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Chinese Chemical Letters 2024年第5期35卷 155-160页

作者： Shuying Li Weiwei ZhuGe Xuan Sun Chongzhen Sun Zhaojun Liu Chenghe Xiong Min Xiao Guofeng Gu National Glycoengineering Research Center and Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology Shandong UniversityQingdao 266237China NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based Medicine Shandong UniversityQingdao 266237China

The galactomannan from Antrodia cinnamomea(AC)is characterized as one of the important bioactive components that exhibits potential immunostimulatory propriety.The biological function of its corresponding oligosaccharide fragments has not been revealed yet.In this study,we reported the first chemical synthesis of the series of oligosaccharide fragments related to AC galactomannan via the convergent glycosylation strategy.The preliminary immunological evaluation of these synthesized AC oligosaccharides disclosed that the backbone tetrasaccharide 1d showed the best immunomodulatory ability on enhancing proliferation,phagocytosis and cytokines secretion of Raw264.7 macrophages in vitro,indicating its immense potential as an immunostimulant candidate.

关键词： Antrodia cinnamomea Galactomannan oligosaccharide Immunostimulatory propriety Chemical synthesis

Expression and Characterization of a Novelλ-Carrageenase Cgl150A_Wa from Wenyingzhuangia aestuarii

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Journal of Ocean University of China 2024年第1期23卷 209-215页

作者： SUN Yuhao CAO Siqi ZHANG Yuying XUE Changhu XIAO Hang CHANG Yaoguang College of Food Science and Engineering Ocean University of ChinaQingdao 266003China Marine Life Research Center Laoshan National LaboratoryQingdao 266237China Department of Food Science University of Massachusetts AmherstMA 01003United States

λ-Carrageenan is a highly sulfated polysaccharide alternating of 1,4-O-α-D-galactopyranose-2,6-sulfate(D2S,6S)and 1,3-O-β-D-galactopyranose-2-sulfate(G2S).λ-Carrageenases are desirable tools forλ-carrageenan degradation.Based on the genome mining,a novelλ-carrageenase Cgl150A_Wa was cloned from the bacterium Wenyingzhuangia aestuarii and expressed in Escherichia coli.Cgl150A_Wa was an endo-acting enzyme and exhibited its maximum activity at 30℃and pH 8.0.By employing a glycomics strategy that combined ultra-performance liquid chromatography-mass spectrometry analysis and glycoinformatics,Cgl150A_Wa was proven to degradeλ-carrageenan octaose and hexaose,and the major hydrolysis product of Cgl150A_Wa wasλ-carrageenan tetrose.In addition to the typicalλ-carrageenan motifs,the active center of Cgl150A_Wa might tolerate desulfatedλ-carrageenan motifs.Cgl150A_Wa is a potential biotechnological tool for preparingλ-carrageenan oligosaccharides and structural investigation.

关键词： carrageenan λ-carrageenase LC-MS oligosaccharide GH150

Structural characterization of oligosaccharide from Spirulina platensis and its effect on the faecal microbiota in vitro

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Food Science and Human Wellness 2022年第1期11卷 109-118页

作者： Bingna Cai Xiangxi Yi Qian Han Jianyu Pan Hua Chen Huili Sun Peng Wan Key Laboratory of Tropical Marine Bio-Resources and Ecology Guangdong Key Laboratory of Marine Materia MedicaSouth China Sea Institute of OceanologyChinese Academy of SciencesGuangzhou510301 GuangdongChina Southern Marine Science and Engineering Guangdong Laboratory(Guangzhou) Guangzhou511458 GuangdongChina School of Pharmacy Guangxi University of Chinese MedicineNanning530200 GuangxiChina Innovation Academy of South China Sea Ecology and Environmental Engineering(ISEE) Chinese Academy of SciencesGuangzhou510000 GuangdongChina

In the present study,an oligosaccharide SPO-1 from Spirulina platensis was prepared by glycosidase from a marine bacterium.The prebiotic activity of SPO-1 on the growth of Lactobacillus paracasei and Bifidobacterium animalis,and its effect on human gut microbiota were examined in vitro.The molecular weight of the tetrasaccharide SPO-1 was 650.2 Da,and it was mainly composed of glucose with α-type glycosidic linkages.The prebiotic activity score of SPO-1 was the highest for the growth of probiotic strains L.paracasei and B.animalis.Furthermore,as fermentation proceeded,SPO-1 was gradually degraded and utilized by intestinal bacteria.The results showed that after treatment with SPO-1,carbohydrate consumption and short-chain fatty acids levels were increased,especially those of i-butyric and i-valeric acids.Moreover,SPO-1 significantly promoted the abundance,diversity and composition of gut microbiota,especially stimulating the growth of Bacteroides,Escherichia-Shigella and Megamonas.In addition,the change in intestinal microbiota function predicted by phylogenetic investigation of communities by reconstruction of unobserved states(PICRUSt)after treatment with SPO-1 is mainly related to the terms“carbohydrate metabolism”and“amino acid metabolism”.These results suggest that SPO-1 is a potential oligosaccharide in regulation of intestinal microbiota.

关键词： oligosaccharide Spirulina platensis Gut microbiota In vitro fermentation

Alginate oligosaccharide-induced intestinal morphology, barrier function and epithelium apoptosis modifications have beneficial effects on the growth performance of weaned pigs

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Journal of Animal Science and Biotechnology 2018年第4期9卷 937-948页

作者： Jin Wan Jiao Zhang Daiwen Chen Bing Yu Xiangbing Mao Ping Zheng Jie Yu Junqiu Luo Jun He Institute of Animal Nutrition Sichuan Agricultural University

Background: Alginate oligosaccharide(AOS), produced from alginate by alginate lyase-mediated depolymerisation, is a potential substitute for antibiotics and possesses growth-enhancing effects. Nevertheless, the mechanisms by which AOS regulates porcine growth remain to be elucidated. Therefore, we investigated the AOS-mediated changes in the growth performance of weaned pigs by determining the intestinal morphology, barrier function,as well as epithelium apoptosis.Methods: Twenty-four weaned pigs were distributed into two groups(n = 12) and received either a basal diet(control group) or the same diet supplemented with 100 mg/kg AOS. On d 15, D-xylose(0.1 g/kg body weight)was orally administrated to eight randomly selected pigs per treatment, and their serum and intestinal mucosa samples were collected 1 h later.Results: Our results showed that inclusion of AOS in the diet for 2 wk increased(P < 0.05) the average daily body weight gain in weaned pigs. Notably, AOS supplementation ameliorated the intestinal morphology and barrier function, as suggested by the enhanced(P < 0.05) intestinal villus height, secretory immunoglobulin A content and goblet cell counts. Compared to the control group, AOS ingestion both decreased(P < 0.05) the total apoptotic percentage and increased(P < 0.05) the proportion of S phase in the intestinal epithelial cells. Furthermore, AOS not only up-regulated(P < 0.05) the B-cell lymphoma-2(BCL2) transcriptional level but also down-regulated(P < 0.05) the B-cell lymphoma-2-associated X protein(BAX), cysteinyl aspartate-specific proteinase-3(caspase-3) and caspase-9 transcriptional levels in the small intestine.Conclusions: In summary, this study provides evidence that supplemental AOS beneficially affects the growth performance of weaned pigs, which may result from the improved intestinal morphology and barrier function,as well as the inhibited enterocyte death, through reducing apoptosis via mitochondria-dependent apoptosis.

关键词： Alginate oligosaccharide Barrier function Cell apoptosis Intestinal morphology Weaned pigs

oligosaccharide and Creatine Supplementation on Glucose and Urea Nitrogen in Blood and Serum Creatine Kinase in Basketball Athletes

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Journal of Huazhong University of Science and Technology(Medical Sciences) 2005年第5期25卷 587-589页

作者：石大玲 Department of Physical Education Tongji Medical College Huazhong University of Science and Technology Wuhan 430030 China

Summary： The effects of oligosaccharide and creatine （Cr） supplementation on glucose, lactic acid and urea nitrogen levels in blood and activity of serum creatine kinase （CK） were explored. Twenty CUBA male athletes were divided into 4 groups： group A （supplementation of Cr alone）, group B （supplementation of oligosaccharide）, group C （supplementation of oligosaccharide and Cr） and group D （placebo control group）. By using orthogonal L4 table （2a ）, the experiment was performed. There were factors including oligosaccharide （carbohydrate, CHO）, Cr and their correlation. Each factor had two levels： supplementation and no-supplementation. The results showed that the supplementation of CliO or Cr alone, combined supplementation of CHO and Cr could significantly reduce the glucose, urea nitrogen levels in blood and serum CK activity after competition in the athletes. Moreover, the effects of combined supplementation of CHO and Cr were more satisfactory. It was concluded that supplementation of CliO and Cr could promote the recovery of physical performance and athletic abilities after athletics in basketball athletes.

关键词： oligosaccharide creatine blood glucose blood urea nitrogen serum creatine kinase basketball athlete

An efficient and facile approach for the construction of chondroitin sulfate E oligosaccharide precursors

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Chinese Chemical Letters 2019年第3期30卷 686-689页

作者： Guangyan Zhang Qi Liu Shuang Yang Zhehui Zhao Pingsheng Lei State Key Laboratory of Bioactive Substance and Function of Natural Medicines Beijing Key Laboratory of Active Substances Discovery and Drug ability Evaluation Department of Medicinal Chemistry Institute of Materia Medica & Peking Union Medical College Chinese Academy of Medical Sciences

An efficient and facile approach has been developed for the construction of chondroitin sulfate E(CS-E)oligosaccharide precursors. In this approach, the disaccharide unit with the GalNAc-GIcA sequence was first elongated to form tetra-and hexasaccharides followed by the introduction of anomeric groups via glycosylation couplings. A number of CS-E tetra-and hexasaccharide precursors were prepared in high yields.

关键词： Chon droitin sulfate E Glycosylation oligosaccharide Anomeric group Modification

Structural Analysis of an oligosaccharide and Glycopeptide Mixture from Panax Ginseng Root with Inhibition SHP-1 Function

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Chemical Research in Chinese Universities 2011年第1期27卷 104-107页

作者： WANG Ying GAO Qi-pin LI Gui-rong CHEN Ying-hong LUO Hao-ming GAO Yang JIANG Rui-zhi College of Light Industry and Food South China University of Technology Guangzhou 510641 P R. China Center for New Medicine Research Changchun University of Chinese Medicine Changchun 130117 P R. China School of Pharmacy Yanbian University Yanji 133000 P. R. China Academy of Chinese Medicine and Material Medica of Jilin Province Changchun 130021 P R. China

A mixture of oligosaccharide and glycopeptide was isolated from the aqueous extract of Panax ginseng roots. The mixture inhibits protein tyrosinc phosphatase（SHP-1） function, implying it enhances immune activity. The peak molecular mass of the oligosaccharide portion is 1800 calculated via GPC software after separation by HPLC. And the structure of the oligosaccharide portion is the backbone of （1→3）- and （1→4）-linked arabinopyranoside, and （1→4）- and （1→6）-linked glucopyranoside, with non-reducing terminals of arabinopyranoside and glucopyranoside. The peak molecular mass of glycopeptide portion is 1900 calculated via GPC software after separation by HPLC. The structure of glycopeptide portion is the backbone of （1→3）- and （1→4）-linked arabinopyranoside, and （1→3,6）-linked glucopyranoside, with non-reducing terminals of galactopyranose and glucopyranoside. The peptide composition is Glu. Asp, Hyp, Set, Arg, Gly , Thr, Pro, Ala, Val, lie, Leu and Lys. The oligosaccharide-peptide linkage is formed by Ara and Hyp.

关键词： Panax ginseng oligosaccharide Glycopeptide Protein tyrosine phosphatase（SHP-1） Methylation analysis

Effects of blocking Le^Y oligosaccharide on cell surface to MMPs secreted by blastocysts and epithelial cells in mouse in vitro

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Chinese Science Bulletin 1998年第17期43卷 1461-1465页

作者： Xiaoqi Wang Yu Liu Enkui Duan Guoqing Zeng Zhengmei Zhu Chinese Acad Sci Inst Zool State Key Lab Reprod Biol Beijing 100080 Peoples R China Dalian Med Univ Dept Biochem Dalian 116027 Peoples R China

In order to understand the role of Le+Y oligosaccharide antigen (Le+Y) during implantation, the relationship of Le+Y on the cell surface with matrix metalloproteinase (MMPs) secreted by blastocysts and monolayer epithelial cells during implantation in the mouse %in vitro% was studied by monoclonal antibody (mAb) AH-6, directed to Le+Y[Fuc α1-2 Gal β1-4 (Fuc α1-3) GlcNAc-], and gelatin zymography. The results showed that MMPs secretion was reduced after Le+Y on the cell surface of either epithelial cells or trophoblasts was blocked. It indicated that MMPs expression which played an important function during the process of implantation were regulated by Le+Y. Therefore, it was considered that Le+Y could regulate embryos invasion by some mechanism.

关键词： mouse Le+Y oligosaccharide antigen matrix metalloproteinases implantation monoclonal antibody.

Ileal profile of non-starch polysaccharides and oligosaccharides in response to exogenous enzymes in broiler chickens offered wheat-or maize-based diets under subclinical necrotic enteritis challenge

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Animal Nutrition 2022年第3期10卷 207-215页

作者： Eunjoo Kim Amy F.Moss Natalie K.Morgan Kosar Gharib-Naseri Peter Ader Mingan Choct School of Environmental and Rural Science University of New EnglandArmidaleNSW2351Australia BASF SE 68623LampertheimGermany

The present study evaluated the impacts of fibre-degrading enzymes on the profiles of non-starch polysaccharides(NSP)and oligosaccharides(OS)in the ileum of broiler chickens offered wheat-or maize-based diets under subclinical necrotic enteritis(NE)challenge.A 224 factorial arrangement of treatments was used.Factors were the following:NE challenge,no or yes;diet type,wheat-or maizebased;and supplemental enzymes,control(no enzyme),family 10 xylanase(XYN10),family 11 xylanase(XYN11)or b-mannanase(MAN).Birds in the challenged group were inoculated with Eimeria on d 9 and Clostridium perfringens on d 14 and 15.A 3-way interaction(P=0.047)occurred on overall(d 0 to 16)weight gain.When NE was present,all the supplemental enzymes increased weight gain in birds fed the wheat-based diet;whereas in those fed the maize-based diet supplemental XYN10 and XYN11 decreased weight gain.When NE was absent,birds fed the wheat-based diet supplemented with XYN10 or MAN presented increased weight gain compared to non-supplemented birds,but no improvements with enzyme addition were observed in birds fed the maize-based diet.A 3-way interaction(P=0.002)was observed on insoluble NSP level in the ileum.When NE was absent,all the supplemental enzymes reduced the ileal level of insoluble NSP,regardless of diet type.In the challenged birds,supplementing XYN10 and MAN reduced insoluble NSP level in the ileum,but only in birds fed the wheat-based diet.Ileal soluble NSP level was reduced by supplemental XYN11 and MAN,but only in birds fed the wheatbased diet,resulting in a 2-way diet typeenzyme interaction(Poligosaccharide release.However,enzyme addition did not improve growth performance in birds fed maize-based diet,with supplemental XYN10 and XYN11 impeding weig

关键词： Broiler chicken Non-starch polysaccharide Subclinical necrotic enteritis oligosaccharide

Pharmacokinetics,distribution,and excretion of sodium oligomannate,a recently approved anti-Alzheimer's disease drug in China

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Journal of Pharmaceutical Analysis 2022年第1期12卷 145-155页

作者： Jiaojiao Lu Qiongqun Pan Jieqiang Zhou Yan Weng Kaili Chen Lv Shi Guanxiu Zhu Chunlin Chen Liang Li Meiyu Geng Zhenqing Zhang Jiangsu Key Laboratory of Translational Research and Therapy for Neuro-Psycho-Diseases College of Pharmaceutical SciencesSoochow UniversitySuzhouJiangsu215021China Shanghai Green Valley Pharma.Corp. Shanghai201203China Medicilon Preclinical Research(Shanghai)LLC Shanghai201299China State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai201203China

The National Medical Products Administration has authorized sodium oligomannate for treating mild-to-moderate Alzheimer’s disease.In this study,an LC-MS/MS method was developed and validated to quantitate sodium oligomannate in different biomatrices.The plasma pharmacokinetics,tissue distribution,and excretion of sodium oligomannate in Sprague-Dawley rats and beagle dogs were systematically investigated.Despite its complicated structural composition,the absorption,distribution,metabolism,and excretion profiles of the oligosaccharides in sodium oligomannate of different sizes and terminal derivatives were indiscriminate.Sodium oligomannate mainly crossed the gastrointestinal epithelium through paracellular transport following oral administration,with very low oral bioavailability in rats(0.6%-1.6%)and dogs(4.5%-9.3%).Absorbed sodium oligomannate mainly resided in circulating body fluids in free form with minimal distribution into erythrocytes and major tissues.Sodium oligomannate could penetrate the blood-cerebrospinal fluid(CSF)barrier of rats,showing a constant area under the concentration-time curve ratio(CSF/plasma)of approximately 5%.The cumulative urinary excretion of sodium oligomannate was commensurate with its oral bioavailability,supporting that excretion was predominantly renal,whereas no obvious biliary secretion was observed following a single oral dose to bile duct-cannulated rats.Moreover,only 33.7%(male)and 26.3%(female)of the oral dose were recovered in the rat excreta within 96 h following a single oral administration,suggesting that the intestinal flora may have ingested a portion of unabsorbed sodium oligomannate as a nutrient.

关键词： Sodium oligomannate Alzheimer’s disease Pharmacokinetics LC-MS/MS oligosaccharide