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Materials · 2020 ·Vol. 13 ·期 3 ·507 · IF 3.057

H3PMo12O40 Immobilized on Amine Functionalized SBA-15 as a Catalyst for Aldose Epimerization

Hui Wang,Meiyin Wang,Jining Shang,Yuanhang Ren,Bin Yue,Heyong He

In this work various amount of phosphomolybdic acid (PMo) were immobilized on amine functionalized SBA-15 and used as heterogeneous catalysts in the epimerization of glucose in aqueous solution. 13.3PMo/NH2-SBA-15 exhibited the best catalytic performance with a glucose conversion of 34.8% and mannose selectivity of 85.6% within two hours at 120 °C. The activation energy of 80.1 ± 0.1 kJ·mol−1was lower than that of 96 kJ·mol−1over the homogeneous H3PMo12O40catalyst. The catalytic activities of 13.3PMo/NH2-SBA-15 for the transformation of some other aldoses including mannose, arabinose and xylose were also investigated.Keywords:aldose epimerization;phosphomolybdic acid;amino-silanization;SBA-15

研究领域: 催化化学 · 生物化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

A Reverse Thinking Based on Partially Methylated Aldononitrile Acetates to Analyze Glycoside Linkages of Polysaccharides Using Liquid Chromatography–Multiple Reaction Monitoring Mass Spectrometry

Jia-Ning Gao,Ye Li,Jun Liang,Li Xiao,Hai-Xue Kuang,Yong-Gang Xia

Glycoside linkage analyses of medicine and food homologous plant polysaccharides have always been a key point and a difficulty of structural characterization. The gas chromatography–mass spectrometry (GC-MS) method is one of the commonly used traditional techniques to determine glycoside linkages via partially methylated alditol acetates and aldononitrile acetates (PMAAs and PMANs). Due to the simplicity of derivatization and the highly structural asymmetry of PMANs, reverse thinking is proposed using liquid chromatography–electrospray ionization–multiple reaction monitoring mass spectrometry (LC-ESI-MRM-MS) for the first time to directly determine the neutral and acidic glycosyl linkages of polysaccharides. The complete characterization of glycoside linkages deduced from PMANs was achieved using a combination of tR values, characteristic MRM ion pairs, diagnostic ESI+–MS/MS fragmentation ions (DFIs), and optimal collision energy (OCE). The DFI and OCE parameters were confirmed to be effective for the auxiliary discrimination of some isomers of the PMANs. The practicality of LC-ESI+-MRM-MS was further verified by analyzing the glycoside linkages of polysaccharides in five medicine and food homologous plants. This method can serve as an alternative to GC-MS for the simultaneous determination of neutral and acidic glycosyl linkages in polysaccharides.

CAS / MDL: 124-41-4
研究领域: 分析化学 · 食品科学 · 药学
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CHINESE CHEMICAL LETTERS · 2014 · IF 1.178

Inhibitory effect of eleven herbal extracts on advanced glycation end-products formation and aldose reductase activity

Guang-Yue Hou,Lu Wang,Shu Liu,Feng-Rui Song,Zhi-Qiang Liu

The formation of advanced glycation end-products (AGEs) and aldose reductase (AR) activity have been implicated in the development of diabetic complications. Our study sought to characterize the capacities of eleven herbal extracts against the formation of AGEs and the AR activity. An ultrahigh performance liquid chromatography and tandem mass spectrometry (UPLC–MS/MS) method was used for the detection of AR activity and the screening of AR inhibitors in this research. The amount of sorbitol from each analyte was directly detected using the multiple reaction monitoring mode and the sorbitol level could be reduced via the addition of an inhibitor. Moreover, the BSA/glucose (fructose) system was applied to investigate their inhibitory activities of AGEs formation in glycation model reactions. Compared with other screened herbs used in our study, Flos Sophorae Immaturus and Radix Scutellariae seemed to be more effective on inhibiting the formation of AGEs and AR activity. The inhibiting capacities of herbal extracts against AR activity and AGEs formation may be correlated with the bioactive components of the herbal extracts. The differences were correlated with the amount of polyphenol and flavonoid components. In the study, we have investigated the potential anti-hyperglycemic bioactivity of eleven herbal extracts in vitro , which could provide a reference for further in vivo research in the prevention and treatment of diabetic complications.

CAS / MDL: 79-17-4
研究领域: 药理学 · 生物化学
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JOURNAL OF CHEMICAL RESEARCH · 2025 · IF 1.2

Design and synthesis of ferulic acid-based aldose reductase inhibitors as hypoglycemic agents

Yulan Zhu,Yuhang Ding

Twelve ferulic acid–based derivatives containing urea groups were synthesized and characterized by elementary analytical,1H and 13C nuclear magnetic resonance and electrospray ionization mass spectrometry spectra. Their hypoglycemic and aldose reductase inhibitory activities were evaluated, several of which showed hypoglycemic activities in vivo comparable with the positive drug glibenclamide. Furthermore, of the tested compounds, 7a and 7b displayed the most potent aldose reductase inhibitory activity in vitro, with an IC50 of 0.55 and 3.88 μM, respectively. Docking simulation indicated compound 7a mainly interact with aldose reductase 2 via three hydrogen bonds with ARG268, SER263, SER210, and one π–π stacking interaction with TYR209.

研究领域: 药物化学 · 生物化学 · 医学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2024 · IF 3.8

Enhanced Selective Oxidation of Glycerol to Dihydroxyacetone over Pt@Sn-MFI Zeolites

Shiwei Wang,Tianhao Li,Yanle Li,Hongfeng Yin,Ziqi Tian,Hongbo Yu

Supported Pt nanoparticles (NPs) exhibit excellent activity for the selective oxidation of glycerol (GL) derived from biodiesel production to high-value dihydroxyacetone (DHA). However, their selectivity to DHA is not satisfactory due to the preferential oxidation of the primary −OH in GL. In this study, Pt@Sn-MFI with ∼4.0 nm Pt NPs and different Si/Sn ratios were synthesized by an in situ encapsulation strategy. The optimized Pt@Sn-MFI-80 catalyst presents a 74.8% selectivity to DHA with a GL conversion of 43.5% at 60 °C. Our experiments and density functional theory (DFT) calculations indicated that the excellent selectivity was ascribed to the synergistic effect between Pt and Sn-MFI. Sn-MFI turned Pt NPs into an electronic-poor state so that suppressed further oxidation of glyceraldehyde (GLD); then, Sn-MFI triggered isomerization of GLD to generate DHA. The core–shell structure not only guaranteed an intimate contact between Pt and Sn-MFI but also enhanced the stability of the active Pt NPs.

CAS / MDL: 107-21-1
研究领域: 化学工程 · 催化 · 材料科学
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RSC Advances · 2025 ·Vol. 15 ·期 31 ·25579-25585 · IF 4.6

Inhibitory mechanism of pterostilbene and pinostilbene on aldose reductase and α-glucosidase: a new insight from inhibition kinetics and molecular docking studies

Lili Jiang,Yanyan Jia,Hang Yin,Yong Liu

Pterostilbene, a dietary polyphenol in blueberries, grapes and wine, possesses an anti-diabetic efficacy. However, the mechanism of anti-diabetic efficacy for pterostilbene is poorly understood. The purpose of the present study was to systematically investigate inhibitory effects and inhibition mechanisms of pterostilbene or its metabolite (pinostilbene) against aldose reductase and α-glucosidase. In the present study, inhibition kinetics and molecular docking were applied to investigate the effect of pterostilbene and pinostilbene on the activity of aldose reductase and α-glucosidase. The results showed that pinostilbene exhibited stronger inhibition on aldose reductase (IC50 = 55.41 ± 4.31 μM) and α-glucosidase (IC50 = 11.69 ± 0.888 μM) in noncompetitive-type manner. Whereas, pterostilbene displayed the weak effect on aldose reductase and α-glucosidase (IC50 = 1569 ± 177.858 μM) inhibition. Moreover, pinostilbene interacted with amino acid residues outside of aldose reductase and α-glucosidase active site to inhibit its activities by van der Waals, π–anion or π–alkyl interactions. The current study has provided comprehensive reference not only for the anti-diabetic mechanism of pterostilbene, but also offered a basis to develop and design adjuvant antidiabetic drugs or novel functional foods.

研究领域: 生物化学 · 药理学 · 分子生物学 · 食品科学 · 药物设计
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ANALYTICA CHIMICA ACTA · 2023 · IF 6.2

In-depth profiling of carbohydrate isomers in biological tissues by chemical derivatization-assisted mass spectrometry imaging

Lei Wang,Yuhao Han,Yaqi Zhang,Haoyuan Geng,Zihan Zhu,Panpan Chen,Xiaoqing Cui,Xiao Wang,Chenglong Sun

Carbohydrates play crucial regulatory roles in various physiological and pathological processes. However, the low ionization efficiency and the presence of linkage pattern, monosaccharide composition and anomeric configuration isomers make their in-depth analysis very challenging, especially for heterogeneous biological tissues. In this study, we propose a high-sensitive and isomer-specific imaging approach to visualize the spatial distributions of monosaccharide and disaccharide isomers by integrating chemical derivatization and matrix-assisted laser desorption/ionization tandem mass spectrometry imaging (MALDI-MS 2 I). 2-Pyridinecarbohydrazide (PYD) is developed as a novel derivatization reagent which can not only improves the MS sensitivity of carbohydrates, but also enables the identification and visualization of ketose and aldose monosaccharide isomers, as well as linkage pattern, monosaccharide composition and anomeric configuration disaccharide isomers by mass spectrometry imaging of isomer-specific MS/MS fragment ions. Moreover, we build quantitative MALDI-MS 2 and MALDI-MS 2 I methods for disaccharide isomers based on the diagnostic fragment ions, and good linear relationships could be achieved both in solution and on glass slides. We expect that this study should provide new ideas for in-depth profiling of the spatial signatures of carbohydrates in biological tissues and lay the foundation for a deeper understanding of carbohydrates’ structure.

研究领域: 分析化学 · 生物化学 · 质谱学 · 分子生物学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2019 · IF 3.571

Degradation of Peptide-Bound Maillard Reaction Products in Gastrointestinal Digests of Glyoxal-Glycated Casein by Human Colonic Microbiota

Dan Xu,Lin Li,Xia Zhang,Hong Yao,Mingquan Yang,Zuoqi Gai,Bing Li,Di Zhao

A large portion of Maillard reaction products (MRPs) cannot be absorbed in the upper gut and therefore may be further decomposed and utilized by colonic microbiota (CM). This work reported the stability of UV-absorbent MRPs, fluorescent MRPs and peptide-bound N(ε)-(carboxymethyl)-lysine (CML) in high molecular weight (HMW, >10 kDa), medium molecular weight (MMW, 1–10 kDa), and low molecular weight (LMW, <1 kDa) gastrointestinal digests of glyoxal-glycated casein in the presence of CM. Fluorescent MRPs showed high stability, whereas UV-absorbent MRPs may be partially decomposed. A higher depletion rate of CML was found in the LMW fraction (38.7%) than in the MMW (21.7%) and HMW (9.6%) fractions. The 16S rRNA sequencing results revealed both beneficial and detrimental changes in CM composition induced by the glycated fractions. Generation of short-chain and branched-chain fatty acids in fermentation solutions with glycated fractions was significantly suppressed compared with that in fermentation solution with unglycated digests. This work revealed the possible interplay between peptide-bound MRPs and CM.

研究领域: 食品科学 · 微生物学 · 营养学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

Simultaneous determination of the monosaccharide types and their absolute configurations in polysaccharides based on UPLC-MS/MS

Yongchun Huang,Jie Bai,Jinman Shui,Zhanhai Su,Chengzhu Cao,Haiyan Wang,Qiong Wu,Shoude Zhang

Analysing monosaccharide composition is an essential step in deciphering polysaccharide structures. However, it presents significant challenges due to the pronounced hydrophilicity and the vast array of monosaccharide isomers. Gas/liquid chromatography, coupled with an aldononitrile acetate derivatisation, has been widely used for monosaccharide composition analysis. However, it poses considerable difficulties in simultaneously determining the D/L configurations of these monosaccharides. In this study, a novel method that can simultaneously determine the composition of polysaccharides and their D/L configuration based on L-cysteine methyl ester derivatisation (CMED) and ultra performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) is developed for the comprehensive analysis of monosaccharide types. This method enables the simultaneous characterization of aldoses, ketoses, alditols, and uronic acids. Furthermore, the reaction mechanisms and by-products were meticulously analysed, offering a robust theoretical basis for this novel methodology. Additionally, the developed method was employed to characterize the monosaccharide composition for six plant polysaccharides. Ultimately, the findings demonstrated that the proposed method is effective for confirming monosaccharide composition, encompassing both structural types and absolute configurations.

研究领域: 分析化学 · 碳水化合物化学 · 生物化学 · 植物科学
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RSC Advances · 2017 ·Vol. 7 ·期 55 ·34448-34460 · IF 3.108

Synthesis and biological evaluation of novel neoflavonoid derivatives as potential antidiabetic agents

Bing Wang,Na Li,Teng Liu,Jie Sun,Xiaojing Wang

Various substituted neoflavonoid derivatives were synthesized using sulfated montmorillonite K-10 as a catalyst. This method is environmental friendly, sustainable and economical, convenient in isolation and purification processes, with little byproducts, using earth-abundant catalysts and has relatively high yield. Those neoflavonoid derivatives were screened for antioxidant, a-glucosidase inhibitory, aldose reductase 2 (ALR2) inhibitory and advanced glycation end-product formation inhibitory effects. Most compounds exhibited significant antioxidant and advanced glycation end-product (AGE) formation inhibitory activities. It was interesting to note that out of thirty compounds, 8k and 8l were found to have greater ALR2 inhibitory activity than the standard drug quercetin. The pharmacological studies suggested neoflavonoid with adjacent 7,8-dihydroxy groups were more effective in inhibiting ALR2. Antidiabetic activity studies had shown that compounds 8l and 8m were equipotent to the standard drug glibenclamide in vivo. In summary, the target compound 8l provided a potential drug design concept for the development of therapeutic or prophylactic agents of diabetes and diabetes complications.

研究领域: 药理学 · 有机化学 · 药物化学
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JOURNAL OF ETHNOPHARMACOLOGY · 2017 · IF 2.981

Gigantol from Dendrobium chrysotoxum Lindl. binds and inhibits aldose reductase gene to exert its anti-cataract activity: An in vitro mechanistic study

Jie Wu,Xue Li,Wencheng Wan,Qiaohong Yang,Weifeng Ma,Dan Chen,Jiangmiao Hu,C.-Y.Oliver Chen,Xiaoyong Wei

Ethnopharmacological relevance Dendrobium . chrysotoxum Lindl is a commonly used species of medicinal Dendrobium which belongs to the family of Orchidaceae , locally known as “Shihu” or “Huangcao”. D. chrysotoxum Lindl is widely known for medicinal values in traditional Chinese medicine as it possesses anti-inflammatory, anti-hyperglycemic induction, antitumor and antioxidant properties. Study aim To characterize the interaction between gigantol extracted from D. chrysotoxum Lindl and the AR gene, and determine gigantol's efficacy against cataractogenesis . Materials and methods Human lens epithelial cells (HLECs) were induced by glucose as the model group. Reverse transcription polymerase chain reaction (RT-PCR) was used to assess AR gene expression. Then, the mode of interaction of gigantol with the AR gene was evaluated by UV–visible spectroscopy, atomic force microscope (AFM) and surface-enhanced Raman spectroscopy (SERS). The binding constant was determined by UV–visible. Results Gigantol depressed AR gene expression in HLECs. UV–visible spectra preliminarily indicated that interaction between the AR gene and gigantol may follow the groove mode, with a binding constant of 1.85×10 3 L/mol. Atomic force microscope (AFM) data indicated that gigantol possibly bound to insert AR gene base pairs of the double helix. Surface-enhanced Raman spectroscopy (SERS) studies further supported these observations. Conclusion Gigantol extracted from D. chrysotoxum Lindl not only has inhibitory effects on aldose reductase, but also inhibits AR gene expression. These findings provide a more comprehensive theoretical basis for the use of Dendrobium for the treatment of diabetic cataract.

CAS / MDL: 919-30-2 50-99-7
研究领域: 药理学 · 民族药理学 · 分子生物学 · 糖尿病研究 · 眼科
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