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Abstract:

Nemalion helminthoides, collected in the Argentine South Atlantic coast, was extracted with hot water and the crude product fractionated using cetrimide. The complexed material was subjected to fractional solubilization in solutions of increasing sodium chloride concentration and seven fractions were separated and analyzed. Structural analysis of the main fractions, those soluble in 3.0 and 4.0 M NaCl (yields 21.0% and 13.8%, respectively) and those insoluble in 4.0 M NaCl (yield 20.0%), indicated that this seaweed biosynthesizes (1 → 3)-linked α-d-mannans that are sulfated at positions 4 and 6. Three mannan fractions comprising considerable amounts of xylose were also isolated in very low total yield (2.0%). The fractions that were soluble in 3.0 and 4.0 M NaCl showed low antiherpetic activity whereas this activity was considerable for the fraction solubilized in 2.0 M NaCl (yield 0.5%) which contained single stubs of β-d-xylose. A xylan, soluble in cetrimide solution, containing (1 → 3, 1 → 4)-linked β-d-xylose residues, was also isolated in minor amount. © 2009 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Sulfated mannans from the red seaweed Nemalion helminthoides of the South Atlantic
Autor:Pérez Recalde, M.; Noseda, M.D.; Pujol, C.A.; Carlucci, M.J.; Matulewicz, M.C.
Filiación:Departamento de Química Orgánica-CIHIDECAR (CONICET-UBA), Facultad de Ciencias, Exactas y Naturales, UBA, Pabellon 2, Ciudad Universitaria, 1428EGA Buenos Aires, Argentina
Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias, Exactas y Naturales, Pabellon 2, Ciudad Universitaria, 1428EGA Buenos Aires, Argentina
Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, P.O. Box 19046, CEP: 81531-990 Curitiba, Parana, Brazil
Palabras clave:Antiherpetic activity; Nemaliales; Nemalion helminthoides; Red seaweed; Sulfated (1 → 3)-linked α-d-mannans; Sulfated mannans; mannan; sulfate; animal; article; Cercopithecus; chemical structure; chemistry; drug effect; Herpes simplex virus; isolation and purification; seaweed; Vero cell; Animals; Cercopithecus aethiops; Mannans; Molecular Structure; Seaweed; Simplexvirus; Sulfuric Acid Esters; Vero Cells; Nemaliales; Nemalion helminthoides
Año:2009
Volumen:70
Número:8
Página de inicio:1062
Página de fin:1068
DOI: http://dx.doi.org/10.1016/j.phytochem.2009.05.001
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:mannan, 51395-96-1, 9036-88-8; sulfate, 14808-79-8; Mannans; Sulfuric Acid Esters
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v70_n8_p1062_PerezRecalde

Referencias:

  • Adams, N.M., Furneaux, R.H., Miller, I.J., Whitehouse, L.A., Xylan from Leptosarca simplex and carrageenans from Iridea, Cenacrum and Nemastoma species from the subantarctic islands of New Zealand (1988) Bot. Mar., 31, pp. 9-14
  • Cerezo, A.S., The fine structure of Chaetangium fastigiatum xylan: studies of the sequence and configuration of the (1 → 3) linkages (1972) Carbohydr. Res., 22, pp. 209-211
  • Cerezo, A.S., The carrageenans from Gigartina skottsbergii S. et G. Part III. Methylation analysis of the fraction precipitated with 0.3-0.4 potassium chloride (1973) Carbohydr. Res., 26, pp. 335-340
  • Cerezo, A.S., Lezerovich, A., Labriola, R., Rees, D.A., A xylan from the red seaweed Chaetangium fastigiatum (1971) Carbohydr. Res., 19, pp. 289-296
  • 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) Curr. Med. Chem., 11, 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
  • Haines, H.H., Matulewicz, M.C., Cerezo, A.S., Sulfated galactans from the red seaweed Nothogenia fastigiata (Nemaliales, Rhodophyta) (1990) Hydrobiologia, 204-205, pp. 637-643
  • Haslin, C. 2000. Chemical composition, structure and antiviral activities of cell-wall polysaccharides from the introduced mediterranean seaweed Asparagopsis armata (Bonnemaisoniales) and four Nemaliales. PhD Thesis Abstract, INIST-CNRS, Cote INIST: T 131593; Kolender, A.A., Polisacáridos de Nothogenia fastigiata y Georgiella confluens (Rhodophyta) (2003) Nuevos métodos de análisis para polisacáridos de algas, , PhD Thesis, Facultad de Ciencias Exactas y Naturales Universidad de Buenos Aires, Argentina
  • Kolender, A.A., Matulewicz, M.C., Cerezo, A.S., Structural analysis of antiviral sulfated α-(1 → 3)-linked mannans (1995) Carbohydr. Res., 273, pp. 179-185
  • 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
  • Kovač, P., Hirsch, J., Shashkov, A.S., Usov, A.I., Yarotsky, S.V., 13C-NMR spectra of xylo-oligosaccharides and their application to the elucidation of xylan structures (1980) Carbohydr. Res., 85, pp. 177-185
  • Lowry, O.H., Rosebrough, N.J., Farr, A.L., Randall, R.J., Protein measurement with the Folin phenol reagent (1951) J. Biol. Chem., 193, pp. 265-275
  • 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. Analysis of the system and the structures of the α-d-(1 → 3)-linked mannans (1987) Carbohydr. Polym., 7, pp. 121-132
  • Matulewicz, M.C., Cerezo, A.S., Jarret, R.M., Syn, N., High resolution 13C-n.m.r. spectroscopy of 'mixed-linkage' xylans (1992) Int. J. Biol. Macromol., 14, pp. 29-32
  • Matulewicz, M.C., Haines, H.H., Cerezo, A.S., Sulphated xylogalactans from Nothogenia fastigiata (1994) Phytochemistry, 36, pp. 97-103
  • Nunn, R., Parolis, H., Russell, H., Polysaccharides of the red algae 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
  • Petruš, L., Gray, D.G., BeMiller, J.N., Homogeneous alkylation of cellulose in lithium chloride/dimethyl sulfoxide with dimsyl sodium activation. A proposal for the mechanism of cellulose dissolution in LiCl/Me2SO (1995) Carbohydr. Res., 268, pp. 319-323
  • 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
  • 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
  • Usov, A.I., Sulfated polysaccharides of the red seaweeds (1992) Food Hydrocoll., 6, pp. 9-23
  • Usov, A.I., Dobkina, I.M., Polysaccharides of algae. 43. A neutral xylan and a sulfated xylomannan from the red alga Liagora valida (1991) Bioorg. Khim., 17, pp. 1051-1058
  • Usov, A.I., Yarotskii, S.V., Polysaccharides of algae. XXI. Alkaline degradation of sulfated mannan from the red alga Nemalion vermiculare Sur (1975) Bioorg. Khim., 1, pp. 919-922
  • 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., Adamyants, K.S., Yarotskii, S.V., Anoshina, A.A., Kochetkov, N.K., Polysaccharides of algae. XIV. Isolation of sulfated mannan and neutral xylan from the red alga Nemalion vermiculare Sur (1974) Z. Obshch. Khim., 44, pp. 416-420
  • Usov, A.I., Adamyants, K.S., Yarotskii, S.V., Polysaccharides of algae. XVIII. Acetolysis of sulfated mannan from Nemalion vermiculare Sur (1975) Z. Obshch. Khim., 45, pp. 1377-1381
  • Usov, A.I., Adamyants, K.S., Yarotskii, S.V., Anoshina, A.A., Polysaccharides of algae. XVI. Study of the structure of the sulfated mannan from the red alga Nemalion vermiculare Sur (1975) Z. Obshch. Khim., 45, pp. 916-921
  • 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

Citas:

---------- APA ----------
Pérez Recalde, M., Noseda, M.D., Pujol, C.A., Carlucci, M.J. & Matulewicz, M.C. (2009) . Sulfated mannans from the red seaweed Nemalion helminthoides of the South Atlantic. Phytochemistry, 70(8), 1062-1068.
http://dx.doi.org/10.1016/j.phytochem.2009.05.001
---------- CHICAGO ----------
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" . Phytochemistry 70, no. 8 (2009) : 1062-1068.
http://dx.doi.org/10.1016/j.phytochem.2009.05.001
---------- MLA ----------
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" . Phytochemistry, vol. 70, no. 8, 2009, pp. 1062-1068.
http://dx.doi.org/10.1016/j.phytochem.2009.05.001
---------- VANCOUVER ----------
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. Phytochemistry. 2009;70(8):1062-1068.
http://dx.doi.org/10.1016/j.phytochem.2009.05.001