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The structures of two sulfated xylomannans extracted from the red alga Nemalion helminthoides were determined. These two fractions plus a sulfated mannan, isolated from the same alga and whose structure was previously reported, were subjected to chemical modification. The mannan was oversulfated with SO 3-pyridine in dimethyl sulfoxide at 60 °C during two and three hours and the xylomannans were subjected to Smith degradation in order to eliminate xylose side-chains. Structural analysis of all derivatives was carried out by methylation analysis and 13C NMR spectroscopy. Antiviral activity against herpes simplex virus type 1 and 2, and dengue virus type 2 of native and modified mannans and xylomannans was estimated. Anticoagulant effect of the active fractions was also determined. © 2011 Elsevier Ltd. All rights reserved.


Documento: Artículo
Título:Chemical modifications of algal mannans and xylomannans: Effects on antiviral activity
Autor:Pérez Recalde, M.; Carlucci, M.J.; Noseda, M.D.; Matulewicz, M.C.
Filiación:Departamento de Química Orgánica-CIHIDECAR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, UBA, Pabellón 2, 1428EGA Buenos Aires, Argentina
Laboratorio de Virología, Departamento de Química Biológica, UBA, Pabellón 2, 1428EGA Buenos Aires, Argentina
Departamento de Bioquimica e Biologia Molecular, Universidade Federal Do Paraná, P.O. Box 19046, CEP: 81531-990, Curitiba-Paraná, Brazil
Palabras clave:Anticoagulant activity; Antiherpetic activity; Nemaliales; Nemalion helminthoides; Oversulfation of mannans; Smith degradation of sulfated xylomannans; Sulfated mannans; Sulfated xylomannans; anticoagulant agent; antivirus agent; mannan; sulfate; xylose; article; chemical structure; chemistry; Dengue virus; drug effect; Herpes simplex virus 1; Herpes simplex virus 2; isolation and purification; nuclear magnetic resonance; red alga; Anticoagulants; Antiviral Agents; Dengue Virus; Herpesvirus 1, Human; Herpesvirus 2, Human; Mannans; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Rhodophyta; Sulfuric Acid Esters; Xylose; algae; Dengue virus; Dengue virus type 2; Human herpesvirus 1; Nemaliales; Nemalion helminthoides; Rhodophyta
Página de inicio:57
Página de fin:64
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
CAS:mannan, 51395-96-1, 9036-88-8; sulfate, 14808-79-8; xylose, 25990-60-7, 58-86-6; Anticoagulants; Antiviral Agents; Mannans; Sulfuric Acid Esters; Xylose


  • Alban, S., Schauerte, A., Franz, G., Anticoagulant sulfated polysaccharides: Part I. Synthesis and structure-activity relationships of new pullulan sulfates (2002) Carbohydrate Polymers, 47 (3), pp. 267-276. , DOI 10.1016/S0144-8617(01)00178-3, PII S0144861701001783
  • Allerhand, A., Berman, E., Systematic approach to the analysis of carbon-13 NMR spectra of complex carbohydrates. 1. α-d-mannopyranosyl residues in oligosaccharides and their implications for studies of glycoproteins and glycopeptides (1984) J. Am. Chem. Soc., 106, pp. 2400-2412
  • Cardoso, M.A., Noseda, M.D., Fujii, M.T., Zibetti, R.G.M., Duarte, M.E.R., Sulfated xylomannans isolated from red seaweeds Chondrophycus papillosus and C. flagelliferus (Ceramiales) from Brazil (2007) Carbohydr. Res., 131, pp. 209-217
  • Chen, Y., Maguire, T., Hileman, R.E., Fromm, J.R., Esko, J.D., Linhardt, R.J., Marks, R.M., Dengue virus infectivity depends on envelope protein binding to target cell heparan sulfate (1997) Nature Medicine, 3 (8), pp. 866-871. , DOI 10.1038/nm0897-866
  • Ciucanu, I., Kerek, F., A simple and rapid method for the permethylation of carbohydrates (1984) Carbohydr. Res., 131, pp. 209-217
  • Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., Sulfated seaweed polysaccharides as antiviral agents (2004) Current Medicinal Chemistry, 11 (18), pp. 2399-2419
  • Dodgson, K.S., Price, R.G., A note on the determination of the ester sulphate content of sulphated polysaccharides (1962) Biochem. J., 84, pp. 106-110
  • 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
  • Estevez, J.M., Ciancia, M., Cerezo, A.S., The system of low-molecular-weight carrageenans and agaroids of room-temperature-extracted fraction of Kappaphycus alvarezii (2000) Carbohydr. Res., 325, pp. 287-299
  • Falshaw, R., Furneaux, R.H., Miller, I.J., The backbone structure of the sulfated galactan from Plocamium costatum (C. Agardh) Hook. f. et Harv. (Plocamiaceae, Rhodophyta) (1999) Botanica Marina, 42 (5), pp. 431-435
  • Haines, H., Matulewicz, M.C., Cerezo, A.S., Sulfated galactans from the red seaweed Nothogenia fastigiata (Nemaliales, Rhodophyta) (1990) Hydrobiology, 204 (205), pp. 637-643
  • 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) Carbohydrate Research, 304 (1), pp. 53-60. , DOI 10.1016/S0008-6215(97)00201-2, PII S0008621597002012
  • Lahaye, M., Yaphe, W., Rochas, C., 13C NMR spectral analysis of sulfated and desulfated polysaccharides of the agar (1985) Carbohydr. Res., 143, pp. 240-245
  • Lee, J., Koizumi, S., Hayashi, K., Hayashi, T., Structure of Rhamnan sulfate from the green alga Monostroma nitidum and its anti-herpetic effect (2010) Carbohydr. Pol., 81, pp. 572-577
  • Mandal, P., Pujol, C.A., Carlucci, M.J., Chattopadhyay, K., Damonte, E.B., Ray, B., Anti-herpetic activity of a sulfated xylomannan from Scinaia hatei (2008) Phytochemistry, 69, pp. 2193-2199
  • Matulewicz, M.C., Cerezo, A.S., Water-soluble sulfated polysaccharides from the red seaweed Chaetangium fastigiatum (1987) Carbohydrate Polymers, 7 (2), pp. 121-132. , DOI 10.1016/0144-8617(87)90054-3
  • Matulewicz, M.C., Haines, H.H., Cerezo, A.S., Sulfated xylogalactans from Nothogenia fastigiata (1994) Phytochemistry, 36, pp. 97-103
  • Montanha, J.A., Bourgougnon, N., Boustie, J., Amoros, M., Antiviral activity of carrageenans from marine red algae (2009) Latin Am. J. Pharmacy, 28, pp. 443-448
  • Nunn, J.R., Parolis, H., Russell, I., Polysaccharides of the red alga Chaetangium erinaceum. Part I. Isolation and characterization of the water-soluble xylan (1973) Carbohydr. Res., 26, pp. 169-180
  • Park, J., Johnson, M., A submicrodetermination of glucose (1949) J. Biol. Chem., 181, pp. 149-151
  • Pérez Recalde, M., Noseda, M.D., Pujol, C.A., Carlucci, M.J., Matulewicz, M.C., Sulfated mannans from the red seaweed Nemalion helminthoides of the South Atlantic (2009) Phytochemistry, 70, pp. 1062-1068
  • 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. Heterocycl. Chem., 11, pp. 259-281
  • Shea, E.M., Carpita, N.C., Separation of partially methylated alditol acetates on SP-2330 and HP-1 vitreous silica capilary columns (1988) J. Chromatogr., 445, pp. 424-428
  • Stevenson, T.T., Furneaux, R.H., Chemical methods for the analysis of sulphated galactans from red algae (1991) Carbohydr. Res., 210, pp. 277-298
  • Sweet, D.P., Shapiro, R.H., Albersheim, P., Quantitative analysis by various g.l.c. response-factor theories for partially methylated and partially ethylated alditol acetates (1975) Carbohydr. Res., 40, pp. 217-225
  • Takano, R., Yoshikawa, S., Ueda, T., Hayashi, K., Hirase, S., Hara, S., Sulfation of polysaccharides with sulfuric acid mediated by dicyclohexylcarbodiimide (1996) Journal of Carbohydrate Chemistry, 15 (4), pp. 449-457
  • Talarico, L.B., Pujol, C.A., Zibetti, R.G.M., Faria, P.C.S., Noseda, M.D., Duarte, M.E.R., Damonte, E.B., The antiviral activity of sulfated polysaccharides against dengue virus is dependent on virus serotype and host cell (2005) Antiviral Research, 66 (2-3), pp. 103-110. , DOI 10.1016/j.antiviral.2005.02.001, PII S0166354205000318
  • Trinchero, J., Ponce, N.M.A., Córdoba, O., Flores, M.L., Pampuro, S., Stortz, C.A., Salomón, H., Turk, G., Antiretroviral activity of fucoidans extracted from the brown seaweed Adenocystis utricularis (2009) Phytoth. Res., 23, pp. 707-712
  • Usov, A.I., Adamyants, K.S., Yarotsky, S.V., Anoshina, A.A., Kochetkov, N.K., The isolation of a sulphated mannan and a neutral xylan from the red seaweed Nemalion vermiculare sur (1973) Carbohydr. Res., 26, pp. 282-283
  • Usov, A.I., Bilan, M.I., Shashkov, A.S., Structure of a sulfated xylogalactan from the calcareous red alga Corallina pilulifera P. et R. (Rhodophyta, Corallinaceae) (1997) Carbohydrate Research, 303 (1), pp. 93-102. , DOI 10.1016/S0008-6215(97)00136-5, PII S0008621597001365
  • Usov, A.I., Dobkina, I.M., Polysaccharides of algae XXXVIII. Polysaccharide composition of the red alga Liagora sp. and structure of the sulfated xylomannan (1988) Bioorg. Khim., 14, pp. 642-651
  • Usov, A.I., Dobkina, I.M., Polysaccharides of algae 43 (1991) A Neutral Xylan and A Sulfated Xylomannan from the Red Alg
  • Usov, A.I., Miroshnikova, L.I., Kochetkov, N.K., Polysaccharides of algae IX. Solvolytic removal of sulfate groups from polysaccharides obtained from the red alga Laingia pacifica (1972) Z. Obshch. Khim., 42, pp. 945-949
  • Usov, A.I., Yarotskii, S.V., Vasyanina, L.K., Synthesis and carbon-13 NMR spectra of methyl 3-O-methyl-α-d- mannopyranoside sulphates (1975) Bioorg. Khim., 1, pp. 1583-1588
  • Vogl, H., Paper, D.H., Franz, G., Preparation of a sulfated linear (1→4)-β-D-galactan with variable degrees of sulfation (2000) Carbohydrate Polymers, 41 (2), pp. 185-190. , DOI 10.1016/S0144-8617(99)00076-4
  • Witvrouw, M., De Clercq, E., Sulfated polysaccharides extracted from sea algae as potential antiviral drugs (1997) General Pharmacology, 29 (4), pp. 497-511. , DOI 10.1016/S0306-3623(96)00563-0, PII S0306362396005630
  • Witvrouw, M., Pannecouque, C., De Clercq, E., Polysulfates: Chemistry and potential as antiviral drugs (1997) Carbohydrates in Drug Design, pp. 157-207. , Z. Witczak, K. Nieforth, Marcel Dekker Inc. New York


---------- APA ----------
Pérez Recalde, M., Carlucci, M.J., Noseda, M.D. & Matulewicz, M.C. (2012) . Chemical modifications of algal mannans and xylomannans: Effects on antiviral activity. Phytochemistry, 73, 57-64.
---------- CHICAGO ----------
Pérez Recalde, M., Carlucci, M.J., Noseda, M.D., Matulewicz, M.C. "Chemical modifications of algal mannans and xylomannans: Effects on antiviral activity" . Phytochemistry 73 (2012) : 57-64.
---------- MLA ----------
Pérez Recalde, M., Carlucci, M.J., Noseda, M.D., Matulewicz, M.C. "Chemical modifications of algal mannans and xylomannans: Effects on antiviral activity" . Phytochemistry, vol. 73, 2012, pp. 57-64.
---------- VANCOUVER ----------
Pérez Recalde, M., Carlucci, M.J., Noseda, M.D., Matulewicz, M.C. Chemical modifications of algal mannans and xylomannans: Effects on antiviral activity. Phytochemistry. 2012;73:57-64.