NMR studies on the occurrence of spirodienone structures in lignins

Journal of Wood Chemistry and Technology

Volumn 26, Issue 1, 2006, Pages 65-79

  Zhang, Liming ^a   Gellerstedt, Göran ^a   Ralph, John ^b   Lu, Fachuang ^b  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b U S DAIRY FORAGE RESEARCH CENTER   (United States)

Author keywords

1 structure; Birch; Kenaf; Lignins; NMR analysis; Spirodienone structure; Spruce

Indexed keywords

HARDWOODS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOFTWOODS; STRUCTURE (COMPOSITION);

GUAIACYL TYPE; LIGNIN ISOLATES; PHENYLPROPANOID; SPIRODIENONE STRUCTURES; STEREOISOMERIC FORMS; SYRINGYL SPIRODIENONES;

LIGNIN;

BETULA; ISOMERS; KENAF; LIGNINS; NUCLEAR MAGNETIC RESONANCE; PICEA; STEREOCHEMISTRY; WOOD STRUCTURE;

EID: 33646355474     PISSN: 02773813     EISSN: 15322319     Source Type: Journal    
DOI: 10.1080/02773810600580271     Document Type: Article

References (28)

1. Nimz, V. (1965) Mild hydrolysis of beech lignin. I. Isolation of dimethylpyrogallylglyceol Chem. Ber., 98(10), pp. 3153-3159.
2. Nimz, V. (1966) Lignin degradation by mild hydrolysis Holzforschung, 20(4), pp. 105-109.
3. Lundquist, K. and Miksche, G. (1965) A new linkage principle for guaiacylpropane units in spruce lignin Tetrahedron Lett., pp. 2131-2136.
4. Lapierre, C. and Pollet, B. and Monties, B. and Rolando, C. (1991) Thioacidolysis of spruce lignin: GC-MS analysis of the main dimers recovered after Raney nickel desulphuration Holzforschung, 45(1), pp. 61-68.
5. Peng, J. and Lu, F. and Ralph, J. (1998) The DFRC method for lignin analysis. 4. Lignin dimers isolated from DFRC-degraded Loblolly pine wood J. Agric. Food Chem., 46(2), pp. 553-560.
6. Lundquist, K. (1987) On the occurrence of β-1 structures in lignins J. Wood Chem. Technol., 7(2), pp. 179-185.
7. Kilpeläinen, I. and Sipilä, J. and Brunow, G. and Lundquist, K. and Ede, R. (1994) Application of two-dimensional NMR spectroscopy to wood lignin structure determination and identification of some minor structural units of hard- and softwood lignins J. Agric. Food Chem., 42(12), pp. 2790-2794.
8. Brunow, G. and Ämmälahti, E. and Niemi, T. and Sipilä, J. and Simola, L. and Ilkka, K. (1998) Labeling of a lignin from suspension cultures of Picea abies Phytochem., 47(8), pp. 1495-1500.
9. Freudenberg, K. and Lehmann, B. (1963) Radioactive isotopes and lignin. X. Investigation of a lignin preparation labeled with C14 Chem. Ber., 96(7), pp. 1850-1854.
10. Freudenberg, K.(1968) The constitution and biosynthesis of lignin. In Constitution and Biosynthesis of Lignin. (pp. 100-101). Berlin: Springer-Verlag.
11. Habu, N. and Matsumoto, Y. and Ishizu, A. and Nakano, J. (1990) The role of the diarylpropane structure as a minor constituent in spruce lignin Holzforschung, 44, pp. 67-71.
12. Lundquist, K. and Miksche, G. and Ericsson, L. and Berndtson, L. (1967) Presence of glyceraldehyde-2-aryl ether structures in lignin Tetrahedron Lett., pp. 4587-4591.
13. Brunow, G. and Lundquist, K. (1991) On the acid-catalyzed alkylation of lignins Holzforshung, 45(1), pp. 37-40.
14. Gellerstedt, G. and Zhang, L. (1991) Reactive lignin structures in high yield pulping. Part 1. Structures of the 1,2-diarylpropane-1,3-diol type Nordic Pulp Pap. Res. J., 3(6), pp. 136-139.
15. Peng, J. and Lu, F. and Ralph, J. (1999) The DFRC method for lignin analysis. Part 5. Isochroman lignin trimers from DFRC-degraded Pinus taeda Phytochem., 50(4), pp. 659-666.
16. Yoshikawa, K. and Kinoshita, H. and Arihara, S. (1997) Woorenol, a novel sesquineolignan with a unique spiro skeleton, from the rhizomes of Coptis japonica var. dissecta J. Nat. Prod., 60(5), pp. 511-513.
17. Setälä, H. and Pajunen, A. and Rummakko, P. and Sipilä, J. and Brunow, G. (1999) A novel type of spiro compound formed by oxidative cross coupling of methyl sinapate with a syringyl lignin model compound. A model system for the β-1 pathway in lignin biosynthesis J. Chem. Soc., Perkin Trans. 1, 4, pp. 461-464.
18. Ämmälahti, E. and Brunow, G. and Bardet, M. and Robert, D. and Kilpeläinen, I. (1998) Identification of side-chain structures in a poplar lignin using three-dimensional HMQC-HOHAHA NMR spectroscopy J. Agric. Food Chem., 46(12), pp. 5113-5117.
19. Zhang, L. and Gellerstedt, G. (2001) NMR observation of a new lignin structure, a spiro-dienone Chem. Commun., pp. 2744-2745.
20. Björkman, A. (1956) Studies on finely devided wood. Part 1. Extraction of lignin with neutral solvents Svensk Papperstidn., 59, pp. 477-485.
21. Ralph, J. (1996) An unsual lignin from kenaf J. Nat. Prod., 59, pp. 341-342.
22. 1H) NMR spectroscopy. In Methods in Lignin Chemistry. (pp. 242-249). Heidelberg: Springer-Verlag.
23. Robert, D. and Chen, C.-L. (1989) Biodegradation of lignin in spruce wood by Phanerochaete chrysosporium: Quantitative analysis of biodegraded spruce lignins by carbon-13 NMR spectroscopy Holzforschung, 43(5), pp. 323-332.
24. 13C spectra using DEPT and quaternary-only sequence J. Magn. Reson., 53, pp. 272-296.
25. Ralph, J. and Marita, J. and Ralph, S. and Hatfield, R. and Lu, F. and Ede, R. and Peng, J. and Quideau, S. and Helm, R. and Grabber, J. and Kim, H. and Jimenez-Monteon, G. and Zhang, Y. and Jung, H. and Landucci, L. and MacKay, J. and Sederoff, R. and Chapple, C. and Boudet, A.(1999) Solution-state NMR of lignins. In Adv. Lignocellul. Charact.. (pp. 55-108). Atlanta GA: Tappi Press.
26. 13C and HSQC NMR techniques. In 6th Eur. Workshop Lignocellul. Pulp. (pp. 7-10). Bordeaux
27. Lu, F. and Ralph, J. (2003) Non-degradative dissolution and acetylation of ball-milled plant cell walls: High-resolution solution-state NMR Plant J., 35(4), pp. 535-544.
28. Gellersrtedt, G. and Zhang, L. (1992) Reactive lignin structures in high yield pulping. Part 2. Monomeric end groups and detached side chain structures Nordic Pulp Pap. Res. J., 7(2), pp. 75-80.