Perez Recalde, M.; Canelón, D.J.; Compagnone, R.S.; Matulewicz, M.C.; Cerezo, A.S.; Ciancia, M. "Carrageenan and agaran structures from the red seaweed Gymnogongrus tenuis" (2016) Carbohydrate Polymers. 136:1370-1378
El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor


The galactan system biosynthesized by the red seaweed Gymnogongrus tenuis (Phyllophoraceae) is constituted by major amounts of κ/ι-carrageenans, with predominance of ι-structures, which were isolated by extraction with hot water in high yield (∼45%). A small amount of non-cyclized carrageenans mostly of the ν-type was also obtained. Besides, 12% of these galactans are agaran structures, which were present in major quantities in the room temperature water extracts, but they were also found in the hot water extract. They are constituted by 3-linked β-d-galactose units partially substituted on C-6 with sulfate or single stubs of β-d-xylose and 4-linked residues that comprise α-l-galactose units partially sulfated or methoxylated on C-3 or sulfated on C-3 and C-6 and 3,6-anhydro-α-l-galactose. Related structural patterns were previously found for agarans synthesized by other carrageenophytes. Results presented here show that these agarans are low molecular weight molecules independent of the carrageenan structures, with strong interactions between them. © 2015 Published by Elsevier Ltd.


Documento: Artículo
Título:Carrageenan and agaran structures from the red seaweed Gymnogongrus tenuis
Autor:Perez Recalde, M.; Canelón, D.J.; Compagnone, R.S.; Matulewicz, M.C.; Cerezo, A.S.; Ciancia, M.
Filiación:Cátedra de Química de Biomoléculas, Departamento de Biología Aplicada y Alimentos, Facultad de Agronomía, Universidad de Buenos Aires, Av. San Martín 4453, Buenos Aires, 1417, Argentina
Escuela de Bioanálisis, Facultad de Medicina, Universidad Central de Venezuela, Ciudad Universitaria, Los Chaguaramos, Av. Carlos Raúl Villanueva, Caracas, 1051, Venezuela
Escuela de Química, Facultad de Ciencias, Universidad Central de Venezuela, Ciudad Universitaria, Los Chaguaramos, Av. Paseo de los Ilustres, Caracas, 1450, Venezuela
Departamento de Química Orgánica - CIHIDECAR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
Palabras clave:Agaran; Carrageenan; Polysaccharide structure; Red seaweed; Sulfated galactan; Polysaccharides; Seaweed; Water; Xylose; Agaran; Carrageenans; Polysaccharide structure; Red seaweeds; Sulfated galactans; Extraction; carrageenan; galactan; water; chemistry; heat; isolation and purification; red alga; seaweed; Carrageenan; Galactans; Hot Temperature; Rhodophyta; Seaweed; Water
Página de inicio:1370
Página de fin:1378
Título revista:Carbohydrate Polymers
Título revista abreviado:Carbohydr Polym
CAS:carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7; galactan, 39300-87-3, 9037-55-2; water, 7732-18-5; Carrageenan; Galactans; Water


  • Bellion, C., Brigand, G., Prome, J.-C., Welti, D., Bociek, S., Identification et caractérisation des précurseurs biologiques des carraghénanes par spectroscopie de r.m.n.-13C (1983) Carbohydate Research, 119, pp. 31-48
  • Cáceres, P.J., Carlucci, M.J., Damonte, E.B., Matsuhiro, B., Zúñiga, E.A., Carrageenans from chilean samples of Stenogramme interrupta (Phyllophoraceae): Structural analysis and biological activity (2000) Phytochemistry, 53, pp. 81-86
  • 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
  • Cases, M.R., Stortz, C.A., Cerezo, A.S., Structure of the 'corallinans' - Sulfated xylogalactans from Corallina officinalis (1994) International Journal of Biological Macromolecules, 16, pp. 93-97
  • Chen, J., Zhou, J., Zhang, L., Chemical structure of the water-insoluble polysaccharide isolated from the fruiting body of Ganoderma incidum (1998) Polymer Journal, 30, pp. 838-842
  • Ciancia, M., Cerezo, A.S., D/L-hybrid galactans from red seaweeds: Do they really exist? (2010) Handbook of Carbohydrate Polymers: Development, Properties and Applications, 10, pp. 355-391. , R. Ito, Y. Matsuo, Nova Science Publishers, Inc. New York, USA
  • Ciancia, M., Matulewicz, M.C., Cerezo, A.S., L-Galactose containing galactans from the carrageenophyte Gigartina skottsbergii (1993) Phytochemistry, 34, pp. 1541-1543
  • Ciancia, M., Matulewicz, M.C., Cerezo, A.S., An unusual l-galactose containing carrageenan from cystocarpic Gigartina skottsbergii (1997) Phytochemistry, 45, pp. 1009-1013
  • Ciancia, M., Matulewicz, M.C., Finch, P., Cerezo, A.S., Determination of the structures of cystocarpic carrageenans from Gigartina skottsbergii by methylation analysis and NMR spectroscopy (1993) Carbohydrate Research, 238, pp. 241-248
  • 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, K., A simple and rapid method for the permethylation of carbohydrates (1984) Carbohydrate Research, 134, pp. 209-217
  • Craigie, J.S., Rivero-Carro, H., Agarocolloids from carrageenophytes. XIVth International Seaweed Symposium, Abstracts (1992) Brest-St. Malo, p. 71
  • Dodgson, K.S., Price, R.G., A note on the determination of the ester sulphate content of sulphated polysaccharides (1962) Biochemistry Journal, 84, pp. 106-110
  • 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 from peralkylated red algal polysaccharides (2001) Botanica Marina, 44, pp. 133-138
  • 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
  • Estevez, J.M., Ciancia, M., Cerezo, A.S., The system of galactans of the red seaweed Kappaphycus alvarezii, with emphasis on its minor constituents (2004) Carbohydrate Research, 339, pp. 2575-2592
  • Estevez, J.M., Ciancia, M., Cerezo, A.S., The system of sulfated galactans from the red seaweed Gymnogongrus torulosus (Phyllophoraceae Rhodophyta): Location and structural analysis (2008) Carbohydrate Polymers, 73, pp. 594-605
  • Flores, M.L., Cerezo, A.S., Stortz, C.A., Alkaline treatment of the carrageenans from the cystocarpic stage of the red seaweed Iridaea undulosa (2002) The Journal of the Argentine Chemical Society, 90, pp. 65-76
  • Furneaux, R.H., Miller, I.J., Water soluble polysaccharides from the New Zealand red algae in the family Phyllophoraceae (1985) Botanica Marina, 28, pp. 419-425
  • Greer, J.W., Rochas, C., Yaphe, W., Iota-carrageenan. Oligosaccharides as model compounds for structural analysis of iota-carrageenan by 13C-NMR spectroscopy (1985) Botanica Marina, 28, pp. 9-14
  • Jouanneau, D., Boulenguer, B., Mazoyer, J., Helbert, W., Complete assignment of 1H and 13C NMR spectra of standard neo-ι-carrabiose oligosaccharides (2010) Carbohydrate Research, 345, pp. 547-551
  • Kapraun, D.F., Dutcher, J.A., Bird, K.T., Capecchi, M.F., Nuclear genome characterization and carrageenan analysis of Gymnogongrus griffithsiae (Rhodophyta) from North Carolina (1993) Journal of Applied Phycology, 5, pp. 99-105
  • 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
  • Kolender, A.A., Matulewicz, M.C., Sulfated polysaccharides from the red seaweed Georgiella confluens (2002) Carbohydrate Research, 337, pp. 57-68
  • Lahaye, M., Yaphe, W., Rochas, C., 13C-N.M.R.-spectral analysis of sulfated and desulfated polysaccharides of the agar type (1985) Carbohydrate Research, 143, pp. 240-245
  • Lowry, O.H., Rosenbrough, N.J., Farr, A.L., Randall, R.J., Protein measurements with the Folin phenol reagent (1951) Journal of Biological Chemistry, 193, pp. 265-275
  • 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
  • McCandless, E.L., Craigie, J.S., Walter, J.A., Carrageenans in the gametophytic and sporophytic stages of Chondrus crispus (1973) Planta, 112, pp. 201-212
  • McCandless, E.L., West, J.A., Guiry, M.D., Carrageenan patterns in the Phyllophoraceae (1982) Biochemistry Systematics & Ecology, 10, pp. 275-284
  • 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, pp. 239-250
  • Miller, I.J., Falshaw, R., Furneaux, R.H., Structural analysis of the polysaccharide from Pachymenia lusoria (Cryptonemiaceae Rhodophyta) (1995) Carbohydrate Research, 268, pp. 219-232
  • Miller, I.J., Falshaw, R.H., Furneaux, R.H., Hemmingson, J.A., Variation in the constituent sugars of the polysaccharides from New Zealand species of Pachimenia (Halymeniaceae) (1997) Botanica Marina, 40, pp. 119-127
  • Navarro, D.A., Flores, M.L., Stortz, C.A., Microwave-assisted desulfation of sulfated polysaccharides (2007) Carbohydrate Polymers, 69, pp. 742-747
  • 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, pp. 2111-2118
  • Navarro, D.A., Stortz, C.A., The system of xylogalactans from the red seaweed Jania rubens (Corallinales Rhodophyta) (2008) Carbohydrate Research, 343, pp. 2613-2622
  • Noseda, M.D., Polissacarídeos sulfatados da fase tetrasporofítica de Gigartina skottsbergii (Rhodophyta, Gigartinales). Ph. D. Thesis (1994) Universidade Federal Do Paraná, Curitiba Brasil
  • Park, J.T., Johnson, M.J., A sub microdetermination of glucose (1949) Journal of Biological Chemistry, 181, pp. 149-151
  • Pernas, A.J., Smidsrød, O., Larsen, B., Haug, A., Chemical heterogeneity of carrageenans as shown by fractional precipitation with potassium chloride (1967) Acta Chemica Scandinavica, 21, pp. 98-110
  • Petruš, L., Gray, D.G., BeMiller, J.N., Homogeneous alkylation of cellulose in lithium chloride/dimethyl sulfoxide solvent with dimsyl sodium activation. A proposal for the mechanism of cellulose dissolution in LiCl/Me2SO (1995) Carbohydrate Research, 268, pp. 319-323
  • Pickmere, S.E., Parsons, M.J., Bailey, R.W., Composition of Gigartina carrageenan in relation to sporophyte and gametophyte stages of the life cycle (1973) Phytochemistry, 12, pp. 2441-2444
  • Prado, H.J., Ciancia, M., Matulewicz, M.C., Agarans from the red seaweed Polysiphonia nigrescens (Rhodomelaceae, Ceramiales) (2008) Carbohydrate Research, 343, pp. 711-718
  • Rios, N.R., Contribución al estudio sistemático de las algas macroscópicas de la costa de Venezuela (1972) Acta Botanica Venezuelica, 7, pp. 219-234
  • 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., Bacon, B.E., 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.R., Cerezo, A.S., The system of agaroids and carrageenans from the soluble fraction of the terasporic stage of the red seaweed Iridaea 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
  • Stortz, C.A., Cerezo, A.S., Novel findings in carrageenans, agaroids and "hibrid" red seaweed galactans (2000) Current Topics in Phytochemistry, 4, pp. 121-134
  • Synytsya, A., Novak, M., Structural diversity of fungal glucans (2013) Carbohydrate Polymers, 92 (2013), pp. 792-809
  • 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
  • Taylor, W., (1960) Marine Algae of the Eastern Tropical and Subtropical Coast of the Americas, , The University of Michigan Press Michigan
  • 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, pp. 93-102
  • Usov, A.I., Elashvili, M.Ya., 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., Shashkov, A.S., Polysaccharides of algae XXXIV: Detection of iota-carrageenan in Phyllophora brodiaei (Turn.) J. Ag. (Rhodophyta) using 13C-NMR spectroscopy (1985) Botanica Marina, 28, pp. 367-373
  • Usov, A.I., Yarotskii, S.V., Shashkov, A.S., 13C-nmr spectroscopy of red algal galactans (1980) Biopolymers, 19, pp. 977-990
  • 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 & Technology, 13, pp. 73-92
  • Welti, D., Carrageenans. Part 12. The 300 MHz proton magnetic resonance spectra of methyl β-d-galactopyranoside, methyl 3,6-anhydro-α-d-galactopyranoside, agarose, kappa-carrageenan, and segments of iota-carrageenan and agarose sulfate (1977) Journal of Chemical Research, pp. 312-313. , (M) 3566-3587


---------- APA ----------
Perez Recalde, M., Canelón, D.J., Compagnone, R.S., Matulewicz, M.C., Cerezo, A.S. & Ciancia, M. (2016) . Carrageenan and agaran structures from the red seaweed Gymnogongrus tenuis. Carbohydrate Polymers, 136, 1370-1378.
---------- CHICAGO ----------
Perez Recalde, M., Canelón, D.J., Compagnone, R.S., Matulewicz, M.C., Cerezo, A.S., Ciancia, M. "Carrageenan and agaran structures from the red seaweed Gymnogongrus tenuis" . Carbohydrate Polymers 136 (2016) : 1370-1378.
---------- MLA ----------
Perez Recalde, M., Canelón, D.J., Compagnone, R.S., Matulewicz, M.C., Cerezo, A.S., Ciancia, M. "Carrageenan and agaran structures from the red seaweed Gymnogongrus tenuis" . Carbohydrate Polymers, vol. 136, 2016, pp. 1370-1378.
---------- VANCOUVER ----------
Perez Recalde, M., Canelón, D.J., Compagnone, R.S., Matulewicz, M.C., Cerezo, A.S., Ciancia, M. Carrageenan and agaran structures from the red seaweed Gymnogongrus tenuis. Carbohydr Polym. 2016;136:1370-1378.