Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 60, Issue 23, Pages 5922-5935Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf301002n
Keywords
wheat straw; Py-GC/MS; TMAH; HSQC; DFRC; milled wood lignin; p-coumarate; ferulate; coniferyl acetate; tricin
Funding
- Spanish project [AGL2011-25379]
- CSIC [201040E075]
- EU [KBBE-244362]
- Fondo Social Europeo (FSE)
- Spanish Ministry of Science and Innovation
- DOE Great Lakes Bioenergy Research Center (DOE Office of Science BER) [DE-FC02-807ER64494]
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The structure of the lignin in wheat straw has been investigated by a combination of analytical pyrolysis, 2D-NMR, and derivatization followed by reductive cleavage (DFRC). It is a p-hydroxyphenyl-guaiacyl-syringyl lignin (with an H:G:S ratio of 6:64:30) associated with p-coumarates and ferulates. 2D-NMR indicated that the main substructures present are beta-O-4'-ethers (similar to 75%), followed by phenylcoumarans (similar to 11%), with lower amounts of other typical units. A major new finding is that the flavone tricin is apparently incorporated into the lignins. NMR and DFRC indicated that the lignin is partially acylated (similar to 10%) at the gamma-carbon, predominantly with acetates that preferentially acylate guaiacyl (12%) rather than syringyl (1%) units; in dicots, acetylation is predominantly on syringyl units. p-Coumarate esters were barely detectable (<1%) on monomer conjugates released by selectively cleaving beta-ethers in DFRC, indicating that they might be preferentially involved in condensed or terminal structures.
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