Abstract:
Background: Many viruses display affinity for cell surface heparan sulfate proteoglycans with biological relevance in virus entry. This raises the possibility of the application of sulfated polysaccharides in antiviral therapy. Methods: In this study, we analysed polysaccharide fractions isolated from Sebdenia polydactyla. Results: The purified xylomannan sulfate and its further sulfated derivatives showed strong activity against herpes simplex virus type-1 (HSV-1). Their 50% inhibitory concentration values were in the range 0.35-2.8 μg/ ml and they lacked cytotoxicity at concentrations up to 1,000 μg/ml. The major polysaccharide, which had 0.6 sulfate groups per monomer unit and an apparent molecular mass of 150 kDa, contained a backbone of α-(1→3)- linked D-mannopyranosyl residues substituted at position 6 with a single stub of β-d-xylopyranosyl residues. Conclusions: The degree of sulfation seemed to play an important role because desulfation and/or further sulfation of the isolated macromolecules largely influenced their in vitro anti-HSV-1 activity. ©2009 International Medical Press.
Registro:
Documento: |
Artículo
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Título: | Sulfated xylomannans from the red seaweed Sebdenia polydactyla: Structural features, chemical modification and antiviral activity |
Autor: | Ghosh, T.; Pujol, C.A.; Damonte, E.B.; Sinha, S.; Ray, B. |
Filiación: | Natural Products Laboratory, Department of Chemistry, University of Burdwan, West Bengal, India Departamento de Química Biológica, Facultad de Ciencias Exactas Y Naturales UBA, Ciudad Universitaria-Pabellón II, Buenos Aires, Argentina
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Palabras clave: | monomer; polysaccharide; unclassified drug; xylomannan derivative; animal cell; antiviral activity; article; chemical modification; drug cytotoxicity; drug isolation; drug selectivity; Herpes simplex virus 1; IC 50; in vitro study; macromolecule; molecular weight; nonhuman; priority journal; seaweed; Sebdenia polydactyla; structure activity relation; sulfation |
Año: | 2009
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Volumen: | 19
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Número: | 6
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Página de inicio: | 235
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Página de fin: | 242
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DOI: |
http://dx.doi.org/10.1177/095632020901900603 |
Título revista: | Antiviral Chemistry and Chemotherapy
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Título revista abreviado: | Antiviral Chem. Chemother.
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ISSN: | 09563202
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CODEN: | ACCHE
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09563202_v19_n6_p235_Ghosh |
Referencias:
- Arad, S.M., Ginzberg, A., Huleihel, M., Antiviral activity of sulfated polysaccharides of marine red algae (2006) Biomaterials from Aquatic and Terrestrial Organizations, pp. 37-62. , Fingerman M, Nagabhusan R Editors, Enfield, NH: Science Publishers
- Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., Sulfated seaweed polysaccharides as antiviral agents (2004) Curr Med Chem, 11, pp. 2399-2419
- Witvrouw, M., De Clercq, E., Sulfated polysaccharides extracted from sea algae as potential antiviral drugs (1997) Gen Pharmacol, 29, pp. 497-511
- Balzarini, J., Van Damme, L., Microbicide drug candidate to prevent HIV infection (2007) Lancet, 369, pp. 787-797
- Kilmarx, P.H., van de Wijgert, J.H.H.M., Chaikummao, S., Safety and acceptability of the candidate microbicide carraguard in Thai women findings from a Phase II clinical trial (2006) J Acquir Immune Defic Syndr, 43, pp. 327-334
- Nikolic, D.S., Garcia, E., Piguet, V., Microbicides and other topical agents in the prevention of HIV and sexually transmitted infections (2007) Expert Rev Anti Infect Ther, 5, pp. 77-88
- Kleymann, G., Agents and strategies in development for improved management of herpes simplex virus infection and disease (2005) Expert Opin Investig Drugs, 14, pp. 135-161
- Pujol, C.A., Carlucci, M.J., Matulewicz, M.C., Damonte, E.B., Natural sulfated polysaccharides for the prevention and control of viral infections (2007) Top Hetero Chem, 11, pp. 259-281
- Ghosh, T., Chattopadhyay, K., Marschall, M., Karmakar, P., Mandal, P., Ray, B., Focus on antivirally active sulfated polysaccharides: From structure-activity analysis to clinical evaluation (2009) Glycobiology, 19, pp. 2-15
- Dubois, M., Gilles, K.A., Hamilton, J.K., Rebers, P.A., Smith, F., Colorimetric method for determination of sugars and related substances (1956) Anal Chem, 28, pp. 350-366
- Ahmed, A., Labavitch, J.M., A simplified method for accurate determination of cell wall uronide content (1977) J Food Biochem, 1, pp. 361-365
- Blakeney, A.B., Harris, P., Henry, R.J., Bruce, A.B., A simple rapid preparation of alditol acetates for monosaccharide analysis (1983) Carbohydr Res, 113, pp. 291-299
- Chattopadhyay, K., Mateu, C.G., Mandal, P., Pujol, C.A., Damonte, E.B., Ray, B., Galactan sulfate of Grateloupia indica: Isolation, structural features and antiviral activity (2007) Phytochemistry, 68, pp. 1428-1435
- York, W.S., Darvill, A.G., O'Neil, M., Stevenson, T.T., Albersheim, P., Isolation and characterisation of plant cell walls and cell wall components (1986) Methods Enzymol, 118, pp. 3-40
- Craigie, J.S., Wen, Z.C., van der Meer, J.P., Interspecific, intraspecific and nutritionally-determined variations in the composition of agars from Gracilaria spp (1984) Bot, 27, pp. 55-61. , Mar
- Rochas, C., Lahaye, M., Yaphe, W., Sulfate content of carrageenan and agar determined by infrared spectroscopy (1986) Bot, 29, pp. 335-340. , Mar
- Falshaw, R., Furneaux, R.H., Structural analysis of carrageenans from the tetrasporic stages of the red algae Gigartina lanceata and Gigartina chapmanii (Gigartinaceae, Rhodophyta) (1998) Carbohydr Res, 307, pp. 325-331
- Mandal, P., Mateu, C.G., Chattopadhyay, K., Pujol, C.A., Damonte, E.B., Ray, B., Structural features and antiviral activity of sulfated fucans from the brown seaweed Cystoseira indica (2007) Antivir Chem Chemother, 18, pp. 153-162
- Chattopadhyay, K., Ghosh, T., Pujol, C.A., Carlucci, M.J., Damonte, E.B., Ray, B., Polysaccharides from Gracilaria corticata: Sulfation, chemical characterization and anti-HSV activities (2008) Int J Biol Macromol, 43, pp. 346-351
- Fry, S.C., (1988) The growing plant cell wall: Chemical and metabolic analysis, p. 333. , Essex: Longman Scientific and Technical, Longman Group UK Limited
- Stevenson, T.T., Furneaux, R.H., Chemical methods for the analysis of sulphated galactans from red algae (1991) Carbohydr Res, 210, pp. 277-298
- Blakeney, A.B., Stone, B.A., Methylation of carbohydrates with lithium methylsulphinyl carbanion (1985) Carbohydr Res, 140, pp. 319-324
- Ray, B., Polysaccharides from Enteromorpha compressa: Isolation, purification and structural features (2006) Carbohydr Polym, 66, pp. 408-416
- Kolender, A.A., Matulewicz, M.C., Cerezo, A.S., Structural analysis of Antiviral sulfated α-D-(1→3)-linked mannans (1995) Carbohydr Res, 273, pp. 179-185
- Mandal, P., Pujol, C.A., Carlucci, M.J., Chattopadhyay, K., Damonte, E.B., Ray, B., Sulfated xylomannan of Scinaia hetai: Isolation, structural features and antiviral activity (2008) Phytochemistry, 69, pp. 2193-2199
- Kolender, A.A., Pujol, C.A., Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., The system of sulfated α-(1→3)-linked D-mannans from the red seaweed Nothogenia fastigiata: Structures, antiherpetic and anticoagulant properties (1997) Carbohydr Res, 304, pp. 53-60
- Percival, E., Wold, J.K., The acid from green seaweed Ulva lactuca. Part II. The site of ester sulphate (1963) J Chem Soc, pp. 5459-5468
- Lloyd, A.G., Dodgson, K.S., Price, R.B., Rose, F.A., Polysaccharide sulphates (1961) Biochim Biophys Acta, 46, pp. 108-115
- Hirst, E., Mackie, W., Percival, E., The water-soluble polysaccharides of Caldophora rupestris and of Chaetomorpha spp. Part II. The site of ester sulphate groups and the linkage between the galactose residues (1965) J Chem Soc, pp. 2958-2967
- Mazumder, S., Ghosal, P.K., Pujol, C.A., Carlucci, M.J., Damonte, E.B., Ray, B., Isolation, chemical investigation and antiviral activity of polysaccharides from Gracilaria corticata (Gracilariaceae, Rhodophyta) (2002) Int J Biol Macromol, 31, pp. 87-95
- Matulewicz, M.C., Cerezo, A.S., Water-soluble sulfated polysaccharides from the red seaweed Chaetangium fastigiatum. Analysis of the system and the structures of the α-D-(1→3)-linked mannans (1987) Carbohydr Polym, 7, pp. 121-132
- McReynolds, K.D., Gervay-Hague, J., Chemotherapeutic interventions targeting HIV interactions with host-associated carbohydrates (2007) Chem Rev, 107, pp. 1533-1552
- Herold, B.C., Gerber, S.I., Belval, B.J., Siston, A.M., Shulman, N., Differences in the susceptibility of herpes simplex virus type 1 and 2 to modified heparin compounds suggest serotype differences in viral entry (1996) J Virol, 70, pp. 3461-3469
- Cohen, J., Microbicide fails to prevent against HIV (2008) Science, 319, pp. 1026-1027
- Grant, R.M., Hamer, D., Hope, T., Whither or wither micobicides? (2008) Science, 321, pp. 532-534
- Klasse, P.J., Shattock, R., Moore, J.P., Antiretorviral drug-based microbicides to prevent HIV-1 sexual transmission (2008) Annu Rev Med, 59, pp. 455-471
- Kilmarx, P.H., Kelly, B., Supaporn, C., A randomized, placebo-controlled trial to assess the safety and acceptability of use of Carraguard vaginal gel by heterosexual couples in Thailand (2008) Sex Transm Dis, 35, pp. 226-232
- Bollen, L.J.M., Kelly, B., Kilmarx, P.H., No increase in cervicovaginal proinflammatory cytokines after Carraguard use in a placebo-controlled randomized clinical trial (2008) J Acquir Immune Defic Syndr, 47, pp. 253-257
- Brache, V., Horacio, C., Régine, S.W., Effect of a single vaginal administration of levonorgestrel in Carraguard® gel on the ovulatory process: A potential candidate for dual protection emergency contraception (2007) Contraception, 76, pp. 111-116
- Liu, S., Lu, H., Neurath, A.R., Jiang, S., Combination of candidate microbicides cellulose acetate 1,2-benzenedicarboxylate and UC781 has synergistic and complementary effects against human immunodeficiency virus type-1 infection (2005) Antimicrob Agents Chemother, 49, pp. 1830-1836
Citas:
---------- APA ----------
Ghosh, T., Pujol, C.A., Damonte, E.B., Sinha, S. & Ray, B.
(2009)
. Sulfated xylomannans from the red seaweed Sebdenia polydactyla: Structural features, chemical modification and antiviral activity. Antiviral Chemistry and Chemotherapy, 19(6), 235-242.
http://dx.doi.org/10.1177/095632020901900603---------- CHICAGO ----------
Ghosh, T., Pujol, C.A., Damonte, E.B., Sinha, S., Ray, B.
"Sulfated xylomannans from the red seaweed Sebdenia polydactyla: Structural features, chemical modification and antiviral activity"
. Antiviral Chemistry and Chemotherapy 19, no. 6
(2009) : 235-242.
http://dx.doi.org/10.1177/095632020901900603---------- MLA ----------
Ghosh, T., Pujol, C.A., Damonte, E.B., Sinha, S., Ray, B.
"Sulfated xylomannans from the red seaweed Sebdenia polydactyla: Structural features, chemical modification and antiviral activity"
. Antiviral Chemistry and Chemotherapy, vol. 19, no. 6, 2009, pp. 235-242.
http://dx.doi.org/10.1177/095632020901900603---------- VANCOUVER ----------
Ghosh, T., Pujol, C.A., Damonte, E.B., Sinha, S., Ray, B. Sulfated xylomannans from the red seaweed Sebdenia polydactyla: Structural features, chemical modification and antiviral activity. Antiviral Chem. Chemother. 2009;19(6):235-242.
http://dx.doi.org/10.1177/095632020901900603