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Nature Communications · 2025 ·Vol. 16 ·期 1 ·1-19 · IF 15.7

FRET imaging of glycoRNA on small extracellular vesicles enabling sensitive cancer diagnostics

Ren Tingju,Zhang Yingzhi,Tong Yuxiao,Zhang Qi,Wang Tianhao,Wang Yue,Yang Chunguang,Xu Zhangrun

Glycosylated RNAs (glycoRNAs), a recently discovered class of membrane-associated glyco-molecules, remain poorly understood in function and clinical value due to limited detection methods. Here, we show a dual recognition Förster resonance energy transfer (drFRET) strategy using nucleic acid probes to detect N-acetylneuraminic acid-modified RNAs, enabling sensitive, selective profiling of glycoRNAs on small extracellular vesicles (sEVs) from minimal biofluids (10 μl initial biofluid). Using drFRET, we identify 5 prevalent sEV glycoRNAs derived from 7 cancer cell lines. In a 100-patient cohort (6 cancer types and non-cancer controls), sEV glycoRNA profiles achieve 100% accuracy (95% confidence interval) in distinguishing cancers from non-cancer cases and 89% accuracy in classifying specific cancer types. Furthermore, drFRET reveal that sEV glycoRNAs specifically interact with Siglec proteins and P-selectin, which is critical for sEV cellular internalization. The drFRET strategy provides a versatile and sensitive platform for the imaging and functional analysis of sEV glycoRNAs, with promising implications for clinical applications.

研究领域: 分子生物学 · 肿瘤学 · 临床医学 · 生物化学
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ANALYTICAL CHEMISTRY · 2011 · IF 5.874

Size-Selective Enrichment of N-Linked Glycans Using Highly Ordered Mesoporous Carbon Material and Detection by MALDI-TOF MS

Hongqiang Qin,Liang Zhao,Ruibin Li,Ren’an Wu,Hanfa Zou

Many diseases are characterized by the changes of either glycan structure or glycosylation site of glycoproteins. The glycan profiling can provide the overview of glycosylation in despite of the absence of the glycosylation sites, which in turn simplifies the complexity of disease diagnosis. Herein, we describe a simple method to profile the N-linked glycans by MALDI-TOF MS with the enrichment using oxidized ordered mesoporous carbon, taking advantages of the size-exclusive effect of mesopore against proteins as well as the interaction between glycans and carbon. Twenty four N-linked glycans derived from ovalbumin could be efficiently detected with high signal-to-noise (S/N) ratios and sufficient peak intensities. In the analysis of complex serum samples, 32 N-linked glycans could be profiled, and 5 (4 core-fucosylated glycans) of them were distinguished from liver cancer and healthy samples.

CAS / MDL: 9007-43-6
研究领域: 分析化学 · 生物医学 · 蛋白质组学
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2012 · IF 3.456

Facile construction of functional biosurface via SI-ATRP and “click glycosylation”

Wantong Song,Chunsheng Xiao,Liguo Cui,Zhaohui Tang,Xiuli Zhuang,Xuesi Chen

Construction of high density glycosylated surfaces is important in the investigation of interactions between pathogens and surface carbohydrates. In this work, we provided a flexible method for glycosyl surface fabrication by combination of surface-initiated atom transfer radical polymerization (SI-ATRP) and copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction. Through this strategy, we got a very high surface glycosyl density of about 4   nmol/cm 2 with the surface “click” efficiency of nearly 50%. Then the carbohydrate decorated surfaces were used to mimic cell surfaces and specific recognition of mannose with Escherichia coli was observed. We believe the methodology provided here can be used as a facile way for construction of a wide range of functional biosurfaces.

CAS / MDL: 109-63-7 920-46-7
研究领域: 生物化学 · 材料科学 · 微生物学
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NEW JOURNAL OF CHEMISTRY · 2019 ·Vol. 43 ·期 43 ·16881-16888 · IF 3.069

Ionic liquid-assisted catalysis for glycosidation of two triterpenoid sapogenins

Tenghe Zhang,Xinlu Li,Hang Song,Shun Yao

In order to both investigate the universality of ionic liquid-based catalytic systems for synthesis of triterpene saponins and explore their effective application methods together with the catalytic behaviors of ionic liquids in related reactions by comparison between different initiators, oleanolic acid and ursolic acid were selected to establish a catalytic system for glycosylation in this study as typical representatives of pentacyclic triterpene sapogenins. As a result, it was found that the system of [C4mim][OTf] + TMSOTf in the reactions between the glycosyl receptors and donors showed obvious catalytic effects; also, the system was stable and could be recycled. The functions of IL include solvent, cocatalyst and stabilizer, simultaneously; thus, the current catalytic system is greener, simpler and more efficient. The reaction time was short, and only β-type products were obtained. This study offers a reference for developing a new glucoside synthesis technology and provides sufficient preliminary exploration and basic data for further large-scale applications.

研究领域: 有机化学 · 药物化学
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Molecular Catalysis · 2022 · IF 5.089

Enzymatic glucosylation of citrus flavonoids to enhance their bioactivity and taste as new food additives

Aolu Liu,Baohua Huang,Shanshan Zuo,Zhihao Li,Jin-Lin Zhou,Wing-Leung Wong,Yu-Jing Lu

Cyclodextrin glucosyltransferase (CGTase) is commonly used to produce cyclodextrins but its utility in flavonoids modification is rarely found. In the present study, an enzymatic transformation of citrus flavonoids by applying CGTase as the catalyst was investigated to produce a number of novel polyglucosylated derivatives from monoglucoside metabolites of citrus flavonoid diglycosides. Under the optimized conditions, the yield of glucosylated products achieved 80%. The water solubility and water partition coefficient of citrus flavonoids before and after the structural modification were compared. The results revealed that the water solubility of the flavonoids modified by glucosylation was significantly increased while the oil-water partition coefficient was just slightly reduced. Moreover, after glucosylation, the products have good anti-inflammatory and antioxidant effects. Interestingly, the taste property (bitterness and sweetness) of the glucosylated products was ameliorated. An evaluation with a Taste-Sensing System showed that the taste of the glucosylated products was strongly correlated with the attached rhamnosyl group (bitter taste) and glucosyl group (sweet taste), indicating that the amelioration of taste of flavonoids could be mainly attributed to the addition of glycosyl groups. The present study demonstrated a novel molecular engineering approach for the enhancement of water solubility and amelioration of taste for some citrus flavonoids, which may have potential applications in the functional food industry.

CAS / MDL: 7783-90-6 87-69-4
研究领域: 食品科学 · 生物化学
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FOOD AND CHEMICAL TOXICOLOGY · 2021 · IF 6.025

Glycated peptides obtained from cultured crocodile meat hydrolysates via Maillard reaction and the anti-aging effects on Drosophila in vivo

Yin Li,Dongyi Hu,Jianlian Huang,Shaoyun Wang

With the aging problems increasing, the discovery of anti-aging compounds has become a popular research direction. Accumulation of free radicals and the consequent oxidative stress are the chief culprit of aging. Given this, cultured crocodile meat peptides-Maillard reaction product (CMP-MRP) with remarkable antioxidant activity was obtained via Maillard reaction of cultured crocodile meat hydrolysates and xylose . The antioxidant activity in vitro and anti-aging activity in vivo of CMP-MRP were investigated. Results indicated that the lifespan and the athletic ability of Drosophila were significantly improved after the administration of CMP-MRP in natural aging, H 2 O 2 - and paraquat-induced models. Furthermore, the antioxidant enzyme activities of Drosophila treated with CMP-MRP were enhanced while the levels of malondialdehyde (MDA) and protein carbonyl (PCO) were reduced in three Drosophila models. With the supplement of 5 mg/mL CMP-MRP in natural aging Drosophila model, the maximum lifespan increased from 61 days to 73 days, athletic ability raised by 95.45%, MDA and PCO reduced by 52.72% and 47.43%, respectively. Taken together, CMP-MRP exhibited outstanding antioxidant and anti-aging capacities in Drosophila models, suggesting that CMP-MRP possesses great potential in the health food and biomedicine fields as a food-derived anti-aging agent.

研究领域: 营养学 · 分子生物学 · 食品科学
✓ 已验证 DOI PubMed 高影响因子
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CARBOHYDRATE POLYMERS · 2023 · IF 11.2

Human milk whey glycoprotein N-glycans varied greatly among different maternal secretor status

Xiaoqin Wang,Wenqing Li,Zhenhua Li,Tianjiao Han,Jinqiao Rong,Jiangbo Fan,Linjuan Huang,Yu Lu,Zhongfu Wang

Human milk glycans are complex carbohydrates , which play a pivotal role in infant health and neonatal development . Maternal secretor status is known to affect free oligosaccharides in milk. Here, the milk N -glycome of secretor (Se+) and nonsecretor (Se−) individuals was qualitatively and quantitatively analyzed by hydrophilic interaction chromatography-electrospray ionization-tandem mass spectrometry. The total glycosylation , fucosylation , and sialylation of N -glycans was three times higher in the Se+ group compared to the Se− group ( p  < 0.001) per equal volume of milk. Importantly, 52 out of 63 N -glycans—including the eight most abundant ones—differed greatly between Se+ and Se− individuals ( p  < 0.05). Moreover, nine N -glycans (H5N3F1, H6N3, H3N5F1, H5N5F1, H5N5F1S1, H5N4F3S1, H6N4F2S1, H6N5F4S1, and H8N7S1) were >10 times more abundant in Se+ milk than in Se− milk. These findings lay a glycomics-basis for designing personalized nutrition supplements for infants.

研究领域: 生物化学 · 儿科医学 · 营养学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Effect of superheated steam on Maillard reaction products, digestibility, and antioxidant activity in β-Lactoglobulin-glucose system

Wen-mei Chen,Yang Wang,Xu-mei Wang,Yan-hong Shao,Zong-cai Tu,Jun Liu

This study analyzes the interactions among Maillard reaction products (MRPs), digestibility and antioxidant activity in a β-lactoglobulin-glucose (βlg-Glu) model system during superheated steam treatment at 120 °C for 1 to 5 min. With an increase in treatment duration, there were significant increases in glucose loss, grafting degree, browning, and the formation of intermediate products in βlg-Glu. Characteristic MRPs, including α-dicarbonyl compounds, 5-hydroxymethylfurfural, and advanced glycation end products (AGEs), were formed through the degradation of sugars and condensation reactions between carbonyls and amines, accompanied by an increase in oxidative products. These changes impacted the molecular weight distribution and conformational structure of βlg-Glu, resulting in decreased digestibility. βLg-Glu with the highest level of glycation exhibited superior antioxidant activity after in vitro digestion, which was closely associated with the increase in AGEs and oxidation products. Therefore, the protein-sugar system treated by superheated steam with different heating time can significantly affect the formation and activity of the products, providing theoretical basis for superheated steam processing nutritious and healthy food.

研究领域: 食品科学 · 营养学 · 生物化学 · 食品加工
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

Deglycosylation significantly affects the activity, stability and appropriate folding of recombinant Aspergillus niger α-L-rhamnosidase expressed in Pichia pastoris

Qihui Lu,Hui Liao,Zedong Jiang,Yanbing Zhu,Yijuan Han,Lijun Li,Hui Ni,Qingbiao Li

Glycosylation plays a critical role in regulating activity, stability, and correct folding of enzymes. In this study, recombinant Aspergillus niger α-L-rhamnosidase (r-Rha1) was employed to explore the impact of glycosylation in Pichia pastoris on the enzymatic properties and protein folding . β-elimination reaction and deglycosylase treatment assays demonstrated that r-Rha1 undergoes primarily N-glycosylation. The deglycosylated r-Rha1 was prepared in two ways: treating with Endoglycosidase F 1 after expression (referred to as r-Rha1- vitro ), or inhibiting intracellular glycosylation using tunicamycin (referred to as r-Rha1- vivo ). Deglycosylation resulted in a 0.22-fold decrease in activity for r-Rha1- vitro and due to its slower turnover rate, r-Rha1- vivo showed a 0.73-fold decrease in activity. r-Rha1- vitro maintained the similar optimal temperature as r-Rha1, r-Rha1- vivo displayed a 10 °C lower optimal temperature. Compared to the decreased extent of r-Rha1- vitro in t 1/2 at 55 °C, 60 °C, and 65 °C and T m , chemical interferent deglycosylation in vivo showed a more profound impact on r-Rha1. Analyses based on circular dichroism, fluorescence spectroscopy, and differential scanning calorimetry revealed significant changes in the structure and thermodynamic stability of r-Rha1- vivo , accounting for its marked decline in activity and stability. The significant and unpredictable structure changes of r-Rha1- vivo proved the essential role of glycosylation for appropriate folding in P. pastoris .

CAS / MDL: 50-01-1
研究领域: 生物化学 · 分子生物学
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FOOD HYDROCOLLOIDS · 2021 · IF 9.147

Sulfated polysaccharides from red seaweed Gelidium amansii: Structural characteristics, anti-oxidant and anti-glycation properties, and development of bioactive films

Gang Yu,Qiaozhi Zhang,Yanbo Wang,Qing Yang,Hejun Yu,Huan Li,Jian Chen,Linglin Fu

Marine red algae are rich sources of sulfated polysaccharides as bioactive ingredients and hydrocolloid molecules. In this study, sulfated polysaccharides (YGAP, EGAP, and NGAP) were extracted from Gelidium amansii s that were harvested from three different sea areas of China. Characterization of these polysaccharides shows that they contain 3.7–4.0% sulfate and are mainly composed of galactose , glucose, fucose, arabinose, and mannose . The FT-IR and 13 C NMR analysis indicate that the sulfated polysaccharides are agar-type galactans containing 3,6 anhydro-α- l -galactopyranose and β- d -galactopyranose residues. By using various in vitro models, all sulfated polysaccharides, particularly EGAP, exhibit the ability to scavenge O 2 •– and OH· radicals and reducing power. Additionally, in a glucose-glycated BSA system, the polysaccharides show an inhibitory effect on protein glycation and formation of specific advanced glycation end-product. Their anti-glycative property is attributed to their anti-oxidant activity and trapping capacity of methylglyoxal. Given that these polysaccharides possess agar-like structures, they were used to prepare bioactive films and expectedly, transparent and homogeneous films were obtained. The films display high water barrier properties with retained antioxidant and anti-glycation activities as above. These results expand the current knowledge of G. amansii s polysaccharides as nutraceuticals and hydrocolloids, which would benefit their applications in the food industry.

研究领域: 食品科学 · 海洋生物学 · 营养学
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FOOD HYDROCOLLOIDS · 2025 · IF 12.4

Oligosaccharide glycosylation of pigskin collagen: Impact on molecular structure, physicochemical properties, and gel functionality

Shengqi Jiang,Huiyu Han,Madina Aitmagambetova,Aidana Rakhimova,Lin Li,Rong Bai,Chunjie Yang,Xiang Ye,Siying Wang,Jing Xi,Wu Ding

This study aimed to investigate the effects of oligosaccharides (xylooligosaccharides (XOS), fructooligosaccharides (FOS), galactooligosaccharides (GOS), and isomaltooligosaccharides (IOS)) with different structures and molecular weights on the glycosylation modification of pigskin collagen (CO). Glycosylated CO was prepared via the Maillard reaction, and its molecular structure, physicochemical, and functional properties were analyzed using various analytical techniques. Results indicated increased glycosylation significantly altered the α-helix and random coil content, intrinsic fluorescence intensity, particle size, and ζ-potential of CO ( P  < 0.05). These modifications enhanced protein-protein and protein-water interactions, improving solubility, thermal stability, rheological properties, and creating a more uniform gel network structure. XOS, composed of the smaller molecular weight five-carbon aldose unit (xylose), exhibited the most significant effects, including enhanced thermal stability, water retention, and gel strength. However, the Maillard reaction-induced glycation browning caused a slight negative impact on the color of CO gels. In conclusion, oligosaccharide glycosylation significantly enhances the functional properties of pigskin CO, providing a promising strategy for its high-value utilization.

研究领域: 食品科学 · 生物化学
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Food & Function · 2015 ·Vol. 6 ·期 10 ·3291-3295 · IF 2.791

Enzymatic transformation of stevioside using a β-galactosidase from Sulfolobus sp.

Hui-da Wan,Yong-mei Xia

Enzymatic hydrolysis and transgalactosylation of stevioside (St) were investigated using a β-galactosidase from Sulfolobus sp. The hydrolysis yielded steviol as the main final product. Under the optimal transgalactosylation conditions, the highest conversion of stevioside was 87.3% with lactose as a donor, several galactosylated products (St-Gals) were obtained. Metal ions such as Na+, K2+, Ca2+, Ba2+, Mn2+ and Mg2+ (2 mM) did not affect the transgalactosylation activity, while Fe2+, Fe3+ and Cu2+ reduced the transgalactosylation activity of β-galactosidase to 64%, 33% and 18%, respectively.

研究领域: 生物化学 · 食品科学
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