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Chemical modification, characterization and bioactivity of a released exopolysaccharide (r-EPS1) from Lactobacillus plantarum 70810

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Abstract

In the present study, a released exopolysaccharide (r-EPS1) from L. plantarum 70810 was modified by acetylation, phosphorylation and carboxymethylation. Scanning electron micrograph (SEM) and thermogravimetric analysis (TGA) showed the r-EPS1 derivatives had different surface morphology and thermal behavior. Compared with r-EPS1, the derivatives exhibited stronger antioxidant and antitumor activities. The study provided experimental evidences that chemical modification could be an effective way to improve the bioactivity of exopolysaccharide from L. plantarum 70810. It is noted that these derivatives could be explored as novel potential antioxidant and antitumor agents.

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References

  1. Sun, Y.X., Kennedy, J.F.: Antioxidant activities of different polysaccharide conjugates (CRPs) isolated from the fruiting bodies of Chroogomphis rutilus (Schaeff.: Fr.) O. K. Miller. Carbohydr Polym 82, 510–514 (2010)

    Article  CAS  Google Scholar 

  2. Liu, J., Luo, J.G., Ye, H., Zeng, X.X.: Preparation, antioxidant and antitumor activities in vitro of different derivatives of levan from endophytic bacterium Paenibacillus polymyxa EJS-3. Food Chem Toxicol 50, 767–772 (2012)

    Article  CAS  PubMed  Google Scholar 

  3. Li, S.Q., Shah, N.P.: Antioxidant and antibacterial activities of sulphated polysaccharides from Pleurotus eryngii and Streptococcus thermophilus ASCC 1275. Food Chem 165, 262–270 (2014)

    Article  CAS  PubMed  Google Scholar 

  4. Valko, M., Leibfritz, D., Moncol, J., Cronin, M.T.D., Mazur, M., Telser, J.: Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol 39, 44–84 (2007)

    Article  CAS  PubMed  Google Scholar 

  5. Shen, S., Cheng, H., Li, X., Li, T., Yuan, M., Zhou, Y., Ding, C.: Effects of extraction methods on antioxidant activities of polysaccharides from camellia seed cake. Eur Food Res Technol 238, 1015–1021 (2014)

    Article  CAS  Google Scholar 

  6. Zhang, K.Y., Ding, W.X., Sun, J., Zhang, B., Lu, F.J., Lai, R., Zou, Y., Yedid, G.: Antioxidant and antitumor activities of 4-arylcoumarins and 4-aryl-3,4- dihydrocoumarins. Biochimie (2014). doi:10.1016/j.biochi.2014.03.014

    Google Scholar 

  7. Zhu, B.W., Wang, L.S., Zhou, D.Y., Li, D.M., Sun, L.M., Yang, J.F., Wu, H.T., Zhou, X.Q., Tada, M.: Antioxidant activity of sulphated polysaccharide conjugates from abalone (Haliotis discus hannai Ino). Eur Food Res Technol 227, 1663–1668 (2008)

    Article  CAS  Google Scholar 

  8. Xu, R.H., Shen, Q., Ding, X.L., Gao, W.G., Li, P.L.: Chemical characterization and antioxidant activity of an exopolysaccharide fraction isolated from Bifidobacterium animalis RH. Eur Food Res Technol 232, 231–240 (2011)

    Article  CAS  Google Scholar 

  9. Chen, Y., Zhang, H., Wang, Y.X., Nie, S.P., Li, C., Xie, M.Y.: Acetylation and carboxymethylation of the polysaccharide from Ganoderma atrum and their antioxidant and immunomodulating activities. Food Chem 156, 279–288 (2014)

    Article  CAS  PubMed  Google Scholar 

  10. Zhang, Z.S., Zhang, Q.B., Wang, J., Zhang, H., Niu, X.Z., Li, P.C.: Preparation of the different derivatives of the low-molecular-weight porphyran from Porphyra haitanensis and their antioxidant activities in vitro. Int J Biol Macromol 45, 22–26 (2009)

    Article  PubMed  Google Scholar 

  11. Liu, W., Xu, J., Jing, P., Yao, W.B., Gao, X.D., Yu, L.L.: Preparation of a hydroxypropyl Ganoderma lucidum polysaccharide and its physicochemical properties. Food Chem 122, 965–971 (2010)

    Article  CAS  Google Scholar 

  12. Tao, Y.Z., Zhang, Y.Y., Zhang, L.N.: Chemical modification and antitumor activities of two polysaccharide–protein complexes from Pleurotus tuber-regium. Int J Biol Macromol 45, 109–115 (2009)

    Article  CAS  PubMed  Google Scholar 

  13. Wei, D.F., Cheng, W.D., Wei, Y.X., Zhang, L.F.: Phosphorylated modification and in vitro antioxidant activity of Radix Hedysari polysaccharide. Glycoconj J 29, 167–172 (2012)

    Article  PubMed  Google Scholar 

  14. Chen, T., Wang, J., Li, Y.Y., Shen, J.M., Zhao, T., Zhang, H.X.: Sulfated modification and cytotoxicity of Portulacaoleracea L. polysaccharides. Glycoconj J 27, 635–642 (2010)

    Article  PubMed  Google Scholar 

  15. Ma, L.S., Chen, H.X., Zhang, Y., Zhang, N., Fu, L.L.: Chemical modification and antioxidant activities of polysaccharide from mushroom Inonotus obliquus. Carbohydr Polym 89, 371–378 (2012)

    Article  CAS  PubMed  Google Scholar 

  16. Wang, K., Li, W., Rui, X., Chen, X.H., Jiang, M., Dong, M.S.: Structural characterization and bioactivity of released exopolysaccharides from Lactobacillus plantarum 70810. Int J Biol Macromol 67, 71–78 (2014)

    Article  PubMed  Google Scholar 

  17. Gröndahl, M., Teleman, A., Gatenholm, P.: Effect of acetylation on the material properties of glucuronoxylan from aspen wood. Carbohydr Polym 52, 359–366 (2003)

    Article  Google Scholar 

  18. Joshi, J.M., Sinha, V.K.: Graft copolymerization of 2-hydroxyethylmethacrylate onto carboxymethyl chitosan using CAN as an initiator. Polymer 47, 2198–2204 (2006)

    Article  CAS  Google Scholar 

  19. Li, W., Ji, J., Chen, X.H., Jiang, M., Rui, X., Dong, M.S.: Structural elucidation and antioxidant activities of exopolysaccharides from Lactobacillus helveticus MB2-1. Carbohydr Polym 102, 351–359 (2014)

    Article  CAS  PubMed  Google Scholar 

  20. Qiao, D.L., Ke, C.L., Hu, B., Luo, J.G., Ye, H., Sun, Y., Yan, X.Y., Zeng, X.X.: Antioxidant activities of polysaccharides from Hyriopsis cumingii. Carbohydr Polym 78, 199–204 (2009)

    Article  CAS  Google Scholar 

  21. Liu, J., Luo, J.G., Ye, H., Sun, Y., Lu, Z.X., Zeng, X.X.: Production, characterization and antioxidant activities in vitro of exopolysaccharides from endophytic bacterium Paenibacillus polymyxa EJS-3. Carbohydr Polym 78, 275–281 (2009)

    Article  CAS  Google Scholar 

  22. Silva, D.A., de Paula, R.C.M., Feitosa, J.P.A., de Brito, A.C.F., Maciel, J.S., Paula, H.C.B.: Carboxymethylation of cashew tree exudate polysaccharide. Carbohydr Polym 58, 163–171 (2004)

    Article  CAS  Google Scholar 

  23. Zhang, Z., Zhang, Q., Wang, J., Song, H., Zhang, H., Niu, X.: Chemical modification and influence of function groups on the in vitro-antioxidant activities of porphyran from Porphyra haitanensis. Carbohydr Polym 79, 290–295 (2010)

    Article  CAS  Google Scholar 

  24. Yang, J.H., Du, Y.M.: Chemical modification, characterization and bioactivity of Chinese lacquer polysaccharides from lac tree Rhus vernicifera against leucopenia induced by cyclophosphamide. Carbohydr Polym 52, 405–410 (2003)

    Article  CAS  Google Scholar 

  25. Ahmed, Z., Wang, Y.P., Anjum, N., Ahmad, H., Ahmad, A., Raza, M.: Characterization of new exopolysaccharides produced by coculturing of L. kefiranofaciens with yoghurt strains. Int J Biol Macromol 59, 377–383 (2013)

    Article  CAS  PubMed  Google Scholar 

  26. Wang, H.J., Wang, H.W., Shi, S.S., Duan, J.Y., Wang, S.C.: Structural characterization of a homogalacturonan from Capparis spinosa L. fruits and anti-complement activity of its sulfated derivative. Glycoconj J 29, 379–387 (2012)

    Article  CAS  PubMed  Google Scholar 

  27. Chatterjee, A., Khatua, S., Chatterjee, S., Mukherjee, S., Mukherjee, A., Paloi, S., Acharya, K., Bandyopadhyay, S.K.: Polysaccharide-rich fraction of Termitomyces eurhizus accelerate healing of indomethacin induced gastric ulcer in mice. Glycoconj J 30, 759–768 (2013)

    Article  CAS  PubMed  Google Scholar 

  28. Cabral, O.V., Téllez, S., Giannerini, C.A., Giannerini, T., Felcman, J.: Fourier-transform infrared spectrum of aspartate hydroxo-aqua nickel (II) complex and DFT-B3LYP/3-21G and 6-311G structural and vibrational calculations. Spectrochim Acta A 61, 337–345 (2005)

    Article  Google Scholar 

  29. Jayakumar, R., Nagahama, H., Furuike, T., Tamura, H.: Synthesis of phosphorylated chitosan by novel method and its characterization. Int J Biol Macromol 42, 335–339 (2008)

    Article  CAS  PubMed  Google Scholar 

  30. Teleman, A., Nordström, M., Tenkanen, M., Jacob, A., Dahlman, O.: Isolation and characterization of O-acetylated glucomannans from aspen and birch wood. Carbohydr Res 338, 525–534 (2003)

    Article  CAS  PubMed  Google Scholar 

  31. Huang, Q.L., Zhang, L.N.: Preparation, chain conformation and anti-tumor activities of water-soluble phosphated (1 → 3)-α-d-glucan from Poria cocos mycelia. Carbohydr Polym 83, 1363–1369 (2011)

    Article  CAS  Google Scholar 

  32. Suflet, D.M., Nicolescu, A., Popescu, I., Chitanu, G.C.: Phosphorylated polysaccharides. 3. Synthesis of phosphorylated curdlan and its polyelectrolyte behaviour compared with other phosphorylated polysaccharides. Carbohydr Polym 84, 1176–1181 (2011)

    Article  CAS  Google Scholar 

  33. Heinze, U., Klemm, D., Unger, E., Pieschel, F.: New starch phosphate carbamides of high swelling ability: synthesis and characterization. Starch-Starke 55, 55–60 (2003)

    Article  CAS  Google Scholar 

  34. Passauer, L., Bender, H., Fischer, S.: Synthesis and characterisation of starch phosphates. Carbohydr Polym 82, 809–814 (2010)

    Article  CAS  Google Scholar 

  35. Xu, J., Liu, W., Yao, W.B., Pang, X.B., Yin, D.K., Gao, X.D.: Carboxymethylation of a polysaccharide extracted from Ganoderma lucidum enhances its antioxidant activities in vitro. Carbohydr Polym 78, 227–234 (2009)

    Article  CAS  Google Scholar 

  36. Qian, J.Y., Chen, W., Zhang, W.M., Zhang, H.: Adulteration identification of some fungal polysaccharides with SEM, XRD, IR and optical rotation: A primary approach. Carbohydr Polym 78, 620–625 (2009)

    Article  CAS  Google Scholar 

  37. Singh, R.P., Shukla, M.K., Mishra, A., Kumari, P., Reddy, C.R.K., Jha, B.: Isolation and characterization of exopolysaccharides from seaweed associated bacteria Bacillus licheniformis. Carbohydr Polym 84, 1019–1026 (2011)

    Article  CAS  Google Scholar 

  38. Liu, J., Wen, X.Y., Lu, J.F., Kan, J., Jin, C.H.: Free radical mediated grafting of chitosan with caffeic and ferulic acids: Structures and antioxidant activity. Int J Biol Macromol 65, 97–106 (2014)

    Article  CAS  PubMed  Google Scholar 

  39. Pasanphan, W., Chirachanchai, S.: Conjugation of gallic acid onto chitosan: An approach for green and water-based antioxidant. Carbohydr Polym 72, 169–177 (2008)

    Article  CAS  Google Scholar 

  40. Huang, D., Ou, B., Prior, R.L.: The chemistry behind antioxidant capacity assays. J Agric Food Chem 53, 1841–1856 (2005)

    Article  CAS  PubMed  Google Scholar 

  41. Yuan, H.M., Zhang, W.W., Li, X.G., Lu, X.X., Li, N., Gao, X.L., Song, J.M.: Preparation and in vitro antioxidant activity of κ-carrageenan oligosaccharides and their oversulfated, acetylated, and phosphorylated derivatives. Carbohydr Res 340, 685–692 (2005)

    Article  CAS  PubMed  Google Scholar 

  42. Qi, H.M., Zhang, Q.B., Zhao, T.T., Hu, R.G., Zhang, K., Li, Z.: In vitro antioxidant activity of acetylated and benzoylated derivatives of polysaccharide extracted from Ulva pertusa (Chlorophyta). Bioorg Med Chem Lett 16, 2441–2445 (2006)

    Article  CAS  PubMed  Google Scholar 

  43. Lillo, L.E., Matsuhiro, B.: Chemical modifications of carboxylated chitosan. Carbohydr Polym 34, 397–401 (1997)

    Article  CAS  Google Scholar 

  44. Stagos, D., Amoutzias, G.D., Matakos, A., Spyrou, A., Tsatsakis, A.M., Kouretas, D.: Chemoprevention of liver cancer by plant polyphenols. Food Chem Toxicol 50, 2155–2170 (2012)

    Article  CAS  PubMed  Google Scholar 

  45. Wang, H., Zhou, H., Wang, C.X., Li, Y.S., Xie, H.Y., Luo, J.D., Zhou, Y.: Paeoniflorin inhibits growth of human colorectal carcinoma HT 29 cells in vitro and in vivo. Food Chem Toxicol 50, 1560–1567 (2012)

    Article  CAS  PubMed  Google Scholar 

  46. Berit, H.F., Terje, E., Liv, R., Bjorn, T.S.: The cytokine stimulating activity of (1 → 3)-β-D-glucans is dependent on the triple helix conformation. Carbohydr Res 329, 587–596 (2000)

    Article  Google Scholar 

  47. Rice, P.J., Kelley, J.L., Kogan, G., Ensley, H.E., Kalbfleisch, J.H., Browder, I.W., Williams, D.L.: Human monocyte scavenger receptors are pattern recognition receptors for (1 → 3)-d-glucans. J Leukoc Biol 72, 140–146 (2002)

    CAS  PubMed  Google Scholar 

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Acknowledgments

This work was co-financed by Specialized Research Fund for the Doctoral Program of Higher Education of China (No. 20130097110022), National Natural Science Foundation of China (No. 31371807; 31201422), Graduate Student Scientific Research Innovation Project of Jiangsu Normal University (No. CXZZ13_0285), and was also supported by the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

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Correspondence to Mingsheng Dong.

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Wang, K., Li, W., Rui, X. et al. Chemical modification, characterization and bioactivity of a released exopolysaccharide (r-EPS1) from Lactobacillus plantarum 70810. Glycoconj J 32, 17–27 (2015). https://doi.org/10.1007/s10719-014-9567-1

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