Structural Studies on ι-Carrageenan Derived Oligosaccharides and Its Application

DOI: 10.4236/aces.2014.41003   PDF   HTML     4,545 Downloads   6,617 Views   Citations


Mild hydrochloric acid hydrolysis of i-carrageenan from Eucheuma spinosum yielded two oligosaccharides of sulfated tetrasaccharide structure. These were characterized by Fourier Transform Infrared Spectroscopy (FT-IR), Nuclear Magnetic Resonance (NMR) and Electrospray Ionization Mass Spectrometry (ESIMS). Both oligosaccharides have structure of b-D-galactopyranose(Galp)4S-(14)-α-D-AnGalp2S-(13)-b-D-galactopyranose Galp)4S-(14)-α-D-AnGalp2S-(13). Application of the resulting oligosaccharides on protein delivery system in terms of encapsulation efficiency was performed.

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Briones, A. and Sato, T. (2014) Structural Studies on ι-Carrageenan Derived Oligosaccharides and Its Application. Advances in Chemical Engineering and Science, 4, 17-22. doi: 10.4236/aces.2014.41003.

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The authors declare no conflicts of interest.


[1] H. Yuan, J. Song, X. Li, N. Li and J. Dai, “Immunomodulation and Antitumor Activity of [κappa]-Carrageenan Oligosaccharides,” Cancer Letters, Vol. 243, No. 2, 2006, pp. 228-234.
[2] N. Volpi and F. Maccari, “Structural Characterization and Antithrombin Activity of Dermatan Sulfate Purified from Marine Clam Scapharca inaequivalvis,” Glycobiology, Vol. 19, No. 4, 2009, pp. 356-367.
[3] H. Zhao, H. Liu, Y. Chen, X. Xin, J. Li, Y. Hou, Z. Zhang, X. Zhang, C. Xie and M. Geng, “Oligomannurarate Sulfate, A Novel Heparanase Inhibitor Simultaneously Targeting Basic Fibroblast Growth Factor, Combats Tumor Angiogenesis and Metastasis,” Cancer Research, Vol. 66, No. 17, 2006, pp. 8779-8787.
[4] J. H. Fitton, M. R. Irhimeh and J. Teas, “14 Marine Algae and Polysaccharides with Therapeutic Applications,” In: C. J. Barrow and F. Shahidi, Eds., Marine Nutraceuticals and Functional Foods, CRC Press, 2008, p. 345.
[5] Q. H. Hou, W. D. Song, H. Wang and L. L. Ji, “Antidiabetic Effect of Thallus laminariae Oligosaccharide on Type 2 Diabetic Rats,” Journal of Zhanjiang Ocean University, Vol. 29, No. 4, 2009, pp. 46-50.
[6] N. R. Sudarshan, D. G. Hoover and D. Knorr, “Antibacterial Action of Chitosan,” Food Biotechnology, Vol. 6, No. 3, 1992, pp. 257-272.
[7] M. N. Alekshun and S. B. Levy, “Targeting Virulence to Prevent Infection: To Kill or Not to Kill?” Drug Discovery Today: Therapeutic Strategies, Vol. 1, No. 4, 2004, pp. 483-489.
[8] W. Xie, P. Xu and Q. Liu, “Antioxidant Activity of Water-Soluble Chitosan Derivatives,” Bioorganic & Medicinal Chemistry Letters, Vol. 11, No. 13, 2001, pp. 1699-1701.
[9] J. Ji, L. C. Wang, H. Wu and H. M. Luan, “Bio-Function Summary of Marine Oligosaccharides,” International Journal of Biology, Vol. 3, No. 1, 2011, pp. 75-86.
[10] H. Yuan and J. Song, “Preparation, Structural Characterization and in Vitro Antitumor Activity of Kappa-Carrageenan Oligosaccharide Fraction from Kappaphycus striatum,” Journal of Applied Phycology, Vol. 17, No. 1, 2005, pp. 7-13.
[11] G. Yu, H. Guan, A. S. Ioanoviciu, S. A. Sikkander, C. Thanawiroon, J. K. Tobacman, T. Toida and R. J. Linhardt, “Structural Studies on κ-Carrageenan Derived Oligosaccharides,” Carbohydrate Research, Vol. 337, 2002, pp. 433-440.
[12] B. M. Henares, E. P. Enriquez, F. M. Dayrit and N. R. L. Rojas, “Iota-Carrageenan Hydrolysis by Pseudoalteromonas carrageenovora IFO12985,” Philippine Journal of Science, Vol. 139, No. 2, 2010, pp. 131-138.
[13] X. Hu, X. Jiang, E. Aubree, P. Boulenguer and A. T. Critchley, “Preparation and in Vivo. Antitumor Activity of κ-Carrageenan Oligosaccharides,” Pharmaceutical Biology, Vol. 44, No. 9, 2006, pp. 646-650.
[14] M. Guibet, S. Colin, T. Barbeyron, S. Genicot, B. Kloareg, G. Michel and W. Helbert, “Degradation of λ-carrageenan by Pseudoalteromonas carrageevora λ-carrageenase: A New Family of Glycoside Hydrolases Unrelated to κand ι-Carrageenases,” Biochemical Journal, Vol. 404, 2007, pp. 105-114.
[15] C. Aguzzi, M. C. Bonferoni, M. R. O. Fortich, S. Rossi, F. Ferrari and C. Caramella, “Influence of Complex Solubility on Formulations Based on Lambda Carrageenan and Basic Drugs,” AAPS PharmSciTech, Vol. 3, No. 3, 2003, pp. 83-89.
[16] A. M. Garcia and E. S. Ghaly, “Preliminary Spherical Agglomerates of Water Soluble Drug Using Natural Polymer and Cross-Linking Technique,” Journal of Controlled Release, Vol. 4, No. 30, 1996, pp. 179-186.
[17] O. Sipahigil and B. Dortunc, “Preparation and in Vitro Evaluation of Verapamil HCl and Ibuprofen Containing Carrageenan Beads,” International Journal of Pharmaceutics, Vol. 228, No. 1, 2001, pp. 119-128.
[18] Y. Ozsoy and N. Bergisadi, “Preparation of Mefenamic Acid Sustained Release Beads Based on Kappa-Carrageenan,” Bollettino Chimico Farmaceutico, Vol. 139, No. 3, 2000, pp. 120-123.
[19] M. R. Mangione, D. Giacomazza, G. Cavallaro, D. Bulone, V. Martorana and P. L. San Biagio, “Relation between Structural and Release Properties in a Polysaccharide Gel System,” Biophysical Chemistry, Vol. 129, No. 1, 2007, pp. 18-22.
[20] G. Ruiz and E. S. Ghaly, “Mucoadhesive Delivery Systems Using Carrageenan and Eudragit RLPO,” VitaeColumbia, Vol. 13, No. 1, 2006, pp. 31-39.
[21] V. K. Gupta, M. Hariharan, T. A. Wheatley and J. C. Price, “Controlled-Release Tablets from Carrageenans: Effect of Formulation, Storage and Dissolution Factors,” European Journal of Pharmaceutics and Biopharmaceutics, Vol. 51, No. 3, 2001, pp. 241-248.
[22] A. Pourjavadi, Sh. Barzegar and F. Zeidabadi, “Synthesis and Properties of Biodegradable Hydrogels of κ-Carrageenan Grafted Acrylic Acid-co-2-acrylamido-2-methylpropanesulfonic Acid as Candidates for Drug Delivery Systems,” Reactive and Functional Polymers, Vol. 67, No. 7, 2007, pp. 644-654.
[23] WHO, “Evaluation of Certain Food Additives and Contaminants,” Sixty-Eighth Report of the Joint FAO/WHO Expert Committee on Food Additives, WHO Technical Report Series 947, 2007, pp. 32-33.
[24] W. M. Heller, “The United States Pharmacopeia,” 22nd Edition, 12601Twinbrook Parkway, Rockville, 1990.
[25] A. V. Briones and T. Sato, “Ability of Chitosan/Carrageenan Complex to Encapsulate Bovine Serum Albumin (BSA) for Potential Use in Protein Delivery,” Asian Journal of Biological and Life Sciences, Vol. 2, No. 2, 2013, pp. 163-169.
[26] S. H. Knutsen, D. E. Myslabodski, B. Larsen and A. I. Usov, “A Modified System of Nomenclature for Red Algal Galactans,” Botanica Marina, Vol. 37, No. 2, 1994, pp. 163-169.
[27] C. W. Greer, C. Rochas and W. Yaphe, “Iota-Carrageenan Oligosaccharides as Model Compounds for Structural Analysis of Iota-Carrageenan by 13C-NMR Spectroscopy,” Botanica Marina, Vol. 28, 1985, pp. 9-14.
[28] C. Mireles, M. Martino, J. Bouzas and J. A. Torres, “Complex Formation of Chitosan and Naturally Occurring Polyanions,” In: C. J. Brine, P. A. Sandford and J. P. Zikakis Eds., Advances in Chitin and Chitosan, Elsevier Applied Science, London, 1991, pp. 506-515.

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