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Rutin
Foods · 2025 ·Vol. 14 ·期 10 ·1672 · IF 5.1

Characterization of Okra Seed Protein/Rutin Covalent Complex and Its Application in Nanoemulsions

Chengyun He,Lu Bai,Yingxuan Zhou,Benguo Liu,Sheng Geng

A covalent complex of okra seed protein (OSP) and rutin was prepared using the alkali-induced method and characterized. Its application in nanoemulsions was also evaluated. Multi-spectral analysis confirmed the formation of the covalent complex, with OSP as the main body. With an increasing rutin dosage during the preparation process, the amount of rutin in the complex progressively ascended, and the α-helix structure and surface hydrophobicity of the complex gradually declined. The complex exhibited remarkable ABTS radical scavenging capacity and reducing power, which were proportional to the total phenolic content. The OSP/rutin complex could be utilized for the fabrication of O/W nanoemulsions, which remained stable in terms of droplet size and appearance after 28 days of storage at both 4 °C and 25 °C. Furthermore, lipid oxidation in the nanoemulsion stabilized by the OSP/rutin covalent complex could be effectively inhibited, and the emulsion could enhance the UV irradiation resistance of lutein loaded in the oil phase. Our results can provide a reference for the development of protein–polyphenol covalent complexes.

CAS / MDL: 28752-68-3
研究领域: 食品科学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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APPLIED ORGANOMETALLIC CHEMISTRY · 2025 ·Vol. 39 ·期 9 ·e70368 · IF 0

Natural Rutin-Based AIE Probes With Enhanced Fe3+ Recognition via Hydroxyl Group Engineering

Kai Wang,Peiwen Lv,Mingyang Liu,Yunjun Mei,Yifan Zhang,Yuqiu Zheng,Jintao Guan

Traditional fluorescent probes have challenges, including aggregation-induced quenching, biological incompatibility, and suboptimal selectivity. In this study, we developed a novel probe derived from natural rutin featuring an aggregation-induced emission (AIE) effect. Through hydroxy engineering of rutin, the optimized probe enables precise detection of Fe 3+ via 2:1 stoichiometric coordination. The probe demonstrates remarkable analytical performance, with a detection limit as low as 0.22 μM. Concentration-dependent responses were observed within 0–20 μM, with significant linearity ( R 2 > 0.99) in the 0–10 μM range. Density functional theory calculations reveal that the binding of Fe 3+ effectively suppresses intramolecular charge transfer. The hydroxy-engineered modification plays a pivotal role in facilitating complexation for bond formation and providing appropriate steric hindrance. This research establishes a new benchmark for natural product-based AIE probes and deepens understanding of the structure–activity relationships governing flavonoid-metal recognition.

研究领域: 分析化学 · 生物无机化学 · 材料科学 · 荧光传感 · 配位化学 · 天然产物化学
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ARCHIVES OF MICROBIOLOGY · 2025 ·Vol. 207 ·期 4 ·1-12 · IF 2.6

Characterization of intestinal bacteria for the production of quercetin and isoquercitrin from rutin

Byambaakhuu Narantsetseg,Duan Shen,Sa Ren,Yang Qing-lan,Xu Hai-Yan,Shan Cheng-Bin,Xu Ri-hua,Ma Chao-Mei

This study was to evaluate the potential of human intestinal bacterial species in the biotransformation of rutin to quercetin and isoquercitrin which is rarer than rutin in nature and could more potently inhibit the growth of some cancer cell lines. Bacterial strains isolated from healthy human fecal samples were identified through 16S rDNA gene sequence analysis and genome analysis. Isoquercitrin and quercetin were identified and quantified by UHPLC-QQQ-MS in multiple reaction monitoring mode. As results, the intestinal bacterial strains, comprising nine Gram-positive rods and one Gram-negative rod, were classified into Enterococcus , Lactococcus , and Escherichia genera. Among the ten isolates , Lactococcus garvieae Y3-2 and Lactococcus petauri Y5-4 produced higher amounts of quercetin compared to other bacteria. Interestingly, all strains of Enterococcus faecium species (Y4-1, Y4-2, Y5-1, and Y5-2) exhibited a relatively strong ability to convert rutin to isoquercitrin, with Y4-2 being particularly efficient. The higher L-rhamnosidase activity observed in E. faecium Y4-1 and E. faecium Y4-2 correlated with their significant yield of isoquercitrin. Four or three genes were probably involved in rutin metabolism according to the analysis of flavonoid pathway based on genome sequences. The results provided information for selecting bacterial species to convert rutin into target bioactive compounds, and for purification of pure enzymes to biosynthesize isoquercitrin.

CAS / MDL: 64-18-6
研究领域: 食品科学 · 微生物学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MICROCHEMICAL JOURNAL · 2025 · IF 5.1

An electrochemical sensor of PBA-grafted Zn-MOF/MIP for sensitive rutin detection

Haoxiang Wang,Yuyang He,Ruoyu Wang,Mengqi Lu,Yuting Luo,Yiwei Sun,Dongpo Xu

An electrochemical sensor with a dual recognition strategy was designed using molecularly imprinted polymers (MIPs) and boric acid for the highly sensitive detection of rutin. The synthesized metal-organic framework (MOFs) is combined with phenylboronic acid, which increases the recognition area of phenylboronic acid and its recognition ability towards adjacent diol compounds. Meanwhile, the molecularly imprinted polymer (MIP) provides specific recognition for rutin. The dual recognition strategy is widely adopted in sensors, enhancing the specificity of the imprinted cavity and effectively addressing the influence of interfering substances in complex matrices. After optimizing the experimental parameters, the detection range of this sensor is from 1 nM to 200 nM, and the limit of detection is 0.43 nM, indicating that this sensor has high potential for practical applications.

CAS / MDL: 10196-18-6 111-30-8
研究领域: 分析化学 · 生物传感 · 药物分析
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Applied Sciences-Basel · 2019 ·Vol. 9 ·期 12 ·2567 · IF 2.217

Light Harvesting and Optical-Electronic Properties of Two Quercitin and Rutin Natural Dyes

Dongpeng Zhao,Qiuchen Lu,Runzhou Su,Yuanzuo Li,Meiyu Zhao

The photovoltaic properties of two dyes (quercitin (Q) and rutin (R)) were experimentally investigated. The results showed that Q had excellent photoelectric properties withJscof 5.480 mA·cm−2,Vocof 0.582 V,ηof 2.151% larger than R withJscof 1.826 mA·cm−2,Vocof 0.547 V, and η of 0.713%. For a better understanding of the photoelectric properties of two molecules and illustrating why the performances of Q is better than R from the micro-level, the UV-VIs spectrum, Fourier transforms infrared (FT-IR) spectrum, and cyclic voltage current characteristics were experimentally investigated. What is more, density functional theory (DFT) and time dependent density functional theory (TD-DFT) have been implemented in theoretical calculation. Based on the calculated results, frontier molecular orbitals (FMOs), charge differential density (CDD), infrared vibration, first hyperpolarizability, projected density orbital analysis (PDOS), electrostatic potential (ESP), and natural bond orbital (NBO) were analyzed. Hole/electron reorganization energies (λh/λe), light harvesting efficiency (LHE), fluorescent lifetime (τ), absorption peak, and the vertical dipole moment (μnormal) were calculated, and the shift of conduction band edge of a semiconductor (ΔECB) has been analyzed, which has a close relationship withJscandVoc. The results demonstrated that, due to the higher LHE, τ,μnormal, and red-shifted absorption peak, Q has better photoelectric properties than R as a promising sensitizer.

研究领域: 光伏技术 · 材料科学 · 计算化学 · 有机电子学 · 染料敏化太阳能电池
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AAPS PHARMSCITECH · 2020 ·Vol. 21 ·期 7 ·1-12 · IF 2.401

Characterization and Evaluation of the Solubility and Oral Bioavailability of Rutin–Ethanolate Solvate

Liu Yanjie,Zhao Xiuhua,Zhang Qian,Wang Lingling,Li Yuanyuan,Li Yuanzuo

Rutin has many biological activities, but poor solubility and absorption limit its oral application. This study aimed to investigate the characterization of metastable rutin–ethanolate and its solubility and oral bioavailability. In this research, a soluble rutin/CH 3 CH 2 OH solvate (Form Π) was prepared by solvent crystallization. High-performance liquid chromatography, gas chromatograph, and 1 H-NMR showed that Form Π was formed by rutin and ethanol in a molar ratio of 1:1. The changes of Fourier transform infrared spectroscopy and 1 H-NMR spectrum and the density functional theory (DFT) calculation predicted hydrogen bond formation between 4’-O of rutin and –OH of ethanol. The results of morphology, solid state CP/MAS 13 C-NMR, X-ray diffraction, and differential scanning calorimetry (DSC) revealed that Form Π is a novel polymorph that differs from Form Ι (rutin trihydrate). Form Π can be stored for a long time under sealed and dry conditions at 40°C but would gradually transform into Form Ι under humid conditions. Although Form Π is a new metastable polymorph relative to Form Ι, Form Π has better solubility and faster dissolution rate. Moreover, the bioavailability of Form Π was 2.04 times higher than that of Form Ι. This outcome implied that Form Π would be a prospective raw material of oral preparation.

CAS / MDL: 153-18-4
研究领域: 药学 · 化学 · 药理学
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Analytical Methods · 2016 ·Vol. 8 ·期 20 ·4056-4063 · IF 1.915

Determination of rutin by chemiluminescence based on a luminol–potassium periodate–ZnSe system

Shifeng Li,Li Zhang,Lei Chen,Yiman Zhong,Yonghong Ni

ZnSe quantum dots (QDs) with a homogeneous size distribution and good stability were synthesized by the reaction of zinc acetate and NaHSe in the presence of glutathione (GSH). The obtained ZnSe QDs were characterized using transmission electron microscopy (TEM) and X-ray powder diffraction (XRD). Simultaneously, UV-visible spectroscopy (UV-vis) was performed and the fluorescence properties of ZnSe QDs were investigated. The effect of ZnSe QDs on the luminol–potassium periodate (KIO4) chemiluminescence (CL) system, a popular model CL system, was researched. It was found that as-prepared ZnSe QDs could strongly enhance the chemiluminescence (CL) of the luminol–KIO4 system. To discuss the mechanism of the CL enhancement, we studied the UV-vis and CL spectra of the luminol–KIO4–ZnSe QDs system. The CL enhancement should be attributed to the oxidation of luminol to its excited state by KIO4, under the catalysis of ZnSe QDs, which caused strong light emission. It was found that rutin, p-t-butylprocatechol, catechol, paracetamol, resorcinol and tryptophan could markedly inhibit the CL of the luminol–KIO4–ZnSe QDs system among 17 kinds of amino acids and 23 other kinds of organics. The above phenomena presented good linear relations. Thus, effective methods to detect them were developed.

CAS / MDL: 70-18-8
研究领域: 分析化学 · 生物医学工程
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Materials · 2016 ·Vol. 9 ·期 7 ·504 · IF 2.728

Incorporation of Rutin in Electrospun Pullulan/PVA Nanofibers for Novel UV-Resistant Properties

Yongfang Qian,Mengjie Qi,Laijiu Zheng,Martin W. King,Lihua Lv,Fang Ye

This study aimed to investigate the incorporation of rutin into electrospun pullulan and poly(vinyl alcohol) (PVA) nanofibers to obtain ultraviolet (UV)-resistant properties. The effect of weight ratios between pullulan and PVA, and the addition of rutin on the nanofibers’ morphology and diameters were studied and characterized by scanning electron microscopy (SEM). Fourier transform infrared (FTIR) analysis was utilized to investigate the interaction between pullulan and PVA, as well as with rutin. The results showed that the inclusion of PVA results in the increase in the fiber’s diameter. The addition of rutin had no obvious effect on the fibers’ average diameters when the content of rutin was less than 7.41%. FTIR results indicated that a hydrogen bond formed between pullulan and PVA, also between these polymers and rutin. Moreover, the addition of rutin could enhance the mechanical properties due to its stiff structure and could decrease the transmittance of UVA and UVB to be fewer than 5%; meanwhile, the value of ultraviolet protection factor (UPF) reached more than 40 and 50 when the content of rutin was 4.46% and 5.67%, respectively. Therefore, the electrospun pullulan/PVA/rutin nanofibrous mats showed excellent UV resistance and have potential applications in anti-ultraviolet packaging and dressing materials.Keywords:pullulan;rutin;electrospinning;nanofiber;UV resistance

CAS / MDL: 153-18-4
研究领域: 材料科学 · 生物医学工程
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LANGMUIR · 2022 · IF 4.331

Supramolecular Vector/Drug Coassemblies of Polyglycerol Dendrons and Rutin Enhance the pH Response

Zhijun Guo,Guangyue Bai,Xize Zhan,Kelei Zhuo,Jianji Wang,Yujie Wang

A coassembly strategy for a supramolecular vector/drug was proposed with a biocompatible ternary dodecyl-bi(third-generation polyglycerol (PG) dendrons) (C12-(G3)2) amphiphile, dodecyl sulfobetaine (SB3-12) surfactant, and poorly water-soluble drug rutin. C12-(G3)2 and rutin will mutually enhance their pH response by protonation and deprotonation of dendritic PG and rutin’s ionization as the pH changes from the acidic gastric lumen to the weakly alkaline intestine. SB3-12 may increase the payload and bring about sustained release for rutin by intermolecular interactions. Self-assembling behaviors of C12-(G3)2, SB3-12, sodium dodecyl sulfate (SDS), and dodecyl trimethylammonium bromide (DTAB) and their hybrids with rutin were characterized by UV–vis spectroscopy, a fluorescence probe, and 1H NMR. UV–vis and 1H NMR were used to identify the position and orientation of rutin in the vectors. The functions of the vector/drug were confirmed by measuring the solubility and in vitro release of rutin. The ternary coassembling vector/drug easily imparted functions of pH-responsive and sustained release without complex synthetic processes. The nanocaves framed by PG dendrons in the micelles provide pH-responsive compartments for rutin and SB3-12 in the supramolecular vector/drug anchors that accommodate rutin by weak interactions. The finely matched supramolecular vector/drug coassemblies exhibit the pH-responsive function for a potential application in the treatment of inflammatory bowel disease.

研究领域: 药学 · 纳米技术 · 药物递送系统
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ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY · 2020 · IF 4.872

New application of rutin: Repair the toxicity of emerging perfluoroalkyl substance to Pseudomonas stutzeri

Yi Qian,Yunhao Zhang,Achuo Anitta Zuh,Weichuan Qiao

Per- and polyfluoroalkyl substances (PFASs) are toxic to microorganisms , thereby affecting microbial communities in sludge and soil, but how to repair the toxicity of microorganisms remains unclear. In this study, rutin, an antioxidant, was added into a culture medium with an aerobic denitrification bacteria, Pseudomonas stutzeri , under the exposure of sodium perfluorononyloxy-benzenesulfonate (OBS) to evaluate the repair mechanisms of rutin to the toxicity of OBS to the bacteria. The results showed that rutin could repair the damage of OBS to cell structures, and reduce the death rates of the bacteria under OBS exposure. The dosage of rutin reduced the effect on the inhibition of denitrification ability of P. stutzeri under OBS exposure. Compared with the bacteria exposed to single OBS, the dosage of rutin resulted in that the death rates recovered from 96.2% to 66.4%, the growth inhibition rate decreased from 46.5% to 15.8%, the total nitrogen removal rate recovered from 66.9% to 100%, and the NO 2 − content recovered from 34.5 mg/L to 0.22 mg/L. The expressions of key denitrification genes ( napA , nirS , norB , nosZ ) were recovered after adding rutin under OBS exposure. Rutin changed the positive rate of reactive oxygen species , the relative superoxide dismutase and catalase activities in the bacteria which exposed to OBS. The mechanism by which rutin repaired the toxicity of OBS to P. stutzeri related to inhibiting the activities of antioxidant and denitrification enzymes rather than affecting the expressions of genes involved in these enzymes. This study sheds light on the repair method of micro-organics and reveals the repair mechanisms under PFASs exposure.

研究领域: 微生物学 · 环境科学 · 分子生物学
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DRUG DELIVERY · 2021 · IF 6.419

Gelatin hydrogel/contact lens composites as rutin delivery systems for promoting corneal wound healing

Lianghui Zhao,Xia Qi,Tao Cai,Zheng Fan,Hongwei Wang,Xianli Du

Corneal wound healing is a highly regulated biological process that is of importance for reducing the risk of blinding corneal infections and inflammations. Traditional eye drop was the main approach for promoting corneal wound healing. However, its low bioavailability required a high therapeutic concentration, which can lead to ocular or even systemic side effects. To develop a safe and effective method for treating corneal injury, we fabricated rutin-encapsulated gelatin hydrogel/contact lens composites by dual crosslinking reactions including in situ free radical polymerization and carboxymethyl cellulose/N-hydroxysulfosuccinimide crosslinking. In vitro drug release results evidenced that rutin in the composites could be sustainedly released for up to 14 days. In addition, biocompatibility assay indicated nontoxicity of the composites. Finally, the effect of rutin-encapsulated composites on the healing of the corneal injury in rabbits was investigated. The injury was basically cured in corneas using rutin-encapsulated composites (healing rate, 98.3% ± 0.7%) at 48 h post-operation, while the damage was still present in corneas using the composite (healing rate, 87.0% ± 4.5%). Further proteomics analysis revealed that corneal wound healing may be promoted by the ERK/MAPK and PI3K/AKT signal pathways. These results inform a potential intervention strategy to facilitate corneal wound healing in humans.

研究领域: 生物材料学 · 眼科医学 · 药剂学
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2019 ·Vol. 30 ·期 5 ·988-996 · IF 1.335

Fluorescent Sensors Based on Cu-Doped Carbon Quantum Dots for the Detection of Rutin

Wang Cheng-ya,Shang Shanzhai,Zheng Xudong,Lei Ping,Han Jingmei,Yuan Linda,Li Zhiqiang,Wang Ru,Gong Weimin,Tang Jianguo,Yang Yaling

In this paper, Cu-doped carbon quantum dots (Cu-CQDs) were prepared by carrying out thermolysis of Na2[Cu(EDTA)] and hydroxylamine hydrochloride at 300 ºC for 2 h. The as-prepared Cu-CQDs were characterized by UV-Vis, Fourier transform infrared (FTIR) spectroscopy, transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and X-ray diffraction (XRD). The Cu-CQDs exhibited good fluorescence property, high stability, excitation-dependent emission behavior and a quantum yield of 9.8%. More significantly, the synthesized Cu-CQDs were developed for sensing rutin (RT) based on the fluorescence quenching of the prepared Cu-CQDs. A good linear relationship between the fluorescence quenching of Cu-CQDs and different concentrations of RT was obtained in the range of 0.1-15 µg mL-1 with a correlation coefficient of 0.9959. The detection limit was as low as 0.05 µg mL-1 (signal-to-noise ratio, S/N = 3). The possible mechanism of fluorescence quenching was explored, which was proved to be inner filter effect. Importantly, the proposed method was successfully applied in the detection of RT tablet samples and with satisfactory results, showing the practical applications.

研究领域: 分析化学 · 材料科学
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