Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_581504,IEDB_983931,SB_192

• Article ID: 3744
  Molinaro A, Newman M, Lanzetta R, Parrilli M "The structures of lipopolysaccharides from plant-associated Gram-negative bacteria" - European Journal of Organic Chemistry 2009(34) (2009) 5887-5896
  

  Gram-negative bacterial lipopolysaccharides (LPSs) have multiple roles in plant-microbe interactions. LPSs contribute to the low permeabilities of bacterial outer membranes, which act as barriers to protect bacteria from plant-derived antimicrobial substances. Conversely, perception of LPSs by plant cells can lead to the triggering of defence responses or to the priming of the plant to respond more rapidly and/or to a greater degree to subsequent pathogen challenge. LPSs are thus key molecules in the interactions between bacteria and plants, either in symbiosis or pathogenesis. Since LPSs are glycoconjugates genetically and chemically consisting of three different molecular regions, their detailed structure elucidation is a very topical and major scientific task for chemists, and is achieved by a combination of state-of-art chemical and spectroscopic techniques. Knowledge of LPSs' chemical structures is an important prerequisite for any further understanding of the biological processes in plant-microbe interactions. Moreover, the LPSs from Gram-negative bacteria - especially those originating from plant-associated bacteria - are a great source of novel monosaccharides with unusual and occasionally astounding chemical structures, never found in the eukaryotic world. This review presents the structures of LPSs from plant-associated bacteria isolated and identified from 2001 onwards.

  lipopolysaccharides, structure elucidation, glycolipids, innate immunity, immunochemistry, plant-associated bacteria

  Publication DOI: 10.1002/ejoc.200900682
  Journal NLM ID: 9805750
  Publisher: Wiley-VCH
  Correspondence: molinaro@unina.it
  Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli “Federico II”, via Cinthia 4, 80126 Napoli, Italy, Fax: +39-081-674393, Faculty of Life Sciences, Department of Plant Biology & Biotechnology, University of Copenhagen, 1871 Frederiksberg, Denmark
  
   
  
  Burkholderia cepacia ASP B 2D
  CSDB ID 24123 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_581504

• Article ID: 4796
  Senchenkova SN, Popova AV, Shashkov AS, Shneider MM, Mei Z, Arbatsky NP, Liu B, Miroshnikov KA, Volozhantsev NV, Knirel YA "Structure of a new pseudaminic acid-containing capsular polysaccharide of Acinetobacter baumannii LUH5550 having the KL42 capsule biosynthesis locus" - Carbohydrate Research 407 (2015) 154-157
  

  The capsular polysaccharide from Acinetobacter baumannii LUH5550 was studied by 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure of the branched trisaccharide repeating unit was established: [structure: see text] where Pse5Ac7RHb indicates 5-acetamido-3,5,7,9-tetradeoxy-7-[(R)-3-hydroxybutanoylamino]-L-glycero-L-manno-non-2-ulosonic acid. The genes in the capsule biosynthesis locus designated KL42 are consistent with the structure established.

  Acinetobacter baumannii, pseudaminic acid, capsular polysaccharide structure, polysaccharide gene locus

  NCBI PubMed ID: 25776191
  Publication DOI: 10.1016/j.carres.2015.02.006
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: yknirel@gmail.com
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, NMR-1D, GPC, bioinformatic analysis
  
   
  
  Acinetobacter baumannii LUH5550
  CSDB ID 30671 (all data & tools)
• Article ID: 4819
  Giguere D "Surface polysaccharides from Acinetobacter baumannii: Structures and syntheses" - Carbohydrate Research 418 (2015) 29-43
  

  The emergence of multidrug-resistance Acinetobacter baumannii requires novel approaches for prevention, treatment and diagnosis. The structures of surface polysaccharides from A. baumannii are valuable tools to understand pathogenesis, virulence and immunogenicity. The synthesis of bacterial mono- or polysaccharides may result in novel probes to become important therapeutic options in the fight against A. baumannii. This report exemplifies the relevance of glycochemistry for the development of new antibiotics.

  lipopolysaccharides, capsular polysaccharides, Acinetobacter, Acinetobacter baumannii, polysaccharide synthesis, surface polysaccharides

  NCBI PubMed ID: 26531136
  Publication DOI: 10.1016/j.carres.2015.10.001
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: denis.giguere@chm.ulaval.ca
  Institutions: Département de Chimie, Université Laval, Québec City, Québec, Canada G1V 0A6
  
   
  
  Acinetobacter baumannii LUH5550
  CSDB ID 30945 (all data & tools)
• Article ID: 5458
  Kenyon JJ, Arbatsky NP, Shashkov AS, Shneider MM, Popova AV, Hall RM, Knirel YA "Production of the K16 capsular polysaccharide by Acinetobacter baumannii ST25 isolate D4 involves a novel glycosyltransferase encoded in the KL16 gene cluster" - International Journal of Biological Macromolecules 128 (2019) 101-106
  

  A new capsular polysaccharide (CPS) biosynthesis gene cluster, KL16, was found in the genome sequence of a clinical Acinetobacter baumannii ST25 isolate, D4. The variable part of KL16 contains a module of genes for synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic acid (5,7-di-N-acetylpseudaminic acid, Pse5Ac7Ac), a gene encoding ItrA3 that initiates the CPS synthesis with d-GlcpNAc, and two glycosyltransferase (Gtr) genes. The K16 CPS was studied by sugar analysis and Smith degradation along with 1D and 2D 1H and 13C NMR spectroscopy, and shown to be built up of linear trisaccharide repeats containing d-galactose (d-Gal), N-acetyl-d-glucosamine (d-GlcNAc), and Pse5Ac7Ac. The d-Galp residue is linked to the d-GlcpNAc initiating sugar via a β-(1→3) linkage evidently formed by a Gtr5 variant, Gtr5K16, encoded in KL16. This reveals an altered or relaxed substrate specificity of this variant as the majority of Gtr5-type glycosyltransferases have previously been shown to form a β-d-Galp-(1→3)-d-GalpNAc linkage. The β-Psep5Ac7Ac-(2→4)-d-Galp linkage is predicted to be formed by the other glycosyltransferase, Gtr37, which does not match members of any known glycosyltransferase family.

  Acinetobacter baumannii, capsular polysaccharide, 5, glycosyltransferase, 7-Di-N-acetylpseudaminic acid, KL16 K locus

  NCBI PubMed ID: 30664967
  Publication DOI: 10.1016/j.ijbiomac.2019.01.080
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: J.J. Kenyon
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Antimicrobial Chemotherapy, Smolensk State Medical University, Smolensk, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, Smith degradation, function analysis of gene clusters
  
   
  
  Acinetobacter baumannii K42
  CSDB ID 1364 (all data & tools)
• Article ID: 5791
  Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" - Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
  

  Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.

  polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component

  Publication DOI: 10.1016/B978-0-12-819475-1.00005-5
  Publisher: Elsevier
  Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
  Editors: Barchi J, Kamerling H
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
  
   
  
  Acinetobacter baumannii K42 LUH5550
  CSDB ID 6700 (all data & tools)
• Article ID: 6411
  Kasimova AA, Sharar NS, Ambrose SJ, Knirel YA, Shneider MM, Timoshina OY, Popova AV, Perepelov AV, Dmitrenok AS, Hsu LY, Hall RM, Kenyon JJ "The Acinetobacter baumannii K70 and K9 capsular polysaccharides consist of related K-units linked by the same Wzy polymerase and cleaved by the same phage depolymerases" - Microbiology Spectrum 11(6) (2023) e0302523
  

  Bacteriophage show promise for the treatment of Acinetobacter baumannii infections that resist all therapeutically suitable antibiotics. Many tail-spike depolymerases encoded by phage that are able to degrade A. baumannii capsular polysaccharide (CPS) exhibit specificity for the linkage present between K-units that make up CPS polymers. This linkage is formed by a specific Wzy polymerase, and the ability to predict this linkage using sequence-based methods that identify the Wzy at the K locus could assist with the selection of phage for therapy. However, little is known about the specificity of Wzy polymerase enzymes. Here, we describe a Wzy polymerase that can accommodate two different but similar sugars as one of the residues it links and phage depolymerases that can cleave both types of bond that Wzy forms.

  Acinetobacter baumannii, capsular polysaccharide, Wzy polymerase, phage depolymerase, K70

  NCBI PubMed ID: 37975684
  Publication DOI: 10.1128/spectrum.03025-23
  Journal NLM ID: 101634614
  Publisher: Washington, DC: ASM Press
  Correspondence: J.J. Kenyon
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, M. M. Shemyakin and Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Centre for Immunology and Infection Control, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, Faculty of Science, University of Sydney, Sydney, Australia, Saw Swee Hock School of Public Health, National University of Singapore, Queenstown, Singapore, Yong Loo Lin School of Medicine, National University of Singapore, Queenstown, Singapore
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, DNA techniques, GLC, Smith degradation, HPLC, GPC, bioinformatic analysis, phage depolymerisation, HR-ESI-MS
  
   
  
  Acinetobacter baumannii K42 LUH5550
  CSDB ID 20754 (all data & tools)
• Article ID: 6413
  Knirel YA, Kasimova AA, Arbatsky NP, Shneider MM, Popova AV, Brovko FA, Shashkov AS, Senchenkova SN, Perepelov AV, Shpirt AM "5,7-Diamino-3,5,7,9-tetradeoxynon-2-ulosonic Acids in the Capsular Polysaccharides of Acinetobacter baumannii" - Biochemistry (Moscow) 88(2) (2023) 202-210
  

  The polysaccharide capsule surrounding bacterial cell plays an important role in pathogenesis of infections caused by the opportunistic pathogen Acinetobacter baumannii by providing protection from external factors. The structures of the capsular polysaccharide (CPS) produced by A. baumannii isolates and the corresponding CPS biosynthesis gene clusters are highly diverse, although many of them are related. Many types of A. baumannii CPSs contain isomers of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acid (DTNA). Three of these isomers, namely acinetaminic acid (l-glycero-l-altro isomer), 8-epiacinetaminic acid (d-glycero-l-altro isomer), and 8-epipseudaminic acid (d-glycero-l-manno isomer), have not been found so far in naturally occurring carbohydrates from other species. In A. baumannii CPSs, DTNAs carry N-acyl substituents at positions 5 and 7; in some CPSs, both N-acetyl and N-(3-hydroxybutanoyl) groups are present. Remarkably, pseudaminic acid carries the (R)-isomer and legionaminic acid carries the (S)-isomer of the 3-hydroxybutanoyl group. The review addresses the structure and genetics of biosynthesis of A. baumannii CPSs containing di-N-acyl derivatives of DTNA.

  Acinetobacter baumannii, capsular polysaccharide, nonulosonic acid, Bacterial polysaccharide, capsule, higher monosaccharide, acyl group

  NCBI PubMed ID: 37072328
  Publication DOI: 10.1134/S0006297923020049
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: Y.A. Knirel
  Institutions: State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, 142279, Russia, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 117913, Russia, Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, 117997, Russia, Branch of the Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry in Pushchino, Russian Academy of Sciences, Pushchino, Moscow Region, 142290, Russia
  
   
  
  Acinetobacter baumannii K42 LUH5550
  CSDB ID 22779 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_136105,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_581504,IEDB_885823,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_88

• Article ID: 5119
  Naumenko OI, Guo X, Senchenkova SN, Geng P, Perepelov AV, Shashkov AS, Liu B, Knirel YA "Structure and gene cluster of the O-antigen of Escherichia coli O54" - Carbohydrate Research 462 (2018) 34-38
  

  Mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O54 afforded an O-polysaccharide, which was studied by sugar analysis, solvolysis with anhydrous trifluoroacetic acid, and 1H and 13C NMR spectroscopy. Solvolysis cleaved predominantly the linkage of β-d-Ribf and, to a lesser extent, that of β-d-GlcpNAc, whereas the other linkages, including the linkage of α-l-Rhap, were stable under selected conditions (40 °C, 5 h). The following structure of the O-polysaccharide was established: →4)-α-d-GalpA-(1 → 2)-α-l-Rhap-(1 → 2)-β-d-Ribf-(1 → 4)-β-d-Galp-(1 → 3)-β-d-GlcpNAc-(1→ The O-antigen gene cluster of E. coli O54 was analyzed and found to be consistent in general with the O-polysaccharide structure established but there were two exceptions: i) in the cluster, there were genes for phosphoserine phosphatase and serine transferase, which have no apparent role in the O-polysaccharide synthesis, and ii) no ribofuranosyltransferase gene was present in the cluster. Both uncommon features are shared by some other enteric bacteria.

  O-antigen, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, O-antigen gene cluster

  NCBI PubMed ID: 29660546
  Publication DOI: 10.1016/j.carres.2018.04.001
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: A.V. Perepelov
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin, 300457, China, Russian Federation, School of Basic Medical Sciences, Tianjin Medical University, Heping District, Tianjin, 300070, PR China
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, GLC, GPC, acetylation, delipidation, function analysis of gene clusters, solvolysis with trifluoroacetic acid
  
   
  
  Escherichia coli O54
  CSDB ID 12457 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: (2->6)lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130644,IEDB_130646,IEDB_130650,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140088,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_143250,IEDB_144556,IEDB_144562,IEDB_144998,IEDB_145669,IEDB_146664,IEDB_147455,IEDB_149555,IEDB_149557,IEDB_149561,IEDB_150092,IEDB_150939,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_2189046,IEDB_2189047,IEDB_461719,IEDB_461720,IEDB_461721,IEDB_581504,IEDB_952752,IEDB_983931,SB_147,SB_154,SB_157,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_34,SB_7,SB_86,SB_88

• Article ID: 5179
  Li H, Tang H, Debowski AW, Stubbs KA, Marshall BJ, Benghezal M "Lipopolysaccharide Structural Differences between Western and Asian Helicobacter pylori Strains" - Toxins 10(9) (2018) 364
  

  Recent structural analysis of the lipopolysaccharide (LPS) isolated from Helicobacter pylori G27 wild-type and O-antigen ligase mutant resulted in the redefinition of the core-oligosaccharide and O-antigen domains. The short core-oligosaccharide (Glc-Gal-Hep-III-Hep-II-Hep-I-KDO) and its attached trisaccharide (Trio, GlcNAc-Fuc-Hep) appear to be highly conserved structures among H. pylori strains. The G27 LPS contains a linear glucan?heptan linker between the core-Trio and distal Lewis antigens. This linker domain was commonly identified in Western strains. In contrast, out of 12 partial LPS structures of Asian strains, none displayed the heptan moiety, despite the presence of Lewis antigens. This raises the question of how Lewis antigens are attached to the Trio, and whether the LPS structure of Asian strains contain another linker. Of note, a riban was identified as a linker in LPS of the mouse-adapted SS1 strain, suggesting that alternative linker structures can occur. In summary, additional full structural analyses of LPS in Asian strains are required to assess the presence or absence of an alternative linker in these strains. It will also be interesting to study the glucan-heptan linker moieties in pathogenesis as H. pylori infections in Asia are usually more symptomatic than the ones presented in the Western world.

  Lipopolysaccharide, structure, Helicobacter pylori

  NCBI PubMed ID: 30205541
  Publication DOI: 10.3390/toxins10090364
  Journal NLM ID: 101530765
  Publisher: Basel: MDPI
  Correspondence: H.T. ; M.B.
  Institutions: West China Marshall Research Center for Infectious Diseases, Center of Infectious Diseases, West China Hospital of Sichuan University, Chengdu 610041, China, Helicobacter pylori Research Laboratory, School of Biomedical Sciences, Marshall Centre for Infectious Disease Research and Training, University of Western Australia, Nedlands, WA 6009, Australia, School of Molecular Sciences, University of Western Australia, Crawley, WA 6009, Australia
  
   
  
  Helicobacter pylori SS1
  CSDB ID 12653 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_581504,IEDB_983931,SB_192

• Article ID: 5796
  Kokoulin MS, Kuzmich AS, Romanenko LA, Chikalovets IV, Chernikov OV "Structure and in vitro Bioactivity against Cancer Cells of the Capsular Polysaccharide from the Marine Bacterium Psychrobacter marincola" - Marine Drugs 18(5) (2020) 268
  

  Psychrobacter marincola KMM 277T is a psychrophilic Gram-negative bacterium that has been isolated from the internal tissues of an ascidian Polysyncraton sp. Here, we report the structure of the capsular polysaccharide from P. marincola KMM 277T and its effect on the viability and colony formation of human acute promyelocytic leukemia HL-60 cells. The polymer was purified by several separation methods, including ultracentrifugation and chromatographic procedures, and the structure was elucidated by means of chemical analysis, 1-D, and 2-D NMR spectroscopy techniques. It was found that the polysaccharide consists of branched hexasaccharide repeating units containing two 2-N-acetyl-2-deoxy-d-galacturonic acids, and one of each of 2-N-acetyl-2-deoxy-d-glucose, d-glucose, d-ribose, and 7-N-acetylamino-3,5,7,9-tetradeoxy-5-N-[(R)-2-hydroxypropanoylamino]- l-glycero-l-manno-non-2-ulosonic acid. To our knowledge, this is the first finding a pseudaminic acid decorated with lactic acid residue in polysaccharides. The biological analysis showed that the capsular polysaccharide significantly reduced the viability and colony formation of HL-60 cells. Taken together, our data indicate that the capsular polysaccharide from P. marincola KMM 277T is a promising substance for the study of its antitumor properties and the mechanism of action in the future.

  capsular polysaccharide, pseudaminic acid, Marine bacteria, lactic acid, Psychrobacter, Antiproliferative activity, HL-60

  NCBI PubMed ID: 32438723
  Publication DOI: 10.3390/md18050268
  Journal NLM ID: 101213729
  Publisher: Basel, Switzerland: Molecular Diversity Preservation International
  Correspondence: maxchem@mail.ru
  Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, 159/2, Prospect 100 let Vladivostoku, 690022 Vladivostok, Russia, Far Eastern Federal University, 8, Sukhanova str., 690950 Vladivostok, Russia
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, partial acid hydrolysis, GC-MS, GC, Smith degradation, composition analysis, HPLC, GPC, PAGE, cell viability assay, soft agar assay
  
   
  
  Psychrobacter marincola KMM 277T
  CSDB ID 5058 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_581504,IEDB_983931,SB_192

• Article ID: 5796
  Kokoulin MS, Kuzmich AS, Romanenko LA, Chikalovets IV, Chernikov OV "Structure and in vitro Bioactivity against Cancer Cells of the Capsular Polysaccharide from the Marine Bacterium Psychrobacter marincola" - Marine Drugs 18(5) (2020) 268
  

  Psychrobacter marincola KMM 277T is a psychrophilic Gram-negative bacterium that has been isolated from the internal tissues of an ascidian Polysyncraton sp. Here, we report the structure of the capsular polysaccharide from P. marincola KMM 277T and its effect on the viability and colony formation of human acute promyelocytic leukemia HL-60 cells. The polymer was purified by several separation methods, including ultracentrifugation and chromatographic procedures, and the structure was elucidated by means of chemical analysis, 1-D, and 2-D NMR spectroscopy techniques. It was found that the polysaccharide consists of branched hexasaccharide repeating units containing two 2-N-acetyl-2-deoxy-d-galacturonic acids, and one of each of 2-N-acetyl-2-deoxy-d-glucose, d-glucose, d-ribose, and 7-N-acetylamino-3,5,7,9-tetradeoxy-5-N-[(R)-2-hydroxypropanoylamino]- l-glycero-l-manno-non-2-ulosonic acid. To our knowledge, this is the first finding a pseudaminic acid decorated with lactic acid residue in polysaccharides. The biological analysis showed that the capsular polysaccharide significantly reduced the viability and colony formation of HL-60 cells. Taken together, our data indicate that the capsular polysaccharide from P. marincola KMM 277T is a promising substance for the study of its antitumor properties and the mechanism of action in the future.

  capsular polysaccharide, pseudaminic acid, Marine bacteria, lactic acid, Psychrobacter, Antiproliferative activity, HL-60

  NCBI PubMed ID: 32438723
  Publication DOI: 10.3390/md18050268
  Journal NLM ID: 101213729
  Publisher: Basel, Switzerland: Molecular Diversity Preservation International
  Correspondence: maxchem@mail.ru
  Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, 159/2, Prospect 100 let Vladivostoku, 690022 Vladivostok, Russia, Far Eastern Federal University, 8, Sukhanova str., 690950 Vladivostok, Russia
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, partial acid hydrolysis, GC-MS, GC, Smith degradation, composition analysis, HPLC, GPC, PAGE, cell viability assay, soft agar assay
  
   
  
  Psychrobacter marincola KMM 277T
  CSDB ID 5059 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_581504,IEDB_983931,SB_192

• Article ID: 5796
  Kokoulin MS, Kuzmich AS, Romanenko LA, Chikalovets IV, Chernikov OV "Structure and in vitro Bioactivity against Cancer Cells of the Capsular Polysaccharide from the Marine Bacterium Psychrobacter marincola" - Marine Drugs 18(5) (2020) 268
  

  Psychrobacter marincola KMM 277T is a psychrophilic Gram-negative bacterium that has been isolated from the internal tissues of an ascidian Polysyncraton sp. Here, we report the structure of the capsular polysaccharide from P. marincola KMM 277T and its effect on the viability and colony formation of human acute promyelocytic leukemia HL-60 cells. The polymer was purified by several separation methods, including ultracentrifugation and chromatographic procedures, and the structure was elucidated by means of chemical analysis, 1-D, and 2-D NMR spectroscopy techniques. It was found that the polysaccharide consists of branched hexasaccharide repeating units containing two 2-N-acetyl-2-deoxy-d-galacturonic acids, and one of each of 2-N-acetyl-2-deoxy-d-glucose, d-glucose, d-ribose, and 7-N-acetylamino-3,5,7,9-tetradeoxy-5-N-[(R)-2-hydroxypropanoylamino]- l-glycero-l-manno-non-2-ulosonic acid. To our knowledge, this is the first finding a pseudaminic acid decorated with lactic acid residue in polysaccharides. The biological analysis showed that the capsular polysaccharide significantly reduced the viability and colony formation of HL-60 cells. Taken together, our data indicate that the capsular polysaccharide from P. marincola KMM 277T is a promising substance for the study of its antitumor properties and the mechanism of action in the future.

  capsular polysaccharide, pseudaminic acid, Marine bacteria, lactic acid, Psychrobacter, Antiproliferative activity, HL-60

  NCBI PubMed ID: 32438723
  Publication DOI: 10.3390/md18050268
  Journal NLM ID: 101213729
  Publisher: Basel, Switzerland: Molecular Diversity Preservation International
  Correspondence: maxchem@mail.ru
  Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, 159/2, Prospect 100 let Vladivostoku, 690022 Vladivostok, Russia, Far Eastern Federal University, 8, Sukhanova str., 690950 Vladivostok, Russia
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, partial acid hydrolysis, GC-MS, GC, Smith degradation, composition analysis, HPLC, GPC, PAGE, cell viability assay, soft agar assay
  
   
  
  Psychrobacter marincola KMM 277T
  CSDB ID 5060 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130644,IEDB_130646,IEDB_130650,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135394,IEDB_135515,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140088,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_143250,IEDB_144556,IEDB_144562,IEDB_144998,IEDB_145669,IEDB_146664,IEDB_147455,IEDB_149555,IEDB_149557,IEDB_149561,IEDB_150092,IEDB_150787,IEDB_150939,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_158546,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_2189046,IEDB_2189047,IEDB_461719,IEDB_461720,IEDB_461721,IEDB_581504,IEDB_952752,IEDB_983931,SB_147,SB_154,SB_157,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_34,SB_7,SB_86,SB_88

• Article ID: 6144
  Silva LM, Correia VG, Moreira ASP, Domingues MRM, Ferreira RM, Figueiredo C, Azevedo NF, Marcos-Pinto R, Carneiro F, Magalhaes A, Feizi T, Ferreira JA, Coimbra MA, Palma AS "Helicobacter pylori lipopolysaccharide structural domains and their recognition by immune proteins revealed with carbohydrate microarrays" - Carbohydrate Polymers 253 (2021) 117350
  

  The structural diversity of the lipopolysaccharides (LPSs) from Helicobacter pylori poses a challenge to establish accurate and strain-specific structure-function relationships in interactions with the host. Here, LPS structural domains from five clinical isolates were obtained and compared with the reference strain 26695. This was achieved combining information from structural analysis (GC-MS and ESI-MSn) with binding data after interrogation of a LPS-derived carbohydrate microarray with sequence-specific proteins. All LPSs expressed Lewisx/y and N-acetyllactosamine determinants. Ribans were also detected in LPSs from all clinical isolates, allowing their distinction from the 26695 LPS. There was evidence for 1,3-d-galactans and blood group H-type 2 sequences in two of the clinical isolates, the latter not yet described for H. pylori LPS. Furthermore, carbohydrate microarray analyses showed a strain-associated LPS recognition by the immune lectins DC-SIGN and galectin-3 and revealed distinctive LPS binding patterns by IgG antibodies in the serum from H. pylori-infected patients.

  lipopolysaccharides, mass spectrometry, Helicobacter pylori, carbohydrate microarrays, host immune receptors, human sera

  NCBI PubMed ID: 33278960
  Publication DOI: 10.1016/j.carbpol.2020.117350
  Journal NLM ID: 8307156
  Publisher: Elsevier
  Correspondence: lisete.silva@ua.pt
  Institutions: LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, Aveiro, Portugal, Glycosciences Laboratory, Department of Metabolism, Digestion and Reproduction, Imperial College London, UK, UCIBIO, Department of Chemistry, School of Science and Technology, NOVA University of Lisbon, Lisbon, Portugal, CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, Aveiro, Portugal, CESAM - Centre for Environmental and Marine Studies, Department of Chemistry, University of Aveiro, Aveiro, Portugal, i3S - Instituto de Investigação e Inovação em Saúde, Universidade do Porto, Porto, Portugal, IPATIMUP - Institute of Molecular Pathology and Immunology of the University of Porto, Porto, Portugal, Faculty of Medicine, University of Porto, Porto, Portugal, LEPABE - Laboratory for Process Engineering, Environment, Biotechnology and Energy, Faculty of Engineering, University of Porto, Porto, Portugal, ICBAS - Institute of Biomedical Sciences Abel Salazar, University of Porto, Porto, Portugal, Department of Gastroenterology, Centro Hospitalar do Porto, Porto, Portugal, Medical Faculty, Centre for Research in Health Technologies and Information Systems, Porto, Portugal, Experimental Pathology and Therapeutics Group, Research Center (CI-IPOP), Portuguese Institute of Oncology, Porto, Portugal
  Methods: methylation, partial acid hydrolysis, GC-MS, SDS-PAGE, ELISA, ESI-MS, composition analysis, serological methods, carbohydrate microarray analysis, carbohydrate microarray construction, extraciton
  
   
  
  Helicobacter pylori SS1
  CSDB ID 9772 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_114701,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_164059,IEDB_167188,IEDB_174332,IEDB_581504,IEDB_983931,SB_192

• Article ID: 6195
  Andrew M, Jayaraman G "Molecular Characterization and Biocompatibility of Exopolysaccharide Produced by Moderately Halophilic Bacterium Virgibacillus dokdonensis from the Saltern of Kumta Coast" - Polymers 14(9) (2022) 3986
  

  The use of natural polysaccharides as biomaterials is gaining importance in tissue engineering due to their inherent biocompatibility. In this direction, the present study aims to explore the structure and biocompatibility of the EPS produced by Virgibacillus dokdonensis VITP14. This marine bacterium produces 17.3 g/L of EPS at 96 h of fermentation. The EPS was purified using ion exchange and gel permeation chromatographic methods. The porous web-like structure and elemental composition (C, O, Na, Mg, P, S) of the EPS were inferred from SEM and EDX analysis. AFM analysis revealed spike-like lumps with a surface roughness of 84.85 nm. The zeta potential value of -10 mV indicates the anionic nature of the EPS. Initial molecular characterization showed that the EPS is a heteropolysaccharide composed of glucose (25.8%), ribose (18.6%), fructose (31.5%), and xylose (24%), which are the monosaccharide units in the HPLC analysis. The FTIR spectrum indicates the presence of functional groups/bonds typical of EPSs (O-H, C-H, C-O-H, C-O, S=O, and P=O). The polymer has an average molecular weight of 555 kDa. Further, NMR analysis revealed the monomer composition, the existence of two α- and six β-glycosidic linkages, and the branched repeating unit as →1)[α-D-Xylp-(1→2)-α-D-Glcp-(1→6)-β-D-Glcp-(1→5)]-β-D-Frup-(2→2)[β-D-Xylp-(1→4)]-β-D-Xylp-(1→6)-β-D-Fruf-(2→4)-β-D-Ribp-(1→. The EPS is thermally stable till 251.4 °C. X-ray diffraction analysis confirmed the semicrystalline (54.2%) nature of the EPS. Further, the EPS exhibits significant water solubility (76.5%), water-holding capacity (266.8%), emulsifying index (66.8%), hemocompatibility (erythrocyte protection > 87%), and cytocompatibility (cell viability > 80% on RAW264.7 and keratinocyte HaCaT cells) at higher concentrations and prolongs coagulation time in APTT and PT tests. Our research unveils the significant biocompatibility of VITP14 EPS for synthesizing a variety of biomaterials.

  exopolysaccharides, fermentation, Marine bacteria, anticoagulant activity, Structural characterization, halophiles, biomaterial, cytocompatibility, hemocompatibility

  NCBI PubMed ID: 36235941
  Publication DOI: 10.3390/polym14193986
  Journal NLM ID: 101545357
  Publisher: Basel: MDPI
  Correspondence: G. Jayaraman
  Institutions: School of Biosciences and Technology, Vellore Institute of Technology, Vellore 632014, Tamil Nadu, India
  Methods: 13C NMR, 1H NMR, NMR-2D, X-ray, FTIR, HPLC, GPC, statistical analysis, zeta potential measurement, cell viability assay, SEM, AFM, emulsifying activity determination, TGA, WHC, X-ray EDX, hemolytic activity, hemolysis activity, anticoagulant activity
  
   
  
  Virgibacillus dokdonensis VITP14
  CSDB ID 8426 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_581504,IEDB_885823

• Article ID: 10332
  Ye W, Shi X, Zhao S, Wu C, Shen W "Chemical constituents of Hupeh anemone (Anemone hupehensis)" - Zhong Cao Yao = Chinese Traditional and Herbal Drugs [Chinese] 23 (1992) 289-291
  
  Journal NLM ID: 9421493
  Publisher: Shao-Yang, China: Chung Tsao Yao Tsa Chih Pien Chi Pu
  
   
  
  Anemone hupehensis
  CSDB ID 150034 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_581504,IEDB_885823

• Article ID: 10332
  Ye W, Shi X, Zhao S, Wu C, Shen W "Chemical constituents of Hupeh anemone (Anemone hupehensis)" - Zhong Cao Yao = Chinese Traditional and Herbal Drugs [Chinese] 23 (1992) 289-291
  
  Journal NLM ID: 9421493
  Publisher: Shao-Yang, China: Chung Tsao Yao Tsa Chih Pien Chi Pu
  
   
  
  Anemone hupehensis
  CSDB ID 150033 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_581504,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10542
  Wang MK, Chen YZ, Wu FE "Triterpenoid saponins from Anemone hupehensis Lemoine" - Hua Xue Xue Bao = Acta Chimica Sinica [Chinese] 52 (1994) 609-612
  
  Journal NLM ID: 0111476
  Publisher: Peking, Ke xue chu ban she
  
   
  
  Anemone hupehensis
  CSDB ID 129816 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1401.6656 [M+Na]+
C₆₆H₁₀₆O₃₀
Trivial name: clemastanoside A
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581504,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10901
  Kizu H, Shimana H, Tomimori T "Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc" - Chemical and Pharmaceutical Bulletin 43(12) (1995) 2187-2194
  

  From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named clemastanin A and B, have been isolated together with three known triterpenoid saponins, huzhangoside B, C and D, and three known lignan glycosides, (+)-lariciresinol 4-O-β-D-glucopyranoside, (+)-lariciresinol 4'-O-β-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-β-D-glucopyranoside. In addition, from the leaves, four new oleanane-type triterpenoid saponins, named clemastanoside D, E, F and G, have been isolated together with five known triterpenoid saponins, hederasaponin B, kizutasaponin K_<12>, huzhangoside B, sieboldianoside B and huzhangoside D, and three known flavonoids, isoquercitrin, rutin and quercetin 3-O-β-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows : clemastanoside A, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-β-D-xylopyranosyl- and 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamno-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanin A, (7S, 8R)-3-methoxy-3', 4,9,9'-tetrahydroxy-4', 7-epoxy-5', 8-lignan 3'-O-β-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-β-D-glucopyranoside.

  Ranunculaceae, lignan glycoside, Clematis stans, oleanolic acid bisdesmoside, hederagenin bisdesmoside, quercetin glycoside

  NCBI PubMed ID: 8582022
  Publication DOI: 10.1248/cpb.43.2187
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Hokuriku University, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, GLC, methanolysis, HPLC, alkaline hydrolysis, UV, enzymatic digestion, CD, HR-FAB-MS
  
   
  
  Clematis stans
  CSDB ID 120688 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: huzhangoside B
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581504,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10901
  Kizu H, Shimana H, Tomimori T "Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc" - Chemical and Pharmaceutical Bulletin 43(12) (1995) 2187-2194
  

  From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named clemastanin A and B, have been isolated together with three known triterpenoid saponins, huzhangoside B, C and D, and three known lignan glycosides, (+)-lariciresinol 4-O-β-D-glucopyranoside, (+)-lariciresinol 4'-O-β-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-β-D-glucopyranoside. In addition, from the leaves, four new oleanane-type triterpenoid saponins, named clemastanoside D, E, F and G, have been isolated together with five known triterpenoid saponins, hederasaponin B, kizutasaponin K_<12>, huzhangoside B, sieboldianoside B and huzhangoside D, and three known flavonoids, isoquercitrin, rutin and quercetin 3-O-β-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows : clemastanoside A, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-β-D-xylopyranosyl- and 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamno-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanin A, (7S, 8R)-3-methoxy-3', 4,9,9'-tetrahydroxy-4', 7-epoxy-5', 8-lignan 3'-O-β-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-β-D-glucopyranoside.

  Ranunculaceae, lignan glycoside, Clematis stans, oleanolic acid bisdesmoside, hederagenin bisdesmoside, quercetin glycoside

  NCBI PubMed ID: 8582022
  Publication DOI: 10.1248/cpb.43.2187
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Hokuriku University, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, GLC, methanolysis, HPLC, alkaline hydrolysis, UV, enzymatic digestion, CD, HR-FAB-MS
  
   
  
  Clematis stans
  CSDB ID 120689 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: huzhangoside C
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_241101,IEDB_581504,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10901
  Kizu H, Shimana H, Tomimori T "Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc" - Chemical and Pharmaceutical Bulletin 43(12) (1995) 2187-2194
  

  From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named clemastanin A and B, have been isolated together with three known triterpenoid saponins, huzhangoside B, C and D, and three known lignan glycosides, (+)-lariciresinol 4-O-β-D-glucopyranoside, (+)-lariciresinol 4'-O-β-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-β-D-glucopyranoside. In addition, from the leaves, four new oleanane-type triterpenoid saponins, named clemastanoside D, E, F and G, have been isolated together with five known triterpenoid saponins, hederasaponin B, kizutasaponin K_<12>, huzhangoside B, sieboldianoside B and huzhangoside D, and three known flavonoids, isoquercitrin, rutin and quercetin 3-O-β-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows : clemastanoside A, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-β-D-xylopyranosyl- and 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamno-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanin A, (7S, 8R)-3-methoxy-3', 4,9,9'-tetrahydroxy-4', 7-epoxy-5', 8-lignan 3'-O-β-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-β-D-glucopyranoside.

  Ranunculaceae, lignan glycoside, Clematis stans, oleanolic acid bisdesmoside, hederagenin bisdesmoside, quercetin glycoside

  NCBI PubMed ID: 8582022
  Publication DOI: 10.1248/cpb.43.2187
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Hokuriku University, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, GLC, methanolysis, HPLC, alkaline hydrolysis, UV, enzymatic digestion, CD, HR-FAB-MS
  
   
  
  Clematis stans
  CSDB ID 120690 (all data & tools)