Journal of Wood Science

, Volume 50, Issue 2, pp 141–150 | Cite as

Isolation of lignin–carbohydrate bonds in wood. Model experiments and preliminary application to pine wood

  • Olov Karlsson
  • Tsutomu Ikeda
  • Takao Kishimoto
  • Kengo Magara
  • Yuji Matsumoto
  • Shuji Hosoya
ORIGINAL ARTICLE

Abstract

A novel method for analysis of benzylic ether type lignin–carbohydrate bonds has been developed by using model compounds. Four diastereomers of model compound 3-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-3-(methyl β-d-glucopyranoside-6-O-yl)-1-propanol (GGMGP), were ozonized in acetic acid/water/methanol 16 : 3 : 1 for 1 h at 0°C. The product from ozonation of each diastereomer was saponified and the corresponding α-etherified tetronic acid (TAMGP) was isolated using ion exchange chromatography. Minor amounts of methyl β-d-glucopyranoside (MGP) and small amounts of a gluconic acid etherified with tetronic acid (TAGLCA), tetronic acid, gluconic acid, and glyceric acid were detected in the product mixture of ozonated benzylic ether type model compounds. The results suggest that a benzyl ether bond between lignin and carbohydrate is rather stable during the ozone treatment. Acid treatments with sulfuric acid or trifluoroacetic acid of the derived TAMGP led to cleavage of the glucosidic bond but only a small amount of products (tetronic acid and glucose) resulting from cleavage of the α-ether bond were formed. The successful chemical treatments were used for studies of benzylic ether bonds in Japanese red pine. The results suggest the presence of benzylic ether bonds to polysaccharides in the wood.

Key words

Ozone Lignin–carbohydrate bond LCC model compound Benzylic ether Threonic/erythronic acid 

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Copyright information

© Springer-Verlag Tokyo 2004

Authors and Affiliations

  • Olov Karlsson
    • 1
  • Tsutomu Ikeda
    • 1
  • Takao Kishimoto
    • 1
  • Kengo Magara
    • 1
  • Yuji Matsumoto
    • 3
  • Shuji Hosoya
    • 1
    • 2
  1. 1.Wood Chemistry Laboratory, Department of Chemical UtilizationForestry and Forest Products Research InstituteIbarakiJapan
  2. 2.Institute of Agricultural and Forest EngineeringUniversity of TsukubaIbarakiJapan
  3. 3.Laboratory of Wood Chemistry, Department of Biomaterial Sciences, Graduate School of Agricultural and Life SciencesThe University of TokyoTokyoJapan

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