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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Structural unit of xylans from sugi (Cryptomeria japonica) and hinoki (Chamaecyparis obtusa)

Journal of Wood Science volume 57, pages 76–84 (2011)Cite this article

Abstract

Arabinoglucuronoxylans (AGXs) isolated from the holocellulose of sugi (Cryptomeria japonica) and hinoki (Chamaecyparis obtusa) contained one 4-O-methyl-d-glucopyranosyluronic acid (4-O-Me-d-GlcAp) residue per 6.2 d-xylopyranose (d-Xylp) residues and one 4-O-Me-d-GlcAp residue per 3.8 d-Xylp residues. These AGXs were subjected to partial acid hydrolysis. Analyses by size exclusion chromatography and electrospray-ionization mass spectroscopy of the neutral sugar fractions in the hydrolysates showed the presence of xylooligosaccharides having a degree of polymerization of 2-8 in addition to d-Xyl, suggesting that the AGXs from sugi and hinoki contained unsubstituted chains consisting of at least eight d-Xyl residues. The acidic sugars in the hydrolysates were separated into two series of aldouronic acids composed of 4-O-Me-d-GlcAp and d-Xylp by ion-exchange chromatography. The first series included aldouronic acids from aldobiouronic acid (4-O-Me-d-GlcAp-Xyl) to aldopentaouronic acids (4-O-Me-d-GlcAp-Xyl4). The second series were aldouronic acids composed of two 4-O-Me-d-GlcAp residues and 2-4 d-Xyl residues. In these acidic sugars, the uronic acid side chains were located on two contiguous d-Xyl residues. These facts indicated that AGXs from sugi and hinoki had a structural unit containing two 4-O-Me-d-GlcAp residues on two contiguous d-Xyl residues as well as AGXs from spruce and larch.

References

  1. Shimizu K (1991) Chemistry of hemicellulose. In: Hon DN-S, Shiraishi N (eds) Wood and cellulosic chemistry. Marcel Dekker, New York, pp 177–214

    Google Scholar 

  2. Ebringerová A, Hromádková Z, Heinze T (2005) Hemicellulose. Adv Polym Sci 186:1–67

    Article  Google Scholar 

  3. Comtat J, Joseleau J-P (1981) Mode of action of a xylanase and its significance for the structural investigation of the branched l-arabino-d-glucurono-d-xylan from redwood (Sequoia sempervirens). Carbohydr Res 95:101–112

    Article  CAS  Google Scholar 

  4. Debeire P, Priem B, Strecker G, Vignon M (1990) Purification and properties of an endo-1,4-xylanase excreted by a hydrolytic thermophilic anaerobe, Clostridium thermolacticum. A proposal for its action mechanism on larch wood 4-O-methylglucuronoxylan. Eur J Biochem 187:573–580

    Article  CAS  PubMed  Google Scholar 

  5. Jacobs A, Larsson PT, Dahlman O (2001) Distribution of uronic acids in xylans from various species of soft- and hardwood as determined by MALDI mass spectrometry. Biomacromolecules 2:979–990

    Article  CAS  PubMed  Google Scholar 

  6. Shimizu K, Samuelson O (1973) An examination of hemicellulose precipitated from spruce neutral sulphite liquor. Svensk Papperstidning 76:156–162

    CAS  Google Scholar 

  7. Shimizu K, Hashi M, Sakurai K (1978) Isolation from a softwood xylan of oligosaccharides containing two 4-O-methyl-d-glucuronic acid residues. Carbohydr Res 62:117–126

    Article  CAS  Google Scholar 

  8. Nakamura A, Hatanaka C, Nagamatsu Y (2000) Ultraviolet spectrometric determination of neutral monosaccharides by HPLC with ethanolamine. Biosci Biotechnol Biochem 64(1):178–180

    Article  Google Scholar 

  9. Japan Wood Research Society (1985) Experimental note of wood science II. Chemistry version (in Japanese). Japan Wood Research Society, Tokyo

    Google Scholar 

  10. Hashi M, Teratani F, Miyazaki K (1970) Studies on hemicellulose. 2. Purification of galactoglucomannan of Japanese larch (Larix leptolepis Gord). Mokuzai Gakkaishi 16:37–41

    CAS  Google Scholar 

  11. Brink DL, Pohlman AA (1972) Wood and pulp analysis by fractionation into component polysaccharides. Tappi 55:380–388

    CAS  Google Scholar 

  12. Clayton DW (1963) The alkaline degradation of some hardwood 4-O-methyl-d-glucuronoxylans. Svensk Papperstidning 66:115–124

    CAS  Google Scholar 

  13. Bryanat RW, Timell TE, Zimbo M, Goring DAI, Yean WQ (1968) The polymolecularity of an aspen xylan. Cellul Chem Technol 2:269–277

    Google Scholar 

  14. Samuelson O (1963) Ion exchange separations in analytical chemistry. Wiley, New York, pp 125–129

    Google Scholar 

  15. Fengel D, Przyklenk M (1975) Studies on the supermolecular structure of cell wall components. Part 3. Fractionation of alkali extract from spruce holocellulose by ion exchange chromatography: Method and first results. Svensk Papperstiding 78:17–21

    CAS  Google Scholar 

  16. Fengel D, Przyklenk M (1975) Studies on the supermolecular structure of cell wall components. Part 4. Composition of the fractions from ion exchange chromatography. Svensk Papperstiding 78:617–620

    CAS  Google Scholar 

  17. Komiyama H, Enomoto A, Sueyoshi Y, Nishio T, Kato A, Ishii T, Shimizu K (2009) Structures of aldouronic acids liberated from kenaf xylan by endoxylanases from Streptomyces sp. Carbohydr Polym 75:521–527

    Article  CAS  Google Scholar 

  18. Shimizu K, Ishihara M, Ishihara T (1976) Hemicellulases of brown rotting fungus, Tyromyces palustris. 2. The oligosaccharides from the hydrolysate of a hardwood xylan by the intracellular xylanases. Mokuzai Gakkaishi 22:618–625

    CAS  Google Scholar 

  19. Komiyama H, Kato A, Aimi H, Ogihara J, Shimizu K (2008) Chemical structure of kenaf xylan. Carbohydr Polym 72:638–645

    Article  CAS  Google Scholar 

  20. Excoffier G, Nardin R, Vignon MR (1986) Détermination de la structure primaire un acide tri-d-xylo-4-O-méthyl-d-glucuronique par R. M. N., à deux dimensions. Carbohydr Res 149:319–328

    Article  Google Scholar 

  21. Cavagna F, Degar H, Puls J (1984) 2D-NMR analysis of the structure of an aldotriouronic acid obtained from birch wood. Carbohydr Res 129:1–8

    Article  CAS  Google Scholar 

  22. Shimizu K, Samuelson O (1973) Uronic acids in birch hemicellulose. Svensk Papperstidning 76:150–155

    CAS  Google Scholar 

  23. Ahlgren PA, Goring DAI (1971) Removal of wood components during chlorite delignification of black spruce. Can J Chem 49:1272–1275

    Article  CAS  Google Scholar 

  24. Andersson SI, Samuelson O, Ishihara M, Shimizu K (1983) Structure of the reducing end-groups in spruce xylan. Carbohydr Res 111:283–288

    Article  CAS  Google Scholar 

  25. Togashi H, Kato A, Shimizu K (2009) Enzymatically derived aldouronic acids from Eucalyptus globulus glucuronoxylan. Carbohydr Polym 78:247–252

    Article  CAS  Google Scholar 

  26. Roy N, Timell TE (1968) The acid hydrolysis of glycosides. X. Hydrolysis of 2-O-(4-O-methyl-α-d-glucopyranosyluronic acid)-d-xylose and related disaccharides. Carbohydr Res 6:488–490

    Article  CAS  Google Scholar 

  27. Ishii T, Konishi T, Yamasaki T, Enomoto A, Yoshida M, Maeda I, Shimizu K (2010) NMR characterization of acidic xylo-oligosaccharides containing two methyl glucuronic acid residues from Japanese cedar and hinoki cypress. Carbohydr Polym 81:964–968

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Graduate School of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa, 252-8510, Japan

    Takashi Yamasaki, Ayumi Enomoto & Kazumasa Shimizu

  2. Department of Biomass Chemistry, Forestry and Forest Products Research Institute, Tsukuba, 305-8685, Japan

    Atsushi Kato & Tadashi Ishii

Authors
  1. Takashi Yamasaki
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  2. Ayumi Enomoto
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  3. Atsushi Kato
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  4. Tadashi Ishii
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  5. Kazumasa Shimizu
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Correspondence to Kazumasa Shimizu.

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Yamasaki, T., Enomoto, A., Kato, A. et al. Structural unit of xylans from sugi (Cryptomeria japonica) and hinoki (Chamaecyparis obtusa). J Wood Sci 57, 76–84 (2011). https://doi.org/10.1007/s10086-010-1139-9

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  • DOI: https://doi.org/10.1007/s10086-010-1139-9

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