Structure and anti-metapneumovirus activity of sulfated galactans from the red seaweed Cryptonemia seminervis

Carbohydrate Polymers

Volumn 101, Issue 1, 2014, Pages 313-323

  Mendes, Gabriella S ^a   Duarte, Maria E R ^b   Colodi, Franciely G ^b   Noseda, Miguel D ^b   Ferreira, Luciana G ^b   Berté, Siliane D ^b   Cavalcanti, Jéssica F ^a   Santos, Norma ^a   Romanos, Maria T V ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

Author keywords

Antiviral activity; Chemical structure; Cryptonemia seminervis; Human metapneumovirus; Partial depolymerization; Sulfated galactans

Indexed keywords

ANTIVIRAL ACTIVITIES; CHEMICAL CHARACTERISTIC; CRYPTONEMIA SEMINERVIS; HUMAN METAPNEUMOVIRUS; MONOSACCHARIDE COMPOSITION; PARTIAL HYDROLYSIS; STRUCTURAL STUDIES; SULFATED GALACTANS;

CELL MEMBRANES; SEAWEED; STRUCTURE (COMPOSITION);

POLYSACCHARIDES;

CRYPTONEMIA SEMINERVIS; HUMAN METAPNEUMOVIRUS; METAPNEUMOVIRUS;

ANTIVIRUS AGENT; GALACTAN; SULFATE;

ANIMAL; ANTIVIRAL ACTIVITY; ARTICLE; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; CRYPTONEMIA SEMINERVIS; DRUG EFFECT; HUMAN; HUMAN METAPNEUMOVIRUS; METAPNEUMOVIRUS; PARTIAL DEPOLYMERIZATION; POLYMERIZATION; RED ALGA; SULFATED GALACTANS;

ANTIVIRAL ACTIVITY; CHEMICAL STRUCTURE; CRYPTONEMIA SEMINERVIS; HUMAN METAPNEUMOVIRUS; PARTIAL DEPOLYMERIZATION; SULFATED GALACTANS;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; GALACTANS; HUMANS; METAPNEUMOVIRUS; POLYMERIZATION; RHODOPHYTA; SULFATES;

EID: 84885333252     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2013.09.026     Document Type: Article

References (57)

1. C.A. Araújo, M.D. Noseda, T.R. Cipriani, A.G. Gonçalves, M.E.R. Duarte, and D.R.B. Ducatti Selective sulfation of carrageenans and the influence of sulfate regiochemistry on anticoagulant properties Carbohydrate Polymers 91 2013 483 491
2. A. Arnott, S. Vong, M. Sek, M. Naughtin, J. Beauté, and S. Rith Genetic variability of human metapneumovirus amongst an all ages population in Cambodia between 2007 and 2009 Infection, Genetics and Evolution 15 2013 43 52
3. 13C NMR assignment of digeneaside, a low-molecular-mass carbohydrate produced by red seaweeds Carbohydrate Research 341 2006 677 682
4. M. Baba, R. Snoeck, R. Pauwels, and E. De Clercq Sulfated polysaccharides are potent and selective inhibitors of various enveloped virus, including Herpes simplex virus, cytomegalovirus, vesicular stomatitis virus, and human immunodeficiency virus Antimicrobial Agents and Chemotherapy 32 1988 1742 1745 (Pubitemid 18267628)
5. E. Borefreund, and J. Puerner Toxicity determined in vitro by morphological alterations and neutral red absorption Toxicology Letters 24 1985 119 124 (Pubitemid 15103513)
6. R. Bouhlal, C. Haslin, J.C. Chermann, S. Colliec-Jouault, C. Sinquin, and G. Simon Antiviral activities of sulfated polysaccharides isolated from Sphaerococcus coronopifolius (Rhodophytha, Gigartinales) and Boergeseniella thuyoides (Rhodophyta Ceramiales) Marine Drugs 9 2011 1187 1209
7. R. Brittain-Long, S. Nord, S. Olofsson, J. Westin, A. Lars-Magnus, and M. Lindh Multiplex Real-time PCR for detection of respiratory tract infections Journal of Clinical Virology 41 2008 53 56 (Pubitemid 50019324)
8. M.A. Cardoso, M.D. Noseda, M.T. Fujii, R.G.M. Zibetti, and M.E.R. Duarte Sulfated xylomannans isolated from red seaweeds Chondrophycus papillosus and C. flagelliferus (Ceramiales) from Brazil Carbohydrate Research 342 2007 2766 2775 (Pubitemid 350123533)
9. M.J. Carlucci, L.A. Scolaro, M.D. Noseda, A.S. Cerezo, and E.B. Damonte Protective effect of a natural carrageenan on genital herpes simplex virus infection in mice Antiviral Research 64 2004 137 141 (Pubitemid 39446136)
10. J.E.F. Cassolato, M.D. Noseda, C.A. Pujol, F.M. Pellizzari, E.B. Damonte, and M.E.R. Duarte Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma Carbohydrate Research 343 2008 3085 3095
11. M. Chen, B.P. Griffith, H.L. Lucia, and G.D. Hsiung Efficacy of S26308 against guinea pig cytomegalovirus infection Antimicrobial Agents and Chemotherapy 32 1988 678 683
12. P.L. Collins, and J.E. Crowe Respiratory syncytial virus and metapneumovirus D.M. Knipe, P.M. Howley, Fields virology 2007 Lippincott Williams & Wilkins Philadelphia, PA, USA 1601 1646
13. P.L. Collins, and J.A. Melero Progress in understanding and controlling respiratory syncytial virus: Still crazy after all these years Virus Research 162 2011 80 99
14. J.S. Craigie, and A. Jurgens Structure of agars from Gracilaria tikvahiae Rhodophyta: Location of 4-O-methyl-l-galactose and sulfate Carbohydrate Polymers 11 1989 265 278
15. E.B. Damonte, M.C. Matulewicz, and A.S. Cerezo Sulfated seaweed polysaccharides as antiviral agents Current Medicinal Chemistry 11 2004 2399 2419 (Pubitemid 39172357)
16. K.S. Dodgson, and R.G. Price A note on determination of the ester sulfate content of sulphated polysaccharides Biochemical Journal 84 1962 106 110
17. M.E.R. Duarte, J.P. Cauduro, D.G. Noseda, M.D. Noseda, A.G. Gonçalves, and C.A. Pujol The structure of the agaran sulfate from Acanthophora spicifera (Rhodomelaceae, Ceramiales) and its antiviral activity. Relation between structure and antiviral activity in agarans Carbohydrate Research 339 2004 335 347 (Pubitemid 38043939)
18. M.E.R. Duarte, M.D. Noseda, M.A. Cardoso, S. Túlio, and A.S. Cerezo The structure of a galactan sulfate from the red seaweed Bostrychia montagnei Carbohydrate Research 337 2001 1137 1144 (Pubitemid 34607686)
19. M.E.R. Duarte, D.G. Noseda, M.D. Noseda, S. Tulio, C.A. Pujol, and E.B. Damonte Inhibitory effect of sulfated galactans from the marine alga Bostrychia montagnei on herpes simplex virus replication in vitro Phytomedicine 8 2001 53 58 (Pubitemid 32242093)
20. M. Dubois, K.A. Gilles, J.K. Hamilton, P.A. Rebers, and F. Smith Colorimetric method for determination of sugars and related substances Analytical Chemistry 28 1956 350 356
21. R. Falshaw, and R.H. Furneaux Carrageenan from the tetrasporic stage of Gigartina decipiens (Gigartinaceae Rhodophyta) Carbohydrate Research 252 1994 171 182 (Pubitemid 24062596)
22. R. Falshaw, and R.H. Furneaux Carrageenans from the tetrasporic stages of Gigartina clavifera and Gigartina alveata (Gigartinaceae Rhodophyta) Carbohydrate Research 276 1995 155 165
23. P.C.S. Faria-Tischer, L.B. Talarico, M.D. Noseda, S.M.P.B. Guimarães, E.B. Damonte, and M.E.R. Duarte Chemical structure and antiviral activity of carrageenans from Meristiella gelidium against herpes simplex and dengue virus Carbohydrate Polymers 63 2006 459 465 (Pubitemid 43375042)
24. L.G. Ferreira, M.D. Noseda, A.G. Gonçalves, D.R.B. Ducatti, M.T. Fujii, and M.E.R. Duarte Chemical structure of the complex pyruvylated and sulfated agaran from the red seaweed Palisada flagellifera (Ceramiales Rhodophyta) Carbohydrate Research 347 2012 83 94
25. F. Feuillet, B. Lina, M. Rosa-Calatrava, and G. Boivin Ten years of human metapneumovirus research Journal of Clinical Virology 53 2012 97 105
26. Freile-Pelegrin, and E. Murano Agars from three species of Gracilaria (Rhodophyta) from Yucatán Peninsula Bioresource Technology 96 2005 295 302 (Pubitemid 39335611)
27. P.J. Garegg, B. Lindberg, and I. Kvarnström Preparation and N.M.R. studies of pyruvic acid and related acetals of pyranosides: Configuration at the acetal carbon atoms Carbohydrate Research 77 1979 71 78
28. A.G. Gonçalves, D.R.B. Ducatti, M.E.R. Duarte, and M.D. Noseda Sulfated and pyruvylated disaccharide alditols obtained from a red seaweed galactan: ESIMS and NMR approaches Carbohydrate Research 337 2002 2443 2453 (Pubitemid 35461938)
29. T. Ghosh, K. Chattopadhyay, M. Marschall, P. Karmakar, P. Mandal, and B. Ray Focus on antivirally active sulfated polysaccharides: From structure-activity analysis to clinical evaluation Glycobiology 19 2009 2 15
30. E.A. Harden, R. Falshaw, S.M. Carnachan, E.R. Kern, and M.N. Prichard Virucidal activity of polysaccharide extracts from four algal species against herpes simplex virus Antiviral Research 83 2009 282 289
31. C. Haslin, M. Lahaye, M. Pellegrini, and J.C. Chermann In vitro anti-HIV activity of sulfated cell-wall polysaccharides from gametic, carposporic and tetrasporic stages of the mediterranean red alga Asparagopsis armata Planta Medica 67 2001 301 305 (Pubitemid 32588562)
32. P.-E. Jansson, L. Kenne, H. Liedgren, B. Lindberg, and J. Lonngren A practical guide to the methylation analysis of carbohydrates Chemical Communications of the University of Stockholm 8 1976 1 76
33. C.N. Jol, T.G. Neiss, B. Penninkhof, B. Rudolph, and G.A. De Ruiter A novel high-performance anion-exchange chromatographic method for the analysis of carrageenans and agars containing 3,6-anhydrogalactose Analytical Biochemistry 268 1999 213 222 (Pubitemid 29147135)
34. S.H. Knutsen, D.E. Myslabodski, B. Larsen, and A.I. Usov A modified system of nomenclature for red algal galactans Botanica Marina 37 1994 163 169
35. 13C-NMR spectroscopic investigation of methylated and charged agarose oligosaccharides and polysaccharides Carbohydrate Research 190 1989 249 265
36. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the folin phenol reagent Journal of Biological Chemistry 193 1951 265 275
37. B. Matsuhiro, A.F. Conte, E.B. Damonte, A.A. Kolender, M.C. Matulewicz, and E.G. Mejías Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta) Carbohydrate Research 340 2005 2392 2402 (Pubitemid 41375758)
38. G.S. Mendes, A.R. Soares, F.O. Martins, M.C. Albuquerque, S.S. Costa, and Y. Yoneshigue-Valentin Antiviral activity of the green marine alga Ulva fasciata on the replication of human metapneumovirus Revista do Instituto de Medicina Tropical de São Paulo 52 2010 3 10
39. G.S. Mendes, A.R. Soares, L. Sigiliano, F. Machado, C. Kaiser, and N. Romeiro In vitro anti-HMPV activity of meroditerpenoids from marine alga Stypopodium zonale (Dictyotales) Molecules 16 2011 8437 8450
40. 13C NMR methods for determining the structure of algal polysaccharides. Part 2. Galactans consisting of mixed diads Botanica Marina 43 2000 251 261 (Pubitemid 30347638)
41. K. Nagasawa, Y. Inoue, and T. Kamata Solvolytic desulfation of glycosaminoglycuronan sulfates with dimethyl sulfoxide containing water or methanol Carbohydrate Research 58 1977 47 55
42. D.A. Navarro, and C.A. Stortz Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans Carbohydrate Research 338 2003 2111 2118 (Pubitemid 37123172)
43. D.A. Navarro, and C.A. Stortz The system of xylogalactans from the red seaweed Jania rubens (Corallinales, Rhodophyta) Carbohydrate Research 343 2008 2613 2622
44. M.T.V. Romanos, M.J. Andrada-Serpa, P.A.S. Mourão, Y. Yoneshigue-Valentin, S.S. Costa, and M.S. Pereira A sulphated fucan from the Laminaria abyssalis inhibits the human T cell lymphotropic virus type 1-induced syncytium formation in HeLa cells Antiviral Chemistry and Chemotherapy 13 2002 219 221 (Pubitemid 36733661)
45. T.T. Stevenson, and R.H. Furneaux Chemical methods for the analysis of sulphated galactans from red algae Carbohydrate Research 210 1991 277 298
46. L.B. Talarico, M.D. Noseda, D.R.B. Ducatti, M.E.R. Duarte, and E.B. Damonte Differential inhibition of dengue virus infection in mammalian and mosquito cells by iota-carrageenan Journal of General Virology 92 2011 1332 1342
47. L.B. Talarico, C.A. Pujol, R.G.M. Zibetti, P.C.S. Faría, M.D. Noseda, and M.E.R. Duarte The antiviral activity of sulfated polysaccharides against dengue virus is dependent on virus serotype and host cell Antiviral Research 66 2005 103 110 (Pubitemid 40720115)
48. L.B. Talarico, R.G.M. Zibetti, P.C.S. Faria, L.A. Scolaro, M.E.R. Duarte, and M.D. Noseda Anti-herpes simplex virus activity of sulfated galactans from the red seaweeds Gymnogongrus griffithsiae and Cryptonemia crenulata Biological Macromolecules 34 2004 63 71 (Pubitemid 38721187)
49. A.I. Usov, and Y.A. Elashvili Polysaccharides of algae: Investigation of sulfated galactan from Laurencia nipponica Yamada (Rhodophyta, Rhodomelaceae) using partial reductive hydrolysis Botanica Marina 34 1991 553 560
50. 13C-NMR spectroscopy Botanica Marina 28 1985 367 373
51. 13C-NMR spectroscopy of red algal galactans Biopolymers 19 1980 977 990
52. B.G. van den Hoogen, S. Herfst, L. Sprong, P.A. Cane, E. Forleo-Neto, and R.L. de Swart Antigenic and genetic variability of human metapneumovirus Emerging Infectious Diseases 10 2004 658 666 (Pubitemid 38420297)
53. B.G. van den Hoogen, J.C. de Jong, J. Groen, T. Kuiken, R. de Groot, and R.A. Fouchier A newly discovered human pneumovirus isolated from young children with respiratory tract disease Nature Medicine 7 2001 719 724 (Pubitemid 32588029)
54. J.V. Williams, K.M. Edwards, and G.A. Weinberg Population-based incidence of human metapneumovirus infection among hospitalized children The Journal of Infectious Diseases 201 2010 1890 1898
55. M. Witvrouw, and E. De Clercq Sulfated polysaccharides extracted from sea algae as potential antiviral drugs General Pharmacology 29 1997 497 511 (Pubitemid 27421412)
56. R.G.M. Zibetti, M.D. Noseda, A.S. Cerezo, and M.E.R. Duarte The system of galactans from Cryptonemia crenulata (Halymeniaceae, Halymeniales) and the structure of two major fractions. Kinetic studies on the alkaline cyclization of the unusual diad G2S→D(L)6S Carbohydrate Research 340 2005 711 722 (Pubitemid 40260918)
57. R.G.M. Zibetti, M.E.R. Duarte, M.D. Noseda, F.G. Colodi, D.R.B. Ducatti, and L.G. Ferreira Galactans from Cryptonemia species. Part II: Studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions Carbohydrate Research 344 2009 2364 2374