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Abstract:

Chemical and spectroscopic methods showed that the major KCl-precipitated galactans from Meristiella gelidium (Solieriaceae) are iota/kappa/nu-hybrid carrageenans with the former one in higher proportion. These carrageenans showed, by HPSEC-MALLS analysis, unimodal symmetrical peaks with MW of 425.6-956.7 kDa. The effectiveness of the crude extracts from M. gelidium against HSV-2 was higher than the corresponding extract from G. griffithsiae, previously determined. However, when considering the homogeneous carrageenans, the fractions obtained from both seaweeds showed the same level of activity. The extracts and carrageenan derived from M. gelidium were more effective inhibitors of DENV-2 if compared with G. griffithsiae samples and reference polysaccharides. The most active fraction obtained from M. gelidium showed a selectivity index against HSV-2 of 25,000, a value high enough to consider this carrageenan as a promising agent to be evaluated for the treatment of genital HSV-2 infections. © 2005 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Chemical structure and antiviral activity of carrageenans from Meristiella gelidium against herpes simplex and dengue virus
Autor:De S.f-Tischer, P.C.; Talarico, L.B.; Noseda, M.D.; Pita B. Guimarães, S.M.; Damonte, E.B.; Duarte, M.E.R.
Filiación:Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, P.O. Box 19046, Curitiba, CEP 81531-990 Parana, Brazil
Laboratorio de Virología, Departamento de Química Biológica, Universidad de Buenos Aires, CP 1428 Buenos Aires, Argentina
Instituto de Botânica, Secretaria do Meio Ambiente do Estado de São Paulo, Seção de Ficologia, P.O. Box 4005, CEP 04301902 São Paulo, SP, Brazil
Palabras clave:Antiviral activity; Chemical structure; Dengue virus; Herpes simplex virus; Iota/kappa-carrageenan; Meristiella gelidium; Solieriaceae; Molecular structure; Polysaccharides; Potassium compounds; Spectroscopy; Antiviral activity; Chemical structures; Dengue virus; Herpes simplex virus; Iota/kappa-carrageenan; Meristiella gelidium; Solieriaceae; Viruses; algae; Dengue virus; Herpes; Human herpesvirus 2; Meristiella gelidium; Simplexvirus; Solieriaceae
Año:2006
Volumen:63
Número:4
Página de inicio:459
Página de fin:465
DOI: http://dx.doi.org/10.1016/j.carbpol.2005.09.020
Título revista:Carbohydrate Polymers
Título revista abreviado:Carbohydr Polym
ISSN:01448617
CODEN:CAPOD
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01448617_v63_n4_p459_DeSfTischer

Referencias:

  • Anderson, N.S., Dolan, T.C.S., Rees, D.A., Carrageenans. Part VII. Polysaccharides from Eucheuma spinosum and Eucheuma cottonii. the covalent structure of ι-carrageenan (1973) Journal of the Chemical Society, 19, pp. 2173-2176
  • Carlucci, M.J., Ciancia, M., Matulewicz, M.C., Cerezo, A.S., Damonte, E.B., Antiherpetic activity and mode of action of natural carrageenans of diverse structural types (1999) Antiviral Research, 43, pp. 93-102
  • Cases, M.R., Cerezo, A.S., Stortz, C.A., Separation and quantification of enantiomeric galactoses and their mono-O-methylethers as their diastereomeric acetylated 1-deoxy-1-(2- hydroxypropylamino) alditols (1995) Carbohydrate Research, 269, pp. 333-341
  • Chen, Y., Maguire, T., Hileman, R.E., Fromm, J.R., Esko, J.D., Linhardt, R.J., Dengue virus infectivity depends on envelope protein binding to target cell heparan sulfate (1997) Nature Medicine, 3, pp. 866-871
  • Chiovitti, A., Bacic, A., Craik, D.J., Kraft, G.T., Liao, M.-L., Falshaw, R., A pyruvated carrageenan from Australian specimens of the red alga Sarconema filiforme (1998) Carbohydrate Research, 310, pp. 77-83
  • Chiovitti, A., Bacic, A., Craik, D.J., Munro, S.L.A., Kraft, G.T., Liao, M.-L., Cell-wall polysaccharides from Australian red algae of the family Solieriaceae (Gigartinales, Rhodophyta): Novel, highly pyruvated carrageenans from the genus Callophycus (1997) Carbohydrate Research, 299, pp. 229-243
  • Chiovitti, A., Bacic, A., Craik, D.J., Munro, S.L.A., Kraft, G.T., Liao, M.-L., Carrageenans with complex substitution patterns from red algae of the genus Erythroclonium (1998) Carbohydrate Research, 305, pp. 243-252
  • Chiovitti, A., Bacic, A., Craik, G.T., D., J., Kraft, G.T., Liao, M.-L., A nearly idealized 6-O-methylated ι-carrageenan from the Australian red alga Claviclonium ovatum (Acrotylaceae, Gigartinales) (2004) Carbohydrate Research, 339, pp. 1459-1466
  • Chiovitti, A., Liao, M.-L., Kraft, G.T., Munro, S.L.A., Craik, D.J., Bacic, A., Cell wall polysaccharides from Australian red algae of the family Solieriaceae (Gigartinales, Rhodophyta): Highly methylated carrageenans from the genus Rhabdonia (1996) Botanica Marina, 39, pp. 47-59
  • Chopin, T., Kerin, B.F., Mazerolle, R., Phycocolloid chemistry as a taxonomic indicator of phylogeny in the Gigartinales, Rhodophyta (1999) Phycology Research, 47, pp. 167-188
  • Ciancia, M., Noseda, M.D., Matulewicz, M.C., Cerezo, A.S., Alkali modification of carrageenans: Mechanism and kinetics in the kappa/iota-, mu/nu- and lambda-series (1993) Carbohydrate Polymers, 20, pp. 95-98
  • Ciucanu, I., Kerek, F., A simple and rapid method for the permethylation of carbohydrates (1984) Carbohydrate Research, 131, pp. 209-217
  • Craigie, J.S., Leigh, C., Carrageenans and agars (1978) Handbook of Phycological Methods: Physiological and Biochemical Methods, pp. 109-131. , J.A. Hellbust J.S. Craigie Cambridge University Press Cambridge
  • Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., Sulfated seaweed polysaccharides as antiviral agents (2004) Current Medicinal Chemistry, 11, pp. 2399-2419
  • Dodgson, K.S., Price, R.G., A note on the determination of the sulfate ester of sulfated polysaccharide (1962) Biochemistry Journal, 84, pp. 106-109
  • Dubois, M., Gilles, K.A., Hamilton, J.K., Rebers, P.A., Smith, F., Colorimetric method for determination of sugars and related substances (1956) Analytical Chemistry, 28, pp. 350-356
  • Errea, M.I., Ciancia, M., Matulewicz, M.C., Cerezo, A.S., Separation and quantification of enantiomeric 3,6-anhydrogalactoses by conversion to the corresponding diastereomeric acetylated sec-butyl 3,6-anhydrogalactonates (1998) Carbohydrate Research, 311, pp. 235-238
  • Estevez, J.M., Ciancia, M., Cerezo, A.S., The system of low-molecular-weight carrageenans and agaroids from the room-temperature-extracted fraction of Kappaphycus alvarezii (2000) Carbohydrate Research, 325, pp. 287-299
  • Estevez, J.M., Ciancia, M., Cerezo, A.S., Dl-Galactan hybrids and agarans from gametophytes of the red seaweed Gymnogongrus torulosus (2001) Carbohydrate Research, 331, pp. 27-41
  • Falshaw, R., Furneaux, R.H., Wong, H., Analysis of pyruvylated β-carrageenan by 2D NMR spectroscopy and reductive partial hydrolysis (2003) Carbohydrate Research, 338, pp. 1403-1414
  • Furneaux, R.H., Miller, I.J., Isolation and 13C-NMR spectral study of the water soluble polysaccharides from four south African red algae (1986) Botanica Marina, 29, pp. 3-10
  • Knutsen, S.H., Myslabodski, D.E., Larsen, B., Usov, A.I., A modified system of nomenclature for red algal galactans (1994) Botanica Marina, 37, pp. 163-169
  • Lowry, O.H., Rosebrough, N.J., Farr, A.L., Randall, R.J., Protein measurement with the folin phenol reagent (1951) The Journal of Biological Chemistry, 193, pp. 265-275
  • McCandless, E.L., West, J.A., Guiry, M.D., Carrageenan patterns in phyllophoraceae (1982) Biochemical Systematics and Ecology, 10, pp. 275-284
  • Renn, D., Biotechnology and the red seaweed polysaccharides industry: Status, needs and prospects (1997) Trends in Biotechnology, 15, pp. 9-14
  • Saito, R., Oliveira, E.C., Chemical screening of Brazilian marine algae producing carrageenans (1990) Hydrobiologia, 204-205, pp. 585-588
  • Stancioff, D.J., Stanley, N.F., Infrared and chemical studies on algal polysaccharides (1969) Proceedings International Seaweed Symposium, 6, pp. 595-609
  • Stevenson, T., Furneaux, R., Chemical methods for the analysis of sulphated galactans from red algae (1991) Carbohydrate Research, 210, pp. 277-298
  • Stortz, C.A., Bacon, C.F., Cherniak, R., Cerezo, A.S., High field NMR spectroscopy of cystocarpic and tetrasporic carrageenans from Iridaea undulosa (1994) Carbohydrate Research, 261, pp. 317-326
  • Stortz, C.A., Cases, M., Cerezo, A.S., The system of agaroids and carrageenans from the soluble fraction of the tetrasporic stage of the red seaweedIridaea undulosa (1997) Carbohydrate Polymers, 34, pp. 61-65
  • Stortz, C.A., Cerezo, A.S., The systems of carrageenans from cystocarpic and tetrasporic stages from Iridaea undulosa: Fractionation with potassium chloride and methylation analysis of the fractions (1993) Carbohydrate Research, 242, pp. 217-227
  • Takano, R., Sakata-Iwane, H., Hayashi, K., Hara, S., Hirase, S., Concurrence of agaroid and carrageenan chains in funoran from the red seaweed Gloiopeltis furcata post. et ruprecht (Cryptonemiales, Rhodophyta) (1998) Carbohydrate Polymers, 35, pp. 81-87
  • Takano, R., Shiomoto, K., Kamei, K., Hara, S., Hirase, S., Occurrence of carrageenan structure in an agar from the red seaweed Digenea simplex (Wulfen) C. Agardh (Rhodomelaceae, Ceramiales) with a short review of carrageenan-agarocolloid hybrid in the florideophycidae (2003) Botanica Marina, 46, pp. 142-150
  • Talarico, L.B., Pujol, C.A., Zibetti, R.G.M., Faria, P.C.S., Noseda, M.D., Duarte, M.E.R., The antiviral activity of sulfated polysaccharides against dengue virus is dependent on virus serotype and host cell (2005) Antiviral Research, 66, pp. 103-110
  • Talarico, L.B., Zibetti, R.G.M., Faria, P.C.S., Scolaro, L.A., Duarte, M.E.R., Noseda, M.D., Anti-herpes simplex virus activity of sulfated galactans from the red seaweeds Gymnogongrus griffithsiae and Cryptonemia crenulata (2004) International Journal of Biological Macromolecules, 34, pp. 63-71
  • Usov, A.I., Structural analysis of red seaweed galactans of agar and carrageenan groups (1998) Food Hydrocolloids, 12, pp. 301-308
  • Usov, A.I., Klochkova, N.G., Polysaccharides of algae. 45. Polysaccharide composition of red seaweeds from Kamchatka coastal waters (Northwestern Pacific) studied by reductive hydrolysis of biomass (1992) Botanica Marina, 35, pp. 371-378
  • Usov, A.I., Shashkov, A.S., Polysaccharides of algae. Detection of iota-carrageenan in Phyllophora brodiaei (Turn.) J. Ag. (Rhodophyta) using 13C-NMR spectroscopy (1985) Botanica Marina, 28, pp. 367-373
  • Van De Velde, F., Knutsen, S.H., Usov, A.I., Rollema, H.S., Cerezo, A.S., 1H and 13C high resolution NMR spectroscopy of carrageenans: Application in research and industry (2002) Trends in Food Science and Technology, 13, pp. 73-92
  • Viana, A.G., Noseda, M.D., Duarte, M.E.R., Cerezo, A.S., Alkali modification of carrageenans. Part V. the iota-nu hybrid carrageenan from Eucheuma denticulatum and its cyclization to iota-carrageenan (2004) Carbohydrate Polymers, 58, pp. 455-460
  • Wudunn, D., Spear, P.G., Initial interaction of herpes simplex virus with cells is binding to heparan sulfate (1989) Journal of Virology, 63, pp. 52-58
  • Yaphe, W., Colorimetric determination of 3,6-anhydrogalactose and galactose in marine algae polysaccharides (1960) Analytical Chemistry, 32, pp. 1327-1330
  • Zibetti, R.G.M., Noseda, M.D., Cerezo, A.S., Duarte, M.E.R., 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 (2005) Carbohydrate Research, 340, pp. 711-722

Citas:

---------- APA ----------
De S.f-Tischer, P.C., Talarico, L.B., Noseda, M.D., Pita B. Guimarães, S.M., Damonte, E.B. & Duarte, M.E.R. (2006) . Chemical structure and antiviral activity of carrageenans from Meristiella gelidium against herpes simplex and dengue virus. Carbohydrate Polymers, 63(4), 459-465.
http://dx.doi.org/10.1016/j.carbpol.2005.09.020
---------- CHICAGO ----------
De S.f-Tischer, P.C., Talarico, L.B., Noseda, M.D., Pita B. Guimarães, S.M., Damonte, E.B., Duarte, M.E.R. "Chemical structure and antiviral activity of carrageenans from Meristiella gelidium against herpes simplex and dengue virus" . Carbohydrate Polymers 63, no. 4 (2006) : 459-465.
http://dx.doi.org/10.1016/j.carbpol.2005.09.020
---------- MLA ----------
De S.f-Tischer, P.C., Talarico, L.B., Noseda, M.D., Pita B. Guimarães, S.M., Damonte, E.B., Duarte, M.E.R. "Chemical structure and antiviral activity of carrageenans from Meristiella gelidium against herpes simplex and dengue virus" . Carbohydrate Polymers, vol. 63, no. 4, 2006, pp. 459-465.
http://dx.doi.org/10.1016/j.carbpol.2005.09.020
---------- VANCOUVER ----------
De S.f-Tischer, P.C., Talarico, L.B., Noseda, M.D., Pita B. Guimarães, S.M., Damonte, E.B., Duarte, M.E.R. Chemical structure and antiviral activity of carrageenans from Meristiella gelidium against herpes simplex and dengue virus. Carbohydr Polym. 2006;63(4):459-465.
http://dx.doi.org/10.1016/j.carbpol.2005.09.020