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MICROCHEMICAL JOURNAL · 2022 · IF 5.304

A greener and sustainable route for medicinal plant analysis: Recycle utilization of hydrophobic deep eutectic solvent

Meichao Liao,Yang Zhao,Xiaoyue Yang,Lin Yang,E-Hu Liu,Bin Lu,Jiye Wang,Xiaopeng Liu,Yanzhong Chang,Li Duan

The green and efficient extraction of bioactive compounds from plant biomass is an extraordinary area of interest in the pharmaceutical industries. In a perspective of sustainable development, we investigate an eco-friendly route using recycle hydrophobic deep eutectic solvent-assisted water extraction (RHD-WE) to effectively and simultaneously extract five main phenolic acids (caftaric acid, chlorogenic acid, caffeic acid, cichoric acid, 3,5-di-O-caffeoylquinic acid) from medicinal plant. In the procedure, 20 mg Taraxacum mongolicum powder was mixed with 800 µL water and 200 µL camphor/p-chlorophenol-based hydrophobic deep eutectic solvent (DES) at a molar ratio of 1:3. After 10 min vortex and centrifugation, the mixture was separated into aqueous phase and DES phase. Compared with other published procedures, phenolic acids were enriched in the aqueous phase. Aqueous solution of phenolic acid could be directly used as raw materials without further purification in pharmaceutical industries. Besides, hydrophobic DES phase could easily be recovered and reused in recycling studies. This is the first study of the recyclability of hydrophobic DES. Generally speaking, the model for the extraction of phenolic acids was well established and verified. The extraction efficiency was higher than other traditional extraction methods, approximately 14 mg/g of phenolic acids were obtained in the aqueous phase. In addition, the extraction mechanism was preliminarily discussed in this research. Such novel RHD-WE method might improve the existing schemes for extraction of bioactive compounds from plant materials. This study suggested that hydrophobic DESs could be used as green and safe auxiliary extractant for pharmaceutical applications.

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JOURNAL OF MEMBRANE SCIENCE · 2022 · IF 10.53

Anionic covalent organic framework engineered high-performance polyamide membrane for divalent anions removal

Guangzhe Wang,Jinqiu Yuan,Junhui Zhao,Yafei Li,Runnan Zhang,Jianliang Shen,Xiaoyao Wang,Hong Wu,Ayman El-Gendi,Yanlei Su,Zhongyi Jiang

Porous framework materials hold great promise in tuning the chemical and physical structure of polyamide membranes for efficient nanofiltration . In this work, anionic covalent organic framework (aCOF) with abundant sulfonic acid groups was embedded into polyamide matrix via interfacial polymerization to modulate both membrane charge property and thickness for the removal of divalent ions. Benefiting from the high negative charged density, aCOF not only enhanced the membrane electronegativity from −25.6 mV to −71.5 mV but also slowed down the diffusion rate of piperazine by electrostatic interaction to decrease the membrane thickness from 93 nm to 18 nm. The enhanced electronegativity can intensify the charge exclusion to divalent anions (Na 2 SO 4 rejection above 97%), while the ultrathin structure endows membrane with high water permeance of up to 39 L m −2  h −1  bar −1 , about 2.4 times higher than that of pristine PA membrane. Our membranes provide a new path to rational design and controllable construction of high-performance nanofiltration membranes.

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LIPIDS · 2022 ·Vol. 57 ·期 3 ·153-162 · IF 1.646

MCFA alleviate H2O2-induced oxidative stress in AML12 cells via the ERK1/2/Nrf2 pathway

Danping Wang,Jinglong Chen,Huangbing Sun,Wenjing Chen,Xiaojing Yang

Oxidative stress is an important factor in the occurrence and development of liver disease. Medium-chain fatty acids (MCFAs) have potential antioxidant function, whereas the exact underlying mechanism of MCFA in oxidative injury of hepatocytes remains unclear. In our present study, three different MCFAs, 8-carbon octanoic acid (OA), 10-carbon capric acid (CA), and 12-carbon lauric acid (LA), have been performed to observe their protective action for hepatocyte under the H 2 O 2 challenge. The result showed that MCFA treatment significantly increased the cell viability, T-AOC, and expression of antioxidant-related genes in AML12 cells under oxidative stress condition, and reduced reactive oxygen species (ROS) production. Moreover, MCFA treatment significantly increased the protein expression of Nrf2 and the phosphorylation level of ERK1/2; LA treatment significantly promoted the Nrf2 nuclear translocation. With a further test, the rescue ability of MCFA was blocked by treating with the ERK inhibitor U0126. Overall, our data suggested that MCFA treatment has positive impact on protecting AML12 cells against oxidative stress through ERK1/2/Nrf2 pathway.

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MOLECULES · 2022 ·Vol. 27 ·期 2 ·352 · IF 4.927

Evolution Analysis of Free Fatty Acids and Aroma-Active Compounds during Tallow Oxidation

Shiqing Song,Feiting Zheng,Xiaoyan Tian,Tao Feng,Lingyun Yao,Min Sun,Lei Shi

To explore the role of fatty acids as flavor precursors in the flavor of oxidized tallow, the volatile flavor compounds and free fatty acid (FFAs) in the four oxidization stages of tallow were analyzed via gas chromatography (GC)–mass spectrometry (MS), the aroma characteristics of them were analyzed by GC–olfactory (GC-O) method combined with sensory analysis and partial least-squares regression (PLSR) analysis. 12 common FFAs and 35 key aroma-active compounds were obtained. Combined with the results of odor activity value (OAV) and FD factor, benzaldehyde was found to be an important component in unoxidized tallow. (E,E)-2,4-Heptadienal, (E,E)-2,4-decadienal, (E)-2-nonenal, octanal, hexanoic acid, hexanal and (E)-2-heptenal were the key compounds involved in the tallow flavor oxidation. The changes in FFAs and volatile flavor compounds during oxidation and the metabolic evolution of key aroma-active compounds are systematically summarized in this study. The paper also provides considerable guidance in oxidation control and meat flavor product development.Keywords:oxidized tallow;aroma-active compounds;solvent-assisted flavor evaporation;gas chromatography-olfactometry;partial least-squares regression

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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2022 ·Vol. 102 ·期 11 ·4714-4723 · IF 4.125

Acidolysis of phospholipids with medium-chain fatty acids over M-SBA-15 (M = Zn, Al) silicas as efficient solid catalysts

Ke Cheng,Jianghua Zhang,Shasha Yang,Fawen Yin,Zixuan Li,Ting Wang,Dayong Zhou

BACKGROUND Efficient and sustainable production of structured phospholipids (SPLs) enriched in medium-chain fatty acids (MCFAs) in a heterogeneous manner is crucial for their potential applications in functional foods and drugs. Herein, for the first time, Zn- and Al-incorporated SBA-15 silicas were prepared by the coprecipitation method and further researched for catalytic synthesis of MCFA-enriched SPLs through acidolysis reaction of natural phospholipids with capric or caprylic acid. RESULTS The as-prepared Zn- and Al-incorporated SBA-15 samples exhibited superior catalytic activities under mild experimental conditions (50 °C, 6 h) to commercial homogeneous Lewis acids and benchmark enzymes. Correspondingly, the capric acid and caprylic acid incorporations were respectively achieved up to ~40.25 ± 0.40% (or 35.08 ± 0.09%) and 37.26 ± 0.38% (or 33.02 ± 0.13%) for Zn- (or Al-) incorporated SBA-15 catalyst. Moreover, various methods such as scanning electron microscopy with energy-dispersive X-ray spectrometry, ultraviolet–visible diffuse reflectance spectroscopy and pyridine–Fourier transform infrared spectroscopy were utilized to characterize the two catalysts in order to elucidate the possible structure–performance relationship. Accordingly, the above-mentioned satisfactory results are most probably due to the well-ordered mesostructures and large amounts of active Lewis acid sites existing in the investigated materials. Noticeably, the two catalysts featured good separation and excellent recyclability as well. CONCLUSION The Zn- and Al-incorporated SBA-15 catalysts studied in this work might shed light on novel, sustainable and economic alternatives for effective SPL production to diminish the applications of conventional homogeneous catalysts and biocatalysts in food industries. © 2022 Society of Chemical Industry.

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CHEMBIOCHEM · 2022 ·Vol. 23 ·期 9 ·e202200063 · IF 3.461

Carving the Active Site of CYP153A7 Monooxygenase for Improving Terminal Hydroxylation of Medium-Chain Fatty Acids

Ya-Li Dong,Gang-Gang Chong,Chun-Xiu Li,Qi Chen,Jiang Pan,Ai-Tao Li,Jian-He Xu

Graphical Make activation of C-H bond feasible : Cytochrome P450 monooxygenases (P450s) catalyze the terminal hydroxylation of fatty acids to form ω-hydroxy fatty acids. To date, available P450s for the terminal hydroxylation of fatty acids stalls at CYP153A subfamily members, which have the limitation of low activity and poor thermostability. We, therefore, adopted directed evolution to generate P450pyr mutants with higher catalytic efficiency toward medium-chain fatty acids. The results show that mutants toward C6−C12 fatty acids display improved analytical yields of ω-hydroxy fatty acids. The P450-mediated terminal hydroxylation of non-activated C−H bonds is a chemically challenging reaction. CYP153A7 monooxygenase, discovered in Sphingomonas sp. HXN200, belongs to the CYP153A subfamily and shows a pronounced terminal selectivity. Herein, we report the significantly improved terminal hydroxylation activity of CYP153A7 by redesign of the substrate binding pocket based on molecular docking of CYP153A7−C 8:0 and sequence alignments. Some of the resultant single mutants were advantageous over the wild-type enzyme with higher reaction rates, achieving a complete conversion of n- octanoic acid (C 8:0, 1 mM) in a shorter time period. Especially, a single-mutation variant, D258E, showed 3.8-fold higher catalytic efficiency than the wild type toward the terminal hydroxylation of medium-chain fatty acid C 8:0 to the high value-added product 8-hydroxyoctanoic acid.

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ACS Applied Nano Materials · 2023 · IF 5.9

Perovskite Quantum Dot Light-Emitting Memcapacitor

Songman Ju,Chaomin Mao,Jinping Zheng,Kaiyu Yang,Lihua Lin,Tailiang Guo,Hailong Hu,Fushan Li

Perovskite quantum dots (PQDs) are promising in the field of light-emitting diodes (LEDs) due to their adjustable band gap, high photoluminescence quantum yield, and high color purity. However, ion migration is prone to occur in the device due to the structural instability of PQDs, resulting in the degradation of external quantum efficiency. In this work, we proposed a strategy to realize a perovskite quantum dot light-emitting memcapacitor (PQLEM) so as to enhance the electroluminescent performance of PQDs. By varying the pre-bias voltage and time, the ion distribution and trap density in the PQD film could be modified, thereby affecting the capacitance value and luminous efficiency of the device. Under the memcapacitive effect, the external quantum efficiency (EQE) of the device increases from an initial 2.81 to 7.95%. This work provides a route for achieving perovskite quantum dot light-emitting devices with high luminous efficiency.

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FOOD CHEMISTRY · 2023 · IF 8.8

The potential of hydroxytyrosol fatty acid esters to enhance oral bioavailabilities of hydroxytyrosol and fatty acids: Continuous and slow-release ability in small intestine and blood

Xinmiao Wang,Qian Wang,Jinghan Yu,Xu Guo,Peiyong Tong,Fawen Yin,Xiaoyang Liu,Dayong Zhou

HPLC-UV analysis in rat everted gut sac and in vitro simulated digestion models indicated that hydroxytyrosol fatty acid esters (HTy-Es) could be hydrolyzed by pancreatic lipase to slow-release of free fatty acids (FAs) and HTy. Meanwhile, the HTy-Es, the liberated FAs and the HTy could cross the membrane and were transported into blood circulation. HTy-Es were further hydrolyzed by carboxylesterase in in vitro rat plasma hydrolysis model, which also showed slow-release of FAs (C1-C4) and HTy. Especially, the rates of hydrolysis and transport initially increased and then decreased with the increasing alkyl chain length. Besides, the above rates of the HTy-Es with a straight chain were greater than those of its isomer with a branched chain. Therefore, the above-mentioned continuous and slow-release of FAs and HTy in small intestine and blood clearly demonstrated that HTy-Es would be an effective approach to enhance oral bioavailabilities of free fatty acids and hydroxytyrosol.

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MICROCHEMICAL JOURNAL · 2023 · IF 4.8

Hexafluoroisopropanol-based supramolecular solvent for liquid phase microextraction of triazole fungicides in drinking water and beverages

Ruiyu Fu,Tingze Ren,Yanhui Zhang,Qingxin Lu,Xiaoli Guo,Xin Di

A new supramolecular solvent (SUPRAS) was synthesized using hexafluoroisopropanol (HFIP) as hydrogen bond donor and undecanol as hydrogen bond acceptor. Then SUPRAS was used as extraction solvent to enrich triazole fungicides in drinking water and beverages by liquid phase microextraction (LPME). Additionally, several variables that influence extraction efficiency were optimized, and the significant factors were investigated by Box-Behnken design. At optimum condition, the method shows desirable precision (RSDs less than 19.4%) and acceptable recovery (63.4%-112.1%). The low limits of detection and limits of quantitation of this method were found to be in the range of 1.0–5.0 μg/L and 5.0–20 μg/L, respectively. Compared with other analytical techniques, the method demonstrated comparable sensitivity, consumed less extractant (750 μL) and a shorter pre-treatment time (10 min). The formation mechanism of SUPRAS was investigated by density functional theory. The proposed methodology was green, sensitive, time-saving and successfully applied to determine triazole fungicides in drinking water and beverages, making it an alternative technique for the analysis of trace analytes with satisfactory sensitivity.

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BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY · 2023 ·Vol. 70 ·期 6 ·1806-1816 · IF 2.8

Quantitative determination of rhamnolipid using HPLC-UV through carboxyl labeling

Jing Zhou,Si-Jia Miao,Shi-Zhong Yang,Jin-Feng Liu,Hong-Ze Gang,Bo-Zhong Mu

Rhamnolipid, as a low-toxic, biodegradable and environmentally friendly biosurfactant, has broad application prospects in many industries. However, the quantitative determination of rhamnolipid is still a challenging task. Here, a new sensitive method for the quantitative analysis of rhamnolipid based on a simple derivatization reaction was developed. In this study, 3-[3′-( l -rhamnopyranosyloxy) decanoyloxy] decanoic acid (Rha-C10-C10) and 3-[3′-(2′- O -α- l -rhamnopyranosyloxy) decanoyloxy] decanoic acid (Rha-Rha-C10-C10) were utilized as the representative rhamnolipids. Liquid chromatography–mass spectrometry and high-performance liquid chromatography-ultra violet results showed that these two compounds were successfully labeled with 1 N1-(4-nitrophenyl)-1,2-ethylenediamine. There was an excellent linear relationship between rhamnolipid concentration and peak area of labeled rhamnolipid. The detection limits of the Rha-C10-C10 and Rha-Rha-C10-C10 were 0.018 mg/L (36 nmol/L) and 0.014 mg/L (22 nmol/L), respectively. The established amidation method was suitable for the accurate analysis of rhamnolipids in the biotechnological process. The method had good reproducibility with the relative standard deviation of 0.96% and 0.79%, respectively, and sufficient accuracy with a recovery of 96%–100%. This method was applied to quantitative analysis of 10 rhamnolipid homologs metabolized by Pseudomonas aeruginosa LJ-8. The single labeling method was used for the quantitative analysis of multiple components, which provided an effective method for the quality evaluation of other glycolipids with carboxyl groups.

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TALANTA · 2023 · IF 6.1

Chiral separation by capillary electrokinetic chromatography with hydrophobic deep eutectic solvents as pseudo-stationary phases

Yu Xu,Ang Li,Song Xue,Sihui Ding,Qi Zhang

This study demonstrated for the first time that hydrophobic deep eutectic solvents (HDESs) can be used in capillary electrophoresis (CE) for chiral separations . We found that the an HDES methyltrioctylammonium chloride :octanoic acid (N 8881 Cl:OctA) can exist in the form of nano-sized microdroplets in CE background electrolyte solutions , and show hydrophobic effects as a new type of pseudo-stationary phase (PSP) during CE separation. When used in combination with various cyclodextrin (CD)-type chiral selectors, the presence of N 8881 Cl:OctA significantly improved the enantioresolutions of several model drugs. Moreover, the migration time of the enantiomers can also be reduced when an anionic CD (e.g., carboxymethyl-β-cyclodextrin (CM-β-CD)) was used. Critical factors influencing the chiral separations were systematically investigated including the HDES concentration, hydrogen-bond acceptor (HBA)/hydrogen-bond donor (HBD) ratio, CD concentration, buffer pH, and applied voltage, etc. An insight into chiral recognition mechanism with HDES is provided for reference. A comparison of the chiral CE performance of HDESs with traditional surfactants was also performed to demonstrate their superiority as a new type of PSP.

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JOURNAL OF MEMBRANE SCIENCE · 2021 · IF 8.742

Charged nanochannels endow COF membrane with weakly concentration-dependent methanol permeability

Chunyang Fan,Li Cao,Chao Yang,Qianxiang Xiao,Xinda You,Xiaoyao Wang,Yan Kong,Hong Wu,Yawei Liu,Zhongyi Jiang

Covalent organic frameworks (COFs) with long-range ordered, rigid, and tailor-made nanochannels hold great promise for energy-related applications. Here, we fabricate COF membranes with one-dimensional charged nanochannels using ionic COF nanosheets decorated with sulfonic acid groups. The free-standing and robust COF membrane exhibits enhanced proton conductivity and suppressed methanol permeability compared to the benchmark Nafion membrane. More interestingly, the methanol permeability of the COF membrane remains almost constant in a wide range of methanol concentrations (5.35 × 10 −7  cm 2  s −1 for the 2 M methanol/water mixture and 5.44 × 10 −7  cm 2  s −1 for the neat methanol). All-atomistic dynamics simulations indicate that the diffusio-osmotic effect arising from the charged nanochannels can account for the low and nearly constant methanol permeability of the COF membranes. These findings suggest that the ionic COF membranes can find potential applications in direct methanol fuel cell with high methanol concentrations, and meanwhile shed light on the mass transport mechanism in the charged, rigid and ordered nanochannels.

CAS / MDL: 124-07-2
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