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Preparation of κ-carra-oligosaccharides with microwave assisted acid hydrolysis method

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Abstract

A rapid method of microwave assisted acid hydrolysis was established to prepare κ-carra-oligosaccharides. The optimal hydrolysis condition was determined by an orthogonal test. The degree of polymerization (DP) of oligosaccharides was detected by high performance thin layer chromatography (HPTLC) and polyacrylamide gel electrophoresis (PAGE). Considering the results of HPTLC and PAGE, the optimum condition of microwave assisted acid hydrolysis was determined. The concentration of κ-carrageenan was 5 mg mL−1; the reaction solution was adjusted to pH 3 with diluted hydrochloric acid; the solution was hydrolyzed under microwave irradiation at 100 for 15 °C min. Oligosaccharides were separated by a Superdex 30 column (2.6 cm × 90 cm) using AKTA Purifier UPC100 and detected with an online refractive index detector. Each fraction was characterized by electrospray ionization mass spectrometry (ESI-MS). The data showed that odd-numbered κ-carra-oligosaccharides with DP ranging from 3 to 21 could be obtained with this method, and the structures of the oligosaccharides were consistent with those obtained by traditional mild acid hydrolysis. The new method was more convenient, efficient and environment-friendly than traditional mild acid hydrolysis. Our results provided a useful reference for the preparation of oligosaccharides from other polysaccharides.

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References

  • Abad, L. V., Kudo, H., Saiki, S., Nagasawa, N., Tamada, M., Katsumura, Y., Aranilla, C. T., Relleve, L. S., and De La Rosa, A. M., 2009. Radiation degradation studies of carrageenans. Carbohydrate Polymers, 78(1): 100–106.

    Article  Google Scholar 

  • Carlucci, M. J., Pujol, C. A., Ciancia, M., Noseda, M. D., Matulewicz, M. C., Damonte, E. B., and Cerezo, A. S., 1997. Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity. International Journal of Biological Macromolecules, 20(2): 97–105.

    Article  Google Scholar 

  • Collen, P. N., Lemoine, M., Daniellou, R., Guegan, J. P., Paoletti, S., and Helbert, W., 2009. Enzymatic degradation of kappa-carrageenan in aqueous solution. Biomacromolecules, 10(7): 1757–1767.

    Article  Google Scholar 

  • Courtois, J., 2009. Oligosaccharides from land plants and algae: Production and applications in therapeutics and biotechnology. Current Opinion in Microbiology, 12(3): 261–273.

    Article  Google Scholar 

  • Hu, T., Li, C., Zhao, X., Li, G., Yu, G., and Guan, H., 2013. Preparation and characterization of guluronic acid oligosa-ccharides degraded by a rapid microwave irradiation method. Carbohydrate Research, 373: 53–58.

    Article  Google Scholar 

  • Hu, X., Jiang, X., Aubree, E., Boulenguer, P., and Critchley, A. T., 2006. Preparation and in vivo antitumor activity of κ-carrageenan oligosaccharides. Pharmaceutical Biology, 44(9): 646–650.

    Article  Google Scholar 

  • Karlsson, A., and Singh, S. K., 1999. Acid hydrolysis of sulphated polysaccharides. Desulphation and the effect on molecular mass. Carbohydrate Polymers, 38(1): 7–15.

    Article  Google Scholar 

  • Mou, H. J., Jiang, X. L., and Guan, H. S., 2003. A κ-carrageenan derived oligosaccharide prepared by enzymatic degradation containing anti-tumor activity. Journal of Applied Phycology, 15(4): 297–303.

    Article  Google Scholar 

  • Myslabodski, D. E., Stancioff, D., and Heckert, R. A., 1996. Effect of acid hydrolysis on the molecular weight of kappa carrageenan by GPC-LS. Carbohydrate Polymers, 31(1–2): 83–92.

    Article  Google Scholar 

  • Navarro, D. A., Flores, M. L., and Stortz, C. A., 2007. Microwave-assisted desulfation of sulfated polysaccharides. Carbohydrate Polymers, 69(4): 742–747.

    Article  Google Scholar 

  • Relleve, L., Nagasawa, N., Luan, L. Q., Yagi, T., Aranilla, C., Abad, L., Kume, T., Yoshii, F., and Dela Rosa, A., 2005. Degradation of carrageenan by radiation. Polymer Degradation and Stability, 87(3): 403–410.

    Article  Google Scholar 

  • Rodriguez-Jasso, R. M., Mussatto, S. I., Pastrana, L., Aguilar, C. N., and Teixeira, J. A., 2011. Microwave-assisted extraction of sulfated polysaccharides (fucoidan) from brown seaweed. Carbohydrate Polymers, 86(3): 1137–1144.

    Article  Google Scholar 

  • Singh, V., Tiwari, A., Kumari, P., and Tiwari, S., 2006. Microwave-promoted hydrolysis of plant seed gums on alumina support. Carbohydrate Research, 341(13): 2270–2274.

    Article  Google Scholar 

  • Singh, V., Tiwari, A., Tripathi, D. N., and Malviya, T., 2003. Microwave promoted methylation of plant polysaccharides. Tetrahedron Letters, 44(39): 7295–7297.

    Article  Google Scholar 

  • Smith, D. B., and Cook, W. H., 1953. Fractionation of carrageenin. Archives of Biochemistry and Biophysics, 45(1): 232–233.

    Article  Google Scholar 

  • Sun, T., Tao, H., Xie, J., Zhang, S., and Xu, X., 2010. Degradation and antioxidant activity of k-carrageenans. Journal of Applied Polymer Science, 117(1): 194–199.

    Google Scholar 

  • Wang, W., Zhang, P., Hao, C., Zhang, X. E., Cui, Z. Q., and Guan, H. S., 2011. In vitro inhibitory effect of carrageenan oligosaccharide on influenza A H1N1 virus. Antiviral Research, 92(2): 237–246.

    Article  Google Scholar 

  • Wu, S., 2012. Degradation of κ-carrageenan by hydrolysis with commercial α-amylase. Carbohydrate Polymers, 89(2): 394–396.

    Article  Google Scholar 

  • Yamada, T., Ogamo, A., Saito, T., Uchiyama, H., and Nakagawa, Y., 2000. Preparation of O-acylated low-molecular-weight carrageenans with potent anti-HIV activity and low anticoagulant effect. Carbohydrate Polymers, 41(2): 115–120.

    Article  Google Scholar 

  • Yang, B., Yu, G., Zhao, X., Jiao, G., Ren, S., and Chai, W., 2009. Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd-numbered oligosaccharides. FEBS Journal, 276(7): 2125–2137.

    Article  Google Scholar 

  • Yu, G., Guan, H., Ioanoviciu, A. S., Sikkander, S. A., Thanawiroon, C., Tobacman, J. K., Toida, T., and Linhardt, R. J., 2002. Structural studies on kappa-carrageenan derived oligosaccharides. Carbohydrate Research, 337(5): 433–440.

    Article  Google Scholar 

  • Yu, G., Li, M., Wang, W., Liu, X., Zhao, X., Lv, Y., Li, G., Jiao, G., and Zhao, X., 2012. Structure and anti-influenza A (H1N1) virus activity of three polysaccharides from Eucheuma denticulatum. Journal of Ocean University of China, 11(4): 527–532.

    Article  Google Scholar 

  • Yu, G., Zhao, X., Yang, B., Ren, S., Guan, H., Zhang, Y., Lawson, A. M., and Chai, W., 2006. Sequence determination of sulfated carrageenan-derived oligosaccharides by high-sensitivity negative-ion electrospray tandem mass spectrometry. Analytical Chemistry, 78(24): 8499–8505.

    Article  Google Scholar 

  • Yu, H., Chen, S., Suree, P., Nuansri, R., and Wang, K., 1996. Effect of microwave irradiation on acid-catalyzed hydrolysis of starch. The Journal of Organic Chemistry, 61(26): 9608–9609.

    Article  Google Scholar 

  • Yuan, H., Song, J., Li, X., Li, N., and Dai, J., 2006. Immunomodulation and antitumor activity of kappa-carrageenan oligosaccharides. Cancer Letters, 243(2): 228–234.

    Article  Google Scholar 

  • Yuan, H., Zhang, W., Li, X., Lu, X., Li, N., Gao, X., and Song, J., 2005. Preparation and in vitro antioxidant activity of kappa-carrageenan oligosaccharides and their oversulfated, acetylated, and phosphorylated derivatives. Carbohydrate Research, 340(4): 685–692.

    Article  Google Scholar 

  • Zhang, Z., Yu, G., Zhao, X., Liu, H., Guan, H., Lawson, A. M., and Chai, W., 2006. Sequence analysis of alginate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry. Journal of the American Society for Mass Spectrometry, 17(4): 621–630.

    Article  Google Scholar 

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Authors and Affiliations

  1. Key Laboratory of Marine Drugs, Ministry of Education, Qingdao, 266003, P. R. China

    Guangsheng Li, Xia Zhao, Youjing Lv, Miaomiao Li & Guangli Yu

  2. Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, P. R. China

    Guangsheng Li, Xia Zhao, Youjing Lv, Miaomiao Li & Guangli Yu

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  1. Guangsheng Li
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  2. Xia Zhao
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  3. Youjing Lv
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  4. Miaomiao Li
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  5. Guangli Yu
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Correspondence to Guangli Yu.

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Li, G., Zhao, X., Lv, Y. et al. Preparation of κ-carra-oligosaccharides with microwave assisted acid hydrolysis method. J. Ocean Univ. China 14, 345–349 (2015). https://doi.org/10.1007/s11802-015-2409-3

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  • DOI: https://doi.org/10.1007/s11802-015-2409-3

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