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Abstract:

The water extracts from red seaweeds Laurencia obtusa and Laurencia filiformis comprise complex sulfated agarans. Those from L. obtusa have 3-linked β-d-galactose units in part sulfated on 2-position or methylated on 6-position, while the 4-linked units are mostly 3,6-anhydro-α-l-galactose and α-l-galactose 6-sulfate, some of the latter units are substituted with β-d-xylose on 3-position, precluding alkaline cyclization. The 3-linked β-d-galactose units of the agarans from L. filiformis are mostly sulfated on 2-position, but approximately half of these residues also carry the 4,6-O-(1-carboxyethylidene) group. The 4-linked 3,6-anhydro-α-l-galactose units are methylated or substituted in part with single stubs of β-d-xylose on 2-position. This is the first time that substitution with xylose of 3,6-anhydro-α-l-galactose is reported. Besides, α-l-galactose 2-sulfate carrying single stubs of β-d-xylose on 3-position was also detected. These galactans have some common structural characteristics with those of other species of this genus, but also others that are specific for these species. © 2013 Elsevier Ltd.

Registro:

Documento: Artículo
Título:Structure of highly substituted agarans from the red seaweeds Laurencia obtusa and Laurencia filiformis
Autor:Canelón, D.J.; Ciancia, M.; Suárez, A.I.; Compagnone, R.S.; Matulewicz, M.C.
Filiación:Escuela de Bioanálisis, Facultad de Medicina, Universidad Central de Venezuela, Av. Carlos Raúl Villanueva, 1051 Caracas, Venezuela
Cátedra de Química de Biomoléculas, Departamento de Biología Aplicada y Alimentos, Universidad de Buenos Aires, Av. San Martín 4453, 1417 Buenos Aires, Argentina
Departamento de Química Orgánica - CIHIDECAR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina
Facultad de Farmacia, Universidad Central de Venezuela, Av. Paseo de los Ilustres, Los Chaguaramos, 1051 Caracas, Venezuela
Escuela de Química, Facultad de Ciencias, Universidad Central de Venezuela, Av. Paseo de los Ilustres, Los Chaguaramos, 1450 Caracas, Venezuela
Palabras clave:Agaran; Galactan structure; Laurencia; Red seaweed polysaccharide; Sulfated polysaccharide; Agaran; Galactans; Laurencia; Red seaweeds; Sulfated polysaccharides; Polysaccharides; Xylose; Seaweed; Laurencia; Laurencia filiformis; Laurencia obtusa; agaran; galactan; polysaccharide sulfate; sulfate; article; chemistry; Galactan structure; isomerism; Laurencia; Red seaweed polysaccharide; species difference; Agaran; Galactan structure; Laurencia; Red seaweed polysaccharide; Sulfated polysaccharide; Galactans; Isomerism; Laurencia; Species Specificity; Sulfates
Año:2014
Volumen:101
Número:1
Página de inicio:705
Página de fin:713
DOI: http://dx.doi.org/10.1016/j.carbpol.2013.09.089
Título revista:Carbohydrate Polymers
Título revista abreviado:Carbohydr Polym
ISSN:01448617
CODEN:CAPOD
CAS:galactan, 39300-87-3, 9037-55-2; polysaccharide sulfate, 79933-28-1; sulfate, 14808-79-8
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01448617_v101_n1_p705_Canelon

Referencias:

  • Ahmed, A.E.R., Labavitch, J.M., A simplified method for accurate determination of cell wall uronide content (1977) Journal of Food Biochemistry, 1, pp. 361-365
  • Bowker, D.M., Turvey, J.R., Water-soluble polysaccharides of the red alga Laurencia pinnatifida. Part I. Constituent units (1968) Journal of the Chemical Society, pp. 983-988
  • Bowker, D.M., Turvey, J.R., Water-soluble polysaccharides of the red alga Laurencia pinnatifida. Part II. Methylation analysis of the galactan sulfate (1968) Journal of the Chemical Society, pp. 989-992
  • 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) Carbohydrate Research, 342 (18), pp. 2766-2775. , DOI 10.1016/j.carres.2007.08.024, PII S0008621507003977
  • Cases, M.R., Stortz, C.A., Cerezo, A.S., Separation and identification of partially ethylated galactoses as their acetylated aldononitriles and alditols by capillary gas chromatography and mass spectrometry (1994) Journal of Chromatography A, 662 (2), pp. 293-299. , DOI 10.1016/0021-9673(94)80517-2
  • Cases, M.R., Cerezo, A.S., Stortz, C.A., Separation and quantitation 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
  • 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 (4), pp. 229-243. , DOI 10.1016/S0008-6215(97)00017-7, PII S0008621597000177
  • Ciucanu, I., Kerek, K., A simple and rapid method for the permethylation of carbohydrates (1984) Carbohydrate Research, 134, pp. 209-217
  • Dodgson, K.S., Price, R.G., A note on the determination of the ester sulphate content of sulphated polysaccharides (1962) Biochemical Journal, 84, pp. 106-110
  • Duarte, M.E.R., Cauduro, J.P., Noseda, D.G., Noseda, M.D., Goncalves, A.G., Pujol, C.A., Damonte, E.B., Cerezo, A.S., The structure of the agaran sulfate from Acanthophora spicifera (Rhodomelaceae, Ceramiales) and its antiviral activity. Relation between structure and antiviral activity in agarans (2004) Carbohydrate Research, 339 (2), pp. 335-347. , DOI 10.1016/j.carres.2003.09.028
  • Duarte, M.E.R., Noseda, M.D., Cardoso, M.A., Tulio, S., Cerezo, A.S., The structure of a galactan sulfate from the red seaweed Bostrychia montagnei (2002) Carbohydrate Research, 337 (12), pp. 1137-1144. , DOI 10.1016/S0008-6215(02)00095-2, PII S0008621502000952
  • Dubois, M., Gilles, K.A., Hamilton, J.K., Rebers, P.A., Smith, F., Colorimetric method of determination of sugars and related substances (1956) Analytical Chemistry, 28, pp. 350-356
  • Errea, M.I., Kolender, A.A., Matulewicz, M.C., Absolute configuration of 2,6-di-O-alkylgalactose obtained from peralkylated red algal polysaccharides (2001) Botanica Marina, 44 (2), pp. 133-138. , DOI 10.1515/BOT.2001.018
  • 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 (1), pp. 27-41. , DOI 10.1016/S0008-6215(01)00015-5, PII S0008621501000155
  • Ferreira, L.G., Noseda, M.D., Gonçalvez, A.G., Ducatti, D.R.B., Fujii, M.T., Duarte, M.E.R., Chemical structure of the complex pyruvylated and sulfated agaran from the red seaweed Palisada flagellifera (Ceramiales, Rhodophyta) (2012) Carbohydrate Research, 347, pp. 83-94
  • Filisetti-Cozzi, T.M., Carpita, N.C., Measurement of uronis acids without interference from neutral sugars (1991) Analytical Biochemistry, 197, pp. 157-162
  • Garegg, P.J., Lindberg, B., Kvarnström, I., Preparation and NMR studies of pyruvic acid and related acetals of pyranosides: Configuration at the acetal carbon atoms (1979) Carbohydrate Research, 77, pp. 71-78
  • Gorin, P.A.J., Mazurek, M., Duarte, H.S., Iacomini, M., Duarte, J.H., Properties of 13C-NMR spectra of O-(1-carboxyethylidene) derivatives of methyl β-d-galactopyranoside: Models for determination of pyruvic acid acetal structures in polysaccharides (1982) Carbohydrate Research, 100, pp. 1-15
  • Guiry, M.D., Guiry, G.M., (2013) AlgaeBase, , http://www.algaebase.org/, World-Wide Electronic Publication, National University of Ireland Galway (assessed 28.05.13)
  • 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
  • Koepsell, H.J., Sharpe, E.S., Microdetermination of pyruvic and α-ketoglutaric acids (1952) Archives of Biochemistry and Biophysics, 38, pp. 443-449
  • Lahaye, M., Yaphe, W., Phan Viet, M.T., Rochas, C., 13C-NMR spectroscopic investigation of methylated and charged agarose oligosaccharides and polysaccharides (1989) Carbohydrate Research, 190, pp. 249-265
  • Lahaye, M., Yaphe, W., Rochas, C., 13C-NMR-spectral analysis of sulfated and desulfated polysaccharides of the agar type (1985) Carbohydrate Research, 143, pp. 240-245
  • Matulewicz, M.C., Ciancia, M., Noseda, M.D., Cerezo, A.S., Carrageenan systems from tetrasporic and cystocarpic stages of Gigartina skottsbergii (1989) Phytochemistry, 28, pp. 2937-2941
  • Miller, I.J., The chemotaxonomic sugnificance of the water-soluble red algal polysaccharides (1997) Recent Research Developments in Phytochemistry, 1, pp. 531-565
  • Miller, I.J., Blunt, J.W., New 13C NMR methods for determining the structure of algal polysaccharides. Part 2. Galactans consisting of mixed diads (2000) Botanica Marina, 43 (3), pp. 251-261
  • Miller, I.J., Blunt, J.W., New 13C NMR methods for determining the structure of algal polysaccharides. Part 1. The effect of substitution on the chemical shifts of simple diad galactans (2000) Botanica Marina, 43 (3), pp. 239-250
  • Miller, I.J., Falshaw, R., Furneaux, R.H., The chemical structures of polysaccharides from New Zealand members of the Rhodomelaceae (1993) Botanica Marina, 36, pp. 203-208
  • Morrison, I.M., Hydrolysis of plant cell walls with trifluoroacetic acid (1988) Phytochemistry, 27, pp. 1097-1100
  • Nam, K.W., Phylogenetic re-evaluation of the Laurencia complex (Rhodophyta) with a description of L. succulenta sp. nov. from Korea (2006) Journal of Applied Phycology, 18 (3-5), pp. 679-697. , DOI 10.1007/s10811-006-9073-3
  • Nam, K.W., Validation of the generic name Palisada (Rhodomelaceae, Rhodophyta) (2007) Algae, 22, pp. 53-55
  • Navarro, D.A., Flores, M.L., Stortz, C.A., Microwave-assisted desulfation of sulfated polysaccharides (2007) Carbohydrate Polymers, 69 (4), pp. 742-747. , DOI 10.1016/j.carbpol.2007.02.009, PII S0144861707001221
  • Navarro, D.A., Stortz, C.A., Determination of the configuration of 3,6-anhydrogalactose and cyclizable α-galactose 6-sulfate units in red seaweed galactans (2003) Carbohydrate Research, 338 (20), pp. 2111-2118. , DOI 10.1016/S0008-6215(03)00345-8
  • Park, J.T., Johnson, M.J., A submicrodetermination of glucose (1949) Journal of Biological Chemistry, 181, pp. 149-151
  • Prado, H.J., Ciancia, M., Matulewicz, M.C., Agarans from the red seaweed Polysiphonia nigrescens (Rhodomelaceae, Ceramiales) (2008) Carbohydrate Research, 343, pp. 711-718
  • Rees, D.A., Estimation of the relative amounts of isomeric sulphate esters in some sulphated polysaccharides (1961) Journal of the Chemical Society, pp. 5168-5171
  • Rios, N.R., Contribución al estudio sistemático de las algas macroscópicas de la costa de Venezuela (1972) Acta Botanica Venezuelica, 7, pp. 219-234
  • Rochas, C., Lahaye, M., Yaphe, W., Phan Viet, M.T., 13C-NMR spectroscopy of agarose oligomers (1986) Carbohydrate Research, 148, pp. 199-207
  • Siddhanta, A.K., Goswami, A.M., Shanmugam, M., Mody, K.H., Ramavat, B.K., Mairh, O.P., Sulphated galactans of marine red alga Laurencia spp. (Rhodomelaceae, Rhodophyta) from the west coast of India (2002) Indian Journal of Marine Sciences, 31, pp. 305-309
  • Stevenson, T.T., Furneaux, R.H., Chemical methods for the analysis of sulphated galactans from red algae (1991) Carbohydrate Research, 210, pp. 277-298
  • Stortz, C.A., Matulewicz, M.C., Cerezo, A.S., Separation and identification of O-acetyl-O-methyl-galactononitriles by gas-liquid chromatography and mass spectrometry (1982) Carbohydrate Research, 111, pp. 31-39
  • Takano, R., Yokoi, T., Kamei, K., Hara, S., Hirase, S., Coexistence of agaroid and carrageenan structures in a polysaccharide from the red seaweed Rhodomela larix (Turner) C. Ag. (1999) Botanica Marina, 42 (2), pp. 183-188
  • Taylor, W., (1960) Marine Algae of the Eastern Tropical and Subtropical Coast of the Americas, , The University of Michigan Press Michigan
  • Usov, A.I., Polysaccharides of the red algae (2011) Advances in Carbohydrate Chemistry and Biochemistry, 65, pp. 115-217
  • Usov, A.I., Ivanova, E.G., Ya Elashvili, M., Polysaccharides of algae 41. Characterization of water-soluble polysaccharides from several representatives of the genus Laurencia (Ceramiales, Rhodophyta) (1989) Bioorganicheskaia Khimia, 15, pp. 1259-1267
  • Usov, A.I., Ya Elashvili, M., Polysaccharides of algae 44. Investigation of sulfated galactan from Laurencia nipponica Yamada (Rhodophyta, Rhodomelaceae) using partial reductive hydrolysis (1991) Botanica Marina, 34, pp. 553-560
  • Usov, A.I., Ya Elashvili, M., Polysaccharides from algae 51. Partial reductive hydrolysis of sulfated galactan from red alga Laurencia coronopus J. Ag. (Rhodophyta, Rhodomelaceae) (1997) Bioorganicheskaia Khimia, 23, pp. 505-511
  • Valiente, O., Fernandez, L.E., Perez, R.M., Marquina, G., Partial methanolysis of the agar-type sulfated galactan of the red seaweed Laurencia gemmifera (1993) Carbohydrate Research, 243 (1), pp. 191-197. , DOI 10.1016/0008-6215(93)84091-J
  • Villanueva, R.D., Romero, J.B., Ragasa, A.L.R., Montaño, M.N.E., Agar from the red seaweed Laurencia flexilis (Ceramiales Rhodohyta) from northern Philippines (2010) Phycological Research, 58, pp. 151-156
  • Welti, D., Carrageenans. Part 12. The 300-MHz proton magnetic resonance of methyl β-d-galactopyranoside, methyl 3,6-anhydro-α-d-galactopyranoside, agarose, kappa-carrageenan, and segments of iota-carrageenan and agarose sulphate (1977) Journal of Chemical Research, , (S) 312-313, (M) 3566-3587

Citas:

---------- APA ----------
Canelón, D.J., Ciancia, M., Suárez, A.I., Compagnone, R.S. & Matulewicz, M.C. (2014) . Structure of highly substituted agarans from the red seaweeds Laurencia obtusa and Laurencia filiformis. Carbohydrate Polymers, 101(1), 705-713.
http://dx.doi.org/10.1016/j.carbpol.2013.09.089
---------- CHICAGO ----------
Canelón, D.J., Ciancia, M., Suárez, A.I., Compagnone, R.S., Matulewicz, M.C. "Structure of highly substituted agarans from the red seaweeds Laurencia obtusa and Laurencia filiformis" . Carbohydrate Polymers 101, no. 1 (2014) : 705-713.
http://dx.doi.org/10.1016/j.carbpol.2013.09.089
---------- MLA ----------
Canelón, D.J., Ciancia, M., Suárez, A.I., Compagnone, R.S., Matulewicz, M.C. "Structure of highly substituted agarans from the red seaweeds Laurencia obtusa and Laurencia filiformis" . Carbohydrate Polymers, vol. 101, no. 1, 2014, pp. 705-713.
http://dx.doi.org/10.1016/j.carbpol.2013.09.089
---------- VANCOUVER ----------
Canelón, D.J., Ciancia, M., Suárez, A.I., Compagnone, R.S., Matulewicz, M.C. Structure of highly substituted agarans from the red seaweeds Laurencia obtusa and Laurencia filiformis. Carbohydr Polym. 2014;101(1):705-713.
http://dx.doi.org/10.1016/j.carbpol.2013.09.089