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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2014 ·Vol. 95 ·期 11 ·2228-2236 · IF 1.879

Oligosaccharides composition in eight food legumes species as detected by high-resolution mass spectrometry

Pei-Hong Fan,Mei-Tong Zang,Jie Xing

BACKGROUND As probiotics, soy oligosaccharides have become popular as healthy foods to reduce disease risk. However, comprehensive information about oligosaccharides in different food legumes is limited. RESULTS In this study, eight oligosaccharides were well detected and quantified in different varieties of eight legume species using high-resolution mass spectrometry. It was determined that species could be distinguished by total content of oligosaccharides and their distribution modes. Among the studied species, Vigna unguiculata is a better resource of non-digestible oligosaccharides, while Vicia faba and black soybean ( Glycine max ) are at a disadvantage. Normally, stachyose predominates in non-digestible oligosaccharides, except in mung bean and broad bean, where verbascose predominates. For mung bean and green soybean, the seed coat should be taken into account for oligosaccharide consumption. The developed high-resolution mass spectrometry method greatly simplified the sample preparation process and permitted the identification of oligosaccharides without reference compounds. CONCLUSION This work involved extensive sample collecting and provided useful information for consumers. The developed method may be useful for rapid quantification of oligosaccharides in related foods. © 2014 Society of Chemical Industry

研究领域: 食品科学 · 植物化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2019 · IF 3.571

Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry Analysis of Human Milk Neutral and Sialylated Free Oligosaccharides Using Girard’s Reagent P On-Target Derivatization

Xi Gao,Yu Lu,Ming Wei,MeiFang Yang,CaiXia Zheng,Chengjian Wang,Ying Zhang,Linjuan Huang,Zhongfu Wang

The functional role of human milk oligosaccharides (HMOs) is closely associated with their type, composition, and structure. However, a detailed analysis of HMOs is difficult because neutral oligosaccharides (NHMOs) are mixed with sialylated oligosaccharides (SHMOs) in milk. Here, NHMOs were separated from SHMOs by DEAE-52 anion chromatography, and lactose was removed by graphite carbon solid-phase extraction. Lactose-free NHMOs were analyzed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) based on Girard’s reagent P on-target derivatization (GPOD), and SHMOs were analyzed by MALDI-TOF-MS following selective sialic acid derivatization and GPOD. Sixty-four oligosaccharides were detected: 36 NHMOs, of which 28 were fucosylated, and 28 SHMOs, of which 8 with α-2,3-linked monosialic acid, 2 with α-2,3-linked disialic acid, 10 with α-2,6-linked monosialic acid, 2 with α-2,6-linked disialic acid, and 5 with both α-2,3- and α-2,6-linked disialic acid. These findings provide the groundwork for further characterization of the structure and activity of HMOs.

研究领域: 生物化学 · 营养学 · 分析化学
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Foods · 2019 ·Vol. 8 ·期 6 ·181 · IF 3.011

Impact of Milk Fortification on the Microbiological and Physicochemical Properties of Set-Type Skimmed Yoghurt Using Three Commercial Soluble Prebiotics

Rui Li,Qi Ding,Xin-Huai Zhao

The impact of milk fortification on the microbiological and physicochemical properties of a set-type skimmed yoghurt using three commercial soluble prebiotics (inulin, iso-malto-oligosaccharides, and xylo-oligosaccharides) at either 3 or 5 g/kg was assessed. The three prebiotics had an insignificant impact on yoghurt fermentation because all yoghurt samples had similar titratable acidity and similar pH values after their lactic acid fermentation. Regarding the control yoghurt samples without prebiotics usage, the prebiotics-fortified yoghurt samples showed no difference in their main chemical compositions, hardness, syneresis extent, and apparent viscosity (p> 0.05), but had a slightly higher lactic acid content and a viable quantity of starter strains. All yoghurt samples had the same acetic acid content, while propionic and butyric acids were not produced. Yoghurt storage at 4 °C for 21 day gave these yoghurt samples decreased pH values and a viable quantity of starter strains (especiallyLactobacillus delbrueckiisubsp.bulgaricus) and unchanged acetic acid; however, it increased lactic acid contents. Overall, prebiotics fortification up to 5 g/kg had a completely insignificant impact on the fermentation and quality attributes of yoghurt samples but could possibly improve the health of consumers due to higher dietary fibers and starter strain populations.Keywords:set-type skimmed yoghurt;inulin;iso-malto-oligosaccharides;xylo-oligosaccharides;yoghurt quality

CAS / MDL: 9005-80-5
研究领域: 食品科学 · 微生物学
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Biomedical Materials · 2019 ·Vol. 14 ·期 2 ·025010 · IF 3.44

Injectable and biocompatible chitosan-alginic acid hydrogels

Yujing You,Yipeng Xie,Zhiqiang Jiang

Injectable and biocompatible polysaccharide hydrogels are ideal scaffolds for drug delivery and tissue engineering. Here, we report a new in situ forming hydrogels by self-crosslinking chitosan and a biocompatible polymeric crosslinker, oxidized alginic acid. The dialdehyde alginic acid was synthesized by the oxidant reaction of alginic acid with sodium periodate. The gel was formed in situ by the Schiff base reactions between their amine groups of chitosan and aldehyde groups of alginic acid. It deformed under stress and kept its shape integrity at the strain of 40%. Sustained cargo release including rhodamine and bovine serum albumin from the hydrogels was obtained. The hydrogels were degraded by chitosanase within 30 d and the pH values of the solution remained neutral. H9c2 cells proliferated the hydrogels and maintained their native state. These results suggested this hydrogel can be promising cell therapy scaffolds for tissue engineering.

研究领域: 生物材料学 · 组织工程学 · 药物递送系统
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JOURNAL OF FOOD SCIENCE · 2021 ·Vol. 86 ·期 7 ·3014-3022 · IF 3.167

Effects of deglycosylation and the Maillard reaction on conformation and allergenicity of the egg ovomucoid

Junjie Ma,Jinru Zhou,Lerong Chen,Hong Zhang,Yanbo Wang,Linglin Fu

Ovomucoid (OVM), known as the major allergen in egg white, has gained increasing concerns in industrialized countries. Here, we found the deglycosylation and Maillard reaction with galactooligosaccharide (GOS) and fructooligosaccharide (FOS) can induce conformational transformation of OVM from other structures (β-turn, strang, and random coils) to α-helix. We also introduced an approach to reduce the allergenicity of Gallus domesticus OVM by Maillard reaction with GOS and FOS. However, the OVM glycated by mannosan (MOS) and deglycosylated OVM exhibited higher allergenicity than native OVM. Therefore, GOS and FOS, especially GOS, could be applied in the reduction of the potential allergenicity of OVM through glycation. Furthermore, these findings may provide new insights into the development of hypoallergenic egg products. Practical Application In this study, the allergenicity and conformation of OVM treated with deglycosylation and glycation (GOS, FOS, and MOS) were investigated. The results would provide a better understanding of the effects of deglycosylation and Maillard reaction with different reducing sugars on the molecular characteristics of OVM and further provide new insights into the development of hypoallergenic egg products.

研究领域: 食品科学 · 过敏学 · 化学
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PURE AND APPLIED CHEMISTRY · 2017 ·Vol. 89 ·期 7 ·921-929 · IF 2.626

1,3-Di(2-dipyridyl)propan-1,3-dione – a new fluorogenic labeling reagent for milk oligosaccharides

Zhi Peng Cai,Wen Li Wang,Louis Conway,Kun Huang,Faisal Nureldin Awad,Li Liu,Josef Voglmeir

We herein demonstrate the use of 1,3-di(2-dipyridyl)propan-1,3-dione (DPPD) as a fluorogenic label for oligosaccharides. A number of milk-derived oligosaccharide standards were successfully labeled with this reagent, with the advantage of greatly simplified sample preparation compared to other commonly used fluorescent tags. DPPD shows a selectivity for oligosaccharides which do not possess a 2-acetamido-2-deoxy-hexose moiety at the reducing terminus, potentially aiding in the identification of complex mixtures of carbohydrates. The use of DPPD for the structural determination of oligosaccharides through exoglycosidase treatment, quantitative analysis of reactions, and in the synthesis of labeled oligosaccharides was also explored. This reagent has, in addition to the analysis of individual and mixed oligosaccharides, potential applications in the study of glycosidases and glycosyltransferases and as such represents a valuable addition to the tools available to the glycoscientist.

CAS / MDL: 10039-26-6
研究领域: 糖生物学 · 分析化学 · 生物化学
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JOURNAL OF CHROMATOGRAPHY A · 2014 · IF 4.258

A dextran-bonded stationary phase for saccharide separation

Qianying Sheng,Xindai Su,Xiuling Li,Yanxiong Ke,Xinmiao Liang

A-saccharide-based stationary phase for hydrophilic interaction liquid chromatography (HILIC) is presented. The method uses carbonyl di-imidazole (CDI) as a cross-linker for dextran in aqueous solution. Different from the traditional immobilized saccharide stationary phase, this method was using a simple way to bond the high molecular of polysaccharide immobilized on the silica gel. The new method avoided the time-consuming process but had a very considerable loading result. With silica-based surface bonded, it will be possible to develop well-defined surface modifications that promote the hydrophilic with dextran and high mechanical strength with silica. For all tested compounds, including polar compounds and carbohydrates, this dextran-bonded stationary phase performed well in terms of separation efficiency and column stability, and the retention mechanism matched that of typical HILIC retention. Moreover, good selectivity was achieved in the separation of oligosaccharides and glycopeptides.

研究领域: 分析化学 · 色谱学
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PROTEIN EXPRESSION AND PURIFICATION · 2022 · IF 2.025

Preparation of chitooligosaccharides with a low degree of polymerization and anti-microbial properties using the novel chitosanase AqCsn1

Chengyao Xia,Ding Li,Mengyi Qi,Yanxin Wang,Yue Zhang,Yiheng Yang,Zejia Hu,Xin Du,Yuqiang Zhao,Kuai Yu,Yan Huang,Zhoukun Li,Xianfeng Ye,Zhongli Cui

Chitosanases hydrolyze chitosan into chitooligosaccharides (COSs) with various biological activities, which are widely employed in many areas including plant disease management. In this study, the novel chitosanase Aq Csn1 belonging to the glycoside hydrolase family 46 (GH46) was cloned from Aquabacterium sp. A7-Y and heterologously expressed in Escherichia coli BL21 (DE3). Aq Csn1 displayed the highest hydrolytic activity towards chitosan with 95% degree of deacetylation at 40 °C and pH 5.0, with a specific activity of 13.18 U/mg. Product analysis showed that Aq Csn1 hydrolyzed chitosan into (GlcN) 2 and (GlcN) 3 as the main products, demonstrating an endo-type cleavage pattern. Evaluation of antagonistic activity showed that the hydrolysis products of Aq Csn1 suppress the mycelial growth of Magnaporthe oryzae and Phytophthora sojae in a concentration-dependent manner, and the inhibition rate of P. sojae reached 39.82% at a concentration of 8 g/L. Our study demonstrates that Aq Csn1 and hydrolysis products with a low degree of polymerization might have potential applications in the biological control of agricultural diseases.

研究领域: 生物技术 · 微生物学 · 植物病理学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

Expression and characterization of colanic acid-degrading enzyme from Escherichia phage phi92 and analysis of its hydrolysate composition and structure

Xiaotong Xu,Xiaoshuang Yan,Xuerong Jin,Juyi Li,Qiaoxia Hu,Dong-Hyun Ahn,Chao Zhong

Colanic acid (CA), an exopolysaccharide synthesized by bacteria, is known for its potential to extend the lifespan of nematodes. However, its high viscosity poses practical application challenges, which can be mitigated by employing colanic acid-degrading enzymes (CAEs). This study presents the expression and characterization of a novel CAE from Escherichia phage phi92, used for the production of CA oligosaccharides (CAOSs). Optimal CAE expression conditions were identified as induction at 20 °C for 24 h with 0.1 mM IPTG. The enzyme showed maximal activity at 55 °C and pH 6.0, with stability in the range of 4–50 °C and pH 4.0–7.0. Structural characterization of CAOSs was performed using GC–MS, LC–MS and NMR spectroscopy, revealing the composition of hexasaccharide and dodecasaccharide units, with CAE cleaving the β-1,4 glycosidic linkage between glucose and fucose. CAOSs were found to mitigate oxidative stress and inflammation induced by H 2 O 2 in RAW 264.7 macrophages, inhibiting NO and MDA production while enhancing CAT activity. Additionally, CAOSs modulated the mRNA expression of pro-inflammatory (IL-1β, COX-2) and anti-inflammatory (IL-10, HO-1) factors. This study deepens the understanding of CAE and facilitates the preparation of CA oligomers for applications in food, cosmetics, and pharmaceuticals.

CAS / MDL: 367-93-1
研究领域: 微生物学 · 生物化学 · 医药科学
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JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES · 2018 · IF 0.827

A discrimination study of Asia ginseng and America ginseng by a comparison of ginsenosides, oligosaccharides and amino acids using a UPLC-MS method

Yang-Fang He,Han-Qing Cai,Wen-Ying Li,Yang Xiu,Wen-Long Liu,Hong-Yue Chi,Hong Shen,Mao-Guang Yang,Jin Pei,Shu-Ying Liu

A quantitative analysis of ginseng chemical ingredients was established using UPLC-MS, in which the concentrations of ginsenosides, oligosaccharides, and amino acids in ginseng were determined. Unlike the C18 column, which showed good performance in the determination of ginsenosides, the NH2 column was used in this method, and it exhibited good separation abilities for three types of compounds, including 6 saponins, 4 oligosaccharides, and 15 amino acids. For each type of compound, a recovery of 88%–111%, with relative standard deviations (RSD) better than 6% (n=6) were obtained; the limits of quantification (LOQ) for three types of substances were less than 1μg/mL. Furthermore, the method showed strong ability on the discrimination Asia Ginseng and America Ginseng, and was confirmed to be robust, selective, sensitive, rapid and inexpensive.GRAPHICAL

研究领域: 药用植物学 · 分析化学 · 中药学
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Marine Drugs · 2021 ·Vol. 19 ·期 11 ·596 · IF 5.118

Expression and Characterization of a Novel Cold-Adapted Chitosanase from Marine Renibacterium sp. Suitable for Chitooligosaccharides Preparation

Lin-Lin Zhang,Xiao-Hua Jiang,Xin-Feng Xiao,Wen-Xiu Zhang,Yi-Qian Shi,Zhi-Peng Wang,Hai-Xiang Zhou

(1) Background: Chitooligosaccharides (COS) have numerous applications due to their excellent properties. Chitosan hydrolysis using chitosanases has been proposed as an advisable method for COS preparation. Although many chitosanases from various sources have been identified, the cold-adapted ones with high stability are still rather rare but required. (2) Methods: A novel chitosanase named CsnY from marine bacteriumRenibacteriumsp. Y82 was expressed inEscherichia coli, following sequence analysis. Then, the characterizations of recombinant CsnY purified through Ni–NTA affinity chromatography were conducted, including effects of pH and temperature, effects of metal ions and chemicals, and final product analysis. (3) Results: The GH46 family chitosanase CsnY possessed promising thermostability at broad temperature range (0–50 °C), and with optimal activity at 40 °C and pH 6.0, especially showing relatively high activity (over 80% of its maximum activity) at low temperatures (20–30 °C), which demonstrated the cold-adapted property. Common metal ions or chemicals had no obvious effect on CsnY except Mn2+and Co2+. Finally, CsnY was determined to be an endo-type chitosanase generating chitodisaccharides and -trisaccharides as main products, whose total concentration reached 56.74 mM within 2 h against 2% (w/v) initial chitosan substrate. (4) Conclusions: The results suggest the cold-adapted CsnY with favorable stability has desirable potential for the industrial production of COS.Keywords:chitosanase;cold adaptation;chitooligosaccharide;Renibacteriumsp.

CAS / MDL: 9012-76-4
研究领域: 生物化学 · 生物技术 · 海洋生物学
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Foods · 2023 ·Vol. 12 ·期 7 ·1369 · IF 5.2

Improving the Yield of Feruloyl Oligosaccharides from Rice Bran through Enzymatic Extrusion and Its Mechanism

Fenghong Deng,Xiuting Hu,Yueru Wang,Shunjing Luo,Chengmei Liu

Rice bran, rich in feruloyl arabinoxylan, is a good source of feruloyl oligosaccharides (FOs). To prepare FOs, bran was often hydrolyzed by amylase and protease to remove starch and protein and then hydrolyzed by xylanase, which was time-consuming and had a low yield. To solve the above problems, enzymatic extrusion was used to treat rice bran, and the effects of traditional hydrolysis, a combination of traditional extrusion and hydrolysis (extrusion-hydrolysis) and enzymatic extrusion on the yield of FOs were investigated and compared in this study. It was found that traditional extrusion and enzymatic extrusion significantly increased the yield of FOs. Particularly, the yield of FOs resulting from enzymatic extrusion was increased to 5.78%, while the yield from traditional hydrolysis was 4.23%. Microscopy analysis showed that extrusion damaged the cell wall of bran, which might increase the accessibility of xylanase to arabinoxylan and the yield of FOs. Spectroscopy analysis suggested that FOs obtained by different pretreatments had similar structures. It was obvious that enzymatic extrusion saved the time for removal of starch and protein and increased the yield of FOs. In addition, the highest yield of FOs was found at the moisture content of 30% and the screw speed of 50 rpm. This study provided an efficient method for the preparation of FOs that is suitable for industrial production.Keywords:rice bran;feruloyl oligosaccharides;enzymatic extrusion;yield

研究领域: 食品科学 · 生物化学
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