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Structure and anti-influenza A (H1N1) virus activity of three polysaccharides from Eucheuma denticulatum

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Abstract

Three polysaccharides (EW, EH and EA) were prepared from a red alga Eucheuma denticulatum by sequential extraction with cold water, hot water and sodium hydroxide water solution. Their monosaccharide compositions, relative molecular mass and structural characterization were determined by gas chromatography, high performance 1iquid chromatography, fourier transform infrared spectroscopy and nuclear magnetic resonance spectroscopy methods. EW was hybrid ı/κ/ν-carrageenan (70 ı/17κ/13ν-carrabiose), EH was mainly ı-carrageenan, and EA was mainly α-1,4-Glucan (88%) but mixed with small amount of ı-carrageenan (12%). The relative molecular mass of EW, EH and EA was 480, 580 and 510 kDa, respectively. The anti-influenza A (H1N1) virus activity of these three polysaccharides was evaluated using the Madin-Darby canine kidney cells model. EW showed good anti-H1N1 virus activity, its IC50 was 276.5 μg mL−1, and the inhibition rate to H1N1 virus was 52% when its concentration was 250 μg mL−1. The IC50 of ı-carrageenan EH was 366.4 μg mL−1, whereas EA showed lower anti-H1N1 virus activity (IC50>430 μg mL−1). Available data obtained give positive evidence that the hybrid carrageenan EW from Eucheuma denticulatum can be used as potential anti-H1N1 virus inhibitor in future.

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References

  • Aguilan, J. T., Broom, J. E., Hemmingson, J. A., Dayrit, F. M., Montano, M., Dancel, M., Ni N Onuevo, M. R., and Furneaux, R. H., 2003. Structural analysis of carrageenan from farmed varieties of Philippine seaweed. Botanica Marina, 46(2): 179–192.

    Article  Google Scholar 

  • Bellion, C., Brigand, G. ì. R., Prome, J., Welti, D., and Bociek, S., 1983. Identification et caracterisation des precurseurs biologiques des carraghenanes par spectroscopie de r.m.n.-13C. Carbohydrate Research, 119: 31–48.

    Article  Google Scholar 

  • Bellion, C., Hamer, G. K., and Yaphe, W., 1982. The degradation of Eucheuma spinosum and Eucheuma cottonii carrageenans by κ-carrageenases and ı-carrageenases from marine bacteria. Canadian Journal of Microbiology, 28(7): 874–880.

    Article  Google Scholar 

  • Buck, C. B., Thompson, C. D., Roberts, J. N., Muller, M., Lowy, D. R., and Schiller, J. T., 2006. Carrageenan is a potent inhibitor of papillomavirus infection. PLoS Pathog, 2(7): e69.

    Article  Google Scholar 

  • Carlucci, M. J., Ciancia, M., Matulewicz, M. C., Cerezo, A. S., and Damonte, E. B., 1999. Antiherpetic activity and mode of action of natural carrageenans of diverse structural types. Antiviral Research, 43(2): 93–102.

    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 

  • Ciancia, M., Noseda, M. D., Matulewicz, M. C., and Cerezo, A. S., 1993. Alkali-modification of carrageenans: mechanism and kinetics in the kappa/iota-, mu/nu- and lambda-series. Carbohydrate Polymers, 20(2): 95–98.

    Article  Google Scholar 

  • Damonte, E. B., Matulewicz, M. C., and Cerezo, A. S., 2004. Sulfated seaweed polysaccharides as antiviral agents. Current Medicinal Chemistry, 11(18): 2399–2419.

    Article  Google Scholar 

  • Dodgson, K. S., and Price, R. G., 1962. A note on the determination of the ester sulphate content of sulphated polysaccharides. Biochemical Journal, 84(1): 106.

    Google Scholar 

  • Dubois, M., Gilles, K. A., Hamilton, J. K., Rebers, P. A., and Smith, F., 1956. Colorimetric method for determination of sugars and related substances. Analytical Chemistry, 28(3): 350–356.

    Article  Google Scholar 

  • Furneaux, R. H., and Miller, I. J., 1985. Water soluble polysaccharides from the New Zealand red algae in the family Phyllophoraceae. Botanica Marina, 28(10): 419–426.

    Article  Google Scholar 

  • Ghosh, T., Chattopadhyay, K., Marschall, M., Karmakar, P., Mandal, P., and Ray, B., 2009. Focus on antivirally active sulfated polysaccharides: from structure-activity analysis to clinical evaluation. Glycobiology, 19(1): 2.

    Article  Google Scholar 

  • Hung, H., Tseng, C., Yang, J., Ju, Y., Tseng, S., Chen, Y., Chao, Y., Hsieh, H., Shih, S., and Hsu, J. T. A., 2009. Aurintricarboxylic acid inhibits influenza virus neuraminidase. Antiviral Research, 81(2): 123–131.

    Article  Google Scholar 

  • Jiao, G., Yu, G., Wang, W., Zhao, X., Zhang, J., and Ewart, S. H., 2012. Properties of polysaccharides in several seaweeds from Atlantic Canada and their potential anti-influenza viral activities. Journal of Ocean University of China, 11(2): 205–212.

    Article  Google Scholar 

  • Jouanneau, D., Boulenguer, P., Mazoyer, J., and Helbert, W., 2010. Complete assignment of 1H and 13C NMR spectra of standard neo-ı-carrabiose oligosaccharides. Carbohydrate Research, 345(4): 547–551.

    Article  Google Scholar 

  • Jouanneau, D., Boulenguer, P., Mazoyer, J., and Helbert, W., 2010. Enzymatic degradation of hybrid iota-/nu-carrageenan by Alteromonas fortis iota-carrageenase. Carbohydrate Research, 345(7): 934–940.

    Article  Google Scholar 

  • Knutsen, S. H., and Grasdalen, H., 1987. Characterization of water-extractable polysaccharides from Norwegian Furcellaria lumbricalis (Huds.) Lamour.(Gigartinales, Rhodophyceae) by IR and NMR spectroscopy. Botanica Marina, 30(6): 497–506.

    Article  Google Scholar 

  • Leibbrandt, A., Meier, C., Konig-Schuster, M., Weinmullner, R., Kalthoff, D., Pflugfelder, B., Graf, P., Frank-Gehrke, B., Beer, M., Fazekas, T., Unger, H., Prieschl-Grassauer, E., and Grassauer, A., 2010. Iota-carrageenan is a potent inhibitor of influenza A virus infection. PLoS One, 5(12): e14320.

    Article  Google Scholar 

  • Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J., 1951. Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193(1): 265–275.

    Google Scholar 

  • Panlasigui, L. N., Baello, O. Q., Dimatangal, J. M., and Dumelod, B. D., 2003. Blood cholesterol and lipid-lowering effects of carrageenan on human volunteers. Asia Pacific Journal of Clinical Nutrition, 12(2): 209–214.

    Google Scholar 

  • Rees, D. A., 1970. Structure, conformation, and mechanism in the formation of polysaccharide gels and networks. Advances in Carbohydrate Chemistry and Biochemistry, 24: 267–332.

    Article  Google Scholar 

  • Semesi, A. K., and Mshigeni, K. E., 1977. Studies on the yield and infrared spectra of phycocolloids from Chondrococcus hornemannii (Lyngbye) Schmitz and Sarconema filiforme (Sonder) Kylin from Tanzania. Botanica Marina, 20(5): 271–276.

    Article  Google Scholar 

  • Stancioff, D. J., and Stanley, N. F., 1969. Infrared and chemical studies on algal polysaccharides. Proceedings of International Seaweed Symposium, (6): 595–609.

    Google Scholar 

  • Stephanie, B., Eric, D., Sophie, F. M., Christian, B., and Yu, G., 2010. Carrageenan from Solieria chordalis (Gigartinales): Structural analysis and immunological activities of the low molecular weight fractions. Carbohydrate Polymers, 81(2): 448–460.

    Article  Google Scholar 

  • Stevenson, T. T., and Furneaux, R. H., 1991. Chemical methods for the analysis of sulphated galactans from red algae. Carbohydrate Research, 210: 277–298.

    Article  Google Scholar 

  • Talarico, L. B., Zibetti, R. G., Faria, P. C., Scolaro, L. A., Duarte, M. E., Noseda, M. D., Pujol, C. A., and Damonte, E. B., 2004. Anti-herpes simplex virus activity of sulfated galactans from the red seaweeds Gymnogongrus griffithsiae and Cryptonemia crenulata. International Journal of Biological Macromolecules, 34(1–2): 63–71.

    Article  Google Scholar 

  • Talarico, L. B., and Damonte, E. B., 2007. Interference in dengue virus adsorption and uncoating by carrageenans. Virology, 363(2): 473–485.

    Article  Google Scholar 

  • Usov, A. I., and Shashkov, A. S., 1985. Polysaccharides of algae. XXXIV: Detection of iota-carrageenan in Phyllophora brodiaei (Turn.) J. Ag. (Rhodophyta) using 13C-NMR spectroscopy. Botanica Marina, 28(9): 367–374.

    Article  Google Scholar 

  • Van de Velde, F., Knutsen, S. H., Usov, A. I., Rollema, H. S., and 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.

    Article  Google Scholar 

  • van de Velde, F., Rollema, H. S., Grinberg, N. V., Burova, T. V., Grinberg, V. Y., and Tromp, R. H., 2002. Coil-helix transition of iota-carrageenan as a function of chain regularity. Biopolymers, 65(4): 299–312.

    Article  Google Scholar 

  • Viana, A. G., Noseda, M. D., Duarte, M. E. R., and Cerezo, A. S., 2004. Alkali modification of carrageenans. Part V. The iota-nu hybrid carrageenan from Eucheuma denticulatum and its cyclization to iota-carrageenan. Carbohydrate Polymers, 58(4): 455–460.

    Article  Google Scholar 

  • Villanueva, R. D., Montaño, M. N. E., and Romero, J. B., 2009. Iota-carrageenan from a newly farmed, rare variety of eucheumoid seaweed ‘endong’. Journal of Applied Phycology, 21(1): 27–30.

    Article  Google Scholar 

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

    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., Hu, Y., Yang, B., Zhao, X., Wang, P., Ji, G., Wu, J., and Guan, H., 2010. Extraction, isolation and structural characterization of polysaccharides from a red alga Gloiopeltis furcata. Journal of Ocean University of China, 9(2): 193–197.

    Article  Google Scholar 

  • Yu, G., Yang, B., Ren, W., Zhao, X., Zhang, J., and Barrow, C., 2007. A comparative analysis of four kinds of polysaccharides purified from Furcellaria lumbricalis. Journal of Ocean University of China, 6(1): 16–20.

    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 

  • Zhou, G., Sun, Y. P., Xin, H., Zhang, Y., Li, Z., and Xu, Z., 2004. In vivo antitumor and immunomodulation activities of different molecular weight lambda-carrageenans from Chondrus ocellatus. Pharmacological Research, 50(1): 47–53.

    Article  Google Scholar 

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Yu, G., Li, M., Wang, W. et al. Structure and anti-influenza A (H1N1) virus activity of three polysaccharides from Eucheuma denticulatum . J. Ocean Univ. China 11, 527–532 (2012). https://doi.org/10.1007/s11802-012-2107-3

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