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Lignin-derived Polyphenols with Enhanced Antioxidant Activities by Chemical Demethylation and Their Structure-Activity Relationship.

International Journal of Biological Macromolecules(2023)SCI 1区SCI 2区

Guangdong Acad Sci | 318 Chebeixi Rd

Cited 8|Views11
Abstract
Lignin valorization to biobased polyphenols antioxidants is increasingly attractive in the modern industry due to their inherent phenolic structures. Herein, lignin-derived polyphenols with enhanced antioxidant activities were prepared from the most available technical lignin including organosolv lignin (OL), alkali lignin (AL), and enzyme lignin (EL) by iodocyclohexane (ICH) chemical demethylation. The structural evolution of lignin indicated that the CAr-OCH3 group and the CAr-O-Calkyl side-chain could be effectively transformed into the CAr-OH group, resulting in a significant increase of the phenolic-OH content and a slight decrease of the molecular weight. The 1,1-diphenyl-2-picrylhydrazyl radical (DPPH·) scavenging activity was in the order of ICHOL-24 > ICHAL-24 > ICHEL-24 ≈ FA > BHT, and the IC50 value of ICHOL-24 was 0.56 times lower than that of BHT. The structure-activity relationship demonstrated the activities were quasi-linearly related to phenolic-OH contents and could be affected by molecular weights. The H/G/S proportions of lignin could be an indicator for accurate screening of efficient lignin-derived polyphenols antioxidants (LPA). It was preliminarily estimated to have economic feasibility for producing LPA from technical lignin by demethylation compared with synthetic or natural antioxidants. This work will help to develop efficient biobased antioxidants for lignin valorization.
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Technical lignin,Polyphenols antioxidants,Chemical demethylation
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要点】:该论文通过化学去甲基化过程,从技术性木质素中制备出具有增强抗氧化活性的源于木质素的多酚类物质,并研究了其结构-活性关系,创新点在于通过化学方法提升了木质素抗氧化剂的效率和活性。

方法】:采用碘代环己烷(ICH)化学去甲基化方法,从最常见的技术性木质素(有机溶剂木质素OL、碱木质素AL和酶木质素EL)中制备抗氧化性增强的木质素衍生物多酚。

实验】:通过1,1-二苯基-2-三硝基苯肼(DPPH·)自由基清除实验,对制备的化合物进行了评估,结果显示,通过ICH化学去甲基化得到的ICHL-24抗氧化活性最强,其IC50值比BHT低约56%,并且其活性与酚羟基含量近似线性相关,而分子重量则略有下降。通过H/G/S比例分析了木质素的特点,作为筛选高效木质素衍生物多酚抗氧化剂(LPA)的指标。研究初步表明,通过去甲基化方法从技术性木质素中生产LPA具有经济可行性,并有助于开发高效的生物基抗氧化剂,从而促进木质素的增值利用。