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Biological Activities of Marine-Derived Oligosaccharides

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Springer Handbook of Marine Biotechnology

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Abstract

Alginate is an acidic copolymer of α-l-guluronate (G) and its C5 epimer β-d-mannuronate (M), is arranged in homopolymer (polyguluronate or polymannuronate) or heteropolymer (a mixed sequence of these residues). Alginates extracted from brown algae are widely used in the food industry, biotechnology, and medical fields. In addition to the many interesting physicochemical properties of alginates, several studies have demonstrated that alginates have various bioactivities such as immunomodulation. Recent studies have demonstrated that alginate oligosaccharides prepared from alginate polymers show even many more improved bioactivities, not only in mammalian systems but also in plant systems. It is considered that the decreased viscosity and the loss of gel-forming properties of alginate oligosaccharides lead to an increase in biocompatibility.

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Abbreviations

AOM:

alginate oligosaccharide mixture

CL:

chemiluminescence

DMPO-OH:

DMPO-hydroxyl

DMPO:

5,5-dimethyl-1-pyrroline N-oxide

DP:

degree of polymerization

ELISA:

enzyme-linked immunosorbent assay

ESR:

electron spin resonance

G-CSF:

granulocyte colony-stimulating factor

G3–G9:

trimer to nonamer of G

GM-CSF:

granulocyte-macrophage colony-stimulating factor

GM:

genetically modified

G:

guluronate

HPX:

hypoxanthine

IL:

interleukin

INF:

interferon

IgE:

immunoglobulin E

KC:

keratinocyte-derived chemokine

LPS:

lipopolysaccharide

M/G:

molar ratio between mannuronic and glucuronic acids in alginates

M3–M9:

trimer to nonamer of M

MCP:

monocyte chemoattractant protein

MG:

heteropolymers of mannuronate and guluronate

MIP:

macrophage inflammatory protein

M:

mannuronate

PBS:

phosphate buffered saline

PG:

homopolymer of guluronate

PHPA:

p-hydroxyphenyl acetic acid

PM:

homopolymer of mannuronate

RANTES:

regulated upon activation, normal T-cell expressed and secreted

ROS:

reactive oxygen species

SOD:

superoxide dismutase

TLR:

toll-like receptor

TNF:

tumor necrosis factor

Th2:

T helper 2 cells

XOD:

xanthine oxidase

i.p.:

intraperitoneal

References

  1. A. Haug: Isolation and fractionation with potassium chloride and manganous ions, Methods Carbohydr. Chem. 5, 69–73 (1965)

    CAS  Google Scholar 

  2. M. Otterlei, K. Østgaard, G. Skjåk-Bæk, O. Smidsrød, P. Soon-Shiong, T. Espevik: Induction of cytokine production from human monocytes stimulated with alginate, J. Immunother. 10(4), 286–291 (1991)

    Article  CAS  Google Scholar 

  3. Y. Kimura, K. Watanabe, H. Okuda: Effects of soluble sodium alginate on cholesterol excretion and glucose tolerance in rats, J. Ethnopharmacol. 54(1), 47–54 (1996)

    Article  CAS  Google Scholar 

  4. D. Logeart, S. Prigent-Richard, J. Jozefonvicz, D. Letourneur: Fucans, sulfated polysaccharides extracted from brown seaweeds, inhibit vascular smooth muscle cell proliferation. I. Comparison with heparin for antiproliferative activity, binding and internalization, Eur. J. Cell Biol. 74(4), 376–384 (1997)

    CAS  Google Scholar 

  5. D. Logeart, S. Prigent-Richard, C. Boisson-Vidal, F. Chaubert, P. Durand, J. Jozefonvicz, D. Letourneur: Fucans, sulfated polysaccharides extracted from brown seaweeds, inhibit vascular smooth muscle cell proliferation. II. Degradation and molecular weight effect, Eur. J. Cell Biol. 74(4), 385–390 (1997)

    CAS  Google Scholar 

  6. M. Asada, M. Sugie, M. Inoue, K. Nakagomi, S. Hongo, K. Murata, S. Irie, T. Takeuchi, N. Tomizuka, S. Oka: Inhibitory effect of alginic acids on hyaluronidase and on histamine release from mast cells, Biosci. Biotechnol. Biochem. 61(6), 1030–1032 (1997)

    Article  CAS  Google Scholar 

  7. H.-J. Jeong, S.-A. Lee, P.-D. Moon, H.-J. Na, R.-K. Park, J.-Y. Um, H.-M. Kim, S.-H. Hong: Alginic acid has anti-anaphylactic effects and inhibits inflammatory cytokine expression via suppression of nuclear factor-κB activation, Clin. Exp. Allergy 36(6), 785–794 (2006)

    Article  CAS  Google Scholar 

  8. B. Fremond, C. Malandain, C. Guyomard, C. Chesne, A. Guillouzo, J.-P. Campion: Correction of bilirubin conjugation in the Gunn rat using hepatocytes immobilized in alginate gel beads as an extracorporeal bioartificial liver, Cell Transplant. 2(6), 453–460 (1993)

    CAS  Google Scholar 

  9. S.C.N. Chang, J.A. Rowley, G. Tobias, N.G. Genes, A.K. Roy, D.J. Mooney, C.A. Vacanti, L.J. Bonassar: Injection molding of chondrocyte/alginate constructs in the shape of facial implants, J. Biomed. Mater. Res. 55(4), 503–511 (2001)

    Article  CAS  Google Scholar 

  10. H.J. Hauselmann, K. Masuda, E.B. Hunziker, M. Neidhart, S.S. Mok, B.A. Michel, E.J. Thonar: Adult human chondrocytes cultured in alginate form a matrix similar to native human articular cartilage, Am. J. Physiol. 271(3), C742–C752 (1996)

    CAS  Google Scholar 

  11. A. Atala, W. Kim, K.T. Paige, C.A. Vacanti, A.B. Retik: Endoscopic treatment of vesicoureteral reflux with a chondrocyte-alginate suspension, J. Urol. 152(2Pt2), 641–643 (1994)

    CAS  Google Scholar 

  12. S. Tajima, H. Inoue, A. Kawada, A. Ishibashi, H. Takahara, N. Hiura: Alginate oligosaccharides modulate cell morphology, cell proliferation and collagen expression in human skin fibroblasts in vitro, Arch. Dermatol. Res. 291(718), 432–436 (1999)

    Article  CAS  Google Scholar 

  13. A. Kawada, N. Hiura, S. Tajima, H. Takahara: Alginate oligosaccharides stimulate VEGF-mediated growth and migration of human endothelial cells, Arch. Dermatol. Res. 291(10), 542–547 (1999)

    Article  CAS  Google Scholar 

  14. A. Kawada, N. Hiura, M. Shiraiwa, S. Tajima, M. Hiruma, K. Hara, A. Ishibashi, H. Takahara: Stimulation of human keratinocyte growth by alginate oligosaccharides, a possible co-factor for epidermal growth factor in cell culture, FEBS Letters 408(1), 43–46 (1997)

    Article  CAS  Google Scholar 

  15. T. Yoshida, A. Hirano, H. Wada, K. Takahashi, M. Hattori: Alginic acid oligosaccharide suppresses Th2 development and IgE production by inducing IL-12 production, Int. Arch. Allergy Immunol. 133(3), 239–247 (2004)

    Article  CAS  Google Scholar 

  16. H. Akiyama, T. Endo, R. Nakakita, K. Murata, Y. Yonemoto, K. Okayama: Effect of depolymerized alginates on the growth of bifidobacteria, Biosci. Biotechnol. Biochem. 56(2), 355–356 (1992)

    Article  CAS  Google Scholar 

  17. Y. Yonemoto, H. Tanaka, T. Yamashita, N. Kitabatake, Y. Ishida, A. Kimura, K. Murata: Promotion of germination and shoot elongation of some plants by alginate oligomers prepared with bacterial alginate lyase, J. Ferment. Bioeng. 75(1), 68–70 (1993)

    Article  CAS  Google Scholar 

  18. Y. Tomoda, K. Umemura, T. Adachi: Promotion of barley root elongation under hypoxic conditions by alginate lyase-lysate (A.L.L.), Biosci. Biotechnol. Biochem. 58(1), 202–203 (1994)

    Article  CAS  Google Scholar 

  19. M. Kurachi, T. Nakashima, C. Miyajima, Y. Iwamoto, T. Muramatsu, K. Yamaguchi, T. Oda: Comparison of the activities of various alginates to induce TNF-alpha secretion in RAW264.7 cells, J. Infect. Chemother. 11(4), 199–203 (2005)

    Article  CAS  Google Scholar 

  20. M. Iwamoto, M. Kurachi, T. Nakashima, D. Kim, K. Yamaguchi, T. Oda, Y. Iwamoto, T. Muramatsu: Structure-activity relationship of alginate oligosaccharides in the induction of cytokine production from RAW264.7 cells, FEBS Letters 579(20), 4423–4429 (2005)

    Article  CAS  Google Scholar 

  21. Y. Yamamoto, M. Kurachi, K. Yamaguchi, T. Oda: Stimulation of multiple cytokines production in mice by alginate oligosaccharides following intraperitoneal administration, Carbohydr. Res. 342(8), 1133–1137 (2007)

    Article  CAS  Google Scholar 

  22. P. Wang, X. Jiang, Y. Jiang, X. Hu, H. Mou, M. Li, H. Guan: In vitro antioxidative activities of three marine oligosaccharides, Nat. Prod. Res. 21(7), 646–654 (2007)

    Article  Google Scholar 

  23. H. Tomida, T. Yasufuku, T. Fujii, Y. Kondo, T. Kai, M. Anraku: Polysaccharides as potential antioxidative compounds for extended-release matrix tablets, Carbohydr. Res. 345(1), 82–86 (2010)

    Article  CAS  Google Scholar 

  24. Y. Iwamoto, H. Hidaka, T. Oda, T. Muramatsu: A study of tryptophan fluorescence quenching of bifunctional alginate lyase from a marine bacterium Pseudoalteromonas sp. strain No. 272 by acrylamide, Biosci. Biotechnol. Biochem. 67(9), 1990–1992 (2003)

    Article  CAS  Google Scholar 

  25. Y. Matsubara, K. Iwasaki, T. Muramatsu: Action of poly (α-l-guluronate) lyase from Corynebacterium sp. ALY-1 strain on saturated oligoguluronates, Biosci. Biotechnol. Biochem. 62(6), 1055–1060 (1998)

    Article  CAS  Google Scholar 

  26. A. Haug, B. Larsen, O. Smidsrød: A study of the constitution of alginic acid by partial acid hydrolysis, Acta Chem. Scand. 20, 183–190 (1966)

    Article  CAS  Google Scholar 

  27. E. Morris, D.A. Rees, D. Thom: Characterization of alginate composition and block-structure by circular dichroism, Carbohydr. Res. 81(2), 305–314 (1980)

    Article  CAS  Google Scholar 

  28. X. Xu, Y. Iwamoto, Y. Kitamura, T. Oda, T. Muramatsu: Root growth-promoting activity of unsaturated oligomeric urinates from alginate on carrot and rice plants, Biosci. Biotechnol. Biochem. 67(9), 2022–2025 (2003)

    Article  CAS  Google Scholar 

  29. M. Ueno, T. Hiroki, S. Takeshita, Z. Jiang, D. Kim, K. Yamaguchi, T. Oda: Comparative study on antioxidative and macrophage-stimulating activities of polyguluronic acid (PG) and polymannuronic acid (PM) prepared from alginate, Carbohydr. Res. 352, 88–93 (2012)

    Article  CAS  Google Scholar 

  30. D. Kim, Y. Yamasaki, T. Yamatogi, K. Yamaguchi, Y. Matsuyama, Y.S. Kang, Y. Lee, T. Oda: The possibility of reactive oxygen species (ROS)-independent toxic effects of Cochlodinium polykrikoides on damselfish (Chromis caerulea), Biosci. Biotechnol. Biochem. 73(3), 613–618 (2009)

    Article  CAS  Google Scholar 

  31. B.L. Millic, S.M. Djilas, J.M. Canadanovic-Brunet: Antioxidative activity of phenolic compounds on the metal-ion breakdown of lipid peroxidation system, Food Chem. 61(4), 443–447 (1998)

    Article  Google Scholar 

  32. H. Chen, Z. Wang, Z. Qu, L. Fu, P. Dong, X. Zhang: Physicochemical characterization and antioxidant activity of a polysaccharide isolated from oolong tea, Eur. Food Res. Technol. 229(4), 629–635 (2009)

    Article  CAS  Google Scholar 

  33. E. Tsiapali, S. Whaley, J. Kalbfleisch, H.E. Ensley, I.W. Browder, D.L. Williams: Glucans exhibit weak antioxidant activity, but stimulate macrophage free radical activity, Free Radic. Bio. Med. 30(4), 393–402 (2001)

    Article  CAS  Google Scholar 

  34. M.Y. Shon, T.H. Kim, N.J. Sung: Antioxidants and free radical scavenging activity of Phellinusbaumii (Phellinus of Hymenochaetaceae) extracts, Food Chem. 82(4), 593–597 (2003)

    Article  CAS  Google Scholar 

  35. C. Smith, B. Halliwell, O.I. Aruoma: Protection by albumin against the pro-oxidant actions of phenolic dietary components, Food Chem. Toxicol. 30(6), 483–489 (1992)

    Article  CAS  Google Scholar 

  36. E.A. Decker, B. Welch: Role of ferritin as a lipid oxidation catalyst in muscle food, J. Agric. Food Chem. 38(3), 674–677 (1990)

    Article  CAS  Google Scholar 

  37. K. Iwasaki, Y. Matsubara: Purification of alginate oligosaccharides with root growth-promoting activity toward lettuce, Biosci. Biotechnol. Biochem. 64(5), 1067–1070 (2000)

    Article  CAS  Google Scholar 

  38. E.D.T. Atkins, I.A. Nieduszynski, W. Mackie, K.D. Parker, E.E. Smolko: Structural components of alginic acid. II. The crystalline structure of poly-α-l-guluronic acid, Results of X-ray diffraction and polarized infrared studies, Biopolymers 12(8), 1879–1887 (1973)

    Article  CAS  Google Scholar 

  39. R. Medzhitov, C. Janeway, Jr.: Innate Immunity, N. Engl. J. Med. 343(5), 338–344 (2000)

    Article  CAS  Google Scholar 

  40. M. Hirschfeld, Y. Ma, J.H. Weis, S.N. Vogel, J.J. Weis: Cutting edge: Repurification of lipopolysaccharide eliminates signaling through both human and murine Toll-like receptor 2, J. Immunol. 165(2), 618–622 (2000)

    Article  CAS  Google Scholar 

  41. S. Yang, S. Sugawara, T. Monodane, M. Nishijima, Y. Adachi, S. Akashi, K. Miyake, S. Hase, H. Takada: Micrococcus luteus teichuronic acids activate human and murine monocytic cells in a CD14- and toll-like receptor 4-dependent manner, Infect. Immun. 69(4), 2025–2030 (2001)

    Article  CAS  Google Scholar 

  42. S. Shoham, C. Hung, J.-M. Chen, D.T. Golenbock, S.M. Levitz: Toll-like receptor 4 mediates intracellular signaling without TNF-α release in response to Cryptococcus neoformans polysaccharide capsule, J. Immunol. 166(7), 4620–4626 (2001)

    Article  CAS  Google Scholar 

  43. T.H. Flo, L. Ryan, E. Latz, O. Takeuchi, B.G. Monks, E. Lien, Ø. Halaas, S. Akira, G. Skjåk-Bræk, D.T. Golenbock, T. Espevik: Involvement of toll-like receptor (TLR) 2 and TLR4 in cell activation by mannuronic acid polymers, J. Biol. Chem. 277(38), 35489–35495 (2002)

    Article  CAS  Google Scholar 

  44. G.D. Demetri, J.D. Griffin: Granulocyte colony-stimulating factor and its receptor, Blood 78(11), 2791–2808 (1991)

    CAS  Google Scholar 

  45. D.C. Dale, L.W. Conrad, W.R. Summer, S. Nelson: Granulocyte colony-stimulating factor–role and relationships in infectious diseases, J. Infect. Dis. 172(4), 1061–1075 (1995)

    Article  CAS  Google Scholar 

  46. J. Martin, S. Navas, J.A. Quiroga, V. Carreno: Recombinant human granulocyte colony-stimulating factor reduces hepatitis C virus replication in mononuclear cells from chronic hepatitis C patients, Cytokine 8(4), 313–317 (1996)

    Article  CAS  Google Scholar 

  47. Ø. Halaas, W.M. Olsen, O.P. Veiby, D. Løvhaug, G. Skjåk-Bræk, R. Vik, T. Espsvik: Mannuronan enhances survival of lethally irradiated mice and stimulates murine haematopoiesis in vitro, Scand. J. Immunol. 46(4), 358–365 (1997)

    Article  CAS  Google Scholar 

  48. M.R. Brown, M. Mular, I. Miller, C. Farmer, C. Trenerry: The vitamine content of microalgae used in aquaculture, J. Appl. Phycol. 11(3), 247–255 (1999)

    Article  CAS  Google Scholar 

  49. R. Vismara, S. Vestri, C. Kusmic, L. Brarsanti, P. Gualtieri: Natural vitamine E enrichment of Artemia salina fed freshwater and marine microalgae, J. Appl. Phycol. 15(1), 75–80 (2003)

    Article  CAS  Google Scholar 

  50. Y. Durmaz: Vitamin E (α-tocopherol) production by the marine microalgae Nannochloropsis oculata (Eustigmatophyceae) in nitrogen limitation, Aquaculture 272(1–4), 717–722 (2007)

    Article  CAS  Google Scholar 

  51. T. Yokose, T. Nishikawa, Y. Yamamoto, Y. Yamasaki, K. Yamaguchi, T. Oda: Growth-promoting effect of alginate oligosaccharides on a unicellular marine microalga, Nannochloropsis oculata, Biosci. Biotechnol. Biochem. 73(2), 450–453 (2009)

    Article  CAS  Google Scholar 

  52. R.R.L. Guillard, J.H. Ryther: Studies on marine planktonic diatoms. I. Cyclotella nana Hustedt and Detonula confervacea (Cleve) Gran., Can. J. Microbiol. 8, 229–239 (1962)

    Article  CAS  Google Scholar 

  53. A. Satoh, L.Q. Vudikaria, N. Kurano, S. Miyachi: Evaluation of the sensitivity of marine microalgal strains to the heavy metals, Cu, As, Sb, Pb and Cd, Environ. Int. 31(5), 713–722 (2005)

    Article  CAS  Google Scholar 

  54. E.E. Farmer, T.D. Moloshok, M.J. Saxton, C.A. Ryan: Oligosaccharide signaling in plants specificity of oligouronide-enhanced plasma membrane protein phosphorylation, J. Biol. Chem. 266(5), 3140–3145 (1991)

    CAS  Google Scholar 

  55. P. Albersheim, A.G. Darvill: Oligosaccharides, Sci. Am. 253, 44–55 (1985)

    Article  Google Scholar 

  56. Y. Yamasaki, T. Yokose, T. Nishikawa, D. Kim, Z. Jiang, K. Yamaguchi, T. Oda: Effects of alginate oligosaccharide mixtures on growth and fatty acid composition of the green alga Chlamydomonas reinhardtii, J. Biosci. Bioeng. 113(1), 112–116 (2012)

    Article  CAS  Google Scholar 

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  1. Division of Biochemistry, Faculty of Fisheries, Nagasaki University, 1-14 Bunkyo-machi, 852-8521, Nagasaki, Japan

    Tatsuya Oda

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  1. Tatsuya Oda
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Correspondence to Tatsuya Oda .

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  1. Department of Marine-Bio. Convergence Science Specialized Graduate School Science & Technology Convergence Marine Bioprocess Research Center, Pukyong National University, Yongdang Campus, 365, Sinseon-ro, Nam-gu, 608-739, Busan, Korea

    Se-Kwon Kim Prof.

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Oda, T. (2015). Biological Activities of Marine-Derived Oligosaccharides. In: Kim, SK. (eds) Springer Handbook of Marine Biotechnology. Springer Handbooks. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-53971-8_47

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