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Structural conversion of the lignin subunit at the cinnamyl alcohol stage in Eucalyptus camaldulensis
Journal of Wood Science volume 45, pages 487–491 (1999)
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
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
Ye Z, Kneusel RE, Matern U, Varner JE (1994) An alternative methylation pathway in lignin biosynthesis in Zinnia. Plant Cell 6:1427–1439
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
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
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
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
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
Whetten R, Sederoff R (1995) Lignin biosynthesis. Plant Cell 7:1001–1013
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
Marcinowski S, Grisebach H (1977) Turnover of coniferin in pine seedlings. Phytochemistry 16:1665–1667
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
Fukushima K, Taguchi S, Matsui N, Yasuda S (1997) Distribution and seasonal changes of monolignol glucosides in Pinus thunbergii. Mokuzai Gakkaishi 43:254–259
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
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
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
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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
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DOI: https://doi.org/10.1007/BF00538958