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Glycoside-specific metabolomics combined with precursor isotopic labeling for characterizing plant glycosyltransferases

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Molecular Plant 2022年第10期15卷 1517-1532页

作者： Jie Wu Wentao Zhu Xiaotong Shan Jinyue Liu Lingling Zhao Qiao Zhao Shenzhen Key Laboratory of Synthetic Genomics Guangdong Provincial Key Laboratory of Synthetic GenomicsCAS Key Laboratory of Quantitative Engineering BiologyShenzhen Institute of Synthetic BiologyShenzhen Institutes of Advanced TechnologyChinese Academy of SciencesShenzhen 518055China Innovation Center of Pesticide Research Department of Applied ChemistryCollege of ScienceChina Agricultural UniversityBeijing 100193China Center for Plant Biology School of Life SciencesTsinghua UniversityBeijing 100084China

Glycosylation by uridine diphosphate-dependent glycosyltransferases(UGTs)in plants contributes to the complexity and diversity of secondary metabolites.UGTs are generally promiscuous in their use of acceptors,making it challenging to reveal the function of UGTs in vivo.Here,we described an approach that combined glycoside-specific metabolomics and precursor isotopic labeling analysis to characterize UGTs in Arabidopsis.We revisited the UGT72E cluster,which has been reported to catalyze the glycosylation of monolignols.Glycoside-specific metabolomics analysis reduced the number of differentially accumulated metabolites in the ugt72e1e2e3 mutant by at least 90%compared with that from traditional untargeted metabolomics analysis.In addition to the two previously reported monolignol glycosides,a total of 62 glycosides showed reduced accumulation in the ugt72e1e2e3 mutant,22 of which were phenylalanine-derived glycosides,including 5-OH coniferyl alcohol-derived and lignan-derived glycosides,as confirmed by isotopic tracing of[^(13)C_(6)]-phenylalanine precursor.Our method revealed that UGT72Es could use coumarins as substrates,and genetic evidence showed that UGT72Es endowed plants with enhanced tolerance to low iron availability under alkaline conditions.Using the newly developed method,the function of UGT78D2 was also evaluated.These case studies suggest that this method can substantially contribute to the characterization of UGTs and efficiently investigate glycosylation processes,the complexity of which have been highly underestimated.

关键词： glycosyltransferases glycosides-specific metabolomics precursor isotopic labeling glucoside Arabidopsis thaliana phenylpropanoid coumarins

glycosyltransferases and non-alcoholic fatty liver disease

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World Journal of Gastroenterology 2016年第8期22卷 2483-2493页

作者： Yu-Tao Zhan Hai-Ying Su Wei An Department of Gastroenterology Beijing Tongren Hospital Capital Medical University Department of Obstetrics and Gynecology Shandong Jining First People’s Hospital Department of Cell Biology Municipal Laboratory for Liver Protection and Regulation of Regeneration Capital Medical University

Non-alcoholic fatty liver disease(NAFLD) is the most common form of chronic liver disease and its incidence is increasing worldwide. However, the underlying mechanisms leading to the development of NAFLD are still not fully understood. glycosyltransferases(GTs) are a diverse class of enzymes involved in catalyzing the transfer of one or multiple sugar residues to a wide range of acceptor molecules. GTs mediate a wide range of functions from structure and storage to signaling, and play a key role in many fundamental biological processes. Therefore, it is anticipated that GTs have a role in the pathogenesis of NAFLD. In this article, we present an overview of the basic information on NAFLD, particularly GTs and glycosylation modification of certain molecules and their association with NAFLD pathogenesis. In addition, the effects and mechanisms of some GTs in the development of NAFLD are summarized.

关键词： Non-alcoholic fatty liver disease Pathogenesis glycosyltransferases Glycosylation

Attractive but Toxic： Emerging Roles of Glycosidically Bound Volatiles and glycosyltransferases Involved in Their Formation

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Molecular Plant 2018年第10期11卷 1225-1236页

作者： Chuankui Song Katja Hartl Kate McGraphery Thomas Hoffmann Wilfried Schwab State Key Laboratory of Tea Plant Biology and Utilization Anhui Agricultural University West Changjiang Road Hefei Anhui 230036 China Biotechnology of Natural Products Technische Universitat Munchen Liesel-Beckmann-Str. 1 Freising 85354 Germany

Plants emit an overabundance of volatile compounds, which act in their producers either as appreciated attractants to lure beneficial animals or as repellent toxins to deter pests in a species-specific and concentration-dependent manner. Plants have evolved solutions to provide sufficient volatiles without poisoning themselves. Uridine-diphosphate sugar-dependent glycosyltransferases （UGTs） acting on vola-tiles is one important part of this sophisticated system, which balances the levels of bioactive metabolites and prepares them for cellular and long-distance transport and storage but enables the remobilization of disarmed toxins for the benefit of plant protection. This review provides an overview of the research history of glycosidically bound volatiles （GBVs）, a relatively new group of plant secondary metabolites, and discusses the role of UGTs in the production of GBVs for plant protection.

关键词： glycosyltransferases terpenoids volatiles plant protection transport storage

Construction of a Rice Glycosyltransferase Phylogenomic Database and Identification of Rice-Diverged glycosyltransferases

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Molecular Plant 2008年第5期1卷 858-877页

作者： Pei-Jian Cao Laura E. Bartley Ki-Hong Jung Pamela C. Ronald Department of Plant Pathology University of California Davis CA 95616 and the Joint BioEnergy Institute Emeryville CA 94710 USA Institute of Bioinformatics Zhejiang University Hangzhou Zhejiang 310029 China

glycosyltransferases （GTs; EC 2.4.x.y） constitute a large group of enzymes that form glycosidic bonds through transfer of sugars from activated donor molecules to acceptor molecules. GTs are critical to the biosynthesis of plant cell walls, among other diverse functions. Based on the Carbohydrate-Active enZymes （CAZy） database and sequence similarity.searches, we have identified 609 potential GT genes （loci） corresponding to 769 transcripts （gene models） in rice （Oryza sativa）, the reference monocotyledonous species. Using domain composition and sequence similarity, these rice GTs were classified into 40 CAZy families plus an additional unknown class. We found that two Pfam domains of unknown function, PF04577 and PF04646, are associated with GT families GT61 and GT31, respectively. To facilitate functional analysis of this important and large gene family, we created a phylogenomic Rice GT Database （http：//ricephylogenomics. ucdavis.edu/cellwalls/gtJ）. Through the database, several classes of functional genomic data, including mutant lines and gene expression data, can be displayed for each rice GT in the context of a phylogenetic tree, allowing for comparative analysis both within and between GT families. Comprehensive digital expression analysis of public gene expression data revealed that most （-80%） rice GTs are expressed. Based on analysis with Inparanoid, we identified 282 ‘rice-diverged＇ GTs that lack orthologs in sequenced dicots （Arabidopsis thaliana, Populus tricocarpa, Medicago truncatula, and Ricinus communis）. Combining these analyses, we identified 33 rice-diverged GT genes （45 gene models） that are highly expressed in above-ground, vegetative tissues. From the literature and this analysis, 21 of these loci are excellent targets for functional examination toward understanding and manipulating grass cell wall qualities. Study of the remainder may reveal aspects of hormone and protein metabolism that are critical for rice biology. This list of 33 genes and the Rice GT Database will facilitate the stud

关键词： glycosyltransferases GT phylogenetic tree orthologs expression pattern mutant lines phylogenomic database rice cell wall.

Dietary fiber in plant cell walls-the healthy carbohydrates

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Food Quality and Safety 2022年第2期6卷 125-141页

作者：安轶陆伟泰李文泽潘浪浪卢孟柱 Igor Cesarino 李争曾为 State Key Laboratory of Subtropical Silviculture College of Forestry and BiotechnologyZhejiang A&F UniversityHangzhouChina State Key Labor atory for Conservation and Utilization of Bio-Resources in Yunnan School of AgricultureYunnan UniversityKunmingChina Department of Botany Institute of BiosciencesUniversity of Sao PauloRua do MataoSao PauloBrazil

Dietary fiber(DF)is one of the major classes of nutrients for humans.It is widely distributed in the edible parts of natural plants,with the cell wall being the main DF-containing structure.DF content varies significantly in different plant species and organs,and the processing procedure can have a dramatic effect on the DF composition of plant-based foods.Given the considerable nutritional value of DF,a deeper understanding of DF in food plants,including its composition and biosynthesis,is fundamental to the establishment of a daily intake reference of DF and is also critical to molecular breeding programs for modifying DF content.In the past decades,plant cell wall biology has seen dramatic progress,and such knowledge is of great potential to be translated into DF-related food science research and may provide future research directions for improving the health benefits of food crops.In this review,to spark interdisciplinary discussions between food science researchers and plant cell wall biologists,we focus on a specific category of DF--cell wall carbohydrates.We first summarize the content and composition of carbohydrate DF in various plant-based foods,and then discuss the structure and biosynthesis mechanism of each carbohydrate DF category,in particular the respective biosynthetic enzymes.Health impacts of DF are highlighted,and finally,future directions of DF research are also briefly outlined.

关键词： Dietary fiber carbohydrate plant cell wall polysaccharide glycosyltransferases healthy food

Filling the Gaps to Solve the Extensin Puzzle

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Molecular Plant 2018年第5期11卷 645-658页

作者： Eliana Marzol Cecilia Borassi Mauro Bringas Ana Sede Diana Rosa Rodriguez Garcia Luciana Capece Jose M. Estevez Fundacion Instituto Leloir and Instituto de Investigaciones Bioquimicas de Buenos Aires (IIBBA-CO.NICEr) Avenida Patricias Argentinas 435 Buenos AiresCP C1405BWE Argentina Departamento de Quimica Inorganica Analitica y Quimica Fisica Facultad de Ciencias Exactas y Naturales Universidad de Buenos Aires (INQUIMAE-CONICET)Buenos Aires CP C1428EGA Argentina Instituto de Investigaciones en Ingenierfa Genetica y Biologia Molecular Dr. Hector Torres (INGEBI-CONICET) Vuelta de Obligado 2490 Buenos Aires C1428ADNArgentina

Extensins （EXTs） are highly repetitive plant O-glycoproteins that require several post-translational modifi- cations （PTMs） to become functional in plant cell walls. First, they are hydroxylated on contiguous proline residues; then they are O-glycosylated on hydroxyproline and serine. After secretion into the apoplast, O-glycosylated EXTs form a tridimensional network organized by inter- and intra-Tyr linkages. Recent studies have made significant progress in the identification of the enzymatic machinery required to process EXTs, which includes prolyl 4-hydroxylases, glycosyltransferases, papain-type cysteine endopeptidases, and peroxidases. EXTs are abundant in plant tissues and are particularly important in rapidly expanding root hairs and pollen tubes, which grow in a polar manner. Small changes in EXT PTMs affect fastgrowing cells, although the molecular mechanisms underlying this regulation are unknown. In this review, we highlight recent advances in our understanding of EXT modifications throughout the secretory pathway, EXT assembly in cell walls, and possible sensing mechanisms involving the Catharanthus roseus cell surface sensor receptor-like kinases located at the interface between the apoplast and the cytoplasmic side of the plasma membrane.

关键词： Arabidopsis thaliana cysteine endopeptidases extensins glycosyltransferases peroxidases prolyl 4-hydroxylases

Developmentally Regulated Glucosylation of Bitter Triterpenoid in Cucumber by the UDP-Glucosyltransferase UGT73AM3

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Molecular Plant 2017年第7期10卷 1000-1003页

作者： Yang Zhong Xiaofeng Xue Zhiqiang Liu Yongshuo Ma Kewu Zeng Lida Han Jingjing Qi Dae-Kyun Ro Soren Bak Sanwen Huang Yuan Zhou Yi Shang Key Laboratory of Biology and Genetic Improvement of Horticultural Crops of the Ministry of Agriculture Sino-Dutch Joint Laboratory of Horticultural Genomics Institute of Vegetables and Flowers Chinese Academy of Agricultural Sciences Beijing 100081 China Agriculturat Genome Institute at Shenzhen Chinese Academy of Agricultural Science Shenzhen 518124 China Tongji School of Pharmacy Huazhong University of Science and Technology 13 Hangkong Road Wuhan 430030 China Institute of Apicuiture Research Chinese Academy of Agricultural Sciences Beijing 100093 China School of Life Science Shanxi University Taiyuan 030006 China School of Pharmaceutical Sciences Peking University Health Science Center Beijing 100191 China Biotechnology Research Institute Chinese Academy of Agricultural Sciences Beijing 100081 China College of Life Sciences Nanjing Agricultural University Nanjing 210095 China Department of Biological Sciences University of Calgary Calgary T2N 1N4 Canada Department of Plant and Environmental Sciences Copenhagen PlantScience Centre University of Copenhagen Copenhagen 1871 Denmark

Dear Editor,Plants have evolved great plasticity to adapt to external environments. A huge number of structurally diverse metabolites gener- ated through the glycosylation process is one potential mechanism that contr... 详细信息

关键词： SATIVUS L glycosyltransferases BIOSYNTHESIS RESISTANCE

Unraveling the serial glycosylation in the biosynthesis of steroidal saponins in the medicinal plant Paris polyphylla and their antifungal action

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Acta Pharmaceutica Sinica B 2023年第11期13卷 4638-4654页

作者： Yuegui Chen Qin Yan Yunheng Ji Xue Bai Desen Li Rongfang Mu Kai Guo Minjie Yang Yang Tao Jonathan Gershenzon Yan Liu Shenghong Li State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China State Key Laboratory of Southwestern Chinese Medicine Resources Innovative Institute of Chinese Medicine and PharmacyChengdu University of Traditional Chinese MedicineChengdu 611137China Key Laboratory for Plant Diversity and Biogeography of East Asia Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China Max Planck Institute for Chemical Ecology Jena D-07745Germany University of Chinese Academy of Sciences Beijing 100049China

Sugar-sugar glycosyltransferases play important roles in constructing complex and bioactive saponins.Here,we characterized a series of UDP-glycosyltransferases responsible for biosynthesizing the branched sugar chain of bioactive steroidal saponins from a widely known medicinal plant Paris polyphylla var.yunnanensis.Among them,a 2'-O-rhamnosyltransferase and three 6'-O-glucosyltrasferases catalyzed a cascade of glycosylation to produce steroidal diglycosides and triglycosides,respectively.These UDP-glycosyltransferases showed astonishing substrate promiscuity,resulting in the generation of a panel of 24 terpenoid glycosides including 15 previously undescribed compounds.A mutant library containing 44 variants was constructed based on the identification of critical residues by molecular docking simulations and protein model alignments,and a mutant UGT91AH1^(Y187A)with increased catalytic efficiency was obtained.The steroidal saponins exhibited remarkable antifungal activity against four widespread strains of human pathogenic fungi attributed to ergosterol-dependent damage of fungal cell membranes,and 2'-O-rhamnosylation appeared to correlate with strong antifungal effects.The findings elucidated the biosynthetic machinery for their production of steroidal saponins and revealed their potential as new antifungal agents.

关键词： Paris polyphylla var.yunnanensis Steroidal saponins glycosyltransferases Sugar chain elongation Antifungal activity

The Cooperative Activities of CSLD2, CSLD3, and CSLD5 Are Required for Normal Arabidopsis Development

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Molecular Plant 2011年第6期4卷 1024-1037页

作者： Lan Yin Yves Verhertbruggen Ai Oikawa Chithra Manisseri Bernhard Knierim Lina Prak Jacob Kriiger Jensen Paul Knox Manfred Auer William G.T. Willatsa and Henrik Vibe Scheller Department of Plant Biology and Biotechnology Faculty of Life Sciences University of Copenhagen DK-1871 Frederiksberg C Denmark Joint BioEnergy Institute Feedstocks Division 5885 Hollis St Emeryville CA 94608 USA Present address： Department of Arctic and Marine Biology University of Tromso 9037 Tromse Norway Physical Biosciences Division Lawrence Berkeley National Laboratory Berkeley CA 94720 USA Present address： Molecular Phytopathology and Genetics University of Hamburg D-22609 Hamburg Germany f Joint BioEnergy Institute Technology Division 5885 Hollis St Emeryville CA 94608 USA Life Sciences Division Lawrence Berkeley National Laboratory Berkeley CA 94720 USA Present address： Department of Plant Biology Michigan State University East Lansing MI 48824 USA Centre for Plant Sciences Faculty of Biological Sciences University of Leeds Leeds LS2 9JT UK Department of Plant and Microbial Biology University of California Berkeley CA 94720 USA Joint BioEnergy Institute Technology Division 5885 Hoilis St Emeryville CA 94608 USA

glycosyltransferases of the Cellulose Synthase Like D （CS/D） subfamily have been reported to be involved in tip growth and stem development in Arabidopsis. The csld2 and csld3 mutants are root hair defective and the csld5 mutant has reduced stem growth. In this study, we produced double and triple knockout mutants of CSLD2, CSLD3, and CSLD5. Unlike the single mutants and the csld2/csld3 double mutant, the csld2/csld5, csld3/csld5, and csld2/csld3/csld5 mutants were dwarfed and showed severely reduced viability. This demonstrates that the cooperative activities of CSLD2, CSLD3, and CSLD5 are required for normal Arabidopsis development, and that they are involved in important processes besides the specialized role in tip growth. The mutant phenotypes indicate that CSLD2 and CSLD3 have overlapping functions with CSLD5 in early plant development, whereas the CSLD2 and CSLD3 proteins are non-redundant. To determine the biochemical function of CSLD proteins, we used transient expression in tobacco leaves. Microsomes containing heterologously expressed CSLD5 transferred mannose from GDP-mannose onto endogenous acceptors. The same activity was detected when CSLD2 and CSLD3 were coexpressed but not when they were expressed separately. With monosaccharides as exogenous acceptors, microsomal preparations from CSLD5-expressing plants mediated the transfer of mannose from GDP-mannose onto mannose. These results were supported by immunodetection studies that showed reduced levels of a mannan epitope in the cell walls of stem interfascicular fibers and xylem vessels of the csld2/csld3/csld5 mutant.

关键词： Cellulose synthase like hemicelluloses mannan glycosyltransferases polysaccharide plant development.