Artículo

La versión final de este artículo es de uso interno de la institución.
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Carrageenans represent one of the major texturising ingredients in the food industry. They are natural ingredients, which are used for decades in food applications. Carrageenan is a generic name for a family of linear, sulfated galactans, obtained by extraction from certain species of red seaweeds (Rhodophyta). Since natural carrageenans are mixtures of different sulfated polysaccharides, their composition differs from batch to batch. Therefore, the quantitative analysis of carrageenan batches is of greatest importance for both ingredient suppliers and food industries to deliver a constant consumer product and to develop new applications based on their unique intrinsic properties. Nowadays NMR spectroscopy is one of the standard tools for the determination of the chemical structure of carrageenan samples. This review gives an overview of NMR-spectroscopy (both 1H- and 13C-NMR) as a powerful tool for the qualitative and quantitative analysis of carrageenan samples. In addition to tables containing chemical shift data for both 1H- and 13C-spectra, details about sample preparation, selective degradation and fractionation techniques are included. © 2002 Elsevier Science Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:1H and 13C high resolution NMR spectroscopy of carrageenans: Application in research and industry
Autor:Van De Velde, F.; Knutsen, S.H.; Usov, A.I.; Rollema, H.S.; Cerezo, A.S.
Filiación:NIZO Food Research, Product Technology Department, PO Box 20, 6710 BA Ede, Netherlands
Wageningen Centre for Food Sciences, PO Box 557, 6700 AN Wageningen, Netherlands
MATFORSK, Norwegian Food Research Institute, Osloveien 1, N-1430 Ås, Norway
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leniskii Prospect 47, Moscow 119991, Russian Federation
Universidad De Buenos Aires, Facultad De Ciencias Exactas Y Naturales, Ciudad Universitaria, 1428, Buenos Aires, Argentina
Palabras clave:Chemical analysis; Degradation; Fractionation; Nuclear magnetic resonance spectroscopy; Polysaccharides; Seaweed; Toxicity; Food industry; Food products; algae; Rhodophyta
Año:2002
Volumen:13
Número:3
Página de inicio:73
Página de fin:92
DOI: http://dx.doi.org/10.1016/S0924-2244(02)00066-3
Título revista:Trends in Food Science and Technology
Título revista abreviado:Trends Food Sci. Technol.
ISSN:09242244
CODEN:TFTEE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09242244_v13_n3_p73_VanDeVelde

Referencias:

  • Anderson, W., Bowtle, W., Determination of iota-carrageenan with 2-thiobarbituric acid (1974) Analyst, 99, pp. 178-183
  • Barbeyron, T., Flament, D., Michel, G., Potin, P., Kloareg, B., The sulphated-galactan hydrolases, agarases and carrageenases: Structural biology and molecular evolution (2001) Cahiers de Biologic Marine, 42, pp. 169-183
  • Bellion, C., Brigand, G., Prome, J.-C., Bociek, D.W.S., Identification et caractérisation des précurseurs biologiques des carraghénanes par spectroscopie de RMN-13C (1983) Carbohydrate Research, 119, pp. 31-48
  • Bhattacharjee, S.S., Yaphe, W., Hamer, G.K., 13C-NMR spectroscopic analysis of agar, kappa-carrageenan and iota-carrageenan (1978) Carbohydrate Research, 60, pp. C1-C3
  • Bixler, H.J., Recent developments in manufacturing and marketing carrageenan (1996) Hydrobiologia, 326-327, pp. 35-57
  • Bock, K., Pedersen, C., Pedersen, H., Carbon-13 nuclear magnetic resonance data for oligosaccharides (1984) Advances in Carbohydrate Chemistry and Biochemistry, 42, pp. 193-225
  • Caram-Lelham, N., Sundelof, L.O., Andersson, T., Preprative separation of oligosaccharides from kappa-carrageenan, sodium hyaluronate, and dextran by Superdex (TM) 30 prep grade (1995) Carbohydrate Research, 273, pp. 71-76
  • 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, pp. 229-243
  • Chiovitti, A., Bacic, A., Craik, D.J., Kraft, G.T., Liao, M.-L., Falshaw, R., Furneaux, R.H., A pyruvated carrageenan from Australian specimens of the red alga Sacronema filiforme (1998) Carbohydrate Research, 299, pp. 229-243
  • Chiovitti, A., Bacic, A., Craik, D.J., Munro, S.L.A., Kraft, G.T., Liao, M.-L., Carrageenans with complex substitution patterns from red algae of the genus Erythroclonium (1998) Carbohydrate Research, 305, pp. 243-252
  • 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., Matulewicz, M.C., Stortz, C.A., Cerezo, A.S., Room temperature, low field 13C NMR spectra of degraded carrageenans. Part II. On the specificity of the autohydrolysis reaction in kappa/iota and mu/nu structures (1991) International Journal of Biological Macromolecules, 13, pp. 337-340
  • 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
  • Colson, P., Jennings, H.J., Smith, J.C.P., Composition, sequence, and conformation of polymers and oligomers of glucose as reveal by carbon-13 nuclear magnetic resonance (1974) Journal of the American Chemistry Society, 96, pp. 8081-8087
  • De Ruiter, G.A., Richard, O., Rudolph, B., Genicot, S., Kloareg, B., Penninkhof, B., Potin, P., (2000), Sulfohydrolases, corresponding amino acid and nucleotide sequences, sulfohydrolase preparations, processes, and products thereof. World Patent application: WO0068395; De Ruiter, G.A., Rudolph, B., Carrageenan biotechnology (1997) Trends in Food Science & Technology, 8, pp. 389-395
  • 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
  • Falshaw, R., Bixler, H.J., Johndro, K., Structure and performance of commercial kappa-2 carrageenan extracts I. Structure analysis (2001) Food Hydrocolloids, 15, pp. 441-452
  • Falshaw, R., Furneaux, R., Carrageenan from the tetrasporic stage of Gigartina decipiens (Gigartinaceae, Rhodophyta) (1994) Carbohydrate Research, 252, pp. 171-182
  • Falshaw, R., Furneaux, R.H., Carrageenans from the tetrasporic stages of Gigartina clavifera and Gigartina alveata (Gigartinaceae, Rhodophyta) (1995) Carbohydrate Research, 276, pp. 155-165
  • Falshaw, R., Furneaux, R.H., Wong, H., Liao, M.-L., Bacic, A., Chandrkrachang, S., Structural analysis of carrageenans from Burnese and Thai samples of Catenella nipae Zanardini (1996) Carbohydrate Research, 285, pp. 81-98
  • Feldman, S.C., Stortz, C.A., Vigna, M.S., Cerezo, A.S., Carrageenans in the "sterile" stage from Gigartina skottsbergii (1994) Anales de la Asociacion Quimica Argentina, 82, pp. 117-124
  • Glicksman, M., (1983) Food Hydrocolloids, Vol. 2: Seaweed Extracts (pp. 89), , Boca Raton: CRC Press Inc
  • Grasdalen, H., High-field, 1H-n.m.r. spectroscopy of alginate: Sequential structure and linkage conformations (1983) Carbohydrate Research, 118, pp. 255-260
  • Grasdalen, H., Painter, T.J., NMR studies of composition and sequence in legume-seed galactomannans (1980) Carbohydrate Research, 81, pp. 59-66
  • Greer, C.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
  • Greer, C.W., Shomer, I., Goldstein, M.E., Yaphe, W., Analysis of carrageenan from Hypnea musciformis by using kappa- and iota-carrageenases and 13C-N. M.R. spectroscopy (1984) Carbohydrate Research, 129, pp. 189-196
  • Hansen, J.H., Larsen, H., Grøndal, J., (2000), Carrageenan compositions and methods for their production. US patent application: US 6,063,915; Hjerde, T., Kristiansen, T.S., Stokke, B.T., Smidsrød, O., Christensen, B.E., Conformation dependent depolymerization kinetics of polysaccharides studied by viscosity measurements (1994) Carbohydrate Polymers, 24, pp. 265-275
  • Imeson, A.P., Carrageenan (2000) Handbook of Hydrocolloids, pp. 87-102. , G.O. Phillips, & P.A. Williams. Cambridge: Woodhead Publishing Ltd
  • Jol, C.N., Neiss, T.G., Penninkhof, B., Rudolph, B., De Ruiter, G.A., A novel high-performance anion-exchange chromatographic method for the analysis of carrageenans and agars containing 3,6-anhydrogalactose (1999) Analytical Biochemistry, 268, pp. 213-222
  • Knutsen, S.H., (1992) Isolation and Analysis of Red Algal Galactans, , PhD thesis, Univerisy of Trondheim, Trondheim, Norway
  • Knutsen, S.H., Grasdalen, H., Characterization of water-extractable polysaccharides from Norwegian Furcellaria lumbricalis (Huds) L. (Gigartinales, Rhodophyceae) by IR and NMR spectroscopy (1987) Botanica Marina, 30, pp. 497-505
  • Knutsen, S.H., Grasdalen, H., The use of neocarrabiose oligosaccharides with different length and sulphate substitution as model compounds for 1H-NMR spectroscopy (1992) Carbohydrate Research, 229, pp. 233-244
  • Knutsen, S.H., Grasdalen, H., Analysis of carrageenans by enzymic degradation, gel filtration and 1H NMR spectroscopy (1992) Carbohydrate Polymers, 19, pp. 199-210
  • Knutsen, S.H., Murano, E., D'Amato, M., Toffanin, R., Rizzo, R., Paoletti, S., Modified procedures for extraction and analysis of carrageenan applied to the red alga Hypnea musciformis (1995) Journal of Applied Phycology, 7, pp. 565-576
  • Knutsen, S.H., Myslabodski, D.E., Grasdalen, H., Characterization of carrageenan fractions from Norwegian Furcellaria lumbricalis (Huds) L. by 1H-NMR spectroscopy (1990) Carbohydrate Research, 206, pp. 367-372
  • 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
  • Knutsen, S.H., Sletmoen, M., Kristensen, T., Barbeyron, T., Kloareg, B., Potin, P., A rapid method for the separation and analysis of carrageenan oligosaccharides released by iota- and kappa-carrageenase (2001) Carbohydrate Research, 331, pp. 101-106
  • Kolender, A.A., Pujol, C.A., Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., The system of sulfated alpha-(1->3)-linked D-mannans from the red seaweed Nothogenia fastigiata: Structures, antiherpetic and anticoagulant properties (1997) Carbohydrate Research, 304, pp. 53-60
  • Kovac, P., Hitsch, J., Shashkov, A.S., Usov, A.I., Yarotsky, S.V., 13C-NMR spectra of xylo-oligosaccharides and their application to the elucidation of xylan structure (1980) Carbohydrate Research, 85, pp. 177-185
  • 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
  • Lahaye, M., Yaphe, W., Viet, M.T.P., Rochas, C., 13C NMR spectroscopic investigation of methylated and charged agarose oligosaccharides and polysaccharides (1989) Carbohydrate Research, 190, pp. 249-265
  • Liao, M.-L., Chiovitti, A., Munro, S.L.A., Craik, D.J., Kraft, G.T., Bacic, A., Sulfated galactans from Australian specimens of the red alga Phacelocarpus peperocarpos (Gigartinales, Rhodophyta) (1996) Carbohydrate Research, 296, pp. 237-247
  • Liao, M.-L., Kraft, G.-T., Munro, S.-L.A., Craik, D.-J., Bacic, A., Beta/kappa-carrageenans as evidence for continued separation of the families Dicranemataceae and Sarcodiaceae (Gigartinales, Rhodophyta) (1993) Journal of Phycology, 29, pp. 833-844
  • McCandless, E.L., West, J.A., Guiry, M.D., Carrageenan patterns in the Gigartinaceae (1982) Biochemical Systematics and Ecology, 10, pp. 275-284
  • McLean, M.W., Williamson, F.B., Kappa-Carrageenase from Pseudomonas carrageenovora (1979) European Journal of Biochemistry, 93, pp. 553-558
  • McNaught, A.D., Nomenclature of carbohydrates (1997) Carbohydrate Research, 297, pp. 1-92
  • Michel, G., Flament, D., Barbeyron, T., Vernet, T., Kloareg, B., Dideberg, O., Expression, purification, crystallization and preliminary X-ray analysis of the i-carrageenase from Alteromonas fortis (2000) Acta Crystallographica Section D - Biological Crystallography, 56, pp. 766-768
  • Miller, I.J., The chemotaxonomic significance of the water-soluble red algal polysaccharides (1997) Recent Research Developments in Phytochemistry, 1, pp. 531-565
  • Miller, I.J., The structure of a pyruvylated carrageenan extracted from Stenogramme interrupta as determined by 13C NMR spectroscopy (1998) Botanica Marina, 41, pp. 305-315
  • Miller, I.J., The structure of the polysaccharide from Hymenocladia sanguinea through 13C NMR spectroscopy (2001) Botanica Marina, 44, pp. 245-251
  • Miller, I.J., The structure of the carrageenan extracted from the tetrasporophytic form of Stenogramme interrupta (2001) Botanica Marina, 44, pp. 583-587
  • Miller, I.J., Blunt, J.W., New C-13 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., Blunt, J.W., New C-13 NMR methods for determining the structure of algal polysaccharides. Part 2. Galactans consisting of mixed diads (2000) Botanica Marina, 43, pp. 251-261
  • Miller, I.J., Blunt, J.W., New C-13 NMR methods for determining the structure of algal polysaccharides. Part 3. The structure of the polysaccharide from Cladhymenia oblongifolia (2000) Botanica Marina, 43, pp. 263-271
  • Morrice, L.M., McLean, M.W., Long, W.F., Williamson, F.B., Porphyran primary structure. An investigation using β-agarase I from Pseudomonas atlantica and 13C NMR spectroscopy (1983) European Journal of Biochemistry, pp. 673-684
  • Noseda, M.D., (1994) Polissacarideos Sulfatados Isolados da Fase Tetrasporofitica de Gigartina Skottsbergii, , PhD thesis, Universidade Federal do Parana, Brasil
  • Noseda, M.D., Cerezo, A.S., Room temperature, low filed 13C NMR spectra of degraded carrageenans. Part III. Autohydrolysis of a lambda carrageenan and of its alkali-treated derivative (1993) International Journal of Biological Macromolecules, 15, pp. 177-181
  • Østgaard, K., Wangen, B.F., Knutsen, S.H., Aasen, I.M., Large-scale production and purification of kappa-carrageenase from Pseudomonas carrageenovora for applications in seaweed biotechnology (1993) Enzyme and Microbial Technology, 15, pp. 326-333
  • Potin, P., Richard, C., Barbeyron, T., Henrissat, B., Gey, C., Petillot, Y., Forest, E., Kloareg, B., Processing and hydrolytic mechanism of the cgkA-encoded kappa-carrageenase of Alteromonas carrageenovora (1995) European Journal of Biochemistry, 228, pp. 971-975
  • Roberts, M.A., Quemener, B., Measurement of carrageenans in food: Challenges, progress, and trends in analysis (1999) Trends in Food Science & Technology, 10, pp. 169-181
  • Rochas, C., Heyraud, A., Acid and enzymic hydrolysis of kappa-carrageenan (1981) Polymer Bulletin, 5, pp. 17-21
  • Rochas, C., Rinaudo, M., Vincendon, M., Spectroscopic characterization and conformation of oligo kappa carrageenans (1983) International Journal of Biological Macromolecules, 5, pp. 111-115
  • Rochas, C., Taravel, F.-R., Turquois, T., NMR studies of synergistic kappa-carrageenan-carob galactomannan gels (1990) International Journal of Biological Macromolecules, 12, pp. 353-358
  • Rudolph, B., Seaweed product: Red algae of economic significance (2000) Marine and Freshwater Products Handbook, pp. 515-529. , R.E. Martin, E.P. Carter, L.M. Davis, & G.J. Flich. Lancaster, USA: Technomic Publishing Company, Inc
  • Sletmoen, M., (2000) Structural Investigation of Oligosaccharides Using Gel Filtration, NMR and MS. A Study of Carrageenan and Specific Carrageenases, , Master-thesis, Agricultural University of Norway, Ås, Norway
  • Stortz, C.A., Bacon, C.E., Cherniak, R., Cerezo, A.S., High-field NMR spectroscopy of cystocarpic and tetrasporic carrageenans form Iridaea undulosa (1994) Carbohydrate Research, 261, pp. 317-326
  • Stortz, C.A., Cerezo, A.S., Room-temperature, low-field C-13-NMR spectra of degraded kappa-iota-carrageenans (1991) International Journal of Biological Macromolecules, 13, pp. 101-104
  • Stortz, C.A., Cerezo, A.S., The 13C NMR spectroscopy of carrageenans: Calculation of chemical shifts and computer-aided structural determination (1992) Carbohydrate Polymers, 18, pp. 237-242
  • Stortz, C.A., Cerezo, A.S., Novel findings in carrageenans, agaroids and "hybrid" red seaweed galactans (2000) Current Topics Phytochemistry, 4, pp. 121-133
  • Therkelsen, G.H., Carrageenan (1993) Industrial Gums: Polysaccharides and their Derivatives, pp. 145-180. , R.L. Whistler, & J.N. BeMiller. San Diego: Academic Press Inc
  • Turquois, T., Acquistapace, S., Arce-Vera, F., Welti, D.H., Composition of carrageenan blends inferred from 13C-NMR and infrared spectroscopy (1996) Carbohydrate Polymers, 31, pp. 269-278
  • Usov, A.I., NMR spectroscopy of red seaweed polysaccharides: Agars, carrageenans, and xylans (1984) Botanica Marina, 27, pp. 189-202
  • Usov, A.I., Structural analysis of red seaweed galactans of agar and carrageenan groups (1998) Food Hydrocolloids, 12, pp. 301-308
  • Usov, A.I., Dobkina, I.M., Polysaccharides of algae. 43. Neutral xylan and sulfated xylomannan from the red alga Liagora valida (1991) Bioorganiceskaja Khimija, 17, pp. 1051-1058
  • Usov, A.I., Shashkov, A.S., Polysaccharides of algae. 34. 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., Yarotsky, S.V., Shashkov, A.S., 13C-NMR spectroscopy of red algal galactans (1980) Biopolymers, 19, pp. 977-990
  • Van de Velde, F., De Ruiter, G.A., Carrageenan (2002) Biopolymers (Vol. 6) Polysaccharide II Polysaccharides from Eukaryotes, pp. 245-274. , A. Steinbüchel, S. DeBaets, & E.J. VanDamme. Weinheim: Wiley-VCH
  • Van de Velde, F., Peppelman, H.A., Rollema, H.S., Tromp, R.H., On the structure of kappa/iota-hybrid carrageenans (2001) Carbohydrate Research, 331, pp. 271-283
  • Van de Velde, F., Rollema, H.S., Grinberg, N.V., Burova, T.V., Grinberg, V.Ya., Tromp, R.H., Coil-helix transition of iota-carrageenan as a function of chain regularity Biopolymers, , in press
  • Welti, D., Carrageenans. Part 12. The 300 MHz proton magnetic resonance spectra of methyl beta-D-galactopyranoside, methyl 3,6-anhydro-alpha-D-galactopyranoside, agarose, kappa-carrageenan, and segments of iota-carrageenan and agarose sulfate (1977) Journal of Chemical Research (M), pp. 3566-3587
  • Wong, K.F., Craigie, J.S., Sulfohydrolase activity and carrageenan biosynthesis in Chondrus crispus (Rhodophyceae) (1978) Plant Physiology, 61, pp. 663-666
  • Yaphe, W., Arsenault, G.P., Improved resorcinol reagent for the determination of fructose, and 3,6-anhydrogalactose in polysaccharides (1965) Analytical Biochemistry, 13, pp. 143-148
  • Yamada, T., Ogamo, A., Saito, T., Watanabe, J., Uchiyama, H., Nakagawa, Y., Preparation and anti-HIV activity of low-molecular-weight carrageenans and their sulfated derivatives (1997) Carbohydrate Polymers, 32, pp. 51-55
  • Yarotsky, S.V., Shashkov, A.S., Usov, A.I., Analysis of 13C-NMR spectra of some red seaweed galactans (1977) Bioorganiceskaja Khimija, 4, pp. 1135-1137

Citas:

---------- APA ----------
Van De Velde, F., Knutsen, S.H., Usov, A.I., Rollema, H.S. & Cerezo, A.S. (2002) . 1H and 13C high resolution NMR spectroscopy of carrageenans: Application in research and industry. Trends in Food Science and Technology, 13(3), 73-92.
http://dx.doi.org/10.1016/S0924-2244(02)00066-3
---------- CHICAGO ----------
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" . Trends in Food Science and Technology 13, no. 3 (2002) : 73-92.
http://dx.doi.org/10.1016/S0924-2244(02)00066-3
---------- MLA ----------
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" . Trends in Food Science and Technology, vol. 13, no. 3, 2002, pp. 73-92.
http://dx.doi.org/10.1016/S0924-2244(02)00066-3
---------- VANCOUVER ----------
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. Trends Food Sci. Technol. 2002;13(3):73-92.
http://dx.doi.org/10.1016/S0924-2244(02)00066-3