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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 (¹³C-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 (DC₂) showed the strongest inhibition of A549 lung cancer cells, with an IC₅₀ of 181.46 ± 28.01 μg/mL. The DC₂ fraction was further purified using medium-pressure liquid chromatography. Anti-cancer analysis revealed that the D₄ and D₅ compounds from DC₂ had better anti-tumor activity, with IC₅₀ 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 D₄ and D₅ were β-5-linked dimers of coniferyl aldehyde, and the ¹³C-NMR and ¹H-NMR analyses confirmed the structure of the D₅. 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.