Advertisement

Russian Chemical Bulletin

, Volume 64, Issue 6, pp 1302–1318 | Cite as

Structural and chemical charactertistics of pectins, arabinogalactans, and arabinogalactan proteins from conifers

  • E. N. Makarova
  • E. G. Shakhmatov
  • E. V. Udoratina
  • A. V. Kutchin
Reviews

Abstract

In this review, we summarized the research data on the contents and chemical structures of pectic polysaccharides, arabinogalactans, and arabinogalactan proteins from coniferous species. The presently known structures of these polymers are given. Special attention is given to the description of chemical structural features of pectic polysaccharides from the Abies sibirica and Picea abies tree verdures (branches and needles). Three models presently suggested for the description of pectin macromolecular structures are discussed.

Key words

softwood polysaccharides pectins arabinogalactans arabinogalactan proteins chemical structure coniferous tree verdure (softwood wood greenery) 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. O. Arifkhodzhaev, Chem. Nat. Compd. (Engl. Transl.), 2000, 36, 229 [Khim. Prir. Soedin, 2000, 185].CrossRefGoogle Scholar
  2. 2.
    N. Trofimova, E. Medvedeva, N. Ivanova, Y. Malkov, V. Babkin, in The Complex World of Polysaccharides, Ed. D. N. Karunaratn, InTech, 2012, 634.Google Scholar
  3. 3.
    Yu. S. Ovodov, Russ. J. Bioorg. Chem. (Engl. Transl.), 1998, 24, 423 [Bioorg. Khim, 1998, 24, 483].Google Scholar
  4. 4.
    E. N. Medvedeva, V. A. Babkin, L. A. Ostroukhova, Khvoinye borealnoi zony [Coniferous of the Boreal Zone], 2003, No. 1, 100 (in Russian).Google Scholar
  5. 5.
    A. L. Galant, G. A. Luzio, W. W. Widmer, R. G. Cameron, Food Hydrocolloids, 2014, 35, 661.CrossRefGoogle Scholar
  6. 6.
    J.-P. Vincken, H. A. Schols, R. J. F. J Oomen, M. C. McCann, P. Ulvskov, A. G. J. Voragen, R. C. F. Visser, Plant Physiol., 2003, 132, 1781.CrossRefGoogle Scholar
  7. 7.
    A. Peaucelle, S. Braybrook, H. Hofte, Front. Plant Sci., 2012, 3, Art. No. 121; 1615; doi: 10.3389/fpls.2012.00121.Google Scholar
  8. 8.
    M. C. Ralet, M. A. K. Williams, A. Tanhatan-Nasseri, D. Ropartz, B. Quéméner, E. Bonnin, Biomacromolecules, 2012, 13, 1615.CrossRefGoogle Scholar
  9. 9.
    A. Tanhatan-Nasseri, M. J. Crepeau, J. F. Thibault, M. C. Ralet, Carbohydr. Polym., 2011, 86, 1236.CrossRefGoogle Scholar
  10. 10.
    Yu. S. Ovodov, Russ. J. Bioorg. Chem. (Engl. Transl.), 2009, 35, 269 [Bioorg. Khim., 2009, 35, 293].CrossRefGoogle Scholar
  11. 11.
    M. A. Atmodjo, Z. Hao, D. Mohnen, Annu. Rev. Plant Biol., 2013, 64, 747.CrossRefGoogle Scholar
  12. 12.
    S. Wolf, G. Mouille, J. Pelloux, Mol. Plant, 2009, 2, 851.CrossRefGoogle Scholar
  13. 13.
    K. H. Caffall, D. Mohnen, Carbohydr. Res., 2009, 344, 1879.CrossRefGoogle Scholar
  14. 14.
    J. Harholt, A. Suttangkakul, H. V. Scheller, Plant Physiol., 2010, 153, 384.CrossRefGoogle Scholar
  15. 15.
    S. Wolf, S. Greiner, Protoplasma, 2012, 249, 169.CrossRefGoogle Scholar
  16. 16.
    B. M. Yapo, Carbohydr. Polym., 2011, 86, 373.CrossRefGoogle Scholar
  17. 17.
    B. M. Yapo, Polym. Rev., 2011, 51, 391.CrossRefGoogle Scholar
  18. 18.
    C. Delattre, T. A. Fenoradosoa, P. Michaud, Braz. Arch. Biol. Technol., 2011, 54, 6.Google Scholar
  19. 19.
    D. Mohnen, C. Opin, Plant. Biol., 2008, 11, 266.Google Scholar
  20. 20.
    T. A. Gorshkova, Rastitel´naya kletochnaya stenka kak dinamichnaya sistema [Plant Cell Wall as a Dynamic System], Nauka, Moscow, 2007, 426 pp. (in Russian).Google Scholar
  21. 21.
    B. L. Ridley, M. A. O´Neill, D. A. Mohnen, Phytochem., 2001, 57, 929.CrossRefGoogle Scholar
  22. 22.
    H. A. Schols, A. G. J. Voragen, Pectins Pectinases, 1996, 5, 3.CrossRefGoogle Scholar
  23. 23.
    J. P. Vincken, H. A. Schols, R. J. F. J. Oomen, G. Beldman, R. G. F. Visser, A. G. J. Voragen, in Advances in Pectin and Pectinase Research, Kluwer Acad. Publ., Dordrecht, 2003, p. 47.CrossRefGoogle Scholar
  24. 24.
    A. J. Ragauskas, M. Nagy, D. H. Kim, C. A. Echert, J. P. Hallett, C. L. Liotta, Ind. Biotechnol., 2006, 2, 55.CrossRefGoogle Scholar
  25. 25.
    B. Bertaud, B. Holmbom, Wood Sci. Technol., 2004, 38, 245.aaaGoogle Scholar
  26. 26.
    E. Sjöström, Wood Chemistry–Fundamentals and Applications, 2nd ed., Acad. Press, San Diego, 1993, 293 pp.Google Scholar
  27. 27.
    S. Willför, A. Sundberg, J. Hemming, B. Holmbom, Wood Sci. Technol., 2005, 39, 245.CrossRefGoogle Scholar
  28. 28.
    J. P. Thornber, D. H. Northcote, Biochem. J., 1961, 81, 449.CrossRefGoogle Scholar
  29. 29.
    J. P. Thornber, D. H. Northcote, Biochem. J., 1961, 81, 455.CrossRefGoogle Scholar
  30. 30.
    N. A. Yartseva, G. V. Permyakova, P. A. Stepen´, Provodol´stvennye i kormovye resursy lesov Sibiri [Food and Feed Supplies of Siberian Forests], Krasnoyarsk, SB AS USSR Publishing House, 1983, 122 (in Russian).Google Scholar
  31. 31.
    G. P. Grigoriuk, Int. Conf. Naturural Products and Physiologically Active Substanses (November, 30–December, 6, Novosibirsk, 1998), p. 79.Google Scholar
  32. 32.
    V. A. Babkin, L. A. Ostroukhova, S. G. D´yachkova, Yu. K. Svyatkin, D. V. Babkin, N. A. Onuchina, Khimiya v interesakh ustoich. razvitiya [Chem. Sustainable Dev.], 1997, No. 5, 105 (in Russian).Google Scholar
  33. 33.
    E. D. Levin, O. B. Denisov, R. Z. Pen, Kompleksnaya pererabotka listvennitsy [Integrated Processing of Larch], Moscow, 1978, 223 pp. (in Russian).Google Scholar
  34. 34.
    V. A. Babkin, L. A. Ostroukhova, N. V. Ivanova, Yu. A. Malkov, S. Z. Ivanova, O. V. Popova, Khvoinye borealnoi zony [Coniferous of the Boreal Zone], 2003, No. 1, 113 (in Russian).Google Scholar
  35. 35.
    A. A. Efremov, T. A. Kondratyuk, Khim. Rast. Syr´ya [Chemistry of Plant Raw Materials], 2008, No. 4, 171 (in Russian).Google Scholar
  36. 36.
    N. V. Ivanova, L. A. Ostroukhova, V. A. Babkin, S. Z. Ivanova, O. V. Popova, Khim. Rast. Syr´ya [Chemistry of Plant Raw Materials], 1999, No, 4, 5.Google Scholar
  37. 37.
    G. V. Permyakova, Territorial Conf. “Study and Ways for Application of Tree Bark” (May 27–31, 1985, Krasnoyarsk), Book of Abstracts, Siberian Technological Institute, Krasnoyarsk, 1985, p. 80 (in Russian).Google Scholar
  38. 38.
    N. V. Ivanova, O. V. Popova, V. A. Babkin, Khim. Rast. Syr´ya [Chemistry of Plant Raw Materials], 2003, No. 4, 43 (in Russian).Google Scholar
  39. 39.
    N. V. Ivanova, R. G. Ovodova, V. A. Babkin, Khim. Rast. Syr´ya [Chemistry of Plant Raw Materials], 2006, No. 1, 15 (in Russian).Google Scholar
  40. 40.
    RF Pat. 2403263; Byull. Izobret., 2010, No. 31 (in Russian).Google Scholar
  41. 41.
    T. A. Kondratyuk, PhD Thesis, Krasnoyarsk State Trade and Economic Institute, Russia, Kemerovo, 2009, 172 pp. (in Russian).Google Scholar
  42. 42.
    Pectosorbin, PVR-2-2.2/01025, State register of medicines and supplement feeds for animals, Ministry of Agriculture of the Russian Federation; http://www.mcx.ru (in Russian).Google Scholar
  43. 43.
    S. S. Bhattacharjee, T. E. Timell, Can. J. Chem., 1965, 43, 9.CrossRefGoogle Scholar
  44. 44.
    A. I. Butylkina, V. A. Levdanskii, B. N. Kuznetsov, Khim. Rast. Syr´ya [Chemistry of Plant Raw Materials], 2011, No. 2, 77 (in Russian).Google Scholar
  45. 45.
    RF Pat. 2364409; Byull. izobret., 2009, No. 23 (in Russian).Google Scholar
  46. 46.
    E. A. Rechkina, G. A. Gubanenko, L. P. Rubchevskaya, Khim. Rast. Syr´ya [Chemistry of Plant Raw Materials], 2010, No. 4, 189 (in Russian).Google Scholar
  47. 47.
    E. A. Rechkina, G. A. Gubanenko, L. P. Rubchevskaya, Sovr. Naukoem. Tekhnologii [Modern High Technologies], 2010, No. 1, 35 (in Russian).Google Scholar
  48. 48.
    R. G. Ovodova, E. A. Kushnikova, S. V. Popov, O. A. Bushneva, in Prolemy khimii drevesiny i lesokhimii [Problems of Wood and Forest Chemistry], Komi Science Center of the Ural Branch of the RAS, Syktyvkar, 1997, 15 (in Russian).Google Scholar
  49. 49.
    E. A. Robakidze, K. S. Bobkova, Russ. J. Plant Physiol. (Engl. Transl.), 2003, 50, 509 [Physiol. Rast., 2003, 50, 573].CrossRefGoogle Scholar
  50. 50.
    E. A. Robakidze, A. I. Patov, Russ. J. Plant Physiol. (Engl. Transl.), 2000, 47, 219 [Physiol. Rast., 2000, 47, 248].Google Scholar
  51. 51.
    E. N. Medvedeva, T. E. Fedorova, A. S. Vanina, A. V. Rokhin, L. A. Es´kova, V. A. Babkin, Khim. Rast. Syr´ya, [Chemistry of Plant Raw Materials], 2006, No. 1, 25 (in Russian).Google Scholar
  52. 52.
    S. Karacsonyi, V. Kovacik, J. Alföldi, M. Kubackova, Carbohydr. Res., 1984, 134, 265.CrossRefGoogle Scholar
  53. 53.
    P. Odonmazig, A. Ebringerová, E. Machová, J. Alföldi, Carbohydr. Res., 1994, 252, 317.CrossRefGoogle Scholar
  54. 54.
    I. M. Borisov, E. N. Shirokova, R. Kh. Mudarisova, R. R. Muslukhov, Yu. S. Zimin, S. A. Medvedeva, G. A. Tolstikov, Yu. B. Monakova, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 318 [Izv. Akad. Nauk, Ser. Khim., 2004, 305].CrossRefGoogle Scholar
  55. 55.
    M. M. Chochieva, I. P. Tsvetaeva, M. K. Yur´eva, A. F. Zaitseva, in Trudy Instituta lesa AN SSSR [Proceedings of the Forest Institute of the Academy of Sciences of USSR], vol. XLV, 1958, p. 31 (in Russian).Google Scholar
  56. 56.
    N. G. Moskovtsev, T. P. Belova, T. A. Valetov, Khim. Drevesiny [Wood Chemistry], 1988, No. 1, 112 (in Russian).Google Scholar
  57. 57.
    V. A. Babkin, L. A. Ostroukhova, N. N. Trofimova, Biomassa listvenitsy: ot khimicheskogo sostava do innovatsionnykh produktov [Larch Biomass: From Chemical Composition to Innovative Products], Ed. A. A. Semenov, SB RAS Publishing House, Novosibirsk, 2011, 236 pp. (in Russian).Google Scholar
  58. 58.
    E. N. Medvedeva, V. A. Babkin, O. A. Makarenko, S. M. Nikolaev, V. B. Khobrakova, A. M. Shulunova, T. E. Fedorova, L. A. Es´kova, Khim. Rast. Syr´ya [Chemistry of Plant Raw Materials] 2004, No. 4, 17 (in Russian).Google Scholar
  59. 59.
    T. L. Putoczki, F. Pettolino, M. D. W. Griffin, R. Möller, J. A. Gerrard, A. Bacic, S. L. Jackson, Planta, 2007, 226, 1131.CrossRefGoogle Scholar
  60. 60.
    F. Bertaud, B. Holmbom, Wood Sci. Technol., 2004, 38, 245.CrossRefGoogle Scholar
  61. 61.
    L. Leppänen, P. Spetz, A. Pranovich, K. Hartonen, V. Kitunen, H. Ilvesniemi, Wood Sci. Technol., 2010, 45, 223.CrossRefGoogle Scholar
  62. 62.
    R. Chandrasekaran, S. Janaswamy, Carbohydr. Res., 2002, 337, 2211.CrossRefGoogle Scholar
  63. 63.
    F. Orsa, B. Holmbom, J. Thornton, Wood Sci. Technol., 1997, 31, 279.CrossRefGoogle Scholar
  64. 64.
    J. Krogell, E. Korotkova, A. Pranovich, T. Salmi, D. Murzin, S. Willför, Bioresour. Technol., 2013, 143, 212.CrossRefGoogle Scholar
  65. 65.
    A. M. Stephen, in The Polysaccharides, Ed. G. O. Aspinall, Academic Press. Inc., New York, 1983, p. 122.Google Scholar
  66. 66.
    S. Willför, R. Sjoholm, C. Laine, B. Holmbom, Wood Sci. Technol., 2002, 36, 101.CrossRefGoogle Scholar
  67. 67.
    S. Willför, B. Holmbom, Wood Sci. Technol., 2004, 38, 173.CrossRefGoogle Scholar
  68. 68.
    T. E. Timell, Adv. Carbohydr. Chem., 1964, 19, 247.Google Scholar
  69. 69.
    T. E. Timell, Adv. Carbohydr. Chem., 1965, 20, 409.Google Scholar
  70. 70.
    T. E. Timell, Wood Sci. Technol., 1967, 1, 45.CrossRefGoogle Scholar
  71. 71.
    S. Haq, G. A. Adams, Can. J. Chem., 1961, 39, 1563.CrossRefGoogle Scholar
  72. 72.
    S. C. Churms, E. H. Merrifield, A. M. Stephen, Carbohydr. Res., 1978, 64, C1.CrossRefGoogle Scholar
  73. 73.
    T. E. Eremeeva, T. O. Bykova, Carbohydr. Polym., 1992, 18, 217.CrossRefGoogle Scholar
  74. 74.
    G. R. Ponder, Carbohydr. Polym., 1998, 36, 1.CrossRefGoogle Scholar
  75. 75.
    J. H. Prescott, E. V. Groman, G. Gulyas, Carbohydr. Res., 1997, 301, 89.CrossRefGoogle Scholar
  76. 76.
    H. Bouveng, B. Lindberg, Acta Chem. Scand., 1958, 12, 1977.CrossRefGoogle Scholar
  77. 77.
    I. Spiridon, V. I. Popa, in Monomers, Polymers and Composites from Renewable Resources, Eds M. N. Belgacem, A. Gandhini, Elsevier, Amsterdam, 2008, p. 289.Google Scholar
  78. 78.
    P. Mäki-Avella, T. Salmi, B. Holmbom, S. Willför, D. Y. Murzin, Chem. Rev., 2011, 111, 5638.CrossRefGoogle Scholar
  79. 79.
    B. P. da Silva, J. P. Parente, Planta Med., 2002, 68, 74.CrossRefGoogle Scholar
  80. 80.
    A. Clarke, R. Anderson, B. Stone, Phytochemistry, 1979, 18, 521.CrossRefGoogle Scholar
  81. 81.
    G. F. Antonova, N. A. Tyukavkina, Khim. Drevesiny, 1976, No. 4, 60 (in Russian).Google Scholar
  82. 82.
    G. F. Antonova, A. I. Usov, Bioorg. Khim., 1984, 10, 1664 [Sov. J. Bioorg. Chem. (Engl. Transl.), 1984, 10].Google Scholar
  83. 83.
    C. Laine, Doct. Dis., Helsinki University of Technology, 2005.Google Scholar
  84. 84.
    G. R. Ponder, G. N. Richards, Carbohydr. Polym., 1997, 34, 251.CrossRefGoogle Scholar
  85. 85.
    G. R. Ponder, G. N. Richards, J. Carbohydr. Chem., 1997, 16, 195.CrossRefGoogle Scholar
  86. 86.
    V. A. Babkin, L. A. Ostroukhova, Yu. A. Malkov, S. Z. Ivanova, N. A. Onuchina, D. V. Babkin, Khimiya v interesakh ustoich. razvitiya [Chem. Sustainable Dev.], 2001, 9, No. 3, 363 (in Russian).Google Scholar
  87. 87.
    G. R. Ponder, G. N. Richards, Carbohydr. Chem., 1997, 16, 181.CrossRefGoogle Scholar
  88. 88.
    I. M. Borisov, E. N. Shirokova, V. A. Babkin, G. A. Tolstikov, Yu. B. Monakov, Dokl. Chem. (Engl. Transl.), 2002, 383, 117 [Dokl. Akad. Nauk, 2002, 383, 774].Google Scholar
  89. 89.
    V. I. Dubrovina, S. A. Medvedeva, G. P. Aleksandrova, N. A. Tyukavkina, E. P. Golubinskii, T. A. Ivanova, Zh. A. Konovalova, Farmatsiya, 2001, No. 5, 26 (in Russian).Google Scholar
  90. 90.
    G. O. Aspinall, T. M. Wood, J. Chem. Soc., 1963, 1686.Google Scholar
  91. 91.
    Š. Karácsonyi, V. Kovácik, D. Kákoniová, Cell. Chem. Technol., 1996, 30, 359.Google Scholar
  92. 92.
    Š. Karácsonyi, V. Pätoprstý, M. Kubacková, Carbohydr. Res., 1998, 307, 271.CrossRefGoogle Scholar
  93. 93.
    E. M. Goellner, J. Utermoehlen, R. Kramer, B. Classen, Carbohydr. Polym., 2011, 86, 1739.CrossRefGoogle Scholar
  94. 94.
    G. A. Adams, Can. J. Chem., 1960, 38, 280.CrossRefGoogle Scholar
  95. 95.
    G. J. Seifert, K. Roberts, Annu. Rev. Plant Biology, 2007, 58, 137.CrossRefGoogle Scholar
  96. 96.
    C. M. Altaner, E. N. Tokareva, M. C. Jarvi, P. J. Harris, Physiology, 2010, 30, 782.Google Scholar
  97. 97.
    Pat. US 6406686; http://patft.uspto.gov/.Google Scholar
  98. 98.
    H. Yamada, H. Kiyohara, in Immunomodulatory Agents from Plants, Ed. H. Wagner, Birkhäuser, Basel, 1999, p. 161.Google Scholar
  99. 99.
    B. S. Paulsen, H. Barsett, Adv. Polym. Sci., 2005, 186, 69.CrossRefGoogle Scholar
  100. 100.
    Y. Kaneo, T. Ueno, H. Twase, Y. Yamaguchi, T. Uemura, Int. J. Pharm., 2000, 201, 59.CrossRefGoogle Scholar
  101. 101.
    M. Ellis, J. Egelund, C. J. Schultz, A. Bacic, Plant Physiol., 2010, 153, 403.CrossRefGoogle Scholar
  102. 102.
    L. Tan, A. M. Showalter, J. Egelund, A. HernandezSanchez, M. S. Doblin, A. Bacic, Front. Plant Sci., 2012, 3, Art. No. 140; doi: 10.3389/fpls.2012.00140.Google Scholar
  103. 103.
    Y. Gaspar, K. L. Johnson, J. A. McKenna, A. Bacic, C. J. Schultz, Plant Mol. Biol., 2001, 47, 161.CrossRefGoogle Scholar
  104. 104.
    T. Tryfona, H.-C. Liang, T. Kotake, S. Kaneko, J. Marsh, H. Ichinose, A. Lovegrove, Y. Tsumuraya, P. R. Shewry, E. Stephens, P. Dupree, Carbohydr. Res., 2010, 345, 2648.CrossRefGoogle Scholar
  105. 105.
    U. Egertsdotter, S. von Arnold, Physiol. Plant., 1995, 93, 334.CrossRefGoogle Scholar
  106. 106.
    J. Bobalek, M. Johnson, Photochem., 1983, 22, 1500.CrossRefGoogle Scholar
  107. 107.
    C. Loopstra, J. Puryear, Planta, 2000, 210, 686.CrossRefGoogle Scholar
  108. 108.
    C. Loopstra, V. R. Sedero, Plant Mol. Biol., 1995, 27, 277.CrossRefGoogle Scholar
  109. 109.
    S. Yang, H. Wang, S. Pratheesh, S. Claudio, C. Loopstra, Physiol. Plant., 2005, 124, 91.CrossRefGoogle Scholar
  110. 110.
    Y. Zhang, G. Brown, R. Whetton, C. A. Loopstra, D. Neale, M. J. Kieliszewski, R. R. Sederoff, Plant. Mol. Biol., 2003, 52, 91.CrossRefGoogle Scholar
  111. 111.
    Y. Akiyama, S. Eda, K. Kato, Agric. Biol. Chem., 1982, 46, 1395.CrossRefGoogle Scholar
  112. 112.
    Y. Tsumuraya, Y. Hashimoto, S. Yamamoto, N. Shibuya, Carbohydr. Res., 1984, 134, 215.CrossRefGoogle Scholar
  113. 113.
    J. Puhlmann, M. H. Zenk, H. Wagner, Phytochem., 1991, 30, 1141CrossRefGoogle Scholar
  114. 114.
    M. D. Serpe, E. A. Nothnagel, Plant Physiol., 1996, 112, 1261.Google Scholar
  115. 115.
    P. Komalavilas, J. Zhu, E. Nothnagel, J. Biol. Chem., 1991, 24, 15956.Google Scholar
  116. 116.
    A. Gane, D. Craik, S. Munro, G. Howlett, A. Clarke, A. Bacic, Carbohydr. Res., 1995, 277, 67.CrossRefGoogle Scholar
  117. 117.
    M. Kreuger, G. van Holst, Plant Mol. Biol., 1996, 30, 1077.CrossRefGoogle Scholar
  118. 118.
    A. Clarke, R. Anderson, B. Stone, Phytochem., 1979, 18, 521.CrossRefGoogle Scholar
  119. 119.
    S. Kuhnel, S. W. A. Hinz, L. Pouvreau, J. Wery, H. A. Schols, H. Gruppen, Bioresour. Technol., 2010, 101, 8300.CrossRefGoogle Scholar
  120. 120.
    F. M. Nunes, A. Reis, A. M. S. Silva, M. Rosario, M. Domingues, M. A. Coimbra, Phytochem., 2008, 69, 1573.CrossRefGoogle Scholar
  121. 121.
    Y. Westphal, S. Kühnel, P. de Waard, S. W. A. Hinz, H. A. Schols, A. G. J. Voragen, H. Gruppen, Carbohydr. Res., 2010, 345, 1180.CrossRefGoogle Scholar
  122. 122.
    A. Oosterveld, G. Beldman, H. A. Schols, A. G. J. Voragen, Carbohydr. Res., 2000, 328, 185.CrossRefGoogle Scholar
  123. 123.
    E. N. Makarova, O. A. Patova, E. G. Shakhmatov, S. P. Kuznetsov, Y. S. Ovodov, Carbohydr. Polym., 2013, 92, 1817.CrossRefGoogle Scholar
  124. 124.
    E. G. Shakhmatov, P. V. Toukach, E. A. Michailowa, E. N. Makarova, Carbohydr. Polym., 2014, 113, 515.CrossRefGoogle Scholar
  125. 125.
    RF Pat. 2448119; Byull. izobret., 2012, No. 11 (in Russian).Google Scholar
  126. 126.
    E. N. Makarova, O. A. Patova, E. A. Mikhailova, V. A. Demin, Khim. Rast. Syr´ya, 2011, No. 2, 35 (in Russian).Google Scholar
  127. 127.
    E. N. Makarova, E. G. Shakmatov, Russ. J. Bioorg. Chem. (Engl. Transl.), 2012, 38, 707 [Khim. Rast. Syr´ya, 2011, No. 3, 59].CrossRefGoogle Scholar
  128. 128.
    N. Khodaei, S. Karboune, Food Chem., 2013, 139, 617.CrossRefGoogle Scholar
  129. 129.
    A. Zykwinska, C. Rondeau-Mouro, C. Garnier, J. F. Thibault, M. C. Ralet, Carbohydr. Polym., 2006, 65, 510.CrossRefGoogle Scholar
  130. 130.
    E. G. Shakhmatov, E. V. Udoratina, K. V. Atukmaev, E. N. Makarova, Carbohydr. Polym., 2015, 123, 228.CrossRefGoogle Scholar
  131. 131.
    M. F. Basanta, M. F. de Escalada Plá, C. A. Stortz, A. M. Rojas, Carbohydr. Polym., 2013, 92, 830.CrossRefGoogle Scholar
  132. 132.
    B. M. Yapo, P. Lerouge, J. F. Thibault, M. C. Ralet, Carbohydr. Polym., 2007, 69, 426.CrossRefGoogle Scholar
  133. 133.
    N. K. Kochetkov, A. F. Bochkov, B. A. Dmitriev, A. I. Usov, O. S. Chizhov, V. N. Shibaev, Khimiya Uglevodov [Chemistry of Carbohydrates], Khimiya, Moscow, 1967, 672 pp. (in Russian).Google Scholar
  134. 134.
    Yu. S. Ovodov, Izbrannye glavy bioorganicheskoi khimii [Selected Topics in Bioorganic Chemistry], SSU, Syktyvkar, 1998, 222 pp. (in Russian).Google Scholar
  135. 135.
    P. J. H. Daas, K. Meyer-Hansen, H. A. Schols, G. A. de Ruiter, A. G. J. Voragen, Carbohydr. Res., 1999, 318, 135.CrossRefGoogle Scholar
  136. 136.
    A. G. J. Voragen, H. A. Schols, H. Gruppen, in Proc. Int. Symp. on Plant Polymeric Carbohydrates, Eds F. Meuser, D. J. Manners, W. Siebel, The Royal Society of Chemistry, Cambridge, 1993, p. 1.Google Scholar
  137. 137.
    P. Azadi, M. A. O´Neill, C. Bergmann, A. G. Darvill, P. Albersheim, Glycobiology, 1995, 5, 783.CrossRefGoogle Scholar
  138. 138.
    M. Mutter, C. M. G. C. Renard, G. Beldman, H. A. Schols, A. G. J. Voragen, Carbohydr. Res., 1998, 311, 155.CrossRefGoogle Scholar
  139. 139.
    E. N. Makarova, PhD Thesis (in Chem.), Institute of Chemistry of the Komi Science Center of the Ural Branch of the RAS, Syktyvkar, 2014, 145 pp. (in Russian).Google Scholar
  140. 140.
    S. M. Cardoso, J. A. Ferreira, I. Mafra, A. M. S. Silva, M. A. Coimbra, J. Agric. Food Chem., 2007, 55, 7124.CrossRefGoogle Scholar
  141. 141.
    M. A. Coimbra, S. M. Cardoso, J. A. Lopes-da-Silva, in Carbohydrates in Sustainable Development I, Sprinder, Berlin–Heidelberg, 2010, p. 129; doi: 10.1007/128_2010_60.Google Scholar
  142. 142.
    H. Kim, J. Ralph, Chemistry, 2010, 8, 576.Google Scholar
  143. 143.
    E. G. Shakmatov, E. N. Makarova, II All-Russian Conference “Fundamental Glycobiology” (July 7–11, 2014, Saratov), Book of Abstracts, Saratov, p. 92. (in Russian).Google Scholar
  144. 144.
    N. R. Swamy, P. V. Salimath, Phytochem., 1991, 30, 263.CrossRefGoogle Scholar
  145. 145.
    D. A. Navarro, A. S. Cerezo, C. A. Stortz, Carbohydr. Res., 2002, 337, 255.CrossRefGoogle Scholar
  146. 146.
    Y. Habibi, M. Mahrouz, M. R. Vignon, Carbohydr. Polym., 2005, 60, 319.CrossRefGoogle Scholar
  147. 147.
    S. Thude, B. Classen, Phytochem., 2005, 66, 1026.CrossRefGoogle Scholar
  148. 148.
    S. Mandal, S. Patra, B. Dey, S. K. Bhunia, K. K. Maity, S. S. Islam, Carbohydr. Polym., 2011, 84, 471.CrossRefGoogle Scholar
  149. 149.
    F. Dourado, S. M. Cardoso, A. M. S. Silva, F. M. Gama, M. A. Coimbra, Carbohydr. Polym., 2006, 66, 27.CrossRefGoogle Scholar
  150. 150.
    I. Simkovic, I. Uhliariková, M. P. Yadav, R. Mendichi, Carbohydr. Polym., 2010, 82, 815.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • E. N. Makarova
    • 1
  • E. G. Shakhmatov
    • 1
  • E. V. Udoratina
    • 1
  • A. V. Kutchin
    • 1
  1. 1.Institute of Chemistry, Komi Science CenterUral Branch of the Russian Academy of SciencesSyktyvkarRussian Federation

Personalised recommendations