A study of the interaction between cell membranes and small molecules derived from lignin, a protective phenolic biopolymer found in vascular plants, is crucial for identifying their potential as pharmacological and toxicological agents. In this work, the interactions of model cell membranes [supported 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) lipid bilayers] are compared for three βO4 dimers of coniferyl alcohol (G lignin monomer): guaiacylglycerol guaiacol ester with a hydroxypropenyl (HOC₃H₄-) tail (G-βO4′-G), a truncated GG dimer without HOC₃H₄- (G-βO4′-truncG), and a benzylated GG dimer (benzG-βO4′-G). The uptake of the lignin dimers (per mass of lipid) and the energy dissipation (a measure of bilayer disorder) are higher for benzG-βO4′-G and G-βO4′-truncG than those for G-βO4′-G in the gel-phase DPPC bilayer, as measured using quartz crystal microbalance with dissipation (QCM-D). A similar uptake of G-βO4′-truncG is observed for a fluid-phase bilayer of 1,2-dioleoyl-sn-glycero-3-phosphocholine, suggesting that the effect of the bilayer phase on dimer uptake is minimal. The effects of increasing lignin dimer concentration are examined through an analysis of density profiles, potential of mean force curves, lipid order parameters, and bilayer area compressibilities (disorder) in the lipid bilayers obtained from molecular dynamics simulations. Dimer distributions and potentials of mean force indicate that the penetration into bilayers is higher for benzG-βO4′-G and G-βO4′-truncG than that for G-βO4′-G, consistent with the QCM-D results. Increased lipid tail disorder due to dimer penetration leads to a thinning and softening of the bilayers. Minor differences in the structure of lignin derivatives (such as truncating the hydroxypropenyl tail) have significant impacts on their ability to penetrate lipid bilayers.

中文翻译：

---

木质素二聚体与模型细胞膜的相互作用：石英晶体微天平和分子动力学模拟研究

研究细胞膜与源自木质素的小分子之间的相互作用，木质素是维管植物中发现的一种保护性酚类生物聚合物，对于确定它们作为药理学和毒理学试剂的潜力至关重要。在这项工作中，比较了松柏醇（G 木质素单体）的三种 βO4 二聚体：愈创木酰甘油愈创木酚酯与羟基丙烯基 (HOC ₃ H ₄ -) 尾 (G- β O4'-G)、不含 HOC ₃ H ₄ - 的截短 GG 二聚体 (G- β O4'- 截断G ) 和苄基化 GG 二聚体 ( benz G- βO4'-G)。苯并G- β O4'-G 和 G- β O4'- trunc G对木质素二聚体的吸收（每质量脂质）和能量耗散（衡量双层紊乱）高于G- β O4凝胶相DPPC双层中的'-G，如使用具有耗散的石英晶体微天平（QCM-D）测量的。G- β O4'- trun的类似摄取对于 1,2-dioleoyl-sn-glycero-3-phosphocholine 的液相双层观察到 cG，表明双层相对二聚体摄取的影响很小。通过分析从分子动力学模拟获得的脂质双层中的密度分布、平均力曲线的潜力、脂质顺序参数和双层面积可压缩性（无序）来检查增加木质素二聚体浓度的影响。二聚体分布和平均力势表明，benz G- β O4'-G 和 G- β O4'- trunc G 比G- β对双层的渗透更高O4′-G，与 QCM-D 结果一致。由于二聚体渗透而增加的脂质尾部紊乱导致双层变薄和软化。木质素衍生物结构的微小差异（例如截断羟基丙烯基尾部）对其穿透脂质双层的能力有显着影响。