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ENVIRONMENTAL SCIENCE & TECHNOLOGY · 2019 · IF 7.149

Enhanced Photooxidation of Hydroquinone by Acetylacetone, a Novel Photosensitizer and Electron Shuttle

Jiyuan Jin,Shujuan Zhang,Bingdang Wu,Zhihao Chen,Guoyang Zhang,Paul G. Tratnyek

Quinones are important electron shuttles as well as micropollutants in the nature. Acetylacetone (AA) is a newly recognized electron shuttle in aqueous media exposed to UV irradiation. Herein, we studied the interactions between AA and hydroquinone (QH2) under steady-state and transient photochemical conditions to clarify the possible reactions and consequences if QH2 and AA coexist in a solution. Steady-state experimental results demonstrate that the interactions between AA and QH2 were strongly affected by dissolved oxygen. In O2-rich solutions, the phototransformation of QH2 was AA-independent. Both QH2 and AA utilize O2 as the electron acceptor, but in O2-insufficient solutions, AA became an important electron acceptor for the oxidation of QH2. In all cases, the coexistence of AA increased the phototransformation of QH2, whereas the decomposition of AA in O2-saturated and oversaturated solutions was inhibited by the presence of QH2. The underlying mechanisms were investigated by a combination of laser flash photolysis (LFP) and reduction potential analysis. The LFP results show that the excited AA serves as a better electron shuttle than QH2. As a consequence, AA might regulate the redox cycling of quinones, leading to significant effects on many processes, ranging from photosynthesis and respiration to photodegradation.

CAS / MDL: 7778-77-0
研究领域: 环境科学 · 光化学
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Journal of Pharmaceutical Analysis · 2025 · IF 8.9

Discovery of anthraquinones as potent Notum inhibitors for treating osteoporosis by integrating biochemical, phytochemical, computational, and experimental assays

Jia Guo,Yuqing Song,Mengru Sun,Jun Qian,Dihang See,Tian Tian,Yunqing Song,Wei Liu,Hongping Deng,Yao Sun,Guangbo Ge,Yongfang Zhao

Osteoporosis, a severe systemic skeletal disorder characterized by decreased bone mineral density, leads to increased risks of bone fragility and fracture. Although some herbal medicines are clinically used for treating osteoporosis, the crucial anti-osteoporotic constituents and their mechanisms have not been well-elucidated. Notum, a negative regulator of Wnt/β-catenin signaling, has been validated as a druggable target for enhancing cortical bone thickness and alleviating osteoporosis. Herein, we showcase an efficient strategy for uncovering the key anti-Notum constituents from herbal medicines via integrating biochemical, phytochemical, computational, and cellular assays. Following screening the anti-Notum potentials of herbal medicines, Polygonum multiflorum Thunb. (PM), a commonly used anti-osteoporosis herb , showed potent and competitive inhibition against Notum. Phytochemical profiling coupling with docking-based virtual screening suggested that three anthraquinones, including rhein, emodin, and chrysophanol, showed high binding-potency towards Notum. Biochemical assays validated that three anthraquinones were strong competitive inhibitors of Notum, while rhein was the most potent one (IC 50 = 9.98 nM). Cellular investigations demonstrated that rhein markedly promoted osteoblast differentiation in dexamethasone-challenged MC3T3-E1 osteoblasts, while RNA sequencing showed that rhein remarkably regulated Wnt signaling-related and osteogenic differentiation-related genes. In vivo tests showed that rhein displayed favorable safety profiles in healthy mice and this agent significantly elevated bone mineral density, augmented trabecula and cortical bone thickness in dexamethasone-induced osteoporotic mice. Collectively, this study showcases an efficient strategy for uncovering the key anti-Notum constituents from herbal medicines, while rhein was identified as a naturally occurring Notum inhibitor that shows favorable safety profiles and impressive anti-osteoporosis effects.

CAS / MDL: 64-18-6
研究领域: 药理学 · 生物化学 · 计算生物学
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DESALINATION · 2024 · IF 8.3

Positively charged loose nanofiltration membranes via the assembly of amino-quinone networks for efficient dye/salt separation

Tian Gao,Ping Fu,Wan-Long Li,Wan-Ting Lin,Yuan-Hui Yu,Xiao-Jun Huang,Zhi-Kang Xu,Ling-Shu Wan

Nanofiltration (NF) membranes with superior permeability and selectivity are highly desirable for the applications. The development of non-polyamide loose NF membranes with high permeability and dye/salt selectivity has aroused great attention in recent years. In this work, 2-hydroxy-1,4-naphthoquinone, a natural compound commonly existed in plants, was chosen to prepare loose NF membranes via the co -deposition with polyethyleneimine (PEI). By optimizing the deposition conditions, we successfully fabricated amine-quinone network coatings on the surface of polyacrylonitrile (PAN) ultrafiltration membranes, and further cross-linked the coatings with glutaraldehyde to improve the compactness and stability. For this kind of loose NF membrane, the rejections to dyes with a molecular weight larger than 600 Da reach 98 %, and the water permeance keeps above 10 L·m −2 ·h −1 ·bar −1 . In contrast, the rejections to inorganic salts (NaCl, Na 2 SO 4 , MgCl 2 , and MgSO 4 ) are only about 10 %, and the selectivity of the dye molecule alcian blue against NaCl can reach 430. These results prove that this novel composite membrane can realize effective separation for dyes with different molecular weights and desalination for dye solutions. The present work will open up an avenue for designing loose NF membranes with novel separation layers.

CAS / MDL: 573-58-0 547-58-0
研究领域: 膜科学 · 材料科学 · 环境工程 · 化学工程
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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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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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ENVIRONMENTAL TOXICOLOGY AND PHARMACOLOGY · 2014 · IF 1.862

Tetrachlorobenzoquinone induces acute liver injury, up-regulates HO-1 and NQO1 expression in mice model: The protective role of chlorogenic acid

Demei Xu,Lihua Hu,Xiaomin Xia,Jianbo Song,Lingrui Li,Erqun Song,Yang Song

Tetrachlorobenzoquinone (TCBQ) is an active metabolite of pentachlorophenol (PCP). Although PCP has been investigated extensively, there are only a few reports describing the toxicity effect of TCBQ, and no report regarding TCBQ-induced liver injury in vivo . In the current study, we aimed to examine the acute hepatic toxicity of TCBQ in the mice model. Chlorogenic acid (CGA) exhibits promising antioxidant activity in the past studies, thus, the second aim of this study was to evaluate the protective effect of CGA on TCBQ-induced liver injury. Our results indicated TCBQ-intoxication caused marked liver cell necrosis and inflammation but not apoptosis, and this damage was alleviated by CGA treatment. Meantime, TCBQ-intoxication enhanced serum ALT, AST activities, TBIL content, hepatic oxidative stress and lipid peroxidation, decreased GSH content and inhibited the activities of antioxidant enzymes. Western blot and immunohistochemical analysis showed that TCBQ marked up-regulated HO-1 and NQO1 expression. On the other hand, pretreatment of CGA reduced TCBQ-induced liver damage remarkably. Taking together, these results revealed that TCBQ has strong hepatic toxic effect, and at least a part of this effect is initiated by free radical and relieved with CGA administration.

研究领域: 毒理学 · 药理学 · 分子生物学
✓ 已验证 DOI PubMed 高影响因子
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Journal of Materials Chemistry A · 2021 ·Vol. 9 ·期 10 ·6131-6138 · IF 12.732

High energy density aqueous zinc–benzoquinone batteries enabled by carbon cloth with multiple anchoring effects

Zhiqiang Luo,Silin Zheng,Shuo Zhao,Xin Jiao,Zongshuai Gong,Fengshi Cai,Yueqin Duan,Fujun Li,Zhihao Yuan

Benzoquinone (BQ) is a desirable cathode for aqueous rechargeable batteries because of its high theoretical capacity and low cost. However, its application is seriously hindered by the high solubility of its discharge product in electrolytes, leading to rapid capacity decay. Here, we report a highly pyridine- and pyrrole-N-doped carbon cloth (NCC) with hierarchical pores as a promising host to anchor BQ and its discharge products. The resultant cathode (BQ-NCC) exhibits an ultrahigh initial capacity of 489 mA h gBQ−1 (excluding the capacity contribution of NCC) at 0.1 A g−1 and a long cycle life with a high capacity retention of 90.4% at 0.5 A g−1 after 500 cycles. Furthermore, a pouch-type cell with a capacity of ∼0.23 A h delivers an energy density of 136.1 W h kg−1 based on the total mass of BQ-NCC and Zn foil. Our study provides a novel strategy to construct high-performance aqueous Zn-ion batteries for potential practical applications.

研究领域: 材料科学 · 电化学
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ENVIRONMENTAL SCIENCE & TECHNOLOGY · 2025 · IF 11.3

A Nationwide Investigation of Substituted p-Phenylenediamines (PPDs) and PPD-Quinones in the Riverine Waters of China

Ningbo Geng,Shijiao Hou,Shuai Sun,Rong Cao,Haijun Zhang,Xianbo Lu,Shusheng Zhang,Jiping Chen,Yanhao Zhang

N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine-quinone (6PPD-Q) has been identified as the cause of the “urban runoff mortality syndrome.” Thus, the ecological risks of substituted p-phenylenediamines (PPDs) and their quinone derivatives (PPD-Qs) in water have gained global attention. However, large-scale observation of their pollution characteristics in surface water is still lacking. Herein, a nationwide investigation revealed the pervasive occurrence of PPDs and PPD-Qs in riverine waters across China, with the mean concentration of ∑5PPD-Qs being 4.9 times higher than their parent ∑5PPDs. Notably, the 6PPD-Q concentrations at eight sampling sites exceeded the median lethal concentration for coho salmon. National annual riverine fluxes were estimated at 113.1 and 276.2 tonnes/year for PPDs and PPD-Qs, respectively, with the Yangtze River contributing more than one-third of the total fluxes. The transformation of PPDs to PPD-Qs was dependent on atmospheric hydroxylation rates and the half-lives of PPDs. A combined multimedia exposure assessment revealed that water exposure accounted for 82.5% of human exposure to PPDs and PPD-Qs, surpassing the contributions from dust and air exposure. This study provides a comprehensive spatial picture of PPDs and PPD-Qs in China. The national atlas highlights their potential ecological risks and implies that targeted actions should be taken to mitigate potential exposure to PPDs and PPD-Qs.

CAS / MDL: 101-54-2
研究领域: 环境科学 · 毒理学 · 生态学
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ENVIRONMENTAL SCIENCE & TECHNOLOGY · 2019 · IF 7.149

Occurrence, Formation, and Oxidative Stress of Emerging Disinfection Byproducts, Halobenzoquinones, in Tea

Jinxiu Lou,Wei Wang,Lizhong Zhu

Halobenzoquinones (HBQs) are frequently detected disinfection byproducts (DBPs) in drinking water with high toxicity and relevance to public health. In this study, we characterized the occurrence, formation, and oxidative stress of the HBQs in tea. 2,6-DCBQ and TetraC-1,2-BQ were identified in all prepared teas at total concentrations of 1.3–2.0 ng/L. 2,6-DCBQ originated from drinking water DBPs, while TetraC-1,2-BQ originated from tea leaves or were generated during tea polyphenol chlorination. HBQs in tea induced the formation of reactive oxygen species and semiquinone radicals, and the oxidative stress could be depleted by tea polyphenols, e.g., (−)-epigallocatechin gallate (EGCG). High-resolution mass spectrometry analysis indicated that the HBQs combined with EGCG and formed adducts at a ratio of 1:1 or 2:1 with the binding sites on the A ring and B ring of EGCG. The viability of HepG2 cells exposed to 50 μM 2,6-DCBQ was increased from 20.0% to 65.2% when 50 μM of EGCG was added. These results demonstrated that various HBQs can occur in tea due to the HBQ DBPs in drinking water, the leachate from tea leaves, and the chlorination of tea polyphenols; furthermore, the oxidative stress and cellular toxicity induced by HBQs in tea could be decreased by tea polyphenols. This is the first study to report HBQs in tea, elucidate the sources of HBQs, and assess relevant health risks.

研究领域: 环境科学 · 公共卫生 · 毒理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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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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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2023 · IF 8.2

Protective effect of thymoquinone on glycation of human myoglobin induced by d-ribose

Jing-Jing Liu,Zhan-Yi Wang,Bin-Bin Jiang,Shu-Qin Gao,Ying-Wu Lin

Nonenzymatic glycation and the subsequent accumulation of advanced glycation end-products (AGEs) in proteins are factors underlying long-term pathogenesis in diabetes. The study of protein glycation is crucial for elucidating their relationship with diabetes mellitus and related disorders. This study explores the interaction between d -ribose and human myoglobin (HMb), as well as the protective effect of thymoquinone (TQ) on glycation. A time-dependent in-vitro glycation study was performed to investigate the mechanism of d -ribose-induced structural interference of HMb in the absence and presence of TQ. Spectroscopic and proteomic analysis indicated that the presence of TQ significantly reduced the total amount of AGEs while maintaining structural characteristics of HMb. 14 glycated sites on HMb were further identified via liquid chromatography-tandem mass spectrometry (LC-MS/MS) after incubation with d -ribose for 12 h, predominantly interacting with lysine residues. TQ was found to disrupt this interaction, reducing the glycated sites from 14 to 12 sites and the percentage of glycated peptides from 26.50 % to 12.97 %. Additionally, there was a significant decrease in the degree of glycation at the same sites. In summary, our findings suggest that TQ has the potential to act as an anti-glycation agent and provide a comprehensive understanding underlying the inhibition mechanism of glycation.

研究领域: 生物化学 · 医学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Sustainable Chemistry and Pharmacy · 2024 · IF 5.5

Development of magnetic ionic liquid-based ultrasound-assisted method for green walnut husk naphthoquinone pigments extraction and application of the pigment to black hair dye

Jing Chen,Jin Zhang,Rundong Liang,Mingyue Ma,Yan Cui

The work established a new method combining MILs with ultrasound to effectively extract naphthoquinone pigments from green walnut husk. With the yield of juglone as the index, some parameters were optimized by single factor experiment with UV. Optimal extraction conditions were determined to be as follows: extraction solvent of [C 4 MIM] [FeCl 4 ], ratio of liquid to material of 10 mL/g, extraction temperature of 60 °C and extraction time of 60 min. Based on this method, the extraction yield of green walnut husk pigment was as high as 85.52% (g/g), which was a lot higher than that of heat-reflux extractions with ethanol and NaOH. Subsequently, the extracted pigment was used as a colorant in the hair dyeing combined with eugenol and tea polyphenol as natural accelerating agent and mordant. The process was optimized by orthogonal experiment, and the hair treated with the extracts got by MB-UA-E was the darkest when pH was kept at 5.0, the pigment concentration was 60%, the dyeing temperature was kept at 70 °C, and the dyeing time was 40 min. Compared to two products obtained by reflux extraction, the extracts got by MB-UA-E showcased superior black dyeing capacity, higher tensile strength, less damage to hair scales or α-keratin and greater UV protection property. It caused less damage to structural of hair fiber than commercial oxidative dye despite participation of conditioner in the oxidative dye. Our study could open new possibilities for using recycled walnut waste in the field of hair dyeing with an eco-friendly and efficient method.

研究领域: 化学 · 材料科学 · 环境科学 · 化妆品科学
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