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Food & Function · 2023 ·Vol. 14 ·期 3 ·1357-1368 · IF 6.1

Noncovalent interaction mechanism and functional properties of flavonoid glycoside-β-lactoglobulin complexes

Min Fu,Lizhi Gao,Qin Geng,Ti Li,Taotao Dai,Chengmei Liu,Jun Chen

The interaction of flavonoid glycosides with milk protein and effects on the functional properties of flavonoid glycoside-β-lactoglobulin complexes are still inexplicit. The noncovalent interactions between flavonoid glycosides including quercetin (QE), quercitrin (QI), and rutin (RU) with β-lactoglobulin (β-LG) were determined by computer molecular docking and multispectral technique analysis. The fluorescence quenching results indicated that the flavonoid glycosides formed stable complexes with β-LG by the static quenching mechanism. The computer molecular docking and thermodynamic parameters analysis conclude that the main interaction of β-LG-QE was via hydrogen bonding, while for β-LG-QI and β-LG-RU it is via hydrophobic forces. The order of binding affinity to β-LG was QE (37.76 × 104 L mol−1) > RU (16.80 × 104 L mol−1) > QI (11.17 × 104 L mol−1), which indicated that glycosylation adversely affected the colloidal complex binding capacity. In this study, the physicochemical properties of the protein-flavonoid colloidal complex were determined. The analysis by circular dichroism spectroscopy demonstrated that flavonoid glycosides made the protein structure looser by inducing the secondary structure of β-LG to transform from the α-helix and β-sheet to random coils. The hydrophobicity of β-LG decreased due to binding with flavonoid glycosides, while functional properties including foaming, emulsification, and antioxidant capacities of β-LG were improved due to the noncovalent interactions. This study presents a part of the insight and guidance on the interactive mechanism of flavonoid glycosides and proteins and is helpful for developing functional protein-based foods.

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INTERNATIONAL JOURNAL OF FOOD PROPERTIES · 2022 · IF 3.388

Comparative phytochemical property and antioxidant activity of sixteen Mei (Prunus mume) fruit cultivars from six provinces in China

Zhihua Liu,Yezi Yang,Chongzhi Sun,Yang Wu,Xiaobo Li

Mei (Prunus mume) is widely planted in Eastern Asian countries. To evaluate the effect of cultivar and producing origin on the quality of Mei fruit, we studied the phytochemical properties and antioxidant activities of the 16 Mei fruit cultivars from 6 provinces in China, as well as their profiles of 121 volatile compounds, 5 organic acids, 13 minerals, 24 amino acids and 3 active peptides. Multivariate analysis revealed that the four Mei fruit cultivars with a drier climate in Yunnan province had the characteristics of low water moistures and proteins contents, high total acids, soluble solids, flavones, and phenols contents, and high antioxidant activities, which could be distinguished from fruits of other producing areas. Further component analysis showed that Mei fruits were rich in volatile compounds, organic acids (such as citric acid and malic acid), minerals (such as K, Ca, Mg, P, and Fe), and amino acids (such as Orn, Asn, and Asp), and the nutrient composition ratio in different cultivars was different. In conclusion, Mei fruits can be used as nutritious health food and different cultivars focus on different nutritional compositions.

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SEPARATION AND PURIFICATION TECHNOLOGY · 2023 · IF 8.6

Partitioning behavior of rutin in novel liquid–liquid biphasic systems formed by choline chloride/ maltose natural deep eutectic solvents and n-propanol

Feng Liu,Li Chen,Kangling Yin,Taotao Fan,Zongcheng Yan

The development of promising environmentally friendly extraction tools has been one of the hottest topics in green chemistry. Among these, natural deep eutectic solvents (NADESs) as green extraction media have received widespread recognition. In this paper, with the aim of exploring the potential applications of NADESs in the extraction field, water-soluble n -propanol was used to form liquid–liquid biphasic systems with choline chloride/ maltose NADESs. The phase behavior of those systems was designed by adjusting the molar proportion of the hydrogen bond acceptors (HBA): hydrogen bond donors (HBD) and temperature. This allows for the systems tailored to the specific requirements of the target molecule, as shown by their application in the extraction of rutin. Investigation of the distribution behavior of rutin suggested that the partition coefficient and the extraction efficiency of rutin in the bottom phase increase significantly with decreasing temperature and increasing HBA : HBD molar ratio. And with the temperature of 288.15 K, the highest TLL of NADES (ChCl: Mal = 1:2) + NPA + water system achieved higher E% of 94.27 %. The interaction force between NADES and rutin was studied using the Hansen solubility parameter, it turned out that Δ δ i , j Δδi,j of the 2:1 and 1:2 M ratio of NADES was only 8.91, 5.12, which meaning that there may be strong interactions between NADES and rutin. In addition, the hydrogen bond ( Δ δ H ΔδH ) of the NADES (HBA: HBD = 1:2) was 25.47, which is greater than other interaction force, revealing that the hydrogen bond is the maximum force between rutin and the NADES (HBA: HBD = 1:2). The energy ( Δ G T ΔGT ), enthalpy ( Δ H T ΔHT ) and entropy ( Δ S T ΔST ) calculated from the partition data of rutin was consistent with the free energy ( Δ G C ) (ΔGC) , enthalpy ( Δ H C ) (ΔHC) and entropy ( Δ S C ) (ΔSC) changes of system, which confirmed that the driving force of the phase separation of the system drives the transfer of rutin to the lower phase. In addition, we used eco-friendly water to regenerate NADES. The recovery efficiency of rutin was explored while NADES was reused in three cycles. This result showed there was no change observed in the extraction capability for rutin in those system. Finally, a larger aggregate of size 1315 nm was observed by dynamic light scattering, which furthermore demonstrated that the hydrogen bonding interaction between NADES (HBA: HBD = 1:2) and rutin is the main driving force tool for enhancing rutin partitioning. This method presents a newly system constructed by NADES and NPA for the green extraction, revealing the feasibility of the system for rutin extraction and facilitating industrial applications.

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INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY · 2023 ·Vol. 58 ·期 5 ·2247-2257 · IF 3.3

Quantification of bioactive components and evaluation of microbial community and antibacterial activity from Heterotrigona itama and Tetrigona binghami honeys

Jiao Wu,Bingjun Han,Xiaoyu Chen,Jinglin Gao,Shan Zhao,Liping Sun,Shijie Wang

Summary Stingless bee honey is a precious food product with therapeutic benefits. In this study, we determined the quality of Malaysian stingless bee honeys ( Heterotrigona itama and Tetrigona binghami ) by the physicochemical characteristics, phenolic compounds, and organic acids. Our results revealed that the major phenolic compounds in all honey samples were chlorogenic acid and myricetin, and the major organic acids contained gluconic acid and trans -cinnamic acid. The microbial community in honeys characterised using 16S rRNA and ITS amplicon sequencing techniques showed that Lactobacillus was assumed to be the predominant bacterium in stingless bee honeys. Furthermore, the antibacterial activity of honeys was examined in order to further demonstrate their health benefits. Our results are intended to pave the road for stingless bee honeys' probiotic capacity to be extended into our daily life.

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ANALYST · 2023 ·Vol. 148 ·期 9 ·2100-2109 · IF 4.2

The facile activation of graphite for the improved determination of dopamine, rutin and acetamidophenol

Yanxue Xu,Guihua Chen,Yunting Qin,Dan Xiao

A glassy carbon electrode (GCE) was modified with graphite powder (G/GCE), and then treated with a solution of sodium peroxide for several minutes to prepare an oxidized G/GCE (OG/GCE). The OG/GCE has prominently improved responses toward dopamine (DA), rutin (RT) and acetamidophenol (APAP), of which the anodic peak current was increased by 2.4, 4.0 and 2.6 fold compared with that obtained using the G/GCE. The redox peaks of DA, RT and APAP on the OG/GCE could be separated sufficiently. The corresponding redox processes were confirmed as diffusion-controlled and parameters such as the charge transfer coefficients (α), saturating adsorption capacity (Γ*) and catalytic rate constant (kcat) were estimated. In individual detection, the linear ranges for DA, RT and APAP were 10 nM–10 μM, 1.00 nM–150 nM and 20 nM–30 μM, respectively, and the LODs for DA, RT and APAP were estimated as 6.23 nM, 0.36 nM and 13.1 nM with 3σ/S, respectively. The contents of RT and APAP in drugs were determined and agreed with the labeled contents. The recoveries of DA in serum and sweat were in the range of 91–107%, indicating that the determination results achieved by the OG/GCE are reliable. The practical use of the method was verified with a graphite-modified screen-printed carbon electrode (G/SPCE), which was also activated by Na2O2 to prepare OG/SPCE. The recovery of DA in sweat achieved using the OG/SPCE was 91.26%.

CAS / MDL: 153-18-4
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2023 ·Vol. 103 ·期 5 ·2367-2377 · IF 4.1

Dietary rutin improves breast meat quality in heat-stressed broilers and protects mitochondria from oxidative attack via the AMPK/PINK1–Parkin pathway

Shun Chen,HuiJuan Liu,JiaQi Zhang,BinBin Zhou,XiaoFang He,Tian Wang,Chao Wang

BACKGROUND This study was conducted to investigate the effect of dietary rutin on the meat quality, antioxidant status and mitochondrial structure and function in the breast muscle of heat-stressed broilers. A total of 192 male broilers were randomly assigned into three groups and treated with normal control (CON), heat stress (34 °C, HS), and HS with 500 mg kg −1 rutin supplementation (HS + Rutin), respectively. RESULTS Dietary rutin significantly reversed HS-induced decrease in body weight, average daily feed intake, average daily gain, and feed efficiency. Rutin supplementation attenuated HS-induced impaired meat quality by decreasing the lightness, drip loss at 24 and 48 h, the peak time of free water ( T 22 ) and the peak area ratio of free water ( P 22 ), and increasing the pH 24h and peak area ratio of immobilized water ( P 21 ). Rutin supplementation promoted superoxide dismutase, glutathione peroxidase activities and total antioxidant capacity, and decreased malondialdehyde levels compared with the HS group. Moreover, rutin attenuated HS-induced mitochondrial damage by increasing the mitochondrial DNA copy number and improving mitochondrial morphology. Dietary rutin significantly increased mitochondrial biogenesis-related mRNA (proliferator-activated γ receptor coactivator-1α [PGC-1α], nuclear respiratory factor 1 [NRF1], and mitochondrial transcription factor A [TFAM]) expression via the AMP-activated protein kinase (AMPK) signaling pathway. HS significantly increased mitophagy-related genes and proteins (Parkin, PTEN-induced putative kinase 1 [PINK1], microtubule associated protein light chain 3-II [LC3-II]) expression, and dietary rutin significantly reversed these alterations. CONCLUSION Dietary rutin attenuated the HS-induced decline in meat quality and antioxidant capacity of broilers, which may be related to inhibition of the AMPK/PINK1–Parkin signaling pathway to attenuate mitochondrial damage. © 2023 Society of Chemical Industry.

CAS / MDL: 153-18-4
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JOURNAL OF HAZARDOUS MATERIALS · 2023 · IF 13.6

Fabrication of double imprinted anchor points in cellulose nanocrystals-based hierarchical porous polyHIPEs for selective separation of flavoniods under physiological pH

Shucheng Liu,Zhi Hu,Xuan Zhang,Hao Huang,Jianming Pan,Hongxiang Ou

Previous research had proved that molecular imprinted polymers can be used as separation material for removing Naringin (NRG) from agricultural pomelo wastes effectively. But the adsorption amounts of NRG molecules from traditional MIPs was quite low by using boronic acid as functional monomer because of single affinity interaction. Therefore, we developed the new combination of bifunctional monomers (i.e. low pKa boronate affinity monomer 2,4-difluoro-3-formylphenylboronic acid and dopamine) based on cellulose nanocrystals (CNCs) mixed with polymerized high internal phase emulsion (polyHIPE, PH) through an double layer surface imprinted method. The introduction of polyethylenimine (PEI) can offer abundant anchor units for the growth of more anchor sites to immobilization template molecules. Importantly, largely improved selective adsorption amounts (50.79 μmol g −1 ), which may be attribute to the fabrication of the uniform growth of double imprinted layers onto the polydopamine (PDA)/boronic acid-based surfaces. In addition, the resulting double recognition molecular imprinted polymers (MIPs) based on hypercrosslinked PH (DR-HCLPH@MIPs) not only exhibited fast adsorption kinetic of NRG molecule, but also possessed excellent selectivity and high adsorption capacities at physiological pH. Meanwhile, the coarse NRG from pomelo waste can be high selectively extracted to 94.74%. Overall, this study provides a versatile approach for fabrication of the sandwich-biscuit-like double imprinting layer porous MIPs for precise identification and ultrafast transport separation of NRG from complex samples.

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MICROCHEMICAL JOURNAL · 2023 · IF 4.8

New theoretical perspective for easy evaluation of the antioxidant properties of typical flavonoids

Tian Yang,Zhong Zhang,Fangjian Ning,Li Yuan,Xingbin Yang,Liping Luo

To intensively investigate the antioxidant property of flavonoids and their different phenolic hydroxyl groups, we selected six types of typical flavonoids and carried out experimental analysis and quantum chemical calculations. By calculating the Mulliken charges, frontier molecular orbitals, molecular dipole moments, and interaction model hydrogen bond lengths of the compounds, the theoretical analysis results were compared with the free radical scavenging assays. Results show that the three flavonoids with different numbers of hydroxyl groups on the B ring are ranked in antioxidant activity as myricetin > quercetin > kaempferol. The glycoside linked in the C ring has a great effect on bioavailability, and the antioxidant activity is ranked as quercetin > isoquercetin > rutin. Besides, the results of the novel interaction model calculations show that quercetin with an meta -hydroxy group on the B ring structure has stronger antioxidant capacity than morin with an ortho -hydroxy group. The theoretical evaluation method established in this work is expected to provide new ideas and references for the evaluation of antioxidant properties of natural active substances from the electronic structure perspective.

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FOOD RESEARCH INTERNATIONAL · 2023 · IF 8.1

Insight into covalent conjugates of β-lactoglobulin with rutin: Characterizing allergenicity, digestibility, and antioxidant properties in vitro

Zhifen Deng,Yuting Xia,Lang Chen,Yi Zhao,Ruihong Wang,Guizhao Liang

β-lactoglobulin (β-LG) is an essential nutrient in milk, but it is the primary allergen causing dairy allergy in humans. Currently, researchers are focusing on using flavonoids to covalently modify β-LG for improving its functionality. However, the impact and underlying mechanisms of rutin covalent modification on the functional properties and allergenicity of β-LG remain unclear. Here, we aim to investigate the changes in allergenicity, digestive characteristics, and antioxidant properties of β-LG after covalent modification using a combination of spectroscopy, enzyme-linked immunosorbent assay (ELISA), simulated digestion, and antioxidant assays. The results indicate that rutin forms covalent bonds with the free amino group, sulfhydryl group, and tryptophan of β-LG, leading to alterations in the secondary structure of β-LG. Furthermore, the modified β-LG exhibits improved antioxidant capacity and decreased allergenicity, along with reduced resistance to pancreatin digestion in vitro . This study provides novel insights and strategies to expand the functional application of β-LG.

CAS / MDL: 153-18-4
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JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY · 2023 · IF 6.1

Near-infrared light-mediated CuS@Rutin nanocomposites for the PTT/PDT synergistic treatment in bacterial infections

Jian Liu,Baoheng Yin,Shuang Li,Lian Mi,Guanghao Yin,Feng Li,Lingmei Zhong,Na Bai,Xue Li

Reactive oxygen species (ROS)-based photodynamic therapy (PDT) and heat-based photothermal therapy (PTT) have garnered significant attention for their non-resistant and minimally invasive characteristics in the treatment of bacterial infections. However, the excessive generation of ROS during treatment can lead to persistent levels of oxidative stress, causing irreversible damage to surrounding tissues. In this study, we successfully synthesized a multifunctional nanocomposite consisting of hollow interior and porous surface nanostructured copper sulfide (Nano CuS) loaded with Rutin, a compound known for its ROS scavenging properties. This nanocomposite effectively eliminates bacteria through PDT and PTT in the initial stage, while simultaneously releasing Rutin to clear ROS at the site of inflammation. This dual therapeutic approach provides antimicrobial and anti-inflammatory effects, making it a promising strategy for combating bacterial infections. Overall, our synthesized nanomaterial demonstrates excellent efficacy in antibacterial and anti-inflammatory applications, offering new insights for future developments in infection treatments.

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Food Chemistry-X · 2023 · IF 6.1

Aqueous two-phase systems coupled with chemometrics-enhanced HPLC-DAD for simultaneous extraction and determination of flavonoids in honey

Xiao-Hua Zhang,Xiang-Dong Qing,Jing-Jing Zheng,Yan Yu,Jiaojiao Huang,Chao Kang,Zhi Liu

In this study, an accurate, rapid, green, and environment friendly method for the extraction and quantitative analysis of flavonoids in honey was established by using the aqueous two-phase extraction combined with the chemometrics-assisted HPLC-DAD. The first purpose of this study was to extract seven flavonoids in five different types of honey using alcohol/salt aqueous two-phase system (ATPS). The system with 2.82 mL sodium citrate (30%), 1.58 mL water, and 3.10 mL isopropanol, showed the highest flavonoids extraction yields in the top phase (87.66–101.50%). Additionally, the three-way array of honey samples based on HPLC-DAD was decomposed mathematically by the alternating trilinear decomposition (ATLD) algorithm to obtain reasonable chromatograms, spectra, and concentration profiles for each analyte. Compared with the traditional solid-phase extraction method, the ATPS-ATLD-based method showed satisfactory spiked recoveries, lower limit of detection, and higher sensitivity, further verifying its accuracy and stability.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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Food Bioscience · 2023 · IF 5.2

Revealing release patterns and availability of phenolics in Tartary buckwheat under simulated digestion

Yong Zhu,Likang Qin,Yue Chen,Shaoqi Zhou

The release patterns of phenolics in digestive tract was elucidated using a simulated digestion protocol, in which the delivery route of rutin was revealed, and the availability of released phenolics was also evaluated using a dialysis membrane absorption model. The results showed that phenolic compounds such as rutin, quercetin , 3,4-dihydroxybenzoic acid (DA), 2,3,4-trihydroxybenzoic acid (TA) and chlorogenic acid (CA) were released from Tartary buckwheat under simulated digestion. The contents of released phenolic compounds in oral-gastrointestinal digestion were significantly higher ( p  < 0.05) than that in oral and oral-stomach digestion phases. Besides, in oral-gastrointestinal digestion, the proportion of available contents of rutin, DA, TA and CA to corresponding released contents were 71.8%, 73.7%, 68.6% and 100%, and the great majority of rutin was sufficiently degraded into quercetin. The contribution of antioxidant activity of available compounds to corresponding total activity were between 62.2% and 68.9%. These results indicated that phenolics in Tartary buckwheat can be adequately released in oral-gastrointestinal digestion, and a great majority of these phenolics are available. This study illustrates the potential bioavailability of phenolic compounds in Tartary buckwheat during gastrointestinal digestion.

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