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Rutin
FOOD AND CHEMICAL TOXICOLOGY · 2020 · IF 4.679

Evaluating the potential risk by probing the site-selective binding of rutin-Pr(III) complex to human serum albumin

Chunlei Zhu,Fengru Liu,Yunlong Wei,Fan Zhang,Ting Pan,Yingwang Ye,Yizhong Shen

Having reported that rare earth elements displayed potential toxicity i n vivo , often be found in soil, plants and etc. , which might be easily chelated with the natural functional molecule rutin to form rutin metal complexes, ultimately entering the human body by means of food chain . However, few reports paid the attention on the toxicology of the complexes consisting of rutin with rare earth ions. Here, we focused on the potential toxicity by probing the site-selective binding of the rutin-rare earth ions complexes to human serum albumin (HSA). As a proof-of-concept, we selected Pr 3+ as the representative to conjugate with rutin to form rutin-Pr(III) complex, which was further applied to interact with HSA in aqueous solution. The results exhibited that the rutin-Pr(III) complex primary bound to the hydrophobic cavity at site II (subdomain IIIA) of HSA through hydrogen bonding and van der Waals force . Through the thermomechanical analysis, we found this binding process was spontaneous because of the negative Δ G. We believe that this work may offer a new insight into understanding the physiological effects ( e.g. toxicology) of rutin and rare earth ions, which could be helpful to guide their rational use in the agriculture and environment-related industries.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2020 · IF 7.1

Electrochemical determination of rutin based on molecularly imprinted poly (ionic liquid) with ionic liquid-graphene as a sensitive element

Yixia Lu,Jian Hu,Yanbo Zeng,Ying Zhu,Hailong Wang,Xiaoling Lei,Shisi Huang,Longhua Guo,Lei Li

A novel electrochemical sensor for rutin determination based on molecularly imprinted poly (ionic liquid) (MIPIL)/ionic liquid-graphene (IL-GR) modified electrode was developed. MIPIL was synthesized via free radical polymerization using rutin as the template, 1-allyl-3-ethyl imidazolium bromide ([AEIm]Br) as the functional monomer and 1,4-butanediyl-3,3′-bis- l -vinylimidazolium dibromide ([V 2 C 4 (mim) 2 ]Br 2 ) as the cross-linker. The composite of IL-GR as an electrode sensitive element was prepared using carboxymethyl-3-methylimidazolium chloride ([HO 2 CMMIm]Cl) by one-step ultrasound method. Fourier transform infrared spectroscopy and scanning electron microscope were used to characterize IL-GR and MIPIL. The increased surface area and conductivity of IL-GR/GCE improved the sensitivity of rutin sensor. Under the optimum condition, good linearity for rutin analysis by the MIPIL-based sensor was obtained from 0.03 to 1 μM. A low limit of detection for rutin was 0.01 μM (S/N = 3). The MIPIL-based sensor demonstrated superiority on DPV response compared to the imprinted sensors based on traditional cross-linkers. The proposed sensor presented good selectivity for rutin and successfully applied for rutin determination in tablets with RSD of 3.05 % and the average recovery range was 98.3 %.

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PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY · 2020 · IF 1.415

Preparation of isoquercitrin by biotransformation of rutin using α-L-rhamnosidase from Aspergillus niger JMU-TS528 and HSCCC purification

Li Jun Li,Xiao Qing Liu,Xi Ping Du,Ling Wu,Ze Dong Jiang,Hui Ni,Qing Biao Li,Feng Chen

Isoquercitrin is a flavonoid with important applications in the pharmaceutical and nutraceutical industries. However, a low yield and high production cost hinders the industrial preparation of isoquercitrin. In the present study, isoquercitrin was prepared by biotransformation of rutin using α-L-rhamnosidase from Aspergillus niger JMU-TS528 combined with high-speed countercurrent chromatography (HSCCC) purification. As a result, the optimum transformation pH, temperature, and time were pH 4.0, 60 °C, and 60 min, respectively. The Km and Vmax were 0.36 mM and 0.460 mmol/min, respectively. For isoquercitrin production, the optimal rutin concentration and transformation time were approximately 1000 mg/L and 60 min. The rutin transformation rate reached 96.44%. The isoquercitrin was purified to a purity of 97.83% using one-step purification with HSCCC. The isoquercitrin was identified using UPLC-Q-TOF-MS. The comprehensive results indicated that the biotransformation procedure using the α-L-rhamnosidase from A. niger JMU-TS528 combined with HSCCC was a simple and effective process to prepare isoquercitrin, which might facilitate the production of isoquercitrin for industrial use.

CAS / MDL: 482-35-9 153-18-4
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD RESEARCH INTERNATIONAL · 2019 · IF 3.579

Effects of dietary cyanidin-3-diglucoside-5-glucoside complexes with rutin/Mg(II) against H2O2-induced cellular oxidative stress

Wei Xu,Nan Zhang,Zhentao Zhang,Pu Jing

Anthocyanins exist likely as complexes with flavones/metal ions in some plants. However, few studies indicate the complexation effects on bioactivities, i.e. antioxidant activities. The aim of this study was to evaluate effects of complexes of cyanidin-3-diglucoside-5-glucoside (CY3D5G) with rutin/Mg(II) on intrinsic antioxidant enzymes and mRNA expressions. All complexes exhibited cellular antioxidant activity in RAW264.7 cells, whereas half maximal effective concentration (EC 50 ) values of CY3D5G complexes were significantly lower than its alone. Combination indexes of CY3D5G-rutin, CY3D5G-Mg(II), and CY3D5G-rutin-Mg(II) complexes were < 1 ( p  < .05), indicating of synergistic effects. Additionally, CY3D5G-Mg(II) rather than others significantly enhanced total antioxidant capacity, superoxide dismutase activity, and glutathione peroxidase activity while reducing malonic dialdehyde contents in H 2 O 2 -induced RAW264.7 cell model ( p  < 0.05), which were further confirmed with the up-regulated mRNA expression of nuclear factor E2-related factor 2 (Nrf2) and heme oxygenase-1 (HO-1), and the down-regulated p21 ( p  < 0.05). Our results demonstrated that CY3D5G and its complexes might enhance cellular antioxidant activities via the Nrf2/HO-1 signaling pathway. Additionally, a synergistic antioxidant effect of CY3D5G in the present of rutin/ Mg(II) as regular food components was evident, suggesting anthocyanin might interact with dietary components such as Mg(II) or rutin in food matrix or biological systems and exhibit a stronger antioxidant activity than it alone. The Mg (II) that exhibited no antioxidant activities alone shows potential as a co-adjuvant for the anthocyanin antioxidant activity.

CAS / MDL: 7722-84-1 153-18-4
✓ 已验证 产品关联 DOI PubMed 高影响因子
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RESEARCH IN VETERINARY SCIENCE · 2025 · IF 1.8

Heat stress relief for broiler chickens: Dietary Rutin improved growth performance, immunity, antioxidant capacity, histopathologic picture and gene expression profile

Mona H. Hafez,Neveen R. Ashoura,Shymaa A. Khatab,Tasnim S. Waheeb,Hebatallah M. Saad,Kariman A. Esmail

Our research aimed to explore the performance, immunity, antioxidants, gene expression, and histopathology of broilers grown at standard temperatures vs those subjected to heat stress (HS) with rutin supplementation. Two hundred forty-one-day-old chicks were randomly allocated into 4 groups. Control group; Rutin group was administered rutin (500 mg/kg food) at ambient temperature; HS group, birds exposed to HS (35 ± 2   °C) for 14 consecutive days; HS + Rutin group was administered the same dosage of rutin, and the birds were then exposed to HS. Molecular docking revealed high binding affinity of rutin toward the growth factors myostatin, insulin-like growth factor receptor-1 (IGFR-1), growth hormone receptor (GHR), heat Shock protein 90 (HSP90), heat Shock factor-1(HSF-1) and HSP70. Rutin not only improved the body weight and feed conversion ratio, but it also considerably reduced the negative effects of HS on growth performance. It also led to decrease in malondialdehyde and pro-inflammatory cytokine levels of interleukin 2 (IL-2), tumor necrosis factor (TNF-α), and IL-6, together with an increase in the antioxidant enzymes CAT, GPX, and SOD activity in addition to a considerable improvement in immunoglobulin (IgM, IgG, and IgA) secretion during HS. Interestingly on molecular level, rutin caused an upregulation in expression of HSP90, HSF-1, HSP70, growth related genes (myostatin, IGFR-1, GHR), and downregulation of immune-related genes chemokines [Lipopolysaccharide-induced TNF-α factor (LITAF), IL-1β, IL-6 gene expression. These changes are further confirmed by histopathological investigation that revealed improvement in hepatic and breast muscle histoarchitecture, increased glycogen and decreased IL-1β immunoexpression after rutin supplementation in HS. In conclusion, rutin is an efficient feed additive that improves antioxidant status, growth, and immunological function in HS.

✓ 已验证 DOI PubMed 高影响因子
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FOOD RESEARCH INTERNATIONAL · 2022 · IF 7.425

Dynamic monitoring of the protein-lipid co-oxidation of algae oil-enriched emulsions coated with soybean protein-rutin covalent conjugates

Yijia Jia,Shiyan Sun,Dongmeng Zhang,Xinyue Yan,Hui Man,Yuyang Huang,Baokun Qi,Yang Li

The stabilities and levels of protein-lipid co-oxidation of algae oil-in water (O/W) emulsions coated with the soybean protein 7S/11S or their rutin covalent conjugates were studied during storage. After 96 h of storage, the emulsions stabilized with the covalent conjugates exhibited decreased droplets sizes and ζ-potentials and increased concentrations of adsorbed proteins. Therefore, the covalent binding of rutin in different mixing ratios (at 7S/11S:rutin molar ratios of 1:10 and 1:20) improved the physical stabilities of the emulsions compared with those of the emulsions stabilized by native 7S/11S. The 7S/11S-rutin covalent conjugates, which formed interfacial barriers and exhibited good free radical scavenging properties, inhibited protein oxidation (with lower contents of protein carbonyls, Nʹ-formyl-L-kynurenine, and Schiff bases, and decreased intensities of intrinsic tryptophan fluorescence) and lipid oxidation (with lower contents of lipid hydroperoxide and malondialdehyde) as storage time increased. The electronic nose test distinguished the flavor characteristics of the emulsions coated with different protein-based stabilizers. These results reveal the viability of utilizing soybean protein-rutin conjugates in protein-stabilized algae oil-fortified emulsions with enhanced storability.

研究领域: 食品科学 · 化学工程 · 生物技术
✓ 已验证 DOI PubMed 高影响因子
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BIOCHEMICAL ENGINEERING JOURNAL · 2023 · IF 3.9

Selective enrichment of Rutin in sunscreen by boronate affinity molecularly imprinted polymer prior to determination by high performance liquid chromatography

Jinyue Chai,Xue Chen,Chengcheng Jin,Fang Chai,Miaomiao Tian

In this study, AgCl was used as the carrier matrix, TiO 2 was introduced on the substrate surface, carboxyphenylboronic acid (CPBA) was used as the boronate affinity functional monomer , and Rutin (RT) as template to prepare molecular imprinted adsorbent AgCl@TiO 2 @B-MIPs (B-MIPs). The effects of synthesis conditions, solid-phase extraction (SPE) conditions, selectivity, competitiveness, reproducibility, and reusability were evaluated in detail. Under the optimum adsorption conditions, the maximum adsorption capacity is 31.70 mg g −1 . The utility of B-MIPs as a SPE adsorbent for RT was supported by an abundance of pore structure, as well as boric acid affinity sites that facilitate rapid binding of adsorbents to templates. The linear range is 0.05–50 mg L −1 , and the limit of detection (LOD) is 0.023 mg L −1 . The method was used for the determination of RT in sunscreen and isolation cream by high-performance liquid chromatography (HPLC). The target analytic recoveries are in the range of 84.7–98.0% (relative standard deviation is less than 2.4%, n  = 3). Furthermore, this work provides a potential possibility to detect other cis -diol containing analytes in the complex matrix.

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Journal of Environmental Sciences · 2022 · IF 6.796

Repairing of rutin to the toxicity of combined F-53B and chromium pollution on the biofilm formed by Pseudomonas aeruginosa

Yunhao Zhang,Yi Qian,Ming Zhang,Weichuan Qiao

The wastewater discharge from the process of chrome plating, which contains 6:2 chlorinated polyfluorinated ether sulfonate (F-53B) and chromium (Cr), may be toxic to biofilm. In this study we found that the biofilm formed by Pseudomonas aeruginosa PAO1 was inhibited by exposure to a combination of F-53B and Cr(VI). The combined pollution damaged the cell membranes and the structure of the biofilm, and inhibited the production of the Pseudomonas quinolone-based signal, which affected biofilm formation. Moreover, the secretion of extracellular polymeric substances decreased as a result of this combined exposure. Exposure to F-53B and Cr(VI) individually or in combination could induce the excessive accumulation of intracellular reactive oxygen species (ROS), and the ROS positive rate of the bacteria increased under the treatment with 0.2 mmol/L of Cr(VI) and 250 nmol/L of F-53B, respectively. In addition, the activities of superoxide dismutase (SOD) and catalase (CAT) were enhanced for scavenging ROS in the bacteria that were exposed to Cr(VI) and F-53B. As an antioxidant, rutin was used to repair the toxicity of Cr(VI) and F-53B towards the biofilm formed by the bacteria. When rutin was added to the bacteria medium, with either Cr(VI) or F-53B as pollutant, or with the combined pollutants, the extracellular protein content of the bacteria recovered to 0.84, 0.94, and 0.85 times that of the control, respectively. Meanwhile, the accumulation of ROS and the activities of SOD and CAT decreased, which indicated that the addition of rutin can alleviate the oxidative stress and promote the antioxidant stress system.

CAS / MDL: 153-18-4
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MICROCHEMICAL JOURNAL · 2022 · IF 5.304

Rutin as a coenzyme of Fe-doped silicon nanozyme with enhanced peroxidase-like activity for a colorimetric β-glucuronidase sensor

Shao-Bin He,Hui-Jing Yang,Liu Yang,Hamada A. A. Noreldeen,Hua-Ping Peng,Hao-Hua Deng,Wei Chen,Guo-Lin Hong

Coenzyme can work with a natural enzyme to achieve the enzymatic catalytic process. Inspired by nature, herein rutin was found to regulate the peroxidase-like activity of Fe-doped silicon nanodots (Fe-OSiNDs) acting as a coenzyme. To be specific, the peroxidase-like activity of Fe-OSiNDs can be activated by rutin at a low concentration (<200 µM), which accelerated the oxidation process between 3, 3′, 5, 5′-tetramethylbenzidine (TMB) and H 2 O 2 . Possibly as a reason, rutin at a low concentration could be easily attracted and oxidized by Fe 3+ in Fe-OSiNDs and then the produced Fe 2+ reacted with H 2 O 2 to form the hydroxyl radicals around the surface of Fe-OSiNDs thereby contributing to an enhancement. More interestingly, the addition of β-glucuronidase can hydrolysis rutin into quercetin and suppress the peroxidase-like activity of rutin-treated Fe-OSiNDs because quercetin is a sugar-free flavonoid with higher anti-oxidant activity than rutin. Thus, a colorimetric sensor for β-glucuronidase could be established. This sensor realizes a linear ranging from 2 to 40 nM (0.58 to 11.6 μg/mL) towards β-glucuronidase with a detection limit of 0.6 nM (0.174 μg/mL). The feasibility of this sensor for β-GUS detection in Escherichia coli has been realized. This work not only provides an interesting concept for coenzyme-dependent nanozyme and expands the promising use of silicon nanomaterials.

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MICROCHEMICAL JOURNAL · 2021 · IF 4.821

Fabrication and application of a rutin electrochemical sensor based on rose-like AuNPs-MoS2-GN composite and molecularly imprinted chitosan

Yuan Wang,Bihong Zhang,Yun Tang,Faqiong Zhao,Baizhao Zeng

A molecularly imprinted polymer/ Au nanoparticles-MoS 2 -graphene/GCE sensor was fabricated and used for the electrochemical detection of rutin. The rose-like Au nanoparticles-MoS 2 -graphene composite (AuNPs-MoS 2 -GN) was fabricated by using a one-pot hydrothermal method. Graphene acted as an efficient matrix for the growth of MoS 2 nanoflower (NF), and the edges of the MoS 2 NF subsequently loaded AuNPs. The AuNPs-MoS 2 -GN composite had large specific surface area, good conductivity and high catalysis, and showed excellent electrochemical response to rutin. To improve the selectivity, rutin imprinted chitosan film was electrodeposited on the AuNPs-MoS 2 -GN/GCE. The obtained molecularly imprinted sensor had strong adsorption capacity for rutin. Under the optimized conditions, the sensor showed a low detection limit (i.e. 4 nmol L −1 ) and a wide detection range (i.e. 0.01–45.0 μmol L −1 ). It also displayed high stability and selectivity. When the sensor was applied to the determination of rutin in real samples satisfactory results were achieved.

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Frontiers in Bioengineering and Biotechnology · 2021 · IF 5.89

Extraction and Application of Natural Rutin From Sophora japonica to Prepare the Novel Fluorescent Sensor for Detection of Copper Ions

Yang Shilong,Sun Lu,Song Zhiwen,Xu Li

Rutin (R), a representative flavonoid found in various biomasses, can be used to prepare different fluorescent sensors for environmental, biological and medical fields. In this work, the natural R in Sophora japonica was extracted and purified to prepare fluorescent-responding sensor systems intended to recognize copper ions with both strong selectivity as well as appropriate sensitivity. Results showed that neat R had no obvious fluorescent emission peak in PBS buffer solution. However, when R and (2-hydroxypropyl)-β-cyclodextrin (CD) were introduced within buffer solution, fluorescent emission intensity was significantly increased due to the resultant R-CD inclusion complex. In addition, the formed R-CD inclusion complex was shown to behave as the aforementioned fluorescent sensor for copper ions through a mechanism of quenched fluorescent emission intensity when R-CD became bound with copper ions. The binding constant value for R-CD with copper ions was 1.33 × 106, allowing for quantification of copper ions between the concentration range of 1.0 × 10–7–4.2 × 10–6mol⋅L–1. Furthermore, the minimum detection limit was found to be 3.5 × 10–8mol⋅L–1. This work showed the prepared R-CD inclusion complex was both highly selective and strongly sensitive toward copper ions, indicating that this system could be applied into various fields where copper ions are of concern.

CAS / MDL: 128446-35-5
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Pharmaceutics · 2026 ·Vol. 18 ·期 7 ·872 · IF 6.9

Hybrid Drug Delivery System Designed from Spatiotemporal Hierarchical Controlled-Release Strategy Co-Delivering Rutin and Resveratrol for Coordinated Anti-Tumor Immunotherapy

Weinan Li,Sisi Yan,Yingying Gao,Yuhan Fu,Yutong Mei,Yanhong Wang,Zhixin Yang

Background: The highly heterogeneous and dynamically evolving tumor microenvironment leads to the development of drug resistance and recurrence in traditional therapies. Although immunotherapy demonstrates unique advantages, its clinical utility remains constrained by the suboptimal immunogenicity and the limited effect of monotherapy. Herein, a hybrid drug delivery system based on a spatiotemporal hierarchical controlled-release strategy was proposed to achieve dual immunotherapy with immune checkpoint blockade (ICB) and immunogenic cell death (ICD) to promote synergistic anti-tumor therapy.Methods: A liposome–micelle hybrid drug delivery system (RUT-RPP-LP) was constructed using a lipid bilayer composed of dioleoyl phosphatidylethanolamine/hemisuccinyl cholesterol to encapsulate rutin (RUT) and to form an inner cavity-encapsulated resveratrol micelle (RPP). RUT-RPP-LP was characterized, and its pH sensitivity and release behavior were investigated. Subsequently, a colon cancer tumor-bearing mouse model was constructed to evaluate the in vivo targeted anti-tumor effect and biological safety. On this basis, the combined mechanism of ICB and ICD was preliminarily explored.Results: RUT-RPP-LP possessed excellent formulation characteristics, stability, and biocompatibility, achieving graded controlled release of drugs via responding to the TME and lysosomal acidity, respectively. Obviously, RUT-RPP-LP could specifically target the tumor site, induce the occurrence of ICD, and simultaneously block the PD-1/PD-L1 immune checkpoint signaling pathway, thereby enhancing the function of T cells and inducing apoptosis of tumor cells.Conclusions: The RUT-RPP-LP based on the hierarchical controlled-release strategy exerted a spatiotemporally coordinated enhancement of anti-tumor immunity, and may provide a novel combinatorial approach to overcome the low response of immunotherapy in solid tumors.

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