Chitin, Chitosan, and Their Derivatives Against Oxidative Stress and Inflammation, and Some Applications

Chapter

Abstract

Chitin, a polymer of N-acetylglucosamine (GlcNAc), (1→4)-linked 2-acetamido-2-deoxy-β-D-glucan, is widely distributed among invertebrates and crustaceans as structural material in their exoskeletons and fungal cell walls. Chitin and its derivatives have important biological properties with potential for a wide variety of applications, such as immunostimulatory, antioxidant, anti-inflammatory, antimicrobial, anticancer, anticholesteremic, anticoagulant, and wound-healing agents. However, chitin is an insoluble polymer in water, and this property is the major limiting factor for its utilization in living systems. Up until now, there have been many reports on the biological activities of derivatives of chitin, which are easily soluble in water, can be used in various applications. Especially, scientists have synthesized many novel derivatives that have activity against oxidative stress and inflammation. Therefore, this chapter reviews the knowledge of some synthetic and productive methods of several derivatives of chitin, chitosan, and, moreover, their antioxidant and anti-inflammation effects as well as potential applications are also presented.

Keywords

Cellulose Oligomer Degenerative Joint Disease Prostaglandin Gelatin 

Notes

Acknowledgment

The author wishes to acknowledge Prof. Se-Kwon Kim, Prof. Moo-Moo Kim, and Vietnam’s National Foundation for Science and Technology Development (NAFOSTED) for the support provided through research grant 106.05.2011.36.

References

  1. Ahn C-B, Jeon Y-J, Kang D-S, Shin T-S, Jung B-M (2004) Free radical scavenging activity of enzymatic extracts from a brown seaweed Scytosiphon lomentaria by electron spin resonance spectrometry. Food Res Int 37:253–258CrossRefGoogle Scholar
  2. Aiba S-i (1989) Studies on chitosan: 2. Solution stability and reactivity of partially N-acetylated chitosan derivatives in aqueous media. Int J Biol Macromol 11:249–252CrossRefGoogle Scholar
  3. Aimin C, Chunlin H, Juliang B, Tinyin Z, Zhichao D (1999) Antibiotic loaded chitosan bar. An in vitro, in vivo study of a possible treatment for osteomyelitis. Clin Orthop Relat Res 366:239–247CrossRefGoogle Scholar
  4. Alexandrova ML, Bochev PG (2005) Oxidative stress during the chronic phase after stroke. Free Radic Biol Med 39:297–316CrossRefGoogle Scholar
  5. Arellano FM, Yood MU, Wentworth CE, Oliveria SA, Rivero E, Verma A, Rothman KJ (2006) Use of cyclo-oxygenase 2 inhibitors (COX-2) and prescription non-steroidal anti-inflammatory drugs (NSAIDS) in UK and USA populations. Implications for COX-2 cardiovascular profile. Pharmacoepidemiol Drug Saf 15:861–872CrossRefGoogle Scholar
  6. Baeuerle PA, Henkel T (1994) Function and activation of NF-kappaB in the immune system. Annu Rev Immunol 12:141–179CrossRefGoogle Scholar
  7. Baumann H, Gauldie J (1994) The acute phase response. Immunol Today 15:74–80CrossRefGoogle Scholar
  8. Bengmark S (2006) Curcumin, an atoxic antioxidant and natural NFkappaB, cyclooxygenase-2, lipooxygenase, and inducible nitric oxide synthase inhibitor: a shield against acute and chronic diseases. JPEN J Parenter Enteral Nutr 30:45–51CrossRefGoogle Scholar
  9. Bhardwaj N, Kundu SC (2011) Silk fibroin protein and chitosan polyelectrolyte complex porous scaffolds for tissue engineering applications. Carbohydr Polym 85:325–333CrossRefGoogle Scholar
  10. Byun H-G, Kim Y-T, Park P-J, Lin XL, Kim S-K (2005) Chitooligosaccharides as a novel β-secretase inhibitor. Carbohydr Polym 61:198–202CrossRefGoogle Scholar
  11. Calabrese V, Lodi R, Tonon C, D’Agata V, Sapienza M, Scapagnini G, Mangiameli A, Pennisi G, Giuffrida Stella AM, Butterfield DA (2005) Oxidative stress, mitochondrial dysfunction and cellular stress response in Friedreich’s ataxia. J Neuro Sci 233:145–162CrossRefGoogle Scholar
  12. Canonica GW (2006) Treating asthma as an inflammatory disease Chest. Chest J 130:21S–28SCrossRefGoogle Scholar
  13. Chen HM, Yan XJ (2005) Antioxidant activities of agaro-oligosaccharides with different degrees of polymerization in cell-based system. Biochim Biophys Acta 1722:103–111CrossRefGoogle Scholar
  14. Chen AS, Taguchi T, Sakai K, Kikuchi K, Wang MW, Miwa I (2003) Antioxidant activities of chitobiose and chitotriose. Biol Pharm Bull 26:1326–1330CrossRefGoogle Scholar
  15. Chen H, Huang J, Yu J, Liu S, Gu P (2011) Electrospun chitosan-graft-poly (ε-caprolactone)/poly (ε-caprolactone) cationic nanofibrous mats as potential scaffolds for skin tissue engineering. Int J Biol Macromol 48:13–19CrossRefGoogle Scholar
  16. Chou T-C, Fu E, Shen EC (2003) Chitosan inhibits prostaglandin E2 formation and cyclooxygenase-2 induction in lipopolysaccharide-treated RAW 264.7 macrophages. Biochem Biophys Res Commun 308:403–407CrossRefGoogle Scholar
  17. Diegelmann RF, Evans MC (2004) Wound healing: an overview of acute, fibrotic and delayed healing. Front Biosci 9:283–289CrossRefGoogle Scholar
  18. Engelmann J, Volk J, Leyhausen G, Geurtsen W (2005) ROS formation and glutathione levels in human oral fibroblasts exposed to TEGDMA and camphorquinone. J Biomed Mater Res Part B Appl Biomater 75:272–276CrossRefGoogle Scholar
  19. Enoch S, Harding K (2003) Wound bed preparation: the science behind the removal of barriers to healing. Wounds 15:213–229Google Scholar
  20. Gao H, Neff T, Ward PA (2006) Regulation of lung inflammation in the model of IgG immune-complex injury. Annu Rev Pathol Mech Dis 1:215–242CrossRefGoogle Scholar
  21. Goswami B, Rajappa M, Sharma M, Sharma A (2008) Inflammation: its role and interplay in the development of cancer, with special focus on gynecological malignancies. Int J Gynecol Cancer 18:591–599CrossRefGoogle Scholar
  22. Green LC, Wagner DA, Glogowski J, Skipper PL, Wishnok JS, Tannenbaum SR (1982) Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids. Anal Biochem 126:131–138CrossRefGoogle Scholar
  23. Guo Z, Liu H, Chen X, Ji X, Li P (2006) Hydroxyl radicals scavenging activity of N-substituted chitosan and quaternized chitosan. Bioorg Med Chem Lett 16:6348–6350CrossRefGoogle Scholar
  24. Han Y, Zhao L, Yu Z, Feng J, Yu Q (2005) Role of mannose receptor in oligochitosan-mediated stimulation of macrophage function. Int Immunopharmacol 5:1533–1542CrossRefGoogle Scholar
  25. Harish Prashanth KV, Tharanathan RN (2005) Depolymerized products of chitosan as potent inhibitors of tumor-induced angiogenesis. Biochim Biophys Acta 1722:22–29CrossRefGoogle Scholar
  26. Hawkey CJ, Jackson L, Harper SE, Simon TJ, Mortensen E, Lines CR (2001) The gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans. Aliment Pharmacol Ther 15:1–9CrossRefGoogle Scholar
  27. Hu SG, Jou CH, Yang MC (2003) Protein adsorption, fibroblast activity and antibacterial properties of poly(3-hydroxybutyric acid-co-3-hydroxyvaleric acid) grafted with chitosan and chitooligosaccharide after immobilized with hyaluronic acid. Biomaterials 24:2685–2693CrossRefGoogle Scholar
  28. Huang R, Du Y, Yang J (2003) Preparation and anticoagulant activity of carboxybutyrylated hydroxyethyl chitosan sulfates. Carbohydr Polym 51:431–438CrossRefGoogle Scholar
  29. Huang SC, Ho CT, Lin-Shiau SY, Lin JK (2005) Carnosol inhibits the invasion of B16/F10 mouse melanoma cells by suppressing metalloproteinase-9 through down-regulating nuclear factor-kappa B and c-Jun. Biochem Pharmacol 69:221–232CrossRefGoogle Scholar
  30. Huang R, Rajapakse N, Kim S-K (2006) Structural factors affecting radical scavenging activity of chitooligosaccharides (COS) and its derivatives. Carbohydr Polym 63:122–129CrossRefGoogle Scholar
  31. Jayakumar R, Prabaharan M, Nair SV, Tokura S, Tamura H, Selvamurugan N (2010) Novel carboxymethyl derivatives of chitin and chitosan materials and their biomedical applications. Prog Mater Sci 55:675–709CrossRefGoogle Scholar
  32. Jayakumar R, Prabaharan M, Sudheesh Kumar PT, Nair SV, Tamura H (2011) Biomaterials based on chitin and chitosan in wound dressing applications. Biotech Adv 29:322–337CrossRefGoogle Scholar
  33. Je J-Y, Kim S-K (2005) Water-soluble chitosan derivatives as a BACE1 inhibitor. Bioorg Med Chem 13:6551–6555CrossRefGoogle Scholar
  34. Je J-Y, Kim S-K (2006) Reactive oxygen species scavenging activity of aminoderivatized chitosan with different degree of deacetylation. Bioorg Med Chem 14:5989–5994CrossRefGoogle Scholar
  35. Je J-Y, Park P-J, Kim B, Kim S-K (2006) Antihypertensive activity of chitin derivatives. Biopolymer 83:250–254CrossRefGoogle Scholar
  36. Je J-Y, Kim E-K, Ahn C-B, Moon S-H, Jeon B-T, Kim BK, Park T-K, Park P-J (2007) Sulfated chitooligosaccharides as prolyl endopeptidase inhibitor. Int J Biol Macromol 41:529–533CrossRefGoogle Scholar
  37. Jeon Y-J, Kim S-K (2002) Antitumor activity of chitosan oligosaccharides produced in ultrafiltration membrane reactor system. J Microbiol Biotechnol 12:503–507Google Scholar
  38. Jeon Y-J, Shahidi F, Kim S-K (2000) Preparation of chitin and chitosan oligomers and their applications in physiological functional foods. Food Rev Int 16:159–176CrossRefGoogle Scholar
  39. Kang KA, Lee KH, Chae SW, Zhang R, Jung MS, Lee YK, Kim SY, Kim HS, Joo HG, Park JW, Ham YM, Lee NH, Hyun JW (2005) Eckol isolated from Ecklonia cava attenuates oxidative stress induced cell damage in lung fibroblast cells. FEBS Lett 579:6295–6304CrossRefGoogle Scholar
  40. Kim KW, Thomas RL (2007) Antioxidative activity of chitosans with varying molecular weights. Food Chem 101:308–313CrossRefGoogle Scholar
  41. Kim S-K, Park P-J, Yang H-P, Han S-S (2001) Subacute toxicity of chitosan oligosaccharide in Sprague-Dawley rats. Arzneimittelforschung 51:769–774Google Scholar
  42. Kim SS, Oh O-J, Min H-Y, Park E-J, Kim Y, Park HJ, Ham YN, Lee SK (2003) Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells. Life Sci 73:337–348CrossRefGoogle Scholar
  43. Kim S-K, Nghiep ND, Rajapakse N (2006) Therapeutic prospectives of chitin, chitosan and their derivatives. J Chitin Chitosan 11:1–10Google Scholar
  44. Levine RL, Garland D, Oliver CN, Amici A, Climent I, Lenz AG, Ahn BW, Shaltiel S, Stadtman ER (1990) Determination of carbonyl content in oxidatively modified proteins. Methods Enzymol 186:464–478CrossRefGoogle Scholar
  45. Li Q, Verma IM (2002) NF-kappaB regulation in the immune system. Nat Rev Immunol 2:725–734CrossRefGoogle Scholar
  46. Li Z, Zhang M (2005) Chitosan–alginate as scaffolding material for cartilage tissue engineering. J Biomed Mater Res Part A 75A:485–493CrossRefGoogle Scholar
  47. Liang T-W, Chen Y-J, Yen Y-H, Wang S-L (2007) The antitumor activity of the hydrolysates of chitinous materials hydrolyzed by crude enzyme from Bacillus amyloliquefaciens V656. Process Biochem 42:527–534CrossRefGoogle Scholar
  48. Matsugo S, Mizuie M, Matsugo M, Ohwa R, Kitano H, Konishi T (1998) Synthesis and antioxidant activity of water-soluble chitosan derivatives. IUBMB Life 44:939–948CrossRefGoogle Scholar
  49. Mendis E, Kim M-M, Rajapakse N, Kim S-K (2007) An in vitro cellular analysis of the radical scavenging efficacy of chitooligosaccharides. Life Sci 80:2118–2127CrossRefGoogle Scholar
  50. Mendis E, Kim M-M, Rajapakse N, Kim S-K (2008) Sulfated glucosamine inhibits oxidation of biomolecules in cells via a mechanism involving intracellular free radical scavenging. Eur J Pharmacol 579:74–85CrossRefGoogle Scholar
  51. Milne L, Nicotera P, Orrenius S, Burkitt MJ (1993) Effects of glutathione and chelating agents on copper-mediated DNA oxidation: pro-oxidant and antioxidant properties of glutathione. Arch Biochem Biophys 304:102–109CrossRefGoogle Scholar
  52. Muzzarelli RAA (2002) The discovery of chitin, a >570 megayear old polymer. In: Chitosan in pharmacy and chemistry. Atec, Italy, pp 1–8Google Scholar
  53. Naito Y, Yoshikawa T, Matsuyama K, Yagi N, Arai M, Nakamura Y, Kaneko T, Yoshida N, Kondo M (1998) Neutrophils, lipid peroxidation, and nitric oxide in gastric reperfusion injury in rats. Free Radic Biol Med 24:494–502CrossRefGoogle Scholar
  54. Ngo D-N, Kim M-M, Kim S-K (2007) Effects of chitin oligosaccharides on production of reactive oxygen species and matrix metalloproteinases in live cells. In: Senel S, Varum KM, Murat SM, Atilla HA (eds) Advances in chitin science. Antalya, Turkey, vol X, pp 355–359Google Scholar
  55. Ngo D-N, Kim M-M, Kim S-K (2008a) Chitin oligosaccharides inhibit oxidative stress in live cells. Carbohydr Polym 74:228–234CrossRefGoogle Scholar
  56. Ngo D-N, Qian Z-J, Je J-Y, Kim M-M, Kim S-K (2008b) Aminoethyl chitooligosaccharides inhibit the activity of angiotensin converting enzyme. Process Biochem 43:119–123CrossRefGoogle Scholar
  57. Ngo D-N, Lee S-H, Kim M-M, Kim S-K (2009) Production of chitin oligosaccharides with different molecular weights and their antioxidant effect in RAW 264.7 cells. J Funct Foods 1:188–198CrossRefGoogle Scholar
  58. Ngo D-N, Kim M-M, Qian Z-J, Jung W-K, Lee S-H, Kim S-K (2010) Free radical-scavenging activities of low molecular weight chitin oligosaccharides lead to antioxidant effect in live cells. J Food Biochem 34(s1):161–177CrossRefGoogle Scholar
  59. Ngo D-H, Qian Z-J, Ngo D-N, Vo T-S, Wijesekara I, Kim S-K (2011a) Gallyl chitooligosaccharides inhibit intracellular free radical-mediated oxidation. Food Chem 128:974–981CrossRefGoogle Scholar
  60. Ngo D-H, Qian Z-J, Vo T-S, Ryu BM, Ngo D-N, Kim S-K (2011b) Antioxidant activity of gallate-chitooligosaccharides in mouse macrophage RAW264.7 cells. Carbohydr Polym 84:1282–1288CrossRefGoogle Scholar
  61. Ngo D-H, Ngo D-N, Vo T-S, Ryu BM, Ta Q-V, Kim S-K (2012a) Protective effects of aminoethyl-chitooligosaccharides against oxidative stress and inflammation in murine microglial BV-2 cells. Carbohydr Polym 88:743–747CrossRefGoogle Scholar
  62. Ngo D-N, Kim M-M, Kim S-K (2012b) Protective effects of aminoethyl-chitooligosaccharides against oxidative stress in mouse macrophage RAW 264.7 cells. Int J Biol Macromol 50:624–631CrossRefGoogle Scholar
  63. Nishimura K, Azuma I (1992) Immunomodulating activities of chitin derivatives. In: Tokura S, Azuma I (eds) Chitin derivatives in life science. Organizing Committee of International Symposium on Chitin Derivatives in Life Sciences and Japanese Society for Chitin/Chitosan, pp 7–11Google Scholar
  64. Okamura Y, Nomura A, Minami S, Okamoto Y (2005) Effects of chitin/chitosan and their oligomers/monomers on release of type I collagenase from fibroblasts. Biomacromolecules 6:2382–2384CrossRefGoogle Scholar
  65. Park P-J, Je J-Y, Kim S-K (2004) Free radical scavenging activities of differently deacetylated chitosans using an ESR spectrometer. Carbohydr Polym 55:17–22CrossRefGoogle Scholar
  66. Pasanphan W, Chirachanchai S (2008) Conjugation of gallic acid onto chitosan: an approach for green and water-based antioxidant. Carbohydr Polym 72:169–177CrossRefGoogle Scholar
  67. Peng HB, Libby P, Liao JK (1995) Induction and stabilization of I kappa B alpha by nitric oxide mediates inhibition of NF-kappa B. J Biol Chem 270:14214–14219CrossRefGoogle Scholar
  68. Perry G, Raina AK, Nunomura A, Wataya T, Sayre LM, Smith MA (2000) How important is oxidative damage? Lessons from Alzheimer’s disease. Free Radic Biol Med 28:831–834CrossRefGoogle Scholar
  69. Poot M, Verkerk A, Koster JF, Jongkind JF (1986) De novo synthesis of glutathione in human fibroblasts during in vitro ageing and in some metabolic diseases as measured by a flow cytometric method. Biochim Biophys Acta 883:580–584CrossRefGoogle Scholar
  70. Rajapakse N, Kim M-M, Mendis E, Kim S-K (2007) Inhibition of free radical-mediated oxidation of cellular biomolecules by carboxylated chitooligosaccharides. Bioorg Med Chem 15:997–1003CrossRefGoogle Scholar
  71. Rajapakse N, Kim M-M, Mendis E, Kim S-K (2008) Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 in lipopolysaccharide-stimulated RAW264.7 cells by carboxybutyrylated glucosamine takes place via down-regulation of mitogen-activated protein kinase-mediated nuclear factor-κB signaling. Immunology 123:348–357CrossRefGoogle Scholar
  72. Rinaudo M (2006) Chitin and chitosan: properties and applications. Prog Polym Sci 31:603–632CrossRefGoogle Scholar
  73. Sambrook J, Russell D (2001) Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory Press, New York, pp 84–87Google Scholar
  74. Sashiwa H, Aiba S-i (2004) Chemically modified chitin and chitosan as biomaterials. Prog Polym Sci 29:887–908CrossRefGoogle Scholar
  75. Sashiwa H, Fujishima S, Yamano N, Kawasaki N, Nakayama A, Muraki E, Hiraga K, Oda K, Aiba S-i (2002) Production of N-acetyl-D-glucosamine from α-chitin by crude enzymes from Aeromonas hydrophila H-2330. Carbohydr Res 337:761–763CrossRefGoogle Scholar
  76. Sashiwa H, Fujishima S, Yamano N, Kawasaki N, Nakayama A, Murakia E, Sukwattanasinitt M, Pichyangkura R, Aiba S-i (2003) Enzymatic production of N-acetyl-D-glucosamine from chitin. Degradation study of N-acetylchitooligosaccharide and the effect of mixing of crude enzymes. Carbohydr Polym 51:391–395CrossRefGoogle Scholar
  77. Seferian PG, Martinez ML (2000) Immune stimulating activity of two new chitosan containing adjuvant formulations. Vaccine 19:661–668CrossRefGoogle Scholar
  78. Seo W-G, Pae H-O, Kim N-Y, Oh G-S, Park I-S, Kim Y-H, Kim Y-M, Lee Y-H, Jun C-D, Chung H-T (2000) Synergistic cooperation between water-soluble chitosan oligomers and interferon-γ for induction of nitric oxide synthesis and tumoricidal activity in murine peritoneal macrophages. Cancer Lett 159:189–195CrossRefGoogle Scholar
  79. Shahidi F, Arachchi JKV, Jeon Y-J (1999) Food applications of chitin and chitosans. Trends Food Sci Technol 10:37–51CrossRefGoogle Scholar
  80. Shikhman AR, Kuhn K, Alaaeddine N, Lotz M (2001) N-acetylglucosamine prevents IL-1 beta-mediated activation of human chondrocytes. J Immunol 166:5155–5160CrossRefGoogle Scholar
  81. Su C-H, Sun C-S, Juan S-W, Ho H-O, Hu C-H, Sheu M-T (1999) Development of fungal mycelia as skin substitutes: effects on wound healing and fibroblast. Biomaterials 20:61–68CrossRefGoogle Scholar
  82. Sun T, Zhou D, Mao F, Zhu Y (2007) Preparation of low-molecular-weight carboxymethyl chitosan and their superoxide anion scavenging activity. Eur Polym J 43:652–656CrossRefGoogle Scholar
  83. Suzuki S (1998) Trends in application studies on chitic substances as drugs. Chitin Chitosan Res 4:1–11Google Scholar
  84. Takahashi M, Shibata M, Niki E (2001) Cytotoxic effect of formaldehyde with free radicals via increment of cellular reactive oxygen species. Free Radic Biol Med 31:164–174CrossRefGoogle Scholar
  85. Tamai Y, Miyatake K, Okamoto Y, Takamori Y, Sakamoto K, Minami S (2002) Enhanced healing of cartilaginous injuries by glucosamine hydrochloride. Carbohydr Polym 48:369–378CrossRefGoogle Scholar
  86. Tamai Y, Miyatake K, Okamoto Y, Takamori Y, Sakamoto K, Minami S (2003) Enhanced healing of cartilaginous injuries by N-acetyl-D-glucosamine and glucuronic acid. Carbohydr Polym 54:251–262CrossRefGoogle Scholar
  87. Usami Y, Minami S, Okamoto Y, Matsuhashi A, Shigemasa Y (1997) Influence of chain length of N-acetyl-D-glucosamine and D-glucosamine residues on direct and complement-mediated chemotactic activities for canine polymorphonuclear cells. Carbohydr Polym 32:115–122CrossRefGoogle Scholar
  88. Valko M, Leibfritz D, Moncol J, Cronin MTD, Mazur M, Telser J (2007) Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol 39:44–84CrossRefGoogle Scholar
  89. VandeVord PJ, Matthew HWT, DeSilva SP, Mayton L, Wu B, Wooley PH (2002) Evaluation of the biocompatibility of a chitosan scaffold in mice. J Biomed Mater Res 59:585–590CrossRefGoogle Scholar
  90. Weiner ML (1992) An overview of the regulatory status and of the safety of chitin and chitosan as food and pharmaceutical ingredients. In: Brine CJ, Sandford PA, Zikakis JP (eds) Advances in chitin and chitosan. Elsevier Applied Science, New York, pp 663–672CrossRefGoogle Scholar
  91. Xie W, Xu P, Liu Q (2001) Antioxidant activity of water-soluble chitosan derivatives. Bioorg Med Chem Lett 11:1699–1701CrossRefGoogle Scholar
  92. Xing R, Liu S, Guo Z, Yu H, Wang P, Li C, Li Z, Li P (2005a) Relevance of molecular weight of chitosan and its derivatives and their antioxidant activities in vitro. Bioorg Med Chem 13:1573–1577CrossRefGoogle Scholar
  93. Xing R, Liu S, Yu H, Guo Z, Wang P, Li C, Li Z, Li P (2005b) Salt-assisted acid hydrolysis of chitosan to oligomers under microwave irradiation. Carbohydr Res 340:2150–2153CrossRefGoogle Scholar
  94. Xue C, Yu G, Hirata T, Terao J, Lin H (1998) Antioxidative activities of several marine polysaccharides evaluated in a phosphatidylcholine-liposomal suspension and organic solvents. Biosci Biotechnol Biochem 62:206–209CrossRefGoogle Scholar
  95. Yuan H, Zhang W, Li X, Lü X, Li N, Gao X, Song J (2005) Preparation and in vitro antioxidant activity of κ-carrageenan oligosaccharides and their oversulfated, acetylated, and phosphorylated derivatives. Carbohydr Res 340:685–692CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Department of Biochemistry, Faculty of BiologyUniversity of Science, Vietnam National University, Ho Chi Minh City (VNU-HCMC)Ho Chi Minh CityVietnam

Personalised recommendations