Skip to main content

Official Journal of the Japan Wood Research Society

Journal of Wood Science Cover Image

Structural conversion of the lignin subunit at the cinnamyl alcohol stage in Eucalyptus camaldulensis

Abstract

The lignin biosynthetic pathway in Eucalyptus camaldulensis was investigated by feeding stems with deuterium-labeled precursor. Pentadeutero[γ,γ-D2 OCD3] coniferyl alcohol was synthesized and supplied to shoots of E. camaldulensis, and incorporation of the labeled precursor into lignin was traced by gas chromatography-mass spectrometry. In addition to the direct incorporation of labeled precursor into the guaiacyl unit, a pentadeuterium-labeled syringyl unit was detected. This finding indicates that the γ-deuterium atoms in the hydroxymethyl group of labeled coniferyl alcohol remain intact during modification of the aromatic ring. The relative level of trideuterium-labeled syringyl monomer (the result of conversion via the cinnamic acid pathway) was negligible, suggesting that the pathway at the monolignol stage is used for conversion of exogenously supplied precursor. Our results provide conclusive evidence of a novel alternative pathway for generation of lignin subunits at the monolignol stage even in plants that do not accumulate coniferin in lignifying tissues.

References

  1. 1.

    Higuchi T (1996) Biosynthesis of wood components. In: Timell TE (ed) Biochemistry and molecular biology of wood. Springer, Berlin Heidelberg New York, pp 156–168

    Google Scholar 

  2. 2.

    Ye Z, Kneusel RE, Matern U, Varner JE (1994) An alternative methylation pathway in lignin biosynthesis in Zinnia. Plant Cell 6:1427–1439

    CAS  Article  Google Scholar 

  3. 3.

    Li L, Popko JL, Zhang X, Osakabe K, Tsai CJ, Joshi CP, Chiang VL (1997) A novel multifunctional O-methyltransferase implicated in a dual methylation pathway associated with lignin biosynthesis in loblolly pine. Proc Natl Acad Sci USA 94:5461–5466

    CAS  Article  Google Scholar 

  4. 4.

    Matsui N, Fukushima K, Kamada K, Nishihawa Y, Yasuda S, Terashima N (1994) On the behavior of monolignol glucosides in lignin biosynthesis. I. Synthesis of monolignol glucosides labeled with 2H at the hydroxymethyl group of side chain, and polymerization of the labeled monolignols in vitro. Holzforschung 48:215–221

    CAS  Article  Google Scholar 

  5. 5.

    Matsui N, Fukushima K, Yasuda S, Terashima N (1994) On the behavior of monolignol glucosides in lignin biosynthesis. II. Synthesis of monolignol glucosides labeled with 3H at the hydroxymethyl group of side chain, and incorporation of the label into magnolia and ginkgo lignin. Holzforschung 48:375–380

    CAS  Article  Google Scholar 

  6. 6.

    Matsui N, Fukushima K, Yasuda S, Terashima N (1996) On the behavior of monolignol glucosides in lignin biosynthesis. III. Synthesis of variously labeled coniferin and incorporation of the label into syringin in the shoot of Magnolia kobus. Holzforschung 50:408–412

    CAS  Article  Google Scholar 

  7. 7.

    Chen F, Yasuda S, Fukushima K (1999) Evidence for a novel biosynthesis pathway that regulates the ratio of syringyl to guaiacyl residues in lignin in the differentiating xylem of Magnolia kobus DC. Planta 207:597–603

    CAS  Article  Google Scholar 

  8. 8.

    Whetten R, Sederoff R (1995) Lignin biosynthesis. Plant Cell 7:1001–1013

    CAS  Article  Google Scholar 

  9. 9.

    Terazawa M, Miyake M (1984) Phenolic compounds in living tissue of woods. II. Seasonal variation of phenolic glycosides in the cambial sap of woods. Mokuzai Gakkaishi 30:329–334

    CAS  Google Scholar 

  10. 10.

    Marcinowski S, Grisebach H (1977) Turnover of coniferin in pine seedlings. Phytochemistry 16:1665–1667

    CAS  Article  Google Scholar 

  11. 11.

    Umezawa T, Davin LB, Lewis NG (1991) Formation of lignans (—)-secoisolariciresinol and (—)-matairesinol with Forsythia intermedia cell-free extracts. J Biol Chem 266:10210–10217

    CAS  PubMed  Google Scholar 

  12. 12.

    Fukushima K, Taguchi S, Matsui N, Yasuda S (1997) Distribution and seasonal changes of monolignol glucosides in Pinus thunbergii. Mokuzai Gakkaishi 43:254–259

    CAS  Google Scholar 

  13. 13.

    Lu F, Ralph J (1997) Derivatization followed by reductive cleavage (DFRC method), a new method for lignin analysis: protocol for analysis of DFRC monomers. J Agric Food Chem 45:2590–2592

    CAS  Article  Google Scholar 

  14. 14.

    Fukushima K, Taguchi S, Matsui N, Yasuda S (1996) Heterogeneous distribution of monolignol glucosides in the stems of Magnolia kobus. Mokuzai Gakkaishi 42:1029–1031

    CAS  Google Scholar 

  15. 15.

    Matsui N, Fukushima K, Yasuda S, Terashia N (1997) On the behavior of monolignol glucosides in lignin biosynthesis. IV. Incorporation of the aglycons of 4-β-d-glucosides of caffeyl alcohol and 5-hydroxyconiferyl alcohol into shoots of Magnolia kobus. Mokuzai Gakkaishi 43:663–668

    CAS  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Kazuhiko Fukushima.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Chen, F., Yasuda, S. & Fukushima, K. Structural conversion of the lignin subunit at the cinnamyl alcohol stage in Eucalyptus camaldulensis . J Wood Sci 45, 487–491 (1999). https://doi.org/10.1007/BF00538958

Download citation

Key words

  • Biosynthetic pathway
  • Coniferyl alcohol
  • Eucalyptus camaldulensis
  • Lignin
  • Sinapyl alcohol