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Isolation and structural characterization of the milled wood lignin, dioxane lignin, and cellulolytic lignin preparations from brewer´s spent grain

AuthorsRencoret, Jorge ; Prinsen, Pepijn ; Gutiérrez Suárez, Ana ; Martínez, Ángel T. ; Río Andrade, José Carlos del
Keywordsbrewer’s spent grain
Issue Date2015
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 63: 603−613 (2015)
AbstractThe structure of the lignin from brewer’s spent grain (BSG) has been studied in detail. Three different lignin preparations, the so-called “milled-wood” lignin (MWL), dioxane lignin (DL), and cellulolytic lignin (CEL), were isolated from BSG and then thoroughly characterized by pyrolysis GC/MS, 2D-NMR, and derivatization followed by reductive cleavage (DFRC). The data indicated that BSG lignin presents a predominance of guaiacyl units (syringyl/guaiacyl ratio of 0.4−0.5) with significant amounts of associated p-coumarates and ferulates. The flavone tricin was also present in the lignin from BSG, as also occurred in other grasses. 2D-NMR (HSQC) revealed that the main substructures present are β-O-4′ alkyl-aryl ethers (77−79%) followed by β-5′ phenylcoumarans (11−13%) and lower amounts of β-β′ resinols (5−6%) and 5-5′ dibenzodioxocins (3−5%). The results from 2D-NMR (HMBC) and DFRC indicated that p-coumarates are acylating the γ-carbon of lignin side chains and are mostly involved in condensed structures. DFRC analyses also indicated a minor degree of γ-acylation with acetate groups, which takes place preferentially on S lignin (6% of S units are acetylated) over G lignin (only 1% of G units are acetylated).
Publisher version (URL)http://pubs.acs.org/doi/abs/10.1021/jf505808c
DOIDOI: 10.1021/jf505808c
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