Research Institute of Pulp & Paper Engineering, Hubei University of Technology, Wuhan 430068, China.
Hubei Provincial Key Laboratory of Green Materials for Light Industry, Hubei University of Technology, Wuhan 430068, China.
Molecules. 2023 Apr 20;28(8):3589. doi: 10.3390/molecules28083589.
In this paper, guaiacyl dehydrogenated lignin polymer (G-DHP) was synthesized using coniferin as a substrate in the presence of β-glucosidase and laccase. Carbon-13 nuclear magnetic resonance (C-NMR) determination revealed that the structure of G-DHP was relatively similar to that of ginkgo milled wood lignin (MWL), with both containing β-O-4, β-5, β-1, β-β, and 5-5 substructures. G-DHP fractions with different molecular weights were obtained by classification with different polar solvents. The bioactivity assay indicated that the ether-soluble fraction (DC) showed the strongest inhibition of A549 lung cancer cells, with an IC of 181.46 ± 28.01 μg/mL. The DC fraction was further purified using medium-pressure liquid chromatography. Anti-cancer analysis revealed that the D and D compounds from DC had better anti-tumor activity, with IC values of 61.54 ± 17.10 μg/mL and 28.61 ± 8.52 μg/mL, respectively. Heating electrospray ionization tandem mass spectrometry (HESI-MS) results showed that both the D and D were β-5-linked dimers of coniferyl aldehyde, and the C-NMR and H-NMR analyses confirmed the structure of the D. Together, these results indicate that the presence of an aldehyde group on the side chain of the phenylpropane unit of G-DHP enhances its anticancer activity.
在本研究中，以松柏醇苷为底物，在β-葡萄糖苷酶和漆酶的存在下合成了愈创木基脱氢木质素聚合物（G-DHP）。碳-13 核磁共振（C-NMR）测定表明，G-DHP 的结构与银杏木粉木质素（MWL）较为相似，两者均含有β-O-4、β-5、β-1、β-β和 5-5 亚结构。通过不同极性溶剂的分级，得到了不同分子量的 G-DHP 级分。生物活性测定表明，醚溶性级分（DC）对 A549 肺癌细胞的抑制作用最强，IC 为 181.46±28.01μg/mL。将 DC 级分进一步用中压液相色谱进行纯化。抗癌分析表明，DC 中的 D 和 D 化合物具有更好的抗肿瘤活性，IC 值分别为 61.54±17.10μg/mL 和 28.61±8.52μg/mL。加热电喷雾串联质谱（HESI-MS）结果表明，D 和 D 均为松柏醛的β-5 连接二聚体，C-NMR 和 H-NMR 分析证实了 D 的结构。综上所述，这些结果表明 G-DHP 苯丙烷单元侧链上醛基的存在增强了其抗癌活性。
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