Show legend Show as text

Structure type: oligomer
Trivial name: variant surface glycoprotein (VSG) GPI anchor
Compound class: GPI-anchor
Contained glycoepitopes: IEDB_115013,IEDB_120354,IEDB_123890,IEDB_130645,IEDB_130651,IEDB_130701,IEDB_131186,IEDB_134624,IEDB_135818,IEDB_136044,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_140116,IEDB_141492,IEDB_141793,IEDB_141794,IEDB_141807,IEDB_141829,IEDB_142346,IEDB_143632,IEDB_144983,IEDB_144987,IEDB_144993,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153201,IEDB_153220,IEDB_156489,IEDB_156493,IEDB_156494,IEDB_156557,IEDB_156983,IEDB_167072,IEDB_176772,IEDB_190606,IEDB_221845,IEDB_241097,IEDB_474450,IEDB_742245,IEDB_742246,IEDB_742247,IEDB_742248,IEDB_918313,IEDB_918314,IEDB_983930,SB_136,SB_163,SB_165,SB_166,SB_187,SB_191,SB_195,SB_196,SB_198,SB_31,SB_44,SB_62,SB_67,SB_7,SB_72,SB_87,SB_88

• Article ID: 5969
  Morotti AMM, Martins-Teixeira MB, Carvalho I "Protozoan Parasites Glycosylphosphatidylinositol Anchors: Structures, Functions and Trends for Drug Discovery" - Current Medicinal Chemistry 26(23) (2019) 4301-4322
  

  Background: Glycosylphosphatidylinositol (GPI) anchors are molecules located on cell membranes of all eukaryotic organisms. Proteins, enzymes, and other macromolecules which are anchored by GPIs are essential elements for interaction between cells, and are widely used by protozoan parasites when compared to higher eukaryotes. Methods: More than one hundred references were collected to obtain broad information about mammalian and protozoan parasites' GPI structures, biosynthetic pathways, functions and attempts to use these molecules as drug targets against parasitic diseases. Differences between GPI among species were compared and highlighted. Strategies for drug discovery and development against protozoan GPI anchors were discussed based on what has been reported on literature. Results: There are many evidences that GPI anchors are crucial for parasite's survival and interaction with hosts' cells. Despite all GPI anchors contain a conserved glycan core, they present variations regarding structural features and biosynthetic pathways between organisms, which could offer adequate selectivity to validate GPI anchors as drug targets. Discussion was developed with focus on the following parasites: Trypanosoma brucei, Trypanosoma cruzi, Leishmania, Plasmodium falciparum and Toxoplasma gondii, causative agents of tropical neglected diseases. Conclusion: This review debates the main variances between parasitic and mammalian GPI anchor biosynthesis and structures, as well as clues for strategic development for new anti-parasitic therapies based on GPI anchors.

  Immunotherapy, protozoan, drug discovery, Glycosylphosphatidylinositol (GPI), lipopeptidophosphoglycans (LPPGs)

  NCBI PubMed ID: 28748758
  Publication DOI: 10.2174/0929867324666170727110801
  Journal NLM ID: 9440157
  Publisher: Saif Zone, Sharjah, U.A.E.: Bentham Science Publishers
  Correspondence: carronal@usp.br
  Institutions: School of Pharmaceutical Sciences of Ribeirão Preto - University of São Paulo, São Paulo, Brazil
  
   
  
  Trypanosoma brucei
  CSDB ID 7339 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 773.7 [M+H]+
Trivial name: cybersan
Compound class: glycolipid
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130651,IEDB_131186,IEDB_134624,IEDB_135818,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_144987,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156489,IEDB_156493,IEDB_156494,IEDB_167072,IEDB_190606,IEDB_221845,IEDB_241097,IEDB_742245,IEDB_742246,IEDB_742247,IEDB_742248,IEDB_918313,IEDB_918314,SB_163,SB_165,SB_166,SB_187,SB_195,SB_31,SB_62,SB_7,SB_87,SB_88

• Article ID: 8750
  Balan SS, Kumar CG, Jayalakshmi S "Physicochemical, structural and biological evaluation of Cybersan (trigalactomargarate), a new glycolipid biosurfactant produced by a marine yeast, Cyberlindnera saturnus strain SBPN-27" - Process Biochemistry 80 (2019) 171-180
  

  Recent attention on marine microbes has gained a renewed interest on natural product-based drug discovery with functional potential. Nevertheless, marine yeasts were less explored from a bioindustrial and biomedical perspective, especially on biosurfactants regardless no novel structures were identified till date. Considering these facts, this study screened biosurfactants from marine yeasts having broad spectrum industrial significance with the basic tensioactive properties, emulsification and non-hemolytic activities. Among the 136 strains isolated from three different stations of Tamil Nadu, India, Cyberlindnera saturnus SBPN-27 exhibited promising features. The biosurfactant from this marine yeast was purified and structurally characterized as Gal-Gal-Gal-Heptadecanoic acid (named as Cybersan) based on different spectral analysis. Further, Cybersan revealed surface tension of 28 mN/m at critical micelle concentration of 30 mg/L and stability over a broad pH and temperature conditions. Cybersan showed appreciable growth inhibition toward the clinical bacterial pathogens and revealed no considerable cytotoxicity against the mammalian 3T3 fibroblast cells suggesting its biocompatible nature. This is the first report on a new biosurfactant from a marine yeast having diverse functional properties and evidenced as promising candidate for mammalian safe antimicrobial therapy and other biomedical applications.

  glycolipid, cytotoxicity, antimicrobial, biosurfactant, marine yeasts, Cyberlindnera saturnus

  Publication DOI: 10.1016/j.procbio.2019.02.005
  Journal NLM ID: 9211419
  Publisher: Barking, Essex: Elsevier Applied Science
  Correspondence: Balan SS ; Balan SS
  Institutions: CAS in Marine Biology, Faculty of Marine Sciences, Annamalai University, Porto Novo, India, Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, India
  Methods: IR, PCR, GC-MS, TLC, MALDI-TOF MS, extraction, EI-MS, column chromatography, cell growth, RNA sequencing, cytotoxicity assay, GC-FID, evaporation, antimicrobial assay, determination of surface tension, MALDI-TOF MS/MS, BLAST
  
   
  
  Cyberlindnera saturnus SBPN-27
  CSDB ID 49794 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure ; 576000
Trivial name: an acidic polysaccharides APS
Contained glycoepitopes: IEDB_114701,IEDB_115013,IEDB_116886,IEDB_130645,IEDB_130651,IEDB_133754,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_136907,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_144825,IEDB_144987,IEDB_149558,IEDB_151528,IEDB_156983,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_221845,IEDB_225177,IEDB_742246,IEDB_742247,IEDB_885823,IEDB_918313,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_31,SB_62,SB_7,SB_87,SB_88

• Article ID: 9373
  Miao M, Yu WQ, Li Y, Sun YL, Guo SD "Structural Elucidation and Activities of Cordyceps militaris-Derived Polysaccharides: A Review" - Frontiers in Nutrition 9 (2022) 898674
  

  Cordyceps militaris is a parasitic edible fungus and has been used as tonics for centuries. Polysaccharides are a major water-soluble component of C. militaris. Recently, C. militaris-derived polysaccharides have been given much attention due to their various actions including antioxidant, anti-inflammatory, anti-tumor, anti-hyperlipidemic, anti-diabetic, anti-atherosclerotic, and immunomodulatory effects. These bioactivities are determined by the various structural characteristics of polysaccharides including monosaccharide composition, molecular weight, and glycosidic linkage. The widespread use of advanced analytical analysis tools has greatly improved the elucidation of the structural characteristics of C. militaris-derived polysaccharides. However, the methods for polysaccharide structural characterization and the latest findings related to C. militaris-derived polysaccharides, especially the potential structure-activity relationship, have not been well-summarized in recent reviews of the literature. This review will discuss the methods used in the elucidation of the structure of polysaccharides and structural characteristics as well as the signaling pathways modulated by C. militaris-derived polysaccharides. This article provides information useful for the development of C. militaris-derived polysaccharides as well as for investigating other medicinal polysaccharides.

  polysaccharide, structure-activity relationship, bioactivity, Cordyceps militaris, mechanisms of action

  NCBI PubMed ID: 35711557
  Publication DOI: 10.3389/fnut.2022.898674
  Journal NLM ID: 101642264
  Publisher: Lausanne, Switzerland: Frontiers Media S.A.
  Correspondence: Y.L. Sun <840915657@qq.com>; S.D. Guo
  Institutions: Institute of Lipid metabolism and Atherosclerosis, Innovative Drug Research Centre, School of Pharmacy, Weifang Medical University, Weifang, China
  Methods: fermentation
  
   
  
  Cordyceps militaris
  CSDB ID 51811 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130651,IEDB_131186,IEDB_134624,IEDB_135818,IEDB_136044,IEDB_136906,IEDB_136907,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_144987,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_156494,IEDB_167072,IEDB_190606,IEDB_221845,IEDB_241097,IEDB_742245,IEDB_742246,IEDB_742247,IEDB_742248,IEDB_918313,IEDB_918314,SB_163,SB_165,SB_166,SB_187,SB_195,SB_31,SB_62,SB_7,SB_87,SB_88

• Article ID: 9566
  Iskenderov GB "Oligosaccharides from Hedera pastuchovii" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] (1971) 514-515
  
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  
   
  
  Hedera pastuchovii
  CSDB ID 142562 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_114704,IEDB_115013,IEDB_130645,IEDB_130651,IEDB_131186,IEDB_134624,IEDB_135818,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_144987,IEDB_149176,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156489,IEDB_156491,IEDB_156492,IEDB_156493,IEDB_156494,IEDB_167072,IEDB_190606,IEDB_221845,IEDB_241097,IEDB_742245,IEDB_742246,IEDB_742247,IEDB_742248,IEDB_885812,IEDB_918313,IEDB_918314,SB_163,SB_165,SB_166,SB_187,SB_195,SB_31,SB_62,SB_7,SB_87,SB_88

• Article ID: 10067
  Lau JM, McNeil M, Darvill AG, Albersheim P "Treatment of rhamnogalacturonan I with lithium in ethylenediamine" - Carbohydrate Research 168 (1987) 245-274
  

  Rhamnogalacturonan I is a pectic polysaccharide that is solubilized from the walls of suspension-cultured sycamore cells (Acer pseudoplatanus) by the action of a highly purified endo-1,4-α-polygalacturonanase. Rhamnogalacturonan I has a linear backbone consisting of the diglycosyl repeating unit, →4)-α-d-GalpA-(1→2)-α-l-Rhap-(1→. Approximately half of the α-l-rhamnosyl residues of the backbone are branched at O-4. Selective cleavage at the galactosyluronic acid residues of the backbone by treatment of rhamnogalacturonan I wit lithium in ethylenediamine resulted in the release of the neutral glycosyl-residue sidechains that had been attached to the backbone. Various analytical techniques, including combined liquid chromatography-mass spectrometry, combined gas-liquid chromatography-mass spectrometry, and 1H-nuclear magnetic resonance spectroscopy, were used to determine the structure of the side chains. The majority of the sidechains were isolated as oligoglycosylalditols, with rhamnitol at the “reducing” end. Terminal 2-, 4-, or 6-linked galactosyl residues were found attached to O-4 of the rhamnitol residues The 2-, 4-, and 6-linked galactosyl residues had terminal or 2-linked arabinosyl, or additional galactosyl, residues attached to them. Based on the results of fast-atom-bombardment mass spectrometry, the side chains were found to range in size from one to fourteen glycosyl residues. The side-chain structures suggest that there are four or more distinct families of side chains attached to the backbone of rhamnogalacturonan I.

  Publication DOI: 10.1016/0008-6215(87)80029-0
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Chemistry, University of Colorado, Boulder, and Complex Carbohydrate Research Center and School of Chemical Sciences, University of Georgia, Athens, GA, U.S.A.
  Methods: gel filtration, 1H NMR, GLC-MS, FAB-MS
  
   
  
  Acer pseudoplatanus
  CSDB ID 265145 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_116886,IEDB_130645,IEDB_130651,IEDB_131186,IEDB_134624,IEDB_135818,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_144987,IEDB_149137,IEDB_149176,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156489,IEDB_156493,IEDB_156494,IEDB_156557,IEDB_156983,IEDB_167072,IEDB_190606,IEDB_221845,IEDB_241097,IEDB_742245,IEDB_742246,IEDB_742247,IEDB_742248,IEDB_885812,IEDB_918313,IEDB_918314,SB_163,SB_165,SB_166,SB_187,SB_195,SB_31,SB_62,SB_7,SB_87,SB_88

• Article ID: 10067
  Lau JM, McNeil M, Darvill AG, Albersheim P "Treatment of rhamnogalacturonan I with lithium in ethylenediamine" - Carbohydrate Research 168 (1987) 245-274
  

  Rhamnogalacturonan I is a pectic polysaccharide that is solubilized from the walls of suspension-cultured sycamore cells (Acer pseudoplatanus) by the action of a highly purified endo-1,4-α-polygalacturonanase. Rhamnogalacturonan I has a linear backbone consisting of the diglycosyl repeating unit, →4)-α-d-GalpA-(1→2)-α-l-Rhap-(1→. Approximately half of the α-l-rhamnosyl residues of the backbone are branched at O-4. Selective cleavage at the galactosyluronic acid residues of the backbone by treatment of rhamnogalacturonan I wit lithium in ethylenediamine resulted in the release of the neutral glycosyl-residue sidechains that had been attached to the backbone. Various analytical techniques, including combined liquid chromatography-mass spectrometry, combined gas-liquid chromatography-mass spectrometry, and 1H-nuclear magnetic resonance spectroscopy, were used to determine the structure of the side chains. The majority of the sidechains were isolated as oligoglycosylalditols, with rhamnitol at the “reducing” end. Terminal 2-, 4-, or 6-linked galactosyl residues were found attached to O-4 of the rhamnitol residues The 2-, 4-, and 6-linked galactosyl residues had terminal or 2-linked arabinosyl, or additional galactosyl, residues attached to them. Based on the results of fast-atom-bombardment mass spectrometry, the side chains were found to range in size from one to fourteen glycosyl residues. The side-chain structures suggest that there are four or more distinct families of side chains attached to the backbone of rhamnogalacturonan I.

  Publication DOI: 10.1016/0008-6215(87)80029-0
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Chemistry, University of Colorado, Boulder, and Complex Carbohydrate Research Center and School of Chemical Sciences, University of Georgia, Athens, GA, U.S.A.
  Methods: gel filtration, 1H NMR, GLC-MS, FAB-MS
  
   
  
  Acer pseudoplatanus
  CSDB ID 265146 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Trivial name: bupleuran 2IIb
Contained glycoepitopes: IEDB_115013,IEDB_116886,IEDB_130645,IEDB_130651,IEDB_131186,IEDB_133754,IEDB_134624,IEDB_135818,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_144987,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156489,IEDB_156493,IEDB_156494,IEDB_156557,IEDB_156983,IEDB_167072,IEDB_190606,IEDB_221845,IEDB_2229966,IEDB_225177,IEDB_241097,IEDB_581506,IEDB_742245,IEDB_742246,IEDB_742247,IEDB_742248,IEDB_885823,IEDB_918313,IEDB_918314,SB_163,SB_165,SB_166,SB_187,SB_195,SB_31,SB_62,SB_7,SB_87,SB_88

• Article ID: 10535
  Yamada H "Pectic polysaccharides from Chinese herbs: Structure and biological activity" - Carbohydrate Polymers 25 (1994) 269-276
  

  Bioactive pectic polysaccharides have been isolated from Chinese herbs, and their structure, activity and modes of action have been studied. Complement-activating pectin from Angelica acutiloba contained a variety of neutral galactosyl chains which attached to the rhamnogalacturonan core (ramified region), and these neutral galactosyl chains were essential for the expression of complement activating activity, but the polygalacturonan moiety modulated the mode of activation by the ramified region. Another pectin-like polysaccharide, bupleuran 2IIb from Bupleurum falcatum showed a potent immune complex clearance-enhancing activity. Bupleuran 2IIb may enhance Fc receptor expression on the macrophage surface via the ramified region as an active site. An anti-ulcer pectin, bupleuran 2IIc from B. falcatum consists mainly of partially branched polygalacturonan in addition to the ramified region and the rhamnogalacturonan II-like region, and the polygalacturonan region may contribute somewhat to the expression of activity. Collectively considered results have indicated that the pharmacological activity of each of the pectic polysaccharides may depend on their fine chemical structure.

  Publication DOI: 10.1016/0144-8617(94)90052-3
  Journal NLM ID: 8307156
  Publisher: Elsevier
  Institutions: Oriental Medicine Research Center, The Kitasato Institute, Minato-ku, Tokyo, Japan
  
   
  
  Angelica acutiloba
  CSDB ID 213032 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Trivial name: bupleuran 2IIb
Contained glycoepitopes: IEDB_115013,IEDB_116886,IEDB_130645,IEDB_130651,IEDB_131186,IEDB_133754,IEDB_134624,IEDB_135818,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_144987,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156489,IEDB_156493,IEDB_156494,IEDB_156557,IEDB_156983,IEDB_167072,IEDB_190606,IEDB_221845,IEDB_2229966,IEDB_225177,IEDB_241097,IEDB_581506,IEDB_742245,IEDB_742246,IEDB_742247,IEDB_742248,IEDB_885823,IEDB_918313,IEDB_918314,SB_163,SB_165,SB_166,SB_187,SB_195,SB_31,SB_62,SB_7,SB_87,SB_88

• Article ID: 10700
  Matsumoto T, Cyong JC, Kiyohara H, Matsui H, Abe A, Hirano M, Danbara H, Yamada H "The pectic polysaccharide from Bupleurum falcatum L. enhances immune-complexes binding to peritoneal macrophages through Fc receptor expression" - International Journal of Immunopharmacology 15 (1993) 683-693
  

  Binding of glucose oxidase-anti-glucose oxidase complexes (GAG), a model of immune complexes, to macrophages was enhanced by treatment with an acidic pectic polysaccharide, bupleuran 2IIb, from Bupleurum falcatum L. GAG binding to macrophages by bupleuran 2IIb increased in a dose-dependent fashion, and was abolished when the Pronase-treated macrophages were incubated with bupleuran 2IIb. The GAG binding enhancing activity of bupleuran 2IIb was reduced by periodate oxidation but not Pronase digestion of bupleuran 2IIb. When bupleuran 2IIb was digested with endo-polygalacturonase, the resulting enzyme resistant carbohydrate portion showed potent activity. Scatchard analysis indicated enhanced expression of the Fc receptor (FcR) on the surface by the action of bupleuran 2IIb. The enhancement of GAG binding by bupleuran 2IIb was inhibited by the presence of actinomycin D or cycloheximide. Bupleuran-2IIb-stimulated cells showed enhanced expression of both FcRI and FcRII mRNA, which were measured as PCR products. These results suggested that the endo-polygalacturonase resistant carbohydrate portion of bupleuran 2IIb is important for the expression of the activity, and that the activity of bupleuran 2IIb on GAG binding was mediated by receptors for polysaccharide on the cells. The up-regulation of the Fc receptor by bupleuran 2IIb was also suggested to mediate by de novo synthesis of the receptor protein.

  NCBI PubMed ID: 8407053
  Publication DOI: 10.1016/0192-0561(93)90141-K
  Journal NLM ID: 7904799
  Publisher: Elsevier
  Institutions: Oriental Medicine Research Center, Kitasato Institute, Tokyo, Japan, Basic Research Center, The Kitasato Institute, Tokyo, Japan, School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan
  
   
  
  Bupleurum falcatum
  CSDB ID 130966 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure ; n=23
Compound class: polysaccharide
Contained glycoepitopes: IEDB_115013,IEDB_116886,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_136907,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_221845,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88

• Article ID: 11697
  Arifkhodzhaev AO "Galactans and galactan-containing polysaccharides of higher plants" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 36(3) (2000) 229-244
  

  Research on the chemical structure and physiological activity of galactan and galactan-containing polysaccharides of higher plants is reviewed. The principal chain in galactan-containing polysaccharides consists of 1–3, 1–4, 1–6, and α- and β-bonded D-galactopyranoses. The side chains contain separate or bonded chains of galactose, arabinose, glucose, rhamnose, and uronic acids. The relationship of chemical structure and physiological activity of the polysaccharides of higher plants is discussed.

  polysaccharides, immunomodulators, galactans, arabino-4-galactans, arabino-3, 6-galactans, mutagenic activity

  Publication DOI: 10.1007/BF02238327
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: S.Yu.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Uzbekistan
  
   
  
  Opuntia dillenii
  CSDB ID 64735 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Compound class: polysaccharide, galactan
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141492,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_156983,IEDB_190606,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88

• Article ID: 11859
  Farias WR, Valente AP, Pereira MS, Mourão PA "Structure and anticoagulant activity of sulfated galactans. Isolation of a unique sulfated galactan from the red algae Botryocladia occidentalis and comparison of its anticoagulant action with that of sulfated galactans from invertebrates" - Journal of Biological Chemistry 275(38) (2000) 29299-29307
  

  We have characterized the structure of a sulfated d-galactan from the red algae Botryocladia occidentalis. The following repeating structure (-4-α-D-Galp-1→3-β-D-Galp-1→) was found for this polysaccharide, but with a variable sulfation pattern. Clearly one-third of the total α-units are 2,3-di-O-sulfated and another one-third are 2-O-sulfated. The algal sulfated D-galactan has a potent anticoagulant activity (similar potency as unfractionated heparin) due to enhanced inhibition of thrombin and factor Xa by antithrombin and/or heparin cofactor II. We also extended the experiments to several sulfated polysaccharides from marine invertebrates with simple structures, composed of a single repeating structure. A 2-O- or 3-O-sulfated l-galactan (as well as a 2-O-sulfated l-fucan) has a weak anticoagulant action when compared with the potent action of the algal sulfated D-galactan. Possibly, the addition of two sulfate esters to a single α-galactose residue has an "amplifying effect" on the anticoagulant action, which cannot be totally ascribed to the increased charge density of the polymer. These results indicate that the wide diversity of polysaccharides from marine alga and invertebrates is a useful tool to elucidate structure/anticoagulant activity relationships.

  anticoagulant activity, Botryocladia occidentalis, red alga, sulfated galactan

  NCBI PubMed ID: 10882718
  Publication DOI: 10.1074/jbc.M002422200
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: pmourao@hucff.ufrj.br
  Institutions: Laboratório de Tecido Conjuntivo, Hospital Universitário Clementino Fraga Filho, Rio de Janeiro, Brazil, Departamento de Bioquímica Médica, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Departamento de Engenharia de Pesca, Universidade Federal do Ceará, Fortaleza, Brazil, Centro Nacional de Ressonância Nuclear Magnética de Macromoléculas, Departamento de Bioquímica Médica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, acid hydrolysis, GLC, anion-exchange chromatography, biological assays, paper chromatography, FPLC, extraction, gel chromatography, acetylation, reduction, dialysis, anticoagulation activity, precipitation, phenol-sulfuric acid assay, derivatization, evaporation, centrifugation, gel electrophoresis
  
   
  
  Botryocladia occidentalis
  CSDB ID 65431 (all data & tools)