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Lignin Modification Supported by DFT-Based Theoretical Study as a Way to Produce Competitive Natural Antioxidants.

ABSTRACT: The valorization of lignins as renewable aromatic feedstock is of utmost importance in terms of the use of sustainable resources. This study provides a deductive approach towards market-oriented lignin-derived antioxidants by ascertaining the direct effect of different structural features of lignin on the reactivity of its phenolic OH groups in the radical scavenging reactions. The antioxidant activity of a series of compounds, modeling lignin structural units, was experimentally characterized and rationalized, using thermodynamic descriptors. The calculated O-H bond dissociation enthalpies (BDE) of characteristic lignin subunits were used to predict the modification pathways of technical lignins. The last ones were isolated by soda delignification from different biomass sources and their oligomeric fractions were studied as a raw material for modification and production of optimized antioxidants. These were characterized in terms of chemical structure, molecular weight distribution, content of the functional groups, and the antioxidant activity. The developed approach for the targeted modification of lignins allowed the products competitive with two commercial synthetic phenolic antioxidants in both free radical scavenging and stabilization of thermooxidative destruction of polyurethane films.

SUBMITTER: Lauberte L

PROVIDER: S-EPMC6539611 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Lignin Modification Supported by DFT-Based Theoretical Study as a Way to Produce Competitive Natural Antioxidants.

Lauberte Liga L Fabre Gabin G Ponomarenko Jevgenija J Dizhbite Tatiana T Evtuguin Dmitry V DV Telysheva Galina G Trouillas Patrick P

Molecules (Basel, Switzerland) 20190509 9

The valorization of lignins as renewable aromatic feedstock is of utmost importance in terms of the use of sustainable resources. This study provides a deductive approach towards market-oriented lignin-derived antioxidants by ascertaining the direct effect of different structural features of lignin on the reactivity of its phenolic OH groups in the radical scavenging reactions. The antioxidant activity of a series of compounds, modeling lignin structural units, was experimentally characterized a ...[more]

PMID: 31075868

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Project description:BackgroundFungal pretreatment for partial separation of lignocellulosic components may reduce lignocellulose recalcitrance during the production of biofuels and biochemicals. Quantitative and qualitative modification of plant lignin through genetic engineering or traditional breeding may also reduce the recalcitrance. This study was conducted to examine the effects of combining these two approaches using three white rot fungi and mulberry wood with an altered lignin structure.ResultsMulberry wood prepared from homozygotes or heterozygotes with a loss-of-function in the cinnamyl alcohol dehydrogenase gene (CAD) was pretreated with three fungal species. Both heterozygous (CAD/cad) and homozygous (cad/cad, null mutant) mulberry plants were derived from the same parents via backcrossing between Sekizaisou (cad/cad, seed parent), a natural lignin mutant, and its F1 progeny (CAD/cad, pollen parent). Homozygote wood and the isolated lignin exhibited an abnormal color. Lignin in homozygotes without fungal pretreatment exhibited a lower syringyl/guaiacyl ratio, molar mass, and thioacidolysis product yield than those in heterozygotes. Pretreatment with Phanerochaete chrysosporium achieved the highest delignification efficiency with a significant reduction in the cellulose content in both mulberry genotypes. In contrast, Ceriporiopsis subvermispora selectively removed lignin, with a weaker reduction in the cellulose content. The degree of delignification by C. subvermispora was significantly higher in homozygotes than in heterozygotes. Trametes versicolor tended to have a lower delignification capacity and smaller effect of subsequent enzymatic sugar release toward the wood from both genotypes than the other two fungi, making it less suitable for fungal pretreatment. Thioacidolysis assays indicated that cinnamaldehyde β-O-4, a typical subunit in the homozygote lignin, did not contribute to the high degradability of the lignin. The saccharification efficiency tended to be higher in homozygote wood than in heterozygote wood under all fungal pretreatment conditions.ConclusionsAlthough further optimization of various system conditions is required, our findings suggest that CAD deficiency promotes delignification and subsequent enzymatic saccharification and may improve the biorefining efficiency of wood when combined with fungal pretreatment.

Dataset Information

Lignin Modification Supported by DFT-Based Theoretical Study as a Way to Produce Competitive Natural Antioxidants.

Publications

Lignin Modification Supported by DFT-Based Theoretical Study as a Way to Produce Competitive Natural Antioxidants.

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