tingming Ye,Weixiao Qi,Xiaoqiang An,Huijuan Liu,Jiuhui Qu

Anthraquinone (AQ), a common oxygenated polycyclic aromatic hydrocarbon (PAH) in the water environment, often occurs with higher concentrations than its parent anthracene as it is the dominant intermediate from anthracene during both wastewater treatment and transformation in natural waters. During the elimination of PAHs and their intermediates, the water matrix often induces positive or negative effects. In this paper, photocatalytic degradation of AQ in the presence of inorganic ions (NO 3 − , HCO 3 − , Fe 3+ ) and organic matter (humic acid) was studied with {101} and {010}-TiO 2 as sunlight-driven photocatalysts. Meanwhile, the effect of dissolved oxygen (DO) on photocatalytic degradation of AQ was evaluated. The results showed that NO 3 − had a slight suppressing effect, while HCO 3 – and Fe 3+ promoted the photocatalytic activity due to formation of new oxidizers (CO 3 − and H 2 O 2 ). Interestingly, HA could envelope {101}-TiO 2 to inhibit photodegradation ; however, it had almost no effect on {010}-TiO 2 due to the different surface structures and properties. High dissolved oxygen content in water could markedly promote the photodegradation of AQ. This was consistent with the results of scavenging experiments, which demonstrated that O 2 – and h + played more important roles than OH did. A small amount of benzene was detected as an intermediate product of AQ by LC-QTOF-MS analysis. Hopefully, this work can contribute to the understanding of the potential of water remediation by faceted photocatalysts.

CAS / MDL: 75-65-0
研究领域: 环境科学 · 化学
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IONICS · 2025 · IF 2.6

Anthraquinone doped CoNi-MOF-74 composites as electrocatalysts for enhanced oxygen evolution reaction

Du Jia,Chen Lixuan,Wu Yiming,Wei Xin,Jia Jingyuan,Sun Kenan,Li Bingke

Nowadays, the advancement of eco-friendly, clean, sustainable and renewable new energy has emerged as a research priority for scientists worldwide. Electrolytic water technology is founded on the principle of electrochemical or photoelectric decomposition of water, is deemed as one of the most promising and most feasible approaches to reach industrial production. Traditional OER (oxygen evolution reaction) electrocatalysts like IrO 2 and RuO 2 are beset by high costs and vulnerability to poisoning. Hence, it is essential to develop more economical, more stable and more efficient materials for the application of OER reactions. In this study, a series of AQ-doped (AQ = anthraquinone) MOF-74 materials were fabricated through a one-step solvothermal approach. The surface loading of the conjugated organic small molecule AQ on CoNi-MOF-74 is capable of effectively boosting the inadequate electrical conductivity of the bulk MOF material, thus significantly enhancing the performance of OER. The optimized ratio of material composition of AQ20@MOF-74 displayed significantly enhanced OER activity. with a lower overpotential of 272 mV at 10 mA cm −2 and a smaller Tafel slope of 78 mV dec −1 . The research findings presented in this thesis provide a novel approach for the design and optimization of highly efficient OER electrocatalysts based on MOFs.

CAS / MDL: 6147-53-1
研究领域: 材料科学 · 能源化学 · 催化化学
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Molecular Catalysis · 2021 · IF 5.062

Performance of carbon-modified Pd/SBA-15 catalyst for 2-ethylanthraquinone hydrogenation

Yue Zhang,Zhiyong Pan,Nan Wang,Li Wang

Silica SBA-15 without removal of template P123 was calcined in an inert atmosphere and the carbon-modified SBA-15 thus obtained was used as the support of Pd catalyst for the hydrogenation of 2-ethylanthraquinone (EAQ). The effects of extraction times of P123 in SBA-15 with water prior to inert calcination and calcination temperature on the structure and catalytic performance of Pd catalyst were studied. The results of elemental analysis, X-ray diffraction, X-ray photoelectron spectroscopy, inductively coupled plasma, Fourier transform infrared spectroscopy, Raman spectra, water contact angle measurement, N 2 adsorption-desorption, transmission electron microscopy and energy dispersive X-ray mapping showed that carbon content of catalysts varied in the range of 3.4 % and 1.1 % with increasing extraction times from 0 to 6 due to the decrease in the residual amount of P123 in uncalcined SBA-15. With rising calcination temperature, the occurrence state of carbon in catalysts was converted from amorphism into graphite. The Pd catalyst supported on SBA-15 extracted for 3 times and calcined at 650 °C had 2.0 % carbon, and exhibited the highest activity (0.37 molH 2 ·gPd −1 ·min −1 ) and selectivity (98.9 %). This is due to the presence of appropriate amount of carbon, which provided a relatively high hydrophobicity without significantly reducing the specific surface area and pore size of SBA-15 support. The high hydrophobicity benefits the adsorption of EAQ from the working solution to the surface of catalyst.

CAS / MDL: 108-67-8
研究领域: 催化化学 · 材料科学
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JOURNAL OF POWER SOURCES · 2021 · IF 9.127

Intramolecular hydrogen bonds induced high solubility for efficient and stable anthraquinone based neutral aqueous organic redox flow batteries

Lixing Xia,Wenbo Huo,Huaizhi Gao,Heng Zhang,Fengming Chu,Hao Liu,Zhan'ao Tan

Solubility of redox active materials (RAMs) is key to realize high volume capacity and energy density in aqueous organic redox flow batteries (AORFBs). In anthraquinone (AQ)-based RAMs, hydrophilic groups substituted at β-sites (2,3,6,7) are expected to improve water-miscibility much better than α-sites (1,4,5,8). In this work, we find an anomalous case: 3-((9,10-dioxo-9.10-dihydroanthracen-2-yl)amino)-N,N,N-trimethylpropan-1-aminium chloride (2-DPAQCl) functioned with the hydrophilic groups surprisingly exhibits poor solubility with less than 0.05 M, however its isomer 3-((9,10-dioxo-9,10-dihydroanthracen-1-yl)amino)-N,N,N-trimethylpropan-1-aminium chloride (1-DPAQCl) shows high solubility at 1.44 M in water. The results from 1 H nuclear magnetic resonance (NMR) and infrared (IR) spectra suggest that intermolecular hydrogen bonds (HBs) are formed between N–H donors and Cl − acceptors in 2-DPAQCl, which is different from the case for 1-DPAQCl that N–H donors interact with neighboring C O acceptors as intramolecular HBs. Benefited from the intramolecular HBs, water is prone to break the interaction between solute molecules than that in 2-DPAQCl, leading to better water-solubility. Electrochemical investigations indicate that the peak-to-peak separations ΔE pp of 1-DPAQCl is very narrow in unbuffered aqueous solution as well as in buffered aqueous solution at pH 7.0, implying its highly electrochemical reversibility and facile reaction kinetics, which further indicates 1-DPAQCl is suitable to serve as a negative RAM for neutral AORFBs.

研究领域: 材料科学 · 电化学
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2016 ·Vol. 27 ·期 11 ·2120-2126 · IF 1.096

Simultaneous, Simple and Rapid Determination of Five Bioactive Free Anthraquinones in Radix et Rhizoma Rhei by Quantitative 1H NMR

Dong Jian-Wei,Cai Le,Fang Yun-Shan,Duan Wei-He,Li Zhen-Jie,Ding Zhong-Tao

Radix et Rhizoma Rhei has been recognized for centuries in traditional medicine for its multiple pharmacological actions. The free anthraquinones including physcion, chrysophanol, emodin, rhein, and aloe-emodin are the main bioactive components in Radix et Rhizoma Rhei. In the present study, a fast quantitative 1H nuclear magnetic resonance (q-HNMR) method for the determination and quantitation of five free anthraquinones in Radix et Rhizoma Rhei was developed. Validation of the quantitative method was performed in terms of specificity, accuracy, precision, and stability. The results showed that the solvent acetone-d6 enabled satisfactory separation of the signals to be integrated. Five anthraquinones in Radix et Rhizoma Rhei could be quantified accurately using featured signals from 1H NMR. This work implied that q-HNMR represents a feasible alternative to high-performance liquid chromatography (HPLC)-based methods for quantitation of anthraquinones in Radix et Rhizoma Rhei and is suitable for the quality control of Radix et Rhizoma Rhei.

研究领域: 中药学 · 分析化学 · 药理学
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PROGRESS IN ORGANIC COATINGS · 2018 · IF 2.955

Synthesis of transparent covalently self-colored polyurethane based on anthraquinone chromophore chain extenders

Yan Xu,Xiaoqian Ji,Fangqing Ge,Chaoxia Wang

The hydroxyl terminated polyurethanes covalently bonded anthraquinone chromophores into skeleton were successfully synthesized based on 1-amino-4-hydroxy-2-(6-hydroxy-hexyloxy) anthraquinone (AHHA) and dimethylolpropionic acid (DMPA) as chain extenders. The UV–visible spectroscopy of polyurethane solution revealed that the conjugated structure of chromophore was not affected after bonding into polyurethane. Owing to the absorption of chromophore in the range of 360–630 nm, the polyurethane with 0.12 wt% AHHA in backbone possessed high transmittance of 94.6% in the range of 630–800 nm and that of polyurethane with 0.89, 1.32, 2.13 wt% AHHA were 87.9%, 82.5%, 78.6%, respectively. Interestingly, the optical transmittance of corresponding polyurethane was 80.5% in the range of 630–800 nm. Transparency was strongly related to the phase separation and crystallization behavior. The DSC curve revealed no endothermic peak and XRD showed a broad diffraction peak, demonstrating that chromophore-incorporated polyurethane with different AHHA amounts had no distinct phase separation and crystallization that accounted for good transparency.

CAS / MDL: 4098-71-9
研究领域: 材料科学 · 化学工程
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Membranes · 2023 ·Vol. 13 ·期 1 ·61 · IF 4.2

The Interaction of Anthracycline Based Quinone-Chelators with Model Lipid Membranes: 1H NMR and MD Study

Olga Yu. Selyutina,Anna V. Mastova,Nikolay E. Polyakov

Anthracycline antibiotics, e.g., doxorubicin, daunomycin, and other anthraquinones, are an important family of antitumor agents widely used in chemotherapy, which is currently the principal method for treating many malignancies. Thus, development of improved antitumor drugs with enhanced efficacy remains a high priority. Interaction of anthraquinone-based anticancer drugs with cell membranes attracts significant attention due to its importance in the eventual overcoming of multidrug resistance (MDR). The use of drugs able to accumulate in the cell membrane is one of the possible ways of overcoming MDR. In the present work, the aspects of interaction of anthraquinone 2-phenyl-4-(butylamino)naphtho[2,3-h]quinoline-7,12-dione) (Q1) with a model membrane were studied by means of NMR and molecular dynamics simulations. A fundamental shortcoming of anthracycline antibiotics is their high cardiotoxicity caused by reactive oxygen species (ROS). The important feature of Q1 is its ability to chelate transition metal ions responsible for ROS generation in vivo. In the present study, we have shown that Q1 and its chelating complexes penetrated into the lipid membrane and were located in the hydrophobic part of the bilayer near the bilayer surface. The chelate complex formation of Q1 with metal ions increased its penetration ability. In addition, it was found that the interaction of Q1 with lipid molecules could influence lipid mobility in the bilayer. The obtained results have an impact on the understanding of molecular mechanisms of Q1 biological activity.Keywords:anthraquinones;NMR;molecular dynamics;lipid membranes

CAS / MDL: 60-33-3
研究领域: 药理学 · 生物物理学
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