NMR structural characterization of quercus alba (White Oak) degraded by the brown rot fungus, laetiporus sulphureus

Journal of Wood Chemistry and Technology

Volumn 30, Issue 1, 2010, Pages 61-85

  Koenig, Amanda B ^a   Sleighter, Rachel L ^b   Salmon, Elodie ^b   Hatcher, Patrick G ^a,b  

^a OHIO STATE UNIVERSITY   (United States)

^b OLD DOMINION UNIVERSITY   (United States)

Author keywords

Cross polarization magic angle spinning; High resolution magic angle spinning; Lignin degradation; Lignin structure; Nuclear magnetic resonance

Indexed keywords

BROWN ROT; BROWN ROT FUNGI; CROSS POLARIZATION MAGIC-ANGLE SPINNINGS; DEUTERATED SOLVENTS; GROUND WOODS; HIGH RESOLUTION MAGIC ANGLE SPINNING; INFORMATION SUPPORT; LAETIPORUS SULPHUREUS; LIGNIN DEGRADATION; LIGNIN STRUCTURE; MODEL COMPOUND; MOLECULAR MOTIONS; NON-INVASIVE; QUERCUS; SIDE CHAINS; STRUCTURAL CHARACTERIZATION; WHITE OAK;

DEUTERIUM; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTODEGRADATION; POLARIZATION; RESONANCE;

LIGNIN;

DEGRADATION; LIGNINS; NUCLEAR MAGNETIC RESONANCE; POLARIZATION; RESONANCE;

EID: 77649153305     PISSN: 02773813     EISSN: 15322319     Source Type: Journal    
DOI: 10.1080/02773810903276668     Document Type: Article

References (48)

1. Monties, B.; Fukushima, K. Occurrence, function and biosynthesis of lignins. In Biopolymers, Volume 1: Lignin, Humic Substances and Coal; Hofrichter, M., Steinbüchel, A., Eds.; Wiley-VCH; Weinheim, 2001; 1-64.
2. Lai, Y.-Z.; Funaoka, M.; Chen, H.-T. Chemical heterogeneity in wood lignins. In Advances in Lignocellulosics Characterization; Argyropoulos, D.S., Ed.; Tappi Press; Atlanta, 1999; 43-53.
3. Stevenson, F.J. Humus Chemistry: Genesis, Composition, Reactions, 2nd Edition; John Wiley & Sons, Inc.: New York, NY, 1994; 188-211.
4. Ralph, J.; Marita, J.M.; Ralph, S.A.; Hatfield, R.D.; Lu, F.; Ede, R.M.; Peng, J.; Quideau, S.; Helm, R.F.; Grabber, J.H.; Kim, H.; Jimenez-Monteon, G.; Zhang, Y.; Jung, H.-J.G.; Landucci, L.L.; MacKay, J.J.; Sederoff, R.R.; Chapple, C.; Boudet, A.M. Solution-state NMR of lignins. In Advances in Lignocellulosics Characterization; Argyropoulos, D.S., Ed.; Tappi Press; Atlanta, 1999; 55-108.
5. Zhang, L.; Henriksson, G.; Gellerstedt, G. The formation of β-β structures in lignin biosynthesis - Are there two different pathways? Org. Biomol. Chem., 2003, 1 (20), 3621-3624.
6. Zhang, L.; Gellerstedt, G.; Ralph, J.; Lu, F. NMR studies on the occurrence of spirodienone structures in lignin. J. Wood Chem. Technol. 2006, 26 (1), 65-79.
7. Holtman, K.M.; Chang, H-M.; Kadla, J.F. An NMR comparison of the whole lignin from milled wood, MWL, and REL dissolved by the DMSO/NMI procedure. J. Wood Chem. Technol. 2007, 27 (3-4), 179-200.
8. 6. Bioener. Res. 2008, 1 (1), 56-66.
9. Yelle, D.J.; Ralph, J.; Frihart, C.R. Characterization of nonderivatized plant cell walls using high-resolution solution-state NMR spectroscopy. Magn. Reson. Chem. 2008, 46 (6), 508-517.
10. Capanema, E.A.; Balakshin, M.Y.; Kadla, J.F. Quantitative characterization of a hardwood milled wood lignin by nuclear magnetic resonance spectroscopy. J. Agr. Food Chem. 2005, 52 (25), 9639-9649.
11. Lundquist, K. Wood. In Methods in Lignin Chemistry; Lin, S.Y., Dence, C.W., Eds.; Springer-Verlag; Berlin, 1992; 65-70.
12. Adler, E. Lignin chemistry - Past, present, and future. Wood Sci. Technol. 1977, 11 (3), 169-218.
13. Hatcher, P.G.; Wilson, M.A.; Vassallo, A.M.; Lerch III, H.E. Studies of angiospermous wood in Australian brown coal by nuclear magnetic resonance and analytical pyrolysis: New insights into the early coalification process. Int. J. Coal Geol. 1989, 13 (1-4), 99-126.
14. Gil, A.M.; Neto, C.P. Solid-state NMR studies of wood and other lignocellulosic materials. Ann. R. NMR S. 1999, 37, 75-117.
15. Ralph, J.; Peng, J.; Lu, F. Isochroman structures in lignin: A new β-1 pathway. Tetrahedron Lett. 1998, 39 (28), 4963-4964.
16. 13C NMR characterization of guaiacyl, guaiacyl/syringyl, and syringyl dehydrogenation polymers. Holzforschung. 1998, 52 (2), 160-170.
17. Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F.; Kim, H.; Schatz, P.F.; Marita, J.M.; Hatfield, R.D.; Ralph, S.A.; Christensen, J.H.; Boerjan, W. Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids. Phytochemistry Rev. 2004a, 3 (1-2), 29-60.
18. 13C NMR. Holzforschung. 1980, 34 (6), 214-217.
19. Maciel, G.E.; O'Donnell, D.J.; Ackerman, J.J.H.; Hawkins, B.H.; Bartuska, V.J. A carbon-13 NMR study of four lignins in the solid and solution states. Makromol. Chem. 1981, 182 (8), 2297-2304.
20. Keifer, P.A.; Baltusis, L.; Rice, D.M.; Tymiak, A.A.; Shoolery, J.N. A comparison of NMR spectra obtained for solid-phase-synthesis resins using conventional high-resolution, magic-angle-spinning, and high-resolution magic-angle-spinning probes. J. Magn. Reson. Ser. A. 1996, 119 (1), 65-75.
21. Millis, K.K.; Maas, W.E.; Cory, D.G.; Singer, S. Gradient, high-resolution, magic-angle spinning nuclear magnetic resonance spectroscopy of human adipocyte tissue. Magnet. Reson. Med. 1997, 38 (3), 399-403.
22. Power, W.P. High resolution magic angle spinning - Applications to solid phase synthetic systems and other semi-solids. Ann. R. NMR S. 2003, 51, 261-295.
23. Simpson, A.J.; Zang, X.; Kramer, R.; Hatcher, P.G. New insights on the structure of algaenan from Botryoccocus braunii race A and its hexane insoluble botryals based on multidimensional NMR spectroscopy and electrospray-mass spectrometry techniques. Phytochemistry. 2003, 62 (5), 783-796.
24. Kelleher, B.P.; Simpson, M.J.; Simpson, A.J. Assessing the fate and transformation of plant residues in the terrestrial environment using HR-MAS NMR spectroscopy. Geochim. Cosmochim. Ac. 2006, 70 (16), 4080-4094.
25. Deshmukh, A.P.; Simpson, A.J.; Hatcher, P.G. Evidence for cross-linking in tomato cutin using HR-MAS NMR spectroscopy. Phytochemistry. 2003, 64 (6), 1163-1170.
26. Deshmukh, A.P.; Simpson, A.J.; Hadad, C.M.; Hatcher, P.G. Insights into the structure of cutin and cutan from Agave americana leaf cuticle using HRMAS NMR spectroscopy. Org. Geochem. 2005, 36 (7), 1072-1085.
27. Salmon, E.; Behar, F.; Lorant, F.; Hatcher, P.G.; Metzger, P.; Marquaire, P.-M. Thermal decomposition processes in algaenan of Botryococcus braunii race L. Part 1: Experimental data and structural evolution. Org. Geochem. 2009, 40 (3), 400-415.
28. Salmon, E.; Behar, F.; Lorant, F.; Hatcher, P.G.; Marquaire, P.-M. Early maturation processes in coal. Part 1: Pyrolysis mass balance and structural evolution of coalified wood from the Morwell Brown Coal seam. Org. Geochem. 2009, 40 (4), 500-509.
29. 13C nuclear magnetic resonance. Org. Geochem. 1987, 11 (1), 31-39.
30. 13C NMR studies of decomposed wood and coal-ified xylem tissue: evidence for chemical structural changes associated with defunctionalization of lignin structural units during coalification. Energ. Fuel. 1988, 2 (1), 48-58.
31. Blanchette, R.A.; Obst, J.R.; Timell, T.E. Biodegradation of compression wood and tension wood by white and brown rot fungi. Holzforschung. 1994, 48 (suppl), 34-42.
32. Dria, K.J.; Sachleben, J.R.; Hatcher, P.G. Solid-state carbon-13 nuclear magnetic resonance of humic acids at high magnetic field strengths. J. Environ. Qual. 2002, 31 (2), 393-401.
33. Ralph, S.A.; Ralph, J.; Landucci, L.L. NMR database of lignin and cell wall model compounds. 2004b, Available at http://ars.usda.gov/Services/docs.htm? docid=10491
34. Kishimoto, T.; Uraki, Y.; Ubukata, M. Synthesis of b-O-4-type artificial lignin polymers and their analysis by NMR spectroscopy. Org. Biomol. Chem. 2008, 6 (16), 2982-2987.
35. Brunow, G.; Ammalahti, E.; Niemi, T.; Sipila, J.; Simola, L.K.; Kilpelainen, I. Labeling of a lignin from suspension cultures of Picea abies. Phytochemistry 1998a, 47 (8), 1495-1500.
36. Boerjan, W.; Ralph, J.; Baucher, M. Lignin biosynthesis. Ann. Rev. Plant Biol. 2003, 54, 519-546.
37. Karhunen, P.; Rummakko, P.; Sipilä, J.; Brunow, G.: Dibenzodioxocins; a novel type of linkage in softwood lignins. Tetrahedron Lett. 1995a, 36 (1), 169-170.
38. Karhunen, P.; Rummakko, P.; Sipilä, J.; Brunow, G. The formation of dibenzodioxocin structures by oxidative coupling. A model reaction for lignin biosynthesis. Tetrahedron Lett. 1995b, 36 (25), 4501-4504.
39. Brunow, G.; Kilpeläinen, I.; Sipilä, J.; Syrjänen, K.; Karhunen, P.; Setälä, H.; Rummakko, P. Oxidative coupling of phenols and the biosynthesis of lignin. In Lignin and Lignan Biosynthesis; Lewis, N.G., Sarkanen, S., Eds.; ACS Symposium Series 697, American Chemical Society; Washington, D.C., 1998b; 131-147.
40. Peng, J.; Lu, F.; Ralph, J. Isochroman lignin trimers from DFRC-degraded Pinus taeda. Phytochemistry. 1999, 50 (4), 659-666.
41. Fagerstedt, K.V. The dibenzodioxocin lignin substructure is abundant in the inner part of the secondary wall in Norway spruce and silver birch xylem. Planta. 2004, 218 (3), 497-500.
42. Argyropoulos, D.S.; Jurasek, L.; Kristofova, L.; Xia, Z.; Sun, Y.; Palus, E. Abundance and reactivity of dibenzodioxocins in softwood lignin. J. Agr. Food Chem. 2002, 50 (4), 658-666.
43. Zhang, L.; Gellerstedt, G. NMR Observations of a new lignin structure, a spiro-dienone. Chem. Commun. 2001, (24), 2744-2745.
44. Filley, T.R.; Cody, G.D.; Goodell, B.; Jellison, J.; Noser, C.; Ostrofsky, A. Lignin demethylation and polysaccharide decomposition in spruce sapwood degraded by brown rot fungi. Org. Geochem. 2002, 33 (2), 111-124.
45. Martínez, A.T.; Almendros, G.; González-Vila, F.J.; Fründ, R. Solid-state spectroscopic analysis of lignins from several Austral hardwoods. Solid State Nucl. Mag. 1999, 15 (1), 41-48.
46. Bates, A.L.; Hatcher, P.G.; Lerch III, H.E.; Cecil, C.B.; Neuzil, S.G.; Supardi. Studies of a peatified angiosperm log cross section from Indonesia by nuclear magnetic resonance spectroscopy and analytical pyrolysis. Org. Geochem. 1991, 17 (1), 37-45.
47. 13C NMR of solid cellulose I. J. Am. Chem. Soc. 1980, 102 (9), 3251-3252.
48. Ralph, J.; Akiyama, T.; Kim, H.; Lu, F.; Schatz, P.F.; Marita, J.M.; Ralph, S.A.; Reddy, M.S.S.; Chen, F.; Dixon, R.A. Effects of coumarate 3-hydroxylase down-regulation on lignin structure. J. Biol. Chem. 2006, 281 (13), 8843-8853.