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ACS Sustainable Chemistry & Engineering · 2023 · IF 8.4

Construction of Sustainable Biomass Bubble Propulsion Micromotor and Selective Recognition/Separation of Shikimic Acid with Open 3D Target Imprinting Cavity

Yao Zhu,Xingqi Shao,Ziyu Yuan,Jian Rong,Tao Zhang,Dongya Yang,Jianming Pan,Fengxian Qiu

Self-propelled nano/micromotors that harvest external energy from the surrounding environment and transform it into the power for autonomous movement have manifested great potential in the separation field. In this work, a bubble-propelled hierarchical bifunctional monomer imprinted micromotor has been demonstrated based on natural cotton fiber (CF) biomass as a platform and MnO2 as the catalytic medium. CF@MnO2 is loaded with Ni(OH)2 nanosheets by a simple hydrothermal reaction, displaying an open three-dimensional structure with a large specific surface area for the construction of an imprinted layer. The covalent functional monomer 3-aminophenylboronic acid (APBA) and noncovalent functional monomer (3-aminopropyl)triethoxysilane (APTES) were used to create imprinted cavities for the target. Such a micromotor (CF@MnO2@Ni(OH)2-MIPs) performs self-propulsion behavior powdered by the decomposition of H2O2 fuel and possesses accessible recognition sites for the selective recognition and separation of shikimic acid (SA), which reinforces the adsorption kinetics process and separation specificity. The micromotor shows a maximal adsorption capacity of 127.1 mg g–1 at pH 7.5 in the presence of H2O2, which has risen by 20.9% compared with the counterpart without H2O2. In addition, the adsorption performance of the micromotor fits well with pseudo-second-order (PSO) kinetics and the Langmuir isotherm model, suggesting that chemisorption is the main rate determination step and the adsorption process is a single-layer adsorption. The adsorption quantity of SA is 4.74 times, 4.58 times, and 4.33 times higher than that of hydroquinone (HDQ), p-hydroxybenzoic acid (PHB), and Quercetin, respectively, implying the bifunctional monomer imprinted strategy enhances the affinity of CF@MnO2@Ni(OH)2-MIPs for SA. After five capture/release cycles, the adsorption capacity remains above 95%. This work provides new insight into the design of potential materials for the adsorption of SA, which may open up new avenues for fabricating advanced adsorbents for the practical separation of natural products.

研究领域: 材料科学 · 化学工程 · 生物技术
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FOOD CONTROL · 2018 · IF 3.667

Antibiofilm activity of shikimic acid against Staphylococcus aureus

Jin-Rong Bai,Kai Zhong,Yan-Ping Wu,Grosu Elena,Hong Gao

The aim of this study was to evaluate the inhibitory activity of shikimic acid (SA) against biofilm formation of Staphylococcus aureus and to explore its potential molecular mechanism. Crystal violet staining assay showed that SA clearly reduced the biomass of the biofilm at its sub-MICs. Light microscopic images and scanning electron microscope (SEM) observations suggested that SA inhibited the biofilm adhesion on glass slides and induced apparent collapse of biofilm architecture. In addition, XTT reduction assay and confocal laser scanning microscopic images illustrated that the metabolic activity and the viability of the SA-treated biofilm cells significantly decreased. Cell mobility of the SA-treated S. aureus was also inhibited. These observations suggested that SA inhibited the initial biofilm formation by interfering the metabolic activity, the cell viability, and the cell mobility of S. aureus . However, SA failed to disrupt the one-day-old mature biofilm of S. aureus even at the concentrations higher than MIC, suggesting that SA disturbed the early steps in the biofilm formation of S. aureus . qRT-PCR analyses showed that SA down-regulated the transcription of sarA , while up-regulated the transcription of agrA , which resulted in the prevention of biofilm formation. So, SA could be a potential antibiofilm agent to inhibit biofilm formation of S. aureus .

研究领域: 微生物学 · 药理学 · 分子生物学
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2023 · IF 9.9

Continuous-imprinted-layer nanofiber membrane with MXene-based precise-designed nanocages for high-accuracy recognition and separation of shikimic acid

Rongxin Lin,Jian Lu,Faguang Ma,Ming Yan,Yilin Wu,Jianming Pan

Ti 3 C 2 T x (MXene) has attracted extensive attention from scholars at home and abroad due to its rich surface termination functional groups and two-dimensional multilayer structure. In this work, MXene was introduced to the membrane by vacuum-assisted filtration processes, and the formed interlayer channel facilitated the construction of recognition sites and molecular transmission. In this paper, PDA@MXene@PDA@SiO 2 -PVDF dual-imprinted mixed matrix membrane (PMS-DIMs) were developed by the cooperative dual-imprinting strategy, which was used for the adsorption of shikimic acid (SA). Firstly, SiO 2 -PVDF nanofiber basement membrane were prepared by electrospinning method and the first Polydopamine (PDA)-based imprinted layer was constructed on the membrane. PDA not only realized the imprinting process, PDA modification was used to give MXene nanosheets better antioxidant properties and to confer the SiO 2 -PVDF nanofiber membrane the interface stability. After that, the second-imprinted sites were constructed on the stacked MXene nanosheets surface as well as between the layers. The SA dual-imprinted sites significantly increased the efficiency of the selective adsorption efficiency, when the template molecule passed through the membrane, the cooperative dual-imprinting strategy enabled multiplex recognition and adsorption of template molecules. As a consequence, which greatly improving the rebinding ability(262.17 g m −2 ), and mselectivity factors ( β Catechol/SA , β P-HB/SA , β P-NP/SA were 2.34, 4.50 and 5.68). High stability proved the potentials of the PMS-DIMs for practical application. Precise SA-recognition sites were constructed on the PMS-DIMs, PMS-DIMs not only exhibit excellent selective rebinding properties but also have high permeability.

研究领域: 材料科学 · 生物化学 · 环境工程
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SEPARATION AND PURIFICATION TECHNOLOGY · 2024 · IF 8.1

Engineering flower-shaped hierarchical micromotors on a sustainable biotemplate by teamed boronate affinity-based surface imprinting for effective separation of shikimic acid

Yao Zhu,Ziyu Yuan,Jian Rong,Tao Zhang,Dongya Yang,Jianming Pan,Fengxian Qiu

Self-propelled nano/micromotors are the frontier of separation materials because they are capable of converting external energy in the surrounding environment into kinetic energy for their autonomous movement. In this work, a bioinspired flower-shaped hierarchical teamed boronate affinity (TBA)-imprinted Pt-free micromotor is introduced based on waste rape pollen as a biotemplate due to its merits of sustainability, rich source and low price. Such micromotor, composed of MnO 2 nanosheets as a catalytic medium, Mg-Al layered double hydroxides (LDH) nanosheets as large surface area substrate and functional surface imprinted polymers as identification subject, exhibits autonomic motor behavior powdered by oxygen bubbles generated by the decomposition of H 2 O 2 and selective recognition and separation for shikimic acid (SA). The hierarchical flower-shaped structure affords more accessible recognition sites for SA, which thus facilitates the separation process. Moreover, in combination with the TBA strategy, the micromotor can precisely recognize the target via boronate affinity between boronic acids and cis -diols from SA while showing strong binding capacity under neutral conditions. Benefiting from the pluripotent role of pioneering boronate affinity-covalent imprinted technique, hydrogen bonds interaction and nanoconfinement effect, the resulting affinity towards SA is evidently enhanced with maximal adsorption capacity of 129.51 mg g −1 at neutral pH in the presence of H 2 O 2 . After five capture/release cycles, the adsorption capacity remains above 85 %. This proposed flower-shaped hierarchical micromotor expands the scope of potential materials for the adsorption of SA and provides a new and promising direction for fabricating adsorbents applied in the separation and purification of natural products.

研究领域: 材料科学 · 生物工程
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JOURNAL OF MEMBRANE SCIENCE · 2023 · IF 9.5

Precise identification and transport of specific molecules through framework-functionalized membranes with multiple binding sites

Kaicheng Zhang,Yue Li,Zequan Diao,Hang Cui,Faguang Ma,Ming Yan,Yilin Wu

Membranes with specific-recognition and superfast-filtration have significant practical applications in water purification and chiral separation. However, membrane technique still remains challenging to high selectivity and permeation in aqueous-and-organic solvents. Here, we reported a new approach to designing framework-functionalized membranes with multiple binding sites (FMMBSs) that enabled structure&size-exclusion selectivity and fast transport performance towards specific compound of shikimic acid (SA). The as-prepared FMMBSs, based on intrinsic core-shell structure of the boronate-affinity sol-gel imprinted polymers, demonstrated that exquisite control over polymerization pattern and functionalization of characteristic membrane construction played important roles in achieving fast molecule transport combined with high molecular selectivity. The superior property of the membrane-based core-shell structure had been initially demonstrated by testing nitrogen adsorption capacity, showing about a 3.0 times higher result (63.65 cm 3 /g) than that of original membrane (20.71 cm 3 /g). These framework-functionalized membranes were then regarded as the platforms to construct the FMMBSs through a first-time-developed boronate-affinity sol-gel imprinting strategy. Therefore, the FMMBSs always kept remarkably static rebinding capacity (45.48 mg g −1 ) and perm-selectivity factors (>10). The dynamic transport results showed that much higher SA-based rebinding capacities than that of other molecules could be still observed under pump-pressure-driven for a long time, which strongly confirmed the preparation of high-efficiency selective membrane separation system. The strategy of introducing framework-functionalized structure on porous membrane would offer a window of opportunity for preparation of high-intensitive selective separation membrane systems not only for continuous high permeability, but also for competitive selectivity.

研究领域: 材料科学 · 环境科学 · 化学工程
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APPLIED SURFACE SCIENCE · 2021 · IF 6.707

Direct growth of boronate based shikimic acid imprinted polymer on porous substrate surface: A stable membrane for specific molecular separation

Yao Zhu,Zhiyuan Pan,Jian Rong,Kaili Mao,Dongya Yang,Tao Zhang,Jicheng Xu,Fengxian Qiu,Jianming Pan,Haixia Yu

Identifiable separation of shikimic acid (SA) compound is important for antiviral drug production. Current separation methods used for shikimic acid remain unsatisfied due to lack of specificity that can accurately and instantly anchor the target molecular from interfering impurities. Membrane separation seems to be feasible with the advantages of low energy consumption and operating convenience. Herein, benefiting from the characteristic cis -diol group in SA, a smart and simple poly(vinylidene fluoride) (PVDF) based molecular imprinted membrane (MIM) is synthesized by using 4-vinylbenzeneboronic acid as functional monomer to form prepolymers with SA. The resulting SA-imprinted boronate affinity molecular imprinted membranes (SA-imprinted-BAMIMs) show enhanced adsorption capacity (51.99 mg g −1 ) compared with reported material. It should be noted that the formation of boronate ester bond between functional monomer and SA can help to specifically capture the target, and the release of combined SA on the membrane becomes easy due to the reversible bind characteristic of boronate ester under different pH condition. Moreover, SA-imprinted-BAMIMs exhibit acceptable stability after ultrasonic for 5 h and satisfactory regeneration performance after 8 cycles of adsorption–desorption experiments (93.02%). This convenient MIMs display great potential in the following work on rapid and specific separation of SA for commercial synthesis of antiviral.

研究领域: 生物化学 · 材料科学 · 制药工程
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PHYTOCHEMICAL ANALYSIS · 2024 ·Vol. 35 ·期 6 ·1428-1442 · IF 3

An effective and comprehensive optimization strategy for preparing Ginkgo biloba leaf extract enriched in shikimic acid by macroporous resin column chromatography

Sijie Zhang,Xingchu Gong,Haibin Qu

Introduction Previously reported preparation methods of Ginkgo biloba leaf extract (EGBL) have mainly focused on the enrichment of flavonoid glycosides (FG) and terpene trilactones (TT), which led to the underutilization of G. biloba leaves (GBL). Objectives To make full use of GBL, in this study, a comprehensive optimization strategy for preparing EGBL by macroporous resin column chromatography was proposed and applied to enrich FG, TT, and shikimic acid (SA) from GBL. Methodology Initially, the static adsorption and desorption were executed to select suitable resin. Then, the influences of solution pH were investigated by the static and dynamic adsorption. Subsequently, eight process parameters were systematically investigated via a definitive screening design (DSD). After verification experiments, scale-up enrichment was carried out, investigating the feasibility of the developed strategy for application on an industrial scale. Results It was found that XDA1 was the most appropriate adsorbent for the preparation of EGBL at solution pH 2.0. Furthermore, based on the constraints of the desired quality attributes, the optimized ranges of operating parameters were successfully acquired, and the verification experiments demonstrated the accuracy and reliability of using DSD to investigate the chromatography process for the preparation of EGBL. Finally, magnified experiments were successfully performed, obtaining the EGBL containing 26.54% FG, 8.96% TT, and 10.70% SA, which reached the SA level of EGB761, an international standard EGBL. Conclusion The present study not only provided an efficient and convenient approach for the preparation of EGBL enriched in SA but also accelerated efforts to high-value utilization of GBL.

CAS / MDL: 7664-38-2
研究领域: 植物化学 · 中药学 · 分离纯化技术
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APPLIED ORGANOMETALLIC CHEMISTRY · 2019 ·Vol. 34 ·期 3 ·e5415 · IF 3.259

Fe3O4@chitosan-bound boric acid composite as pH-responsive reusable adsorbent for selective recognition and capture of cis-diol-containing shikimic acid

Yao Zhu,Jian Rong,Kaili Mao,Dongya Yang,Tao Zhang,Fengxian Qiu,Jianming Pan

Recently, shikimic acid (SA) has aroused great concern as the starting raw material for the synthesis of antiviral drug (Tamiflu) against the spread of influenza virus in the body. In this work, magnetic chitosan composite modified with boric acid and its application in SA recognition and separation was described. Chitosan (CT) with plenty of hydroxyl and amino groups was first coated on the surface of magnetic core Fe 3 O 4 , then carboxylic groups were grafted to the surface of Fe 3 O 4 @CT via anhydride modification, followed by the introduction of 3-aminophenylboronic acid (APBA). The uniform morphology and composition analysis of the adsorbent (Fe 3 O 4 @CT-COOH-BA) were characterized by FT-IR, XRD, XPS, SEM, TEM and UV–visible spectroscopy. The adsorption capacity of as-prepared material was explored in detail by batch mode experiments. The adsorption kinetics fitted well with a pseudo-second order model, and the adsorption isotherms was well described by the Langmuir model with a maximum adsorption capacity of 23.8 mg g −1 at 25 °C. Solution pH plays a crucial role in adsorption process and the optimized pH was 8.0. In addition, Fe 3 O 4 @CT-COOH-BA could be easily reused through an external magnet and the adsorption capacity reduced by only 4% after five adsorption–desorption cycles. These results prove that boric acid modified magnetic chitosan composite is an effective and practical adsorbent for specific recognition and selective adsorption of cis-diol-containing compounds.

研究领域: 生物化学 · 材料科学 · 药物合成
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2021 · IF 4.952

Comparative study on antibacterial mechanism of shikimic acid and quinic acid against Staphylococcus aureus through transcriptomic and metabolomic approaches

Jinrong Bai,Yanping Wu,Qian Bu,Kai Zhong,Hong Gao

Shikimic acid (SA) and quinic acid (QA), widely found in many natural plants, have been reported to exhibit prominent antibacterial activity in our previous studies. In this study, their inhibitory mechanism against Staphylococcus aureus was comparatively investigated for the first time by combined transcriptomic and metabolomic analyses. Bioinformatic analysis results revealed SA and QA had remarkably different action mechanism against S. aureus at multi-targets and multi-pathways. These two organic acids disturbed oxidative phosphorylation pathway, and changed glycerophospholipids and fatty acids levels to interfere with the membrane fluidity. Besides, only SA affected the normal functions of potassium channel and calcium channel. After penetrated cell membrane, SA and QA influenced the ribosome functions and aminoacyl-tRNA synthesis, thus disordering the protein synthesis. Furthermore, SA interfered with the pyruvate metabolic pathways, while QA damaged the synthesis of l -lysine and peptidoglycan to inhibit cell wall synthesis and cell division. This study lays theoretical foundations for the application of SA and QA as novel natural antibacterial agents in foods.

研究领域: 微生物学 · 生物信息学 · 食品科学
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JOURNAL OF MATERIALS SCIENCE · 2021 ·Vol. 56 ·期 23 ·13043-13055 · IF 4.22

Boronate affinity-modified magnetic β-cyclodextrin polymer for selective separation and adsorption of shikimic acid

Zhu Yao,Rong Jian,Mao Kaili,Yang Dongya,Zhang Tao,Qiu Fengxian,Pan Jianming,Pu Zhilong

Polymer of cyclodextrin (CD) is still of great sustainable interest in the scientific research attributing to its excellent physicochemical properties. Owing to its water solubility and superior binding capacity, CD is usually modified through various strategies to exploit its application area. Herein, for the first time, magnetic β-cyclodextrin (β-CD) polymer is endowed with boronate affinity property via mild chemical modifications to specifically separate natural drug raw material shikimic acid (SA). The uniform morphology, magnetic response ability and composition analysis of the porous adsorbent were highly supported by the characterizations. The capture process towards SA depending on the pH value is explored in detail by adsorption kinetics, equilibrium, selectivity and reusability. It is found that specific recognition sites decorated on the surface of magnetic β-CD provides strength support for selective adsorption and separation of shikimic acid. The prepared adsorbent shows high adsorption quantity ( Q , mg g −1 ) of 31.60 mg g −1 at 25 °C, high specific recognition and good adsorption capacity (above 83.7%) and stability after five cycles. This study gives a new sight on the utilization of porous β-CD-based material by grafting functional boric acid group for specific capture of natural cis-diol-containing compounds.

研究领域: 材料科学 · 药物化学
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JOURNAL OF MOLECULAR LIQUIDS · 2021 · IF 6.165

Boronate affinity surface imprinted polymers supported on dendritic fibrous silica for enhanced selective separation of shikimic acid via covalent binding

Yao Zhu,Zhiyuan Pan,Jian Rong,Kaili Mao,Dongya Yang,Tao Zhang,Jicheng Xu,Fengxian Qiu,Jianming Pan

In this work, a surface molecular imprinted polymers (MIPs)-based boronate affinity adsorbent was prepared on dendritic fibrous silica particle (DFSP) for rapid recognition and selective separation of shikimic acid for the first time. Double recognition of both imprinted cavity and boronate affinity endowing the MIPs material high adsorption capacity and superior selectivity, which could reach 43.708 mg g −1 at 308 K and pH 8, relatively higher than other reported materials. In addition, pH response adsorption towards SA was achieved in the work. Under the optimum condition, the experimental kinetics data is confirmed to the pseudo-second order model ( R 2  = 0.9957), and the adsorption process of shikimic acid is well fitted with the Langmuir model ( R 2  > 0.99). In contrast, the adsorption quantity of MIPs based adsorbent was 3.75 times higher than that of non-imprinted samples. Moreover, the as-obtained MIPs showed comparable reusability after five cycles of continuous adsorption–desorption, which maintained 86.38% of the initial adsorption quantity. The enhanced selectivity property and good regeneration performance makes the boronate affinity MIPs a promising and practical material for rapid recognition and specific capture of shikimic acid. Therefore, the strategy posed in this work sheds new light on the role of boronate affinity MIPs in the adsorption of shikimic acid.

研究领域: 生物化学 · 材料科学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2023 · IF 8.6

Boronate-affinity sol–gel-imprinted membranes with MOFs-functionalized rotary-evaporating layers for high-precision specific recognition

Faguang Ma,Ming Yan,Rongxin Lin,Yilin Wu,Jianming Pan

Compared to traditional separation methods, membrane-based separation can reduce environmental impact while reducing energy consumption. However, traditional adsorbents have issues with low selectivity and adsorption capacity because they enclose the majority of their functional sites in their thick structures. In this research, molecularly imprinted nanocomposite membranes were inventively integrated with boronate-affinity sol–gel imprinting technique (BSIT). It is important to note that in this work, the metal–organic frameworks (MOFs) mixed-matrix membrane (MMMs) served as the initial platform for the polydopamine (PDA)-based imprinting layer. The key to the fabrication of the MOFs MMMs was the employment of the rotary evaporation technique. The prepared boronate-affinity sol–gel molecularly imprinted membranes (BS-MIMs) played an important role in the high selectivity of the specific compound shikimic acid (SA) through covalent (boronate-affinity) and non-covalent (–OH and –NH 2 ) effect. This new approach provides a more precise combination of simultaneously increasing selectivity (greater than 5.0) and adsorption capacity (up to 107.87 mg g −1 ). The efficiency of BSIT makes it extremely competitive for the development of selective separation membranes.

研究领域: 材料科学 · 生物化学
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