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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2014 · IF 3.107

Wightianines A–E, Dihydro-β-agarofuran Sesquiterpenes from Parnassia wightiana, and Their Antifungal and Insecticidal Activities

Dong-Mei Wang,Cheng-Chen Zhang,Qiang Zhang,Nusrat Shafiq,Gennaro Pescitelli,Deng-Wu Li,Jin-Ming Gao

Five new sesquiterpene polyol esters with a dihydro-β-agarofuran skeleton, designated as wightianines A–E (1–5), besides two known compounds, were isolated from the methanolic extract of the whole plant of the traditional herbal medicine Parnassia wightiana Wall. The structures of the isolated compounds were elucidated on the basis of spectroscopic analyses, including two-dimensional nuclear magnetic resonance techniques (correlation spectroscopy, heteronuclear multiple-quantum coherence, nuclear Overhauser effect spectrometry, and heteronuclear multiple-bond correlation) and electronic circular dichroism studies. The antifungal and insecticidal activities of five compounds were evaluated against several plant pathogenic fungi and armyworm larvae (Mythimna separata Walker). Among the test metabolites, compounds 2 and 7 both exhibited potent antifungal activity against the phytopathogenic fungus Cytospora sp. with minimum inhibitory concentration values of 0.78 μg/mL, which are equal to the two positive controls, hymexazol and carbendazim. However, no insecticidal activity of the test compounds was observed in the present study. Compounds 2 and 7 could be promising leads for developing new fungicides against agriculturally important fungus Cytospora sp.

CAS / MDL: 10605-21-7 10004-44-1
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MOLECULES · 2014 ·Vol. 19 ·期 6 ·7459-7479 · IF 2.095

Organic Liquids-Responsive β-Cyclodextrin-Functionalized Graphene-Based Fluorescence Probe: Label-Free Selective Detection of Tetrahydrofuran

Huawen Hu,John H. Xin,Hong Hu,Xiaowen Wang,Xinkun Lu

In this study, a label-free graphene-based fluorescence probe used for detection of volatile organic liquids was fabricated by a simple, efficient and low-cost method. To fabricate the probe, a bio-based β-cyclodextrin (β-CD) was firstly grafted on reduced graphene surfaces effectively and uniformly, as evidenced by various characterization techniques such as Ultraviolet/Visible spectroscopy, Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy and transmission electron microscopy. The subsequent inclusion of Rhodamine B (RhB) into the inner cavities of the β-CD grafted on the graphene surfaces was achieved easily by a solution mixing method, which yielded the graphene-based fluorescent switch-on probe. In addition, the gradual and controllable quenching of RhB by Fluorescence Resonance Energy Transfer from RhB to graphene during the process of stepwise accommodation of the RhB molecules into the β-CD-functionalized graphene was investigated in depth. A wide range of organic solvents was examined using the as-fabricated fluorescence probe, which revealed the highest sensitivity to tetrahydrofuran with the detection limit of about 1.7 μg/mL. Some insight into the mechanism of the different responsive behaviors of the fluorescence sensor to the examined targets was also described.Keywords:β-cyclodextrin;graphene oxide;chemical reduction and functionalization;functionalized graphene;Rhodamine B;fluorescence quenching;fluorescence switch-on;fluorescence probe;sensor;sensing platform

CAS / MDL: 7585-39-9
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FOOD RESEARCH INTERNATIONAL · 2015 · IF 2.818

Preparation, physicochemical characterization and release behavior of the inclusion complex of trans-anethole and β-cyclodextrin

Wenwen Zhang,Xinying Li,Taocheng Yu,Lun Yuan,Gang Rao,Defu Li,Changdao Mu

Trans -anethole (AT) has a variety of antimicrobial properties and is widely used as food functional ingredient. However, the applications of AT are limited due to its low water solubility, strong odor and low physicochemical stability. Therefore, the aim of this work was to encapsulate AT with β-cyclodextrin (β-CD) for obtaining inclusion complex by co-precipitation method. The measurements effectively confirmed the formation of inclusion complex between AT and β-CD. The results showed that the inclusion complex presented new solid crystalline phases and was more thermally stable than the physical mixture and β-CD. The phase solubility study showed that the aqueous solubility of AT was increased by being included in β-CD. The calculated stability constant of inclusion complex was 1195   M −   1 , indicating the strong interaction between AT and β-CD. Furthermore, the release study suggested that β-CD provided the protection for AT against evaporation. The release behavior of AT from the inclusion complex was controlled.

CAS / MDL: 4180-23-8 7585-39-9
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JOURNAL OF LUMINESCENCE · 2013 · IF 2.144

A novel FRET-based fluorescent chemosensor of β-cyclodextrin derivative for TNT detection in aqueous solution

Lijuan Feng,Cuiyan Tong,Yao He,Bingxin Liu,Chunyu Wang,Jie Sha,Changli Lü

A new fluorescent sensor based on single water-soluble β-cyclodextrin (β-CD) molecule as the support carrier of donor and acceptor complex was designed, and used for TNT detection by fluorescence resonance energy transfer (FRET). In this sensing platform, per-6-amino-β-CD (per-6-NH 2 -β-CD) was used as the detection vehicle. The probe dye of fluorescein 5(6)-isothiocyanate (FITC) was covalently linked onto the per-6-NH 2 -β-CD rim with the grafting molar ratio of 1:1, the residual amino groups of per-6-NH 2 -β-CD can adsorb TNT molecules by forming Meisenheimer complex (TNT–amine complex) with TNT. The absorbtion spectrum of this complex has a spectral overlapping with the emission of FITC in aqueous solution, so it can strongly suppress the fluorescence emission of the adjacent FITC through FRET on β-CD vehicle. This FRET-based fluorescent sensing technique provides a facile, ultrasensitive and selective detection method for TNT molecule. The observed linear fluorescence intensity change could allow the quantitative detection TNT with the detection limit of 20   nM in water.

CAS / MDL: 27072-45-3 118-96-7
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NANO · 2015 · IF 1.09

Voltammetric Sensor for Sudan I Based on Glassy Carbon Electrode Modified by SWCNT/β-Cyclodextrin Conjugate

Yu Cao,Zhihui Fang,Duanguang Yang,Yong Gao,Huaming Li

We reported a sensitive voltammetric sensor for Sudan I determination by modifying glassy carbon electrode (GCE) with single-walled carbon nanotubes (SWCNTs)/β-cyclodextrin conjugate. The cyclic voltammetry results showed that the modified GCE exhibited strong catalytic activity toward the electro-reduction of Sudan I with a well-defined cyclic voltammetric peak at -673 mV. Differential pulse voltammetry measurement showed that the response current exhibited a linear range between 50 nM and 5 μM, and the detection limit was as low as 2.22 nM (S/N = 3). The enhanced electrochemical performance of the fabricated sensor was attributed to the combination of the excellent electrocatalytic properties of SWCNTs and the molecular recognition ability of β-cyclodextrin to Sudan I. The sensor was successfully applied to determine Sudan I in real food samples with satisfactory results.

CAS / MDL: 842-07-9
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INORGANIC CHEMISTRY · 2015 · IF 4.762

Mitochondria Targetable Time-Gated Luminescence Probe for Singlet Oxygen Based on a β-Diketonate–Europium Complex

Jingyan Sun,Bo Song,Zhiqiang Ye,Jingli Yuan

Singlet oxygen (1O2) plays a key role in the photodynamic therapy (PDT) technique of neoplastic diseases. In this work, by using a 9,10-dimethyl-2-anthryl-containing β-diketone, 1,1,1,2,2-pentafluoro-5-(9′,10′-dimethyl-2′-anthryl)-3,5-pentanedione (Hpfdap), as a 1O2-recognition ligand, a novel β-diketonate–europium(III) complex that can act as a luminescence probe for 1O2, [Eu(pfdap)3(tpy)] (tpy = 2,2′,2″-terpyridine), has been designed and synthesized for the time-gated luminescence detection of 1O2 in living cells. The complex is weakly luminescent due to the quenching effect of 9,10-dimethyl-2-anthryl groups. After reaction with 1O2, accompanied by the formation of endoperoxides of 9,10-dimethyl-2-anthryl groups, the luminescence quenching disappears, so that the long-lived luminescence of the europium(III) complex is switched on. The complex showed highly selective luminescence response to 1O2 with a remarkable luminescence enhancement. Combined with the time-gated luminescence imaging technique, the complex was successfully used as a luminescent probe for the monitoring of the time-dependent generation of 1O2 in 5-aminolevulinic acid (a PDT drug) loaded HepG2 cells during the photodynamic process. In addition, by coloading the complex and a mitochondrial indicator, Mito-Tracker Green, into HepG2 cells, the specific localization of [Eu(pfdap)3(tpy)] molecules in mitochondria of HepG2 cells was demonstrated by confocal fluorescence imaging measurements.

CAS / MDL: 9003-99-0
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Journal of Materials Chemistry B · 2015 ·Vol. 4 ·期 1 ·141-151 · IF 4.726

Unimolecular micelles of camptothecin-bonded hyperbranched star copolymers via β-thiopropionate linkage: synthesis and drug delivery

Liang Qiu,Qing Liu,Chun-Yan Hong,Cai-Yuan Pan

In order to develop pH- and redox-responsive unimolecular micelles composed of camptothecin (CPT)-conjugated hyperbranched star copolymers via acid-labile β-thiopropionate linkage, a new monomer, methacryloyloxy-3-thiohexanoyl–CPT, is synthesized through conjugation of CPT with methacrylate via β-thiopropionate linkage, and then used in synthesis of the CPT-conjugated hyperbranched star copolymers by two steps of atom transfer radical polymerization (ATRP): self-condensation vinyl polymerization of the CPT-based monomer, 2-hydroxypropyl methacrylate and inimer, and subsequent ATRP of oligo(ethylene glycol) methacrylate using the obtained hyperbranched polymers as the macroinitiator. The obtained polymers dissolve in water to form unimolecular micelles, and their release of CPT in water at various pHs and their anticancer efficacy are studied. The CPT-loaded unimolecular micelles with diameters of 3.56–6.08 nm are quite stable under neutral environment, and are easily triggered by mild acidic pH, such as 6.0 and 5.0. They can be easily internalized by the tumor cells, releasing the CPT. The CPT-conjugated unimolecular micelles via acid-labile β-thiopropionate linkage have potential for application as tumor-targeted drug release systems.

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CARBON · 2017 · IF 6.337

Monolayer polymerization of polyhedral oligomeric silsesquioxane on graphene oxide for highly efficient adsorption of β-lactoglobulin

Yue Zhang,Zhiyong Guo,Lu Han,Yang Zhang,Xuwei Chen,Jianhua Wang

We report the self-assembly of monolayer polyhedral oligomeric silsesquioxane (POSS) on graphene oxide (GO), where GO acts as a directing template along with the assembly of POSS into a three-dimensional porous framework structure, shortly termed as PPG. The PPG framework contains ultrathin nanopetals with a thickness of ca. 1.95 nm, giving rise to reduced restacking and high surface area. The PPG framework exhibits a high adsorption capacity of up to 1570.3 mg g −1 towards β-lactoglobulin, in addition to a favorable selectivity against other protein species with similar isoelectric points to that of β-lactoglobulin. This might be attributed to the specific hydrogen-bonding donor-acceptor interaction between the calyx structure of β-lactoglobulin and the PPG framework. Satisfactory separation performance of PPG is confirmed by the selective discrimination and isolation of β-lactoglobulin from complex biological sample matrixes, e.g., milk whey. This observation provides a promising approach for the construction of monolayer polymer-modified three-dimensional graphene oxide composites with specific biological application potentials.

CAS / MDL: 919-30-2 7722-84-1
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RSC Advances · 2017 ·Vol. 7 ·期 25 ·15315-15320 · IF 3.108

Nanopore sensor for copper ion detection using a polyamine decorated β-cyclodextrin as the recognition element

Yanli Guo,Feifei Jian,Xiaofeng Kang

A novel and simple nanopore sensing method has been developed for the detection of CuII ions using polyamine decorated cyclodextrin as the recognition element. The strong binding affinity between CuII and the amino groups of cyclodextrin inside an α-hemolysin pore causes the new current blockade events. The event frequency is linear for concentrations of CuII in the range 0.08–20 μM. The detection limit is as low as 12 nM. More significantly, the sensing system is highly specific for CuII and does not respond to other metal ions with concentrations up to 10 fold that of CuII. The applicability of this sensor has also been verified by the analysis of CuII ions in running water, suggesting the potential application of this sensing system.

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ACS Applied Materials & Interfaces · 2025 · IF 8.2

Enantioselective Recognition Driven Photocatalytic Degradation of d-Tryptophan Enantiomers Based on l-Cysteine-Modified β-Cyclodextrin

Hongfang Zhao,Jianrong Wang,Hongxia Li,Xiaohui Niu,Hui Xu,Kunjie Wang

The enantioselective recognition and separation of racemic tryptophan are of significant importance in the fields of medicine, pharmaceutics, and biochemistry. However, conventional methods are costly, energy intensive, and environmentally unfriendly. In this case, l-Cys with amino (−NH2) and sulfhydryl (−SH) groups was chosen to modify β-CD with a chiral cavity to achieve self-assembly via hydrogen bonding, which not only serves as an electrochemical chiral sensor with enhanced chiral sites at the sensing interface but also achieves a higher enantioselectivity for d-tryptophan enantiomers through hydrogen bonding between the host and guest. Moreover, the d-tryptophan enantiomers were subsequently degraded under catalytic conditions simulating visible light, which was a new approach to introduce chiral properties in photocatalysis without organic synthesis. The use of inclusion-complex formation with β-CD combined with simple electrochemical technology and photocatalytic degradation techniques to efficiently and rapidly identify and degrade harmful d-type amino acid enantiomers offers new avenues, which would have great potential in future studies.

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Food Bioscience · 2024 · IF 4.8

Encapsulation and protection of β-carotene in Pickering emulsions stabilized by chitosan-phytic acid-cyclodextrin nanoparticles

Qianzhu Lin,Han Jiang,Xiaojing Li,David Julian McClements,Shangyuan Sang,Jinpeng Wang,Aiquan Jiao,Zhengyu Jin,Chao Qiu

β-Carotene is a hydrophobic molecule that can be isolated from plants that acts as a natural pigmen and nutraceutical. However, the limited water-solubility, oxidative-stability, and bioavailability limit its utilization in functional food, supplement, and pharmaceutical products. Pickering emulsions stabilized by chitosan-phytic acid-cyclodextrin (CS-PA-CD) nanoparticles were prepared to improve the delivery, stability, and bioavailability of β-carotene. The impact of nanoparticle concentration (0.1%, 0.5%, 1.0%, 1.5%, 2.0% w/v) and oil phase fraction (30%, 40%, 50%, 60%, 70% v/v) on the stability of β-carotene-loaded Pickering emulsions was investigated. The Pickering emulsions that were most stable to phase separation were formed at intermediate oil concentrations (50%-60% v/v). The encapsulated β-carotene exhibited improved resistance to heating (70 °C) and UV light exposure. Moreover, the bioaccessibility of β-carotene was also improved using a simulated gastrointestinal model. Overall, our findings highlight the potential of CS-PA-CD nanoparticles for forming and stabilizing Pickering emulsion-based delivery carrier for hydrophobic bioactive substances.

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LWT-FOOD SCIENCE AND TECHNOLOGY · 2024 · IF 6

Encapsulation of resveratrol in nanosheet structured sodium caseinate dialdehyde β-cyclodextrin conjugate with enhanced physicochemical properties

Yanli Fu,Peipei Zhu,Hong Lin,Chun Hu,Lijuan Han,Weinong Zhang,Junbo He

The poor solubility and stability of resveratrol (Res) represent significant obstacles to its utilization and efficacy. Encapsulating in sodium caseinate (NaCas) has also faced issues concerning low encapsulation efficiency and stability. This study presented the synthesis of a novel NaCas and dialdehyde β-cyclodextrin (DA-β-CD) conjugate through the Schiff base reaction using a wet-heating method, which was then utilized to encapsulate resveratrol. Results showed the DA-β-CD was formed in the form of needle-like crystals, whereas the NaCas-DA-β-CD conjugate had a nanosheet structure. The NaCas-DA-β-CD exhibited a substantial increase in surface hydrophobicity, emulsifying activity index, and emulsion stability index. The incorporation of resveratrol into NaCas-DA-β-CD demonstrated a consistent and uniform dispersion at the nanoscale level. It achieved an encapsulation efficiency of 96.8% and exhibited excellent chemical stability, which surpasses those of the NaCas system. Furthermore, the water solubility and antioxidant capacity of resveratrol in NaCas-DA-β-CD exhibited characteristics similar to those in NaCas. The compacted nanosheet structure of the Res-NaCas-DA-β-CD complex, as observed in TEM and SEM, is likely responsible for those enhancements. Hence, the DA-β-CD can serve as an effective polysaccharide for protein modification, while the NaCas-DA-β-CD conjugate can function as an innovative delivery carrier for resveratrol and other hydrophobic bioactives.

CAS / MDL: 7585-39-9 7790-28-5
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