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COLORATION TECHNOLOGY · 2016 ·Vol. 133 ·期 1 ·65-72 · IF 1.127

A novel strategy to improve the dyeing properties in laccase-mediated coloration of wool fabric

Ting Zhang,Rubing Bai,Qiang Wang,Xuerong Fan,Ping Wang,Jiugang Yuan,Yuanyuan Yu

Enzymatic coloration of fabrics has received worldwide attention in recent years. In order to improve the dyeing properties of enzymatically coloured fabrics, a novel strategy using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), a biological coupling agent, to pretreat wool fabric was employed in this paper. Enzymatic coloration of wool fabrics with syringic acid was carried out in the presence of laccase from Trametes versicolor . The effect of different periods on laccase-catalysed polymerisation of syringic acid was examined by UV-vis spectroscopy. Enzymatic coloration results of dyed wool fabrics were evaluated by means of K / S value and colour difference ( ∆E* ). Process parameters, including the dosages of syringic acid and incubation time, that influenced the colour depth were studied. Meanwhile, the colour fastness and levelness of dyed wool fabrics were tested. The results showed that the UV-vis absorbance of reaction solution increased as oxidation time elapsed, and a new peak appeared at 360 nm. After pretreatment, the K / S values and colour difference values of wool fabrics dyed with poly(syringic acid) improved appreciably compared with the control samples without any pretreatment. Moreover, pretreated wool fabrics showed better dyeing fastness and levelness than control samples.

CAS / MDL: 25952-53-8 530-57-4
研究领域: 生物化学 · 纺织科学
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Current Pharmaceutical Analysis · 2018 ·Vol. 14 ·期 1 ·41-52 · IF 0.859

An Efficient HPLC Method for Determination of Syringic Acid Liposome in Rats Plasma and Mice Tissues: Pharmacokinetic and Biodistribution Application

Sun Congyong,Yuan Yangyang,Omari-Siaw Emmanuel,Tong Shanshan,Zhu Yuan,Wang Qilong,Wang Yuanwen,Wei Qiuyu,Yu Jiangnan,Xu Ximing

Objective: This study aims to establish an efficient, sensitive and specific analytical method (in vitro and in vivo) for syringic acid. Method: Syringic acid loaded liposome was prepared and characterized. In vitro and in vivo chromatographic conditions for the determination of syringic acid were investigated, with the application verified by pharmacokinetics and biodistribution studies. Results: The developed liposomal formulation produced homogeneous regular, spherical and multilamellar- shaped liposome. Efficient HPLC method for the analysis of syringic acid was established and validated. The chromatographic separation was performed on a Waters symmetry C18 column (4.6 150 mm, 5 μm) at 25 °C by using mobile phases of 30 % methanol and 70 % acetic acid solution (0.1 %) (in vitro) and 28 % methanol and 72 % acetic acid solution (0.1 %) (in vivo) at a flow rate of 0.8 mL/min. The wavelength was set at 272 nm. Vanillin was used as internal standard for the in vivo analysis. The established linearity ranges of SA were 1 - 100 μg/mL (R2 = 0.9997) in vitro and 0.125 – 64 μg/mL (R2 = 0.9991) in vivo. In vitro accuracy of the method was > 99%, and in vivo accuracies were between 91.23 % - 109.54 %, while the precisions met the acceptance criterion. In vivo HPLC method was also confirmed by pharmacokinetics and biodistribution studies. Conclusion: Established HPLC method exhibited high linearity, precision, accuracy and specificity, could be used for quantitative determination of SA in vitro and in vivo.

研究领域: 药物分析 · 药理学 · 分析化学
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SCIENCE OF THE TOTAL ENVIRONMENT · 2020 · IF 6.551

Aqueous-phase oxidation of syringic acid emitted from biomass burning: Formation of light-absorbing compounds

Fenghua Li,Narcisse T. Tsona,Jianlong Li,Lin Du

Syringic acid is a methoxyphenol model compound derived from biomass burning , and its photooxidation processes have important effects on atmospheric chemistry . However, its aqueous-phase photochemistry remains unclear. In this study, we systematically report the photooxidation of syringic acid induced by OH radicals in the aqueous phase. Employing the relative rate technique, the bimolecular rate constant for syringic acid reaction with OH radicals was acquired to be (1.1 ± 0.3) × 10 10  M −1  s −1 . Notably, colored products were formed as the reaction progressed. Furthermore, the UV–vis and fluorescence spectra confirmed the formation of light-absorbing organic species, and the results agreed well with previous results on atmospheric and natural humic-like substances (HULIS). The photooxidation products were detected by high performance liquid chromatography mass spectrometry (HPLC/MS), and a possible reaction mechanism was proposed. The aqueous-phase reaction of syringic acid would undergo functionalization process forming a hydroxylation product that enhances the degree of oxidation of aqueous secondary organic aerosol (aqSOA), and goes through dimerization process by C-C or C-O coupling of phenoxy radicals which may conduce to the formation of HULIS. These findings suggest that the photooxidation of syringic acid is an important pathway for highly oxygenated phenolic aqSOA formation , providing a secondary source for HULIS in a liquid phase or in deliquescent particles surrounded by a layer of water.

研究领域: 大气化学 · 环境科学
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CRYSTAL GROWTH & DESIGN · 2022 · IF 4.01

Directional Self-Assembly of Ofloxacin and Syringic Acid: The First Salt Cocrystal of Ofloxacin with Phenolic Acid Displays Superior In Vitro/Vivo Biopharmaceutical Property and Enhanced Antibacterial Activity

Su-Su Meng,Yue-Ming Yu,Fan-Zhi Bu,Cui-Wei Yan,Zhi-Yong Wu,Yan-Tuan Li

A cocrystallization tactic of double optimization and synergistic enhancement efficacy has been proposed, aiming at maximizing the benefits of phenolic acid nutriment syringic acid (HSA) to perfect biopharmaceutical features of antibacterial drug ofloxacin (OA). This strategy utilizes the salt-forming function and cocrystallization ability of HSA interplaying with OA to assemble into a salt cocrystal, thus ameliorating OA’s physicochemical properties in vitro, which, in turn, can optimize its pharmacokinetic characteristics in vivo, making OA’s pharmaceutical peculiarities be doubly optimized on both in vivo and in vitro levels. Ulteriorly, the antibacterial potency of OA is heightened by stimulating the auxiliary antibacterial ability of HSA, fulfilling the cooperativeness of OA and HSA in antibacterial efficacy. Taking this tactic as orientation, the first OA– nutriment salt cocrystal, viz., [HOA+-SA–]-HSA-H2O, is directionally synthesized and structurally identified. Single-crystal X-ray diffraction substantiates that the salt cocrystal has a bilayer hole structure, wherein, a hexahelical hydrogen-bonding motif of [HOA+-SA–] salts situates outside with a double spiral of neutral HSA and H2O molecules inside, thus endowing the salt cocrystal with the capacity to simultaneously enhance solubility and permeability compared with OA itself, which achieves positive correlations with theoretical investigations. Intriguingly, the strengthened in vitro properties of the salt cocrystal have been effectually turned into in vivo pharmacokinetic advantages, displaying an advanced peak plasma concentration and protracted half-life along with raised relative bioavailability. More meaningfully, the antibacterial capacity of the salt cocrystal has also attained significant enhancement owing to the congenerous antibacterial action of OA and HSA. Therefore, this investigation not only offers a novice strategy for optimizing in vitro/vivo pharmaceutical characteristics and concurrently elevating antibacterial efficacy of OA through formation of the salt cocrystal but also fulfills a breakthrough in developing new salt cocrystal systems of antibacterial drugs.

研究领域: 药学 · 生物医学工程
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AAPS PHARMSCITECH · 2019 ·Vol. 20 ·期 3 ·1-10 · IF 2.608

Preparation and Characterization of Syringic Acid–Loaded TPGS Liposome with Enhanced Oral Bioavailability and In Vivo Antioxidant Efficiency

Liu Yingkun,Sun Congyong,Li Wenjing,Adu-Frimpong Michael,Wang Qilong,Yu Jiangnan,Xu Ximing

In this study, syringic acid–loaded TPGS liposome (SA-TPGS-Ls) was successfully prepared to improve oral bioavailability of syringic acid (SA). SA is a natural and notable antioxidant activity compound with its limited bioavailability ascribable to its poor aqueous solubility and fast elimination. Recently, TPGS has become a perfect molecular biomaterial in developing several carrier systems with sustained, controlled, and targeted the drug delivery. SA-TPGS-Ls was prepared via thin-film dispersion method and characterized in terms of particle size, stability, morphology, and encapsulation efficiency (EE). The results showed that SA-TPGS-Ls had regular spherical-shaped nanoparticles with EE of 96.48 ± 0.76%. The pharmacokinetic studies demonstrated a delayed MRT and prolonged t 1/2 , while relative oral bioavailability increased by 2.8 times. Tissue distribution showed that SA-TPGS-Ls maintained liver drug concentration while delayed elimination was also observed in the kidney. In CCl 4 -induced hepatotoxicity study, the activities of hepatic T-AOC, GSH-Px, CAT, GSH, and SOD were greatly elevated, while serum biological markers ALT, AST, and AKP were reduced after treatment of mice with SA-TPGS-Ls. Histopathological studies confirmed that SA-TPGS-Ls could remarkably improve the status of hepatic tissues. Collectively, SA-TPGS-Ls significantly improved the drug encapsulation efficiency, stability coupled with bioavailability of SA, hence increasing in vivo antioxidant activity of the drug.

CAS / MDL: 8002-43-5 9002-96-4
研究领域: 药剂学 · 生物医学 · 药物代谢动力学
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CRYSTAL GROWTH & DESIGN · 2022 · IF 4.01

The First Cocrystallization of Milrinone with Nutraceuticals: The Adjusting Effects of Hydrophilicity/Hydrophobicity in Cavities on the In Vitro/In Vivo Properties of the Cocrystals

Lu Liu,Yue-Ming Yu,Fan-Zhi Bu,Yan-Tuan Li,Cui-Wei Yan,Zhi-Yong Wu

To give full prominence to the superiority of phenolic acid nutraceuticals syringic acid (SYRA) and gallic acid (GALA) in perfection of in vitro and in vivo performances for cardiotonic drug milrinone (MLN), and ulteriorly attain novice insights in the development of cardiotonic drug-nutraceutical cocrystals, two new solid forms of MLN including one cocrystal with SYRA, and one cocrystal hydrate with GALA─namely, MLN-SYRA (1) and MLN-GALA- H2O (2)─are first assembled and thoroughly characterized. The single-crystal X-ray diffraction showcases that both cocrystal 1 and cocrystal hydrate 2 have three-dimensional supramolecular structures controlled by hydrogen-bonding and aromatic packing interactions, where the hydrogen-bonding dimers of MLN itself still remain in 1 but are broken in 2, forming hydrophobic cavities in the former and hydrophilic ones in the latter. Such structural characteristics and aggregation motifs, because of the introduction of different phenolic acids in the crystalline lattices, have important influence on the improvements of dissolvability and permeability for the two crystalline forms, and in accordance with the theoretical studies. Intriguingly, the optimized in vitro biopharmaceutical properties can be effectually transformed to satisfactory in vivo pharmacokinetic peculiarity, performing the increased bioavailability and extended half-life. Thus, the current research not only offers promising solid-state forms for MLN with development foregrounds, but opens up new applications for nutraceutical phenolic acids in cardiotonic pharmaceutical cocrystals.

研究领域: 药剂学 · 药物化学 · 药物递送 · 生物药剂学
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JOURNAL OF FOOD SCIENCE · 2024 ·Vol. 89 ·期 11 ·7534-7548 · IF 3.2

Effects of preheat treatment and syringic acid binding on the physicochemical, antioxidant, and antibacterial properties of black soybean protein isolate before and after in vitro digestion

Yiqing He,Haiwen Sun,Bingyao Han,Tosin Michael Olajide,Minxin Yang,Qianqian Miao,Xianyan Liao,Junyi Huang

This study investigated the effects of preheat treatment (70–100 °C) and syringic acid (SA) grafting on the antioxidant, antibacterial, and physicochemical properties of black soybean protein isolate (BSPI) before and after in vitro digestion. The results revealed that both preheat treatment and SA grafting increased the digestibility and the absolute zeta potential value of BSPI. However, as the preheating temperature increased, the antioxidant ability of BSPI decreased, which was improved by SA grafting. During in vitro digestion, the absolute zeta potential and antioxidant activities of preheated BSPI and preheated BSPI–SA complex followed the order: intestine > gastric > before digestion. Compared with before digestion, preheated BSPI with its SA complex after in vitro digestion exhibited excellent antibacterial activities. Importantly, the preheated BSPI–SA complex enhanced the SA recovery rate during digestion and SA stability, with the highest recovery rate observed for the SA-grafted BSPI with preheat treatment at 100°C (BSPI100–SA). The principal component analysis sufficiently distinguished preheated BSPI and preheated BSPI–SA complexes. There were partitions between BSPI and BSPI–SA treated at different preheating temperatures. This study contributes to expanding the potential applications of BSPI with its SA complex in food products and offers guidance for designing SA delivery systems. Practical Application Preheated BSPI–SA complexes could serve as functional ingredients in food or health products. Besides, preheated BSPI has application potential as a carrier for SA delivery.

CAS / MDL: 9001-62-1 9005-38-3
研究领域: 食品科学 · 营养学 · 蛋白质化学 · 抗菌技术
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ENVIRONMENTAL POLLUTION · 2013 · IF 3.73

Covalent bonding of chloroanilines to humic constituents: Pathways, kinetics, and stability

Deyang Kong,Qing Xia,Guoqiang Liu,Qingguo Huang,Junhe Lu

Covalent coupling to natural humic constituents comprises an important transformation pathway for anilinic pollutants in the environment. We systematically investigated the reactions of chlorine substituted anilines with catechol and syringic acid in horseradish peroxidase (HRP) catalyzed systems. It was demonstrated that although nucleophilic addition was the mechanism of covalent bonding to both catechol and syringic acid, chloroanilines coupled to the 2 humic constituents via slightly different pathways. 1,4-addition and 1,2-addition are involved to catechol and syringic acid, respectively. 1,4-addition showed empirical 2nd order kinetics and this pathway seemed to be more permanent than 1,2-addition. Stability experiments demonstrated that cross-coupling products with syringic acid could be easily released in acidic conditions. However, cross-coupling with catechol was relatively stable at similar conditions. Thus, the environmental behavior and bioavailability of the coupling products should be carefully assessed.

研究领域: 环境化学 · 有机化学 · 环境科学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2023 · IF 6.1

Syringic Acid Alleviates Dextran Sulfate Sodium-Induced Colitis in Mice by Modulating Gut Microbiota

Qiaoqiao Luo,Pengfei Gong,Ruoyu Shi,Wei Chen,Chengtao Wang,Chan Zhang,Zhe Wu

Inflammatory bowel disease is known to be associated with alterations in gut microbiota. The bioactive compound syringic acid has been shown to alleviate inflammatory bowel disease, but its interaction with gut microbiota and mechanism of action remain unclear. To address this, we conducted a study in which we investigated the potential benefits of syringic acid in a mouse model of dextran sulfate sodium-induced colitis through gut microbiota modulation. Our results show that oral administration of syringic acid effectively reduced symptoms of colitis, as indicated by reduced disease activity index, and histopathology scores. Moreover, syringic acid administration enriched the abundance of Alistipes and norank_f__norank_o__Gastranaerophilales in mice, suggesting a restoration of impaired gut microbiota. Notably, we found that the effects of syringic acid were similar to those of fecal microbiota transplantation in dextran sulfate sodium-induced mice. Further analysis revealed that syringic acid inhibited the NLRP3-Cas-1-GSDMD-IL-1β inflammatory vesicle signaling pathway, leading to amelioration of colonic inflammation in a gut microbiota-dependent manner. Our findings demonstrate the potential of syringic acid as a preventive and therapeutic agent for inflammatory bowel disease.

CAS / MDL: 30525-89-4
研究领域: 胃肠病学 · 免疫学 · 微生物学 · 药理学
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FOOD HYDROCOLLOIDS · 2020 · IF 7.053

Characterization the non-covalent interactions between beta lactoglobulin and selected phenolic acids

Xin Li,Taotao Dai,Peng Hu,Chenghao Zhang,Jun Chen,Chengmei Liu,Ti Li

The interactions between β-lactoglobulin (β-LG) and two types of phenolic acids , including 3,4-dihydroxybenzoic acid, gallic acid, syringic acid, caffeic acid, ferulic acid, and chlorogenic acid, were investigated by spectroscopy and molecular docking. The fluorescence quenching suggested the formation of a stable phenolic acid-β-LG complex. The thermodynamic parameters suggested that hydrophobic forces dominated the interaction process and the interaction was studied by the molecular docking. The circular dichroism spectra showed the selected phenolic acid induced secondary structure transition of the β-LG from β-sheet to β-turn and α-helix. Interestingly, two types of selected phenolic acids had different effects on the surface hydrophobicity of β-LG. Furthermore, the binding affinity decreased in the order CaA > ChA > FA > SA > DA > GA, which revealed that hydroxylation, methylation , steric hindrance and the type of phenolic acids affected the binding affinity. Cinnamic acid derivatives (CaA, FA, and ChA) exhibited a stronger binding affinity with β-LG than benzoic acid derivatives (DA, GA, and SA). The influence of methylation and the number of hydroxyl groups on the phenolic acids depended on phenolic acid type, the steric hindrance effects reduced their binding ability. The findings obtained herein are helpful to bring out the binding mechanism of phenolic acids and β-lactoglobulin.

研究领域: 食品科学 · 生物化学 · 分子生物学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Fabrication and characterization of dual-functional porous starch with both emulsification and antioxidant properties

Ruixi Chen,Yunxiang Ma,Zidi Chen,Zhipeng Wang,Jinfeng Chen,Yue Wang,Shenggui Zhang

Starchy materials with good antioxidant, emulsification and adsorption properties have potential applications in industry. To improve these properties, a Dual-functional porous starch was prepared through one-pot synthesis. In this case, octenyl succinic anhydride (OSA) and syringic acid (SA) were selected to modify the porous starch (PS) by esterification, with subsequent signals recorded by 1 H NMR at 1.2 ppm and FT-IR at 1743 cm −1 , indicating the formation of Dual-functional porous starch grafted by OSA and SA. N 2 adsorption analysis further proved that the porous structure (2.9 m 2 g −1 ) was still maintained after modification. This was followed by measurements of droplet size distribution (34.18 ± 3.80 μm), zeta potential (−39.62 ± 1.89 mV) and emulsion index (85.10 ± 1.76 %), all of which indicated good emulsifying capacity. Meanwhile, results of radical scavenging assay proved that the Dual-functional porous starch had considerable antioxidant properties due to the introduction of SA groups. Besides, the Dual-functional porous starch also showed good resistance to digestion. These findings not only provide a novel strategy for constructing multi-functionalized starchy materials, but also open up potential applications of starch in the food and pharmaceutical industries.

CAS / MDL: 9032-08-0 9000-90-2
研究领域: 食品科学 · 材料科学 · 化学
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Food & Function · 2022 ·Vol. 13 ·期 20 ·10759-10768 · IF 6.317

Gut microbiota derived structural changes of phenolic compounds from colored rice and its corresponding fermentation property

Meng Jia,Dengdeng Li,Rui Wang,Anqi Wang,Padraig Strappe,Qinghai Wu,Wenting Shang,Xuanyu Wang,Min Zhuang,Chris Blanchard,Zhongkai Zhou

The influence of phenolic compound extracts from three colored rice cultivars on the gut microbiota was investigated. The results revealed that protocatechuic acid, chlorogenic acid, caffeic acid and p-coumaric acid were the major metabolites after gut microbiota fermentation. The presence of phenolic compounds led to a significantly decreased ratio of Firmicutes and Bacteroidetes, while the abundance of Proteobacteria decreased. At the genus level, phenolic compounds promoted an increase of Prevotella, Megamonas and Bifidobacterium, while the abundance of Bacteroides and Escherichia–Shigella was inhibited. The concentration of ferulic acid and syringic acid was positively correlated with Bifidobacterium, while Megamonas was positively correlated with catechin and caffeic acid. The abundance of Escherichia–Shigella and Citrobacter was found to be significantly negatively correlated with chlorogenic acid. More importantly, this study revealed that the presence of phenolic compounds generated more propionate, followed by acetate, but not butyrate after gut microbiota fermentation.

研究领域: 营养学 · 微生物学 · 食品科学 · 生物化学
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