Research Institute of Pulp and 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. 2022 Feb 22;27(5):1466. doi: 10.3390/molecules27051466.
The lignin precursors of coniferin and syringin were synthesised, and guaiacyl-type and guaiacyl-syringyl-type oligomeric lignin dehydrogenation polymers (DHP and DHP-GS) were prepared with the bulk method. The carbon-13 nuclear magnetic resonance spectroscopy showed that both DHP-G and DHP-GS contained β-O-4, β-5, β-β, β-1, and 5-5 substructures. Extraction with petroleum ether, ether, ethanol, and acetone resulted in four fractions for each of DHP-G (C-C) and DHP-GS (C-C). The antibacterial experiments showed that the fractions with lower molecular weight had relatively strong antibacterial activity. The ether-soluble fractions (C of DHP-G and C of DHP-GS) had strong antibacterial activities against and . The C and C fractions were further separated by preparative chromatography, and 10 bioactive compounds (G-G and GS-GS) were obtained. The overall antibacterial activities of these 10 compounds was stronger against than . Compounds G, G, G, and GS, which had the most significant antibacterial activities, contained β-5 substructures. Of these, G had the best antibacterial activity. Its inhibition zone diameter was 19.81 ± 0.82 mm, and the minimum inhibition concentration was 56.3 ± 6.20 μg/mL. Atmospheric pressure chemical ionisation mass spectrometry (APCI-MS) showed that the antibacterial activity of G was attributable to a phenylcoumarin dimer, while the introduction of syringyl units reduced antibacterial activity.
松柏醇和丁香苷的木质素前体被合成,并用本体法制备了愈创木基型和愈创木基-丁香基型低聚木质素脱氢聚合物(DHP 和 DHP-GS)。碳-13 核磁共振光谱表明,DHP-G 和 DHP-GS 均含有 β-O-4、β-5、β-β、β-1 和 5-5 亚结构。用石油醚、乙醚、乙醇和丙酮萃取,得到 DHP-G(C-C)和 DHP-GS(C-C)的四个馏分。抗菌实验表明,分子量较低的馏分具有相对较强的抗菌活性。乙醚可溶部分(DHP-G 的 C 部分和 DHP-GS 的 C 部分)对 和 具有很强的抗菌活性。C 和 C 馏分进一步通过制备色谱分离,得到 10 种具有生物活性的化合物(G-G 和 GS-GS)。这 10 种化合物对 的整体抗菌活性强于 。抗菌活性最强的化合物 G、G、G 和 GS 均含有β-5 亚结构。其中,G 的抗菌活性最好。其抑菌圈直径为 19.81±0.82mm,最小抑菌浓度为 56.3±6.20μg/mL。大气压化学电离质谱(APCI-MS)表明,G 的抗菌活性归因于苯并呋喃二聚体,而丁香基单元的引入降低了抗菌活性。