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Structure type: polymer chemical repeating unit
Trivial name: mannan, neutral mannan, BCG-PSN (Bacillus Calmette-Guérin polysaccharide and nucleic acid), α-mannan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 3780
  Shashkov AS, Tul'skaya EM, Streshinskaia GM, Senchenkova SN, Avtukh AN, Evtushenko LI "New cell wall glycopolymers of the representatives of the genus Kribbella" - Carbohydrate Research 344(16) (2009) 2255-2262
  

  Each of the cell walls of four representatives of the genus Kribbella (order Actinomycetales; suborder Propionibacterineae; family Nocardioidaceae) contains a neutral polysaccharide and an acidic polysaccharide with unusual structures. Common to all four strains studied is a mannan with the following repeating unit: In the cell wall of the strain VKM Ac-2541, a teichulosonic acid was identified with a monosaccharide component that has not hitherto been found in Gram-positive bacteria, viz., pseudaminic acid, and an unusual linkage type in the polymeric chain, where R = H (45%), α-D-Galp3OMe (37%) or α-D-Galp2,3OMe (18%). The anionic cell wall components of three other strains are represented by teichuronic acids with a rare constituent, viz., a diaminosugar, 2,3-diacetamido-2,3-dideoxyglucopyranose. The structures of their repeating units differ in the nature of the acidic components: →4)-β-D-Manp2,3NAcA-(1→6)-α-D-Glcp2,3NAc-(1→ (VKM Ac-2538 and VKM Ac-2540) and →4)-β-D-ManpNAcA-(1→6)-α-D-Glcp2,3NAc-(1→ (VKM Ac-2539). The structures of all the glycopolymers were established by chemical and NMR spectroscopic methods; they are identified in Gram-positive bacteria for the first time.

  NMR spectroscopy, mannan, teichuronic acid, teichulosonic acid, Actinomycetales, Kribbella

  NCBI PubMed ID: 19762009
  Publication DOI: 10.1016/j.carres.2009.08.010
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: em_tulskaya@mail.ru
  Institutions: School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, Russian Federation, All-Russian Collection of Microorganisms (VKM), G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, GLC, Smith degradation, paper chromatography, composition analysis, electrophoresis, GPC
  
   
  
  Kribbella sp. VKM Ac-2538, Kribbella sp. VKM Ac-2539, Kribbella sp. VKM Ac-2540, Kribbella sp. VKM Ac-2541
  CSDB ID 23841 (all data & tools)
• Article ID: 4122
  Tul'skaya EM, Shashkov AS, Streshinskaia GM, Senchenkova SN, Potekhina NV, Kozlova YI, Evtushenko LI "Teichuronic and teichulosonic acids of actinomycetes" - Biochemistry (Moscow) 76(7) (2011) 736-744
  

  The subject of the present review is the structural diversity and abundance of cell wall teichuronic and teichulosonic acids of representatives of the order Actinomycetales. Recently found teichulosonic acids are a new class of natural glycopolymers with ald-2-ulosonic acid residues: Kdn (3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid) or di-N-acyl derivatives of Pse (5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic or pseudaminic acid) as the obligatory component. The structures of teichuronic and teichulosonic acids are presented. Data are summarized on the occurrence of the glycopolymers of different nature in the cell wall of the studied actinomycetes. The biological role of the glycopolymers and their possible taxonomic implication are discussed. The comprehensive tables given in the Supplement show (13)C NMR spectroscopic data of teichuronic and teichulosonic acids obtained by the authors.

  NMR spectroscopy, cell wall, teichuronic acid, actinomycetes, teichulosonic acid

  NCBI PubMed ID: 21999534
  Publication DOI: 10.1134/S0006297911070030
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: em_tulskaya@mail.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, All-Russian Collection of Microorganisms (VKM), Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Lomonosov Moscow State University, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia
  Methods: NMR, ESI-MS, MALDI-TOF MS
  
   
  
  Kribbella sp. VKM Ac-2500, Kribbella sp. VKM Ac-2568, Kribbella sp. VKM Ac-2572, Kribbella sp. VKM Ac-2575, Kribbella sp. VKM Ac-2541, Kribbella sp. VKM Ac-2527, Kribbella sp. VKM Ac-2538, Kribbella sp. VKM Ac-2539, Kribbella sp. VKM Ac-2540
  CSDB ID 26532 (all data & tools)
• Article ID: 4123
  Tul'skaya EM, Streshinskaya GM, Shashkov AS, Senchenkova SN, Avtukh AN, Baryshnikova LM, Evtushenko LI "Novel teichulosonic acid from cell walls of some representatives of the genus Kribbella" - Carbohydrate Research 346(13) (2011) 2045-2051
  

  Cell walls of each of five bacterial strains belonging to the genus Kribbella (family Nocardioidaceae, order Actinomycetales) contain a neutral polysaccharide (mannan) and teichulosonic acid of novel structure in different proportions. The novel teichulosonic acid found in strains VKM Ac-2500, VKM Ас-2568, VKM Ас-2572, and VKM Ас-2575 is a heteropolymer with an irregular structure where fragments I (predominant) alternate with fragments II (minor): The teichulosonic acid from Kribbella sp. VKM Ac-2527 has in general a structure similar to that above with the exception that the Pse residue is randomly glycosylated at O-4 with β-l-Rhap (along with α-d-Galp3OMe or α-d-Galp2,3OMe). The strain VKM Ac-2572 contained additionally teichuronic acid with the disaccharide repeating unit consisted of aminomannuronic acid and 2,3-diacetamido-2,3-dideoxy-α-glucopyranose. The mannan, a polysaccharide common to all of the strains, is built of (1→6)-linked α-d-mannopyranose substituted with α-d-mannopyranose at O-2. The structures of all the glycopolymers were established by a combination of chemical and NMR spectroscopic methods.

  NMR spectroscopy, cell wall, teichulosonic acid, Kribbella

  NCBI PubMed ID: 21718973
  Publication DOI: 10.1016/j.carres.2011.06.003
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: em_tulskaya@mail.ru
  Institutions: School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, acid hydrolysis, GLC, Smith degradation, paper chromatography, de-O-acetylation, NMR-1D, electrophoresis
  
   
  
  Kribbella sp. VKM Ac-2500, Kribbella sp. VKM Ac-2568, Kribbella sp. VKM Ac-2572, Kribbella sp. VKM Ac-2575
  CSDB ID 26534 (all data & tools)
• Article ID: 6273
  Luo L, Song X, Chang X, Huang S, Zhou Y, Yang S, Zhu Y, Zhang L, Wu Y, Zhang J, Zhou Z, Wu M "Detailed Structural Analysis of the Immunoregulatory Polysaccharides from the Mycobacterium Bovis BCG" - Molecules 27(17) (2022) 5691
  

  Bacillus Calmette-Guérin polysaccharide and nucleic acid (BCG-PSN), extracted from Mycobacterium bovis, is an immunoregulatory medicine commonly used in clinic. However, the structural characteristics and potential pharmacological efficacy of the polysaccharides from BCG-PSN remain unclear. Herein, two polysaccharides (BCG-1 and BCG-2) were purified and their structures were characterized. Monosaccharide composition analysis combined with methylation analysis and NMR data indicated that BCG-1 and BCG-2 were an α-D-(1→4)-mannan with (1→2)-linked branches, and an α-D-(1→4)-glucan with (1→6)-linked branches, respectively. Herein, the mannan from BCG-PSN was first reported. Bioactivity assays showed that BCG-1 and BCG-2 dose-dependently and potently increased the production of inflammatory mediators (NO, TNF-α, IL-6, IL-1β, and IL-10), as well as their mRNA expressions in RAW264.7 cells; both have similar or stronger effects compared with BCG-PSN injection. These data suggest that BCG-1 and BCG-2 are very likely the active ingredients of BCG-PSN.

  immunomodulator, mannan, glucan, active ingredients, Mycobacterium Bovis BCG, polysaccharide purification

  NCBI PubMed ID: 36080458
  Publication DOI: 10.3390/molecules27175691
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: M. Wu
  Institutions: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China, University of Chinese Academy of Sciences, Beijing 100049, China, Hunan Jiuzhitang Siqi Biological Pharmaceutical Co., Ltd., Changsha 410329, China, Jiuzhitang Co., Ltd., Changsha 410205, China
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, ESI-MS, MALDI-TOF MS, FTIR, composition analysis, HPLC, UV, statistical analysis, SEC, determination of NO production, cytokine production, cell viability assay, HPGPC, RT-qPCR
  
   
  
  Mycobacterium bovis
  CSDB ID 8506 (all data & tools)
• Article ID: 6635
  Jiménez-Barbero J, Bernabé M, Leal JA, Prieto A, Gomez-Miranda B "Chemical structure and conformational features of cell-wall polysaccharides isolated from Aphanoascus mephitalus and related species" - Carbohydrate Research 250 (1993) 289-299
  

  The structures of cell-wall mannans isolated from Aphanoascus mephitalus, A. fulvescens, A. verrucosus, and A. reticulisporus have been investigated by chemical analyses and 1D and 2D 1H and 13C NMR techniques. It was found that all of them consists of a relatively simple comb-like structure of the disaccharide repeating block [→6)-[α-Manp-(1→2)]-α-Manp-(1→]. The conformations around the α-(1→2) and α-(1→6) linkages in these kinds of polymers were also studied by using molecular mechanics and dynamics calculations, together with NOE data. The results are similar to those found within the oligosaccharide chains of glycoproteins, with a well-defined conformation for the α-(1→2) linkage and a certain restriction around the α-(1→6) bonding imposed by the 2-substitution.

  NCBI PubMed ID: 8131160
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Instituto de Química Orgánica, CSIC, Madrid, Spain
  Methods: 13C NMR, 1H NMR, molecular mechanics, molecular dynamics
  
   
  
  Aphanoascus fulvescens, Aphanoascus reticulisporus, Aphanoascus verrucosus, Aphanoascus mephitalis
  CSDB ID 117549 (all data & tools)
• Article ID: 6782
  Leal JA, Gomez-Miranda B, Bernabé M, Cano J, Guarro J "The chemical composition of the wall of six species of Aphanoascus: the taxonomic significance of the presence of a-(1-2) (1-6) mannan and a-(1-4) glucan" - Mycological Research 96 (1992) 363-368
  
  Journal NLM ID: 8913481
  Publisher: Cambridge University Press
  
   
  
  Aphanoascus fulvescens
  CSDB ID 144154 (all data & tools)
• Article ID: 6842
  Bahia MC, Bahia MCFD, Vieira RP, Mulloy B, Hartmann R, Bergter EB "The structures of polysaccharides and glycolipids of Aspergillus fumigatus grown in the presence of human serum" - Mycopathologia 137(1) (1997) 17-25
  

  A study was made of polysaccharides and glycosphingolipids isolated from Aspergillus fumigatus grown in media supplemented with human serum from healthy donors. Fractionation of Cetavlon-precipitated polysaccharides on Sephacryl S-400 gave rise to an excluded fraction (Fraction I) with molecular weight of >400 kDa and an included peak (Fraction II) with an averagemolecular weight of 30-80 kDa. Fraction I comprises about 5% of total polysaccharide and was identified as a glycogen-like molecule. Its structure was deduced from methylation data, treatment with amyloglucosidase, a red-browncoloration produced with an iodine solution and by 1Hand 13C NMR spectroscopy. It was previously suggested that higher amounts of glycogen-like polysaccharide (20%) were present in A. fumigatus grown in serum-free medium. Fraction II was identified as a galactomannan and was the main polysaccharide of A. fumigatus grown in serum-supplemented medium. Its structure was elucidated mainly by 13C NMR spectroscopy combined with partial acetolysis and methylation analysis. The 13C NMR spectrum of the galactomannan showed a much greater complexity in the b-D-galf and a-D-manp C-1 regions, than was evident for galactomannan from serum-free cultures previously described, reflecting differences in the glycosylation pattern, stimulated in serum-supplemented medium. No differences in A. fumigatus glycosphingolipid could be detected between serum-containing and serum-free growth conditions. Our results demonstrate that the change in polysaccharide structure is a more specific response to the altered growth conditions and not merely a symptom of more general changes.

  structure, human, polysaccharide, polysaccharides, glycolipid, serum, glycolipids, human serum, Galactomannan, glucan, Aspergillus fumigatus

  NCBI PubMed ID: 9299754
  Journal NLM ID: 7505689
  Publisher: Kluwer Academic Publishers
  Institutions: Departamento de Microbiologia Geral, Instituto de Microbiologia and Departamento de Bioquimica, Instituto de Ciencias Biomedicas, Universidade Federal do Rio de Janeiro, National Institute for Biological Standards and Control, Blanche Lane, South Mimms, Potters Bar, Hertfordshire, ENG 3QG, UK, Institut fur Physiologische Chemie der Universitaet Bonn, Germany
  Methods: methylation, NMR-2D, FAB-MS, GC-MS, partial acetolysis, hydrolysis, iodine reacion
  
   
  
  Aspergillus fumigatus NCPF2140
  CSDB ID 190 (all data & tools)
• Article ID: 9562
  Tang N, Wang X, Yang R, Liu Z, Liu Y, Tian J, Xiao L, Li W "Extraction, isolation, structural characterization and prebiotic activity of cell wall polysaccharide from Kluyveromyces marxianus" - Carbohydrate Polymers 289 (2022) 119457
  

  In this study, three yeast α-mannans (LZ-MPS, MC-MPS, and G-MPS) were extracted from different sources of Kluyveromyces marxianus. The total sugar content of the three α-mannans ranged from 91.13–97.10%, whereas no proteins were detected. A structural arrangement was proposed using ultraviolet spectroscopy, Fourier-transform infrared spectroscopy, and one-dimensional and two-dimensional nuclear magnetic resonance. The main chain of the three yeast α-mannans was formed by a →6)-α-D-Manp-(1→ unit, which was slightly different from the repeating unit of the branch structure. The prebiotic potential of LZ-MPS, MC-MPS, and G-MPS was assessed using in vitro fermentation with pure and faecal cultures. The three yeast α-mannans could be utilised as substrates for the growth of Lactobacillus and Lactococcus strains. In addition, the three yeast α-mannans markedly regulated the intestinal microbiota composition by increasing the relative abundances of Bacteroides, Parabacteroides, and Phascolarctobacterium and decreasing the abundance of pathogenic bacteria.

  Lactobacillus, Structural characterization, gut microbiota, in vitro fermentation, prebiotic activity, Kluyveromyces marxianus, yeast cell wall polysaccharide

  Publication DOI: 10.1016/j.carbpol.2022.119457
  Journal NLM ID: 8307156
  Publisher: Elsevier
  Correspondence: W. Li
  Institutions: College of Food Science and Technology, Nanjing Agricultural University, Nanjing, Jiangsu 210095, PR China
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, anion-exchange chromatography, FTIR, HPLC, HPSEC, UV, extraction, statistical analysis, analysis of gut microbiota, In vitro fermentation
  
   
  
  Kluyveromyces marxianus MC-S-E
  CSDB ID 51835 (all data & tools)