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.
Similar content being viewed by others
References
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)
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)
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)
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)
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)
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
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Gröndahl, M., Teleman, A., Gatenholm, P.: Effect of acetylation on the material properties of glucuronoxylan from aspen wood. Carbohydr Polym 52, 359–366 (2003)
Joshi, J.M., Sinha, V.K.: Graft copolymerization of 2-hydroxyethylmethacrylate onto carboxymethyl chitosan using CAN as an initiator. Polymer 47, 2198–2204 (2006)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Passauer, L., Bender, H., Fischer, S.: Synthesis and characterisation of starch phosphates. Carbohydr Polym 82, 809–814 (2010)
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)
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)
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)
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)
Pasanphan, W., Chirachanchai, S.: Conjugation of gallic acid onto chitosan: An approach for green and water-based antioxidant. Carbohydr Polym 72, 169–177 (2008)
Huang, D., Ou, B., Prior, R.L.: The chemistry behind antioxidant capacity assays. J Agric Food Chem 53, 1841–1856 (2005)
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)
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)
Lillo, L.E., Matsuhiro, B.: Chemical modifications of carboxylated chitosan. Carbohydr Polym 34, 397–401 (1997)
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)
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)
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)
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)
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).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10719-014-9567-1