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JOURNAL OF MEMBRANE SCIENCE · 2014 · IF 4.908

A novel free-standing flexible molecularly imprinted membrane for selective separation of synephrine in methanol–water media

Jie-Ping Fan,Lie Li,Ze-You Tian,Chun-Fang Xie,Fa-tian Song,Xue-Hong Zhang,Jian-Hang Zhu

Flexibility was very important for molecularly imprinted membrane (MIM) to apply to practical use. A novel free-standing flexible MIM was prepared using methacrylic acid (MAA) and 2-hydroxyethyl acrylate (HEA) as co-functional monomer , and ionic liquid as porogen. HEA was able to effectively improve the flexibility of MIM. Ionic liquid, 1-butyl-3-methylimidazolium bromide, was able to accelerate the synthesis process and improve the selectivity and adsorption of the MIM. The properties of MIM were characterized by scanning electron microscopy (SEM), Fourier transform infrared (FT-IR), thermo gravimetric analysis (TGA), differential thermal analysis (DTA) and X-ray photoelectron spectroscopy (XPS). Two structurally similar compounds (octopamine and tyramine) were selected as competitors to examine the selective recognition of MIM to synephrine (SYN). The competitive adsorption and permeation selectivity experiments showed that the MIM could selectively recognize SYN, and was able to be used to selectively separate SYN from the standard mixtures or the extract of stir-baked Aurantii Fructus Immaturus in methanol/water (4:1, v / v ) media.

CAS / MDL: 97-90-5 60-18-4
研究领域: 化学工程 · 生物技术
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JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS · 2017 · IF 3.255

Rapid analysis of Aurantii Fructus Immaturus (Zhishi) using paper spray ionization mass spectrometry

Xuemei Liu,Zhixin Gu,Yuan Guo,Jingjing Liu,Ming Ma,Bo Chen,Liping Wang

Paper spray-mass spectrometry (PS-MS) is a rapid, solvent-efficient, and high-throughput analytical method for analyzing complex samples. In this study, a PS-MS method was developed to obtain MS profiles of Aurantii Fructus Immaturus ( aka Zhishi in Chinese) in positive and negative ion modes. In combination with multivariate analyses, including principal component analysis and cluster analysis, the PS-MS profiles of 25 batches of Zhishi were discriminated in 25 batches of Citri Reticulatae Pericarpium Viride ( aka Qingpi in Chinese; an adulterant of Zhishi). Moreover, a rapid quantitative analysis of synephrine, a prescriptive quality control component of Zhishi listed in the Chinese Pharmacopoeia, was conducted with PS-MS using synephrine-d2 as an internal standard (IS). The linearity range was 1.68–16.8   μg/mL (R 2   =   0.9985), the limit of quantitation was 0.5   μg/mL. Relative standard deviations in the intra- and inter-day precision of the MS were 4.87 and 4.90%, respectively. Compared with HPLC results, there was no significant difference in the quantitation of synephrine. This study demonstrated that the PS-MS method is useful for the rapid discrimination and quality control of Zhishi samples.

CAS / MDL: 10236-47-2
研究领域: 中药学 · 分析化学 · 药理学
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2011 ·Vol. 402 ·期 3 ·1337-1346 · IF 3.841

Molecularly imprinted polymers for selective extraction of synephrine from Aurantii Fructus Immaturus

Fan Jie-Ping,Zhang Lu,Zhang Xue-Hong,Huang Jun-zhong,Tong Sheng,Kong Tao,Tian Zhe-You,Zhu Jian-Hang

In this work, molecularly imprinted solid-phase extraction (MISPE) has been used to selectively enrich, purify, or remove synephrine from Aurantii Fructus Immaturus . To this end, a molecularly imprinted polymer (MIP) was prepared by self-assembly from the template synephrine, the functional monomer methacrylic acid, and the crosslinker ethylene glycol dimethacrylate in 1:4:20 molar ratio. Subsequent molecular interrogation of the MIP binding sites revealed preferential structural selectivity for synephrine relative to other structurally related naturally occurring compounds (i.e. octopamine and tyramine ). This selectivity was subsequently exploited to achieve substantial sample clean-up of extracts of crude Aurantii Fructus Immaturus and Aurantii Fructus Immaturus stir-baked with bran. The purity of synephrine in the extracts after MISPE represented approximately 24.21-fold enrichment of the synephrine in the untreated extracts of Aurantii Fructus Immaturus stir-baked with bran. High recoveries (85–90%) from the samples proved that the method was valid for selective enrichment, purification, or removal of synephrine from Aurantii Fructus Immaturus . The Molecularly imprinted polymers for the selective extraction of synephrine

CAS / MDL: 97-90-5 60-18-4
研究领域: 药物分析 · 天然产物化学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2023 · IF 8.2

Load mechanism and release behaviour of synephrine-loaded calcium pectinate beads: Experiments characterizations, theoretical calculations and mathematical modeling

Peng Zhou,Min Zheng,Xiangzhou Li,Jun Zhou,Wensheng Li,Yanhong Yang

It is an appropriate strategy to construct the carrier material with polysaccharide pectin, which is the characteristics of good bio-compatible, safe and non-toxic, avoiding the functional loss of bioactive ingredients and achieve sustained release . However, the loading mechanism of the active ingredient and the release behaviour of the active ingredient from the carrier material is still at the stage of conjecture. In this study, a kind of synephrine-loaded calcium pectinate beads (SCPB) with high encapsulation efficiency (95.6 %), loading capacity (11.5 %) and excellent controlled release behaviour was constructed. The interaction between synephrine (SYN) and quaternary ammonium fructus aurantii immaturus pectin (QFAIP) was revealed by FTIR, NMR and density functional theory (DFT) calculation. An inter-molecular hydrogen bond and Van der Waals forces between 7-OH, 11-OH and 10-NH of SYN and -OH, -C=O and N + (CH 3 ) 3 of QFAIP were formed. The release experiment in vitro showed that the QFAIP could effectively avoid the release of SYN in gastric fluid, and also realized the slow and full release of SYN in intestinal tract. Moreover, the release mechanism of SCPB in simulated gastric fluid (SGF) was Fickian diffusion, while in simulated intestinal fluid (SIF) was a non-Fickian diffusion controlled by both diffusion and skeleton dissolution.

CAS / MDL: 3033-77-0
研究领域: 药剂学 · 食品科学
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FOOD CHEMISTRY · 2013 · IF 3.334

A novel molecularly imprinted polymer of the specific ionic liquid monomer for selective separation of synephrine from methanol–water media

Jie-Ping Fan,Ze-You Tian,Sheng Tong,Xue-Hong Zhang,Yan-Long Xie,Rui Xu,Yu Qin,Lie Li,Jian-Hang Zhu,Xiao-Kun Ouyang

A novel molecularly imprinted polymer (MIP) using the specific ionic liquid (i.e. 1-vinyl-3-carboxymethylimidazolium bromide, 1-vinyl-3-carboxyethylimidazolium bromide, 1-viny-3-carboxybutylimidazolium bromide, or 1-vinyl-3-carboxypentylimidazolium bromide) as functional monomer was prepared via precipitation polymerization, which can be used to selectively separate synephrine (SYN) from methanol–water media. Ionic liquids are facile to be designed with varying the cation or anion, which enables the specific ionic liquid to be effectively designed to be a functional monomer for the preparation of MIP. The MIP showed a good selectivity and high adsorption capacity for SYN in methanol–water media. The adsorption process could be described by the pseudo-first-order model, which meant that the adsorption kinetics described a diffusion-controlled process. The equilibrium data fitted well to the Freundlich model, indicating multilayer adsorption . Finally, the MIP were successfully applied as sorbent to selectively enrich and separate SYN from the extracts of Aurantii Fructus Immaturus with a relatively high recovery (80–90%).

研究领域: 分析化学 · 药物化学
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SEPARATION SCIENCE AND TECHNOLOGY · 2014 · IF 1.2

Synthesis and Evaluation of Uniformly Sized Synephrine-Imprinted Microparticles Prepared by Precipitation Polymerization

Jie-Ping Fan,Lie Li,Ze-You Tian,Chun-Fang Xie,Yuan Xue,Yan-Long Xie,Rui Xu,Yu Qin,Xue-Hong Zhang,Jian-Hang Zhu

Uniformly sized synephrine molecularly imprinted polymer (MIP) microparticles were prepared via precipitation polymerization. The presence of the template, the amount of monomer, crosslinker, and porogenic solvent could affect the size distribution and morphology of the polymers. The pseudo-second-order kinetic model could provide a better correlation for the adsorption than the pseudo-first-order model. The intraparticle diffusion study showed that the sorption involved intraparticle diffusion, but that was not the only rate-controlling step. The equilibrium data better fit the Freundlich model than the Langmuir model. The Scatchard plot of MIPs revealed MIPs had two groups of sites with different affinities. Subsequent recognition selectivity experiments demonstrated preferential structural selectivity for synephrine with respect to other structurally similar compounds (i.e., octopamine and tyramine). Compared with the bulk MIP of SYN, the SYN MIP microparticles in this work had higher adsorption selectivity and capacity due to their smaller particle sizes; moreover, the precipitation polymerization was time-saving due to not using a crash-and-sieve process.

CAS / MDL: 97-90-5 51-67-2
研究领域: 材料科学 · 药物化学 · 分析化学
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Analytical Methods · 2013 ·Vol. 5 ·期 19 ·5317-5323 · IF 1.855

A highly sensitive sensor for synephrine detection based on multi-walled carbon nanotubes modified glass carbon electrodes

Jie Liu,Wei Zhang,Yinfeng Li,Lingxi Yang,Baoxian Ye

A sensitive, fast and cheap sensor, based on a glassy carbon electrode (GCE) modified with a multiwalled carbon nanotubes (MWCNTs)/Nafion film, is reported for the quantitative determination of synephrine in the Chinese traditional herbal drug Pericarpium citri reticulatae using . The electrochemical behavior of synephrine at this sensor was explored in Britton–Robinson buffer solution using cyclic voltammetry. An oxidation peak at 1027 mV was observed for synephrine when a bare GCE was used, whereas an oxidation peak at 998 mV with greatly enhanced peak current was obtained at the MWCNTs/Nafion/GCE, showing the electrocatalytic nature of the modified electrode. Moreover, cyclic voltammetric studies indicated that the oxidation of synephrine at the modified electrode was irreversible, adsorption controlled and involved two electrons. A calibration plot of oxidation peak current versus synephrine concentration was linear in the range of 1 × 10−8 to 1 × 10−5 mol L−1. The detection limit of synephrine was found to be 8 × 10−9 mol L−1 by linear sweep voltammetry . The effect of pH and scan rate of synephrine were studied. This is currently the first report on the determination of trace synephrine by a purely electroanalytical method. The analytical performance of this sensor was also evaluated for the detection of synephrine in real samples.

研究领域: 分析化学 · 药学 · 中药学
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REACTIVE & FUNCTIONAL POLYMERS · 2023 · IF 5.1

A molecular imprinting polymer based on computer-aided design: Selective enrichment and purification of synephrine from the extract waste liquid of Citrus aurantium L

Peng Zhou,Xiangzhou Li,Jun Zhou,Wensheng Li,Liqun Shen

A molecularly imprinted polymer (MIPs) was prepared based on a computer-aided design, which was used to selectively enrich and purify synephrine (SYN) from the extract waste liquid of Citrus aurantium L. The suitable functional monomers , cross-linkers and reaction systems for preparing MIPs were quickly screened with density functional theory (DFT) calculation to effectively avoid the design blindness of molecularly imprinted material. The synephrine molecularly imprinted polymer (SYN-MIPs) with imprinted holes and magnetic properties were prepared with nano Fe 3 O 4 as the core, and the structure, morphology, magnetic property and adsorption behavior were studied and the interaction mechanism of the adsorption process was clarified by DFT calculations. The saturated adsorption of SYN-MIPs for SYN was as high as 47.38–53.68 mg/g within 298 K to 308 K. The adsorption behavior of SYN-MIPs for SYN was well fit for the Freundlich adsorption and the pseudo-second-order kinetic model. It was worth mentioning that SYN-MIPs showed distinguished re-usability and specific recognition. The imprinting factor and selection factor to SYN were 3.13 and 2.43, respectively. The selective enrichment and purification of SYN from the extract waste liquid of Citrus aurantium L. achieved satisfactirily, and the purity of SYN enriched to 93.73% while the concentration of SYN was only 1.73% in the extract waste liquid. The study provides not only an efficient adsorption separation polymer materials but also a practical for the enrichment and purification process of SYN from the extract waste liquid of citrus plants.

研究领域: 化学工程 · 药物化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2021 · IF 5.279

Biotransformation and Quantification of Sinensetin and Its Metabolites in Plasma, Urine, and Feces of Rats

Xiaoqi Wang,Dongli Li,Yong Cao,Chi-Tang Ho,Qingrong Huang

As one of the major polymethoxyflavones in citrus peels, sinensetin (Sin) has been reported to possess numerous bioactivities. However, its detailed in vivo metabolic fate has not been uncovered yet. In the present study, the possible metabolites of Sin were synthesized, and all five mono-demethylated metabolites were successfully identified via ultraperformance liquid chromatography–tandem mass spectrometry (UPLC–MS/MS) analysis in rats fed with 100 mg/(kg·bw) Sin. The excretion and pharmacokinetic studies were then carried out to quantitatively investigate their variation in content with time in urine, feces, and plasma samples. Results showed that 4′-demethylsinensetin, 6-demethylsinensetin, and 3′-demethylsinensetin were the three most abundant metabolites generated in the above-mentioned biological samples. In addition, the total amount of Sin with its metabolites showed a significantly higher content in urine than in feces, indicating that Sin may be easily absorbed in the small intestine.

CAS / MDL: 8001-30-7
研究领域: 药理学 · 分析化学 · 生物化学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Polyphenol improve the foaming properties of soybean isolate protein: Structural, physicochemical property changes and application in angel cake

Yi-Lun Wang,Shi-Cheng Dai,Zi-Teng Lian,Xiao-Yi Cheng,Xiao-Hong Tong,Huan Wang,Liang Li,Lian-Zhou Jiang

With the increasing demand for food foaming, how to enhance the foaming properties of protein has gradually become the research focus. This work studied the effect of synephrine (SY) on foaming properties, structure properties, and physicochemical properties of soybean protein isolate (SPI). When the mass ratio of SY to SPI was 1:2, compared with SPI alone, the foam capacity and foam stability of the SY-SPI complex were significantly enhanced. Optical microscopy and confocal laser scanning microscope showed that the improvement in foaming performance was mainly due to the reduction of bubble size and uniform protein distribution. Circular dichroism spectrum and fluorescence spectra indicated that the hydrogen bond of SPI was destroyed and blue shifted with the addition of SY. What's more, the absolute value of Zeta potential, solubility, and hydrophobicity all increased, while the particle size decreased. As a result of molecular docking, surface hydrogen bonds, Van der Waals forces and hydrophobic interactions are the main driving forces. The addition of SY and SPI improved the specific volume and texture of angel cake. This study shows that SY has the potential to be developed into a new type of blowing agent.

CAS / MDL: 7558-80-7
研究领域: 食品科学 · 蛋白质化学 · 烘焙科学
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Food & Function · 2023 ·Vol. 14 ·期 11 ·5417-5428 · IF 6.1

Effects of hesperidin combined with synephrine on the capture of acrolein in a mouse model, or in humans by citrus consumption

Mengwei Jia,Huihui Gu,Yongling Lu,Lishuang Lv

Acrolein (ACR) is a highly reactive α,β-unsaturated aldehyde that plays a key role in the pathogenesis of human diseases, such as atherosclerosis and pulmonary, cardiovascular, and neurodegenerative disorders. We investigated the capture capacity of hesperidin (HES) and synephrine (SYN) on ACR by individual and combined means in vitro, in vivo (utilizing a mouse model), and via a human study. After proving that HES and SYN could efficiently capture ACR by generating ACR adducts in vitro, we further detected the adducts of SYN-2ACR, HES-ACR-1, and hesperetin (HESP)-ACR in mouse urine by ultraperformance liquid chromatography-tandem mass spectrometry. Quantitative assays revealed that adduct formation occurred in a dose-dependent manner, and that there was a synergistic effect of HES and SYN on capturing ACR in vivo. Moreover, quantitative analysis suggested that SYN-2ACR, HES-ACR-1, and HESP-ACR were formed and excreted through the urine of healthy volunteers consuming citrus. The maximum excretions of SYN-2ACR, HES-ACR-1, and HESP-ACR were at 2–4, 8–10, and 10–12 h, respectively, after dosing. Our findings propose a novel strategy for eliminating ACR from the human body via the simultaneous consumption of a flavonoid and an alkaloid.

CAS / MDL: 9005-27-0
研究领域: 药理学 · 毒理学 · 生物化学 · 营养学
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Frontiers in Plant Science · 2024 · IF 4.1

Effects of rootstocks and developmental time on the dynamic changes of main functional substances in ‘Orah’ (Citrus reticulata Blanco) by HPLC coupled with UV detection

Li Shuang,Yang Lei,Wang Min,Chen Yang,Yu Jianjun,Chen Hao,Yang Haijian,Wang Wu,Cai Zhiyong,Hong Lin

Introduction: Citrus fruit is rich in important functional constituents such as flavonoids, phenolic acids terpenes and other functional substances that play an important role for treating clinical diseases or controlling major agricultural diseases and pests. Plant secondary metabolites have become one of the most important resources of novel lead compounds, especially young citrus fruits contain multiple functional substances. ‘Orah’, a type of citrus reticulata, is known for its fine appearance, productivity, delicious sweetness, late-maturing characteristics, and is widely cultivated in China. Fruit thinning and rootstock selection are commonly used agronomic measures in its production to ensure its quality and tree vigor. However, few studies have demonstrated the effects of these agronomic measures on the functional substances of ‘Orah’.Methods: In this study, we used HPLC coupled with UV to detect the dynamic changes of fruit quality, 13 main flavonoids, 7 phenolic acids, 2 terpenes, synephrine and antioxidant capacity in both peel and pulp of citrus fruits grafted on four rootstocks (Red orange Citrus reticulata Blanco cv. red tangerine, Ziyang xiangcheng Citrus junos Sieb. ex Tanaka, Trifoliate orange Poncirus trifoliata L. Raf, and Carrizo citrange Citrus sinensis Osb.×P.trifoliate Raf) at six different developmental stages (from 90 DAF to 240 DAF).Results: The results indicated that rootstock can significantly affect the contents of functional constituents and antioxidant capacity in ‘Orah’. Additionally, it was found that pruning at either 90 DAF (days after flowering) or 150 DAF produced the most favorable outcomes for extracting functional substances. We also identified rootstock ‘Trifoliate orange’ has the highest total soluble solids (TSS) and ‘Ziyang xiangcheng’ to be the optimal in terms of comprehensive sensory of fruit quality, while ‘Red orange’ and ‘Ziyang xiangcheng’ are optimal in terms of functional substance quality, and ‘Red orange’ excels in antioxidant capacity.Discussion: Overall, the findings demonstrate the important role of rootstocks and developmental stage in shaping fruit sensory quality and functional substance synthesis, providing valuable insights for guiding rootstock selection, determining thinning time, and utilizing pruned fruits in a more informed manner.

研究领域: 农业 · 植物科学 · 食品科学 · 药理学
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