Preparation of Lignin-like Polymers by Dehydrogenation of Lignin Precursors and Structure-activity Relationships of the Resulting Polymers against Live Cancer HepG2 Cells
Lignin can be used as a natural anticancer drug because of its potential biological activity and low cytotoxicity. This research focuses on oligomeric dehydrogenation polymers (DHPs) of lignin. The lignin precursor coniferin was used to yield Zulaufverfahren dehydrogenation polymers (ZL-DHPs) and Zu...
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North Carolina State University
2025-02-01
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| author | Boxuan Zhao Zhijian Li Zhi Wang Yunbo Zhao Yimin Xie |
| author_facet | Boxuan Zhao Zhijian Li Zhi Wang Yunbo Zhao Yimin Xie |
| author_sort | Boxuan Zhao |
| collection | DOAJ |
| description | Lignin can be used as a natural anticancer drug because of its potential biological activity and low cytotoxicity. This research focuses on oligomeric dehydrogenation polymers (DHPs) of lignin. The lignin precursor coniferin was used to yield Zulaufverfahren dehydrogenation polymers (ZL-DHPs) and Zutropfverfahren dehydropolymers (ZT-DHPs) catalyzed by mixed enzymes. The 13C-NMR determination showed that the DHPs obtained were similar to natural lignin, and ZL-DHP had a slightly higher β-5 content than ZT-DHP. ZL-DHPs and ZT-DHPs were subjected to organic solvent extraction with different polarities to obtain eight fractions, i.e., ZL-1-ZL-4 and ZT-1-ZT-4. The antitumor activity showed ZL-2 (IC50 181.99 μg/mL) and ZT-2 (IC50 246.76 μg/mL) had significant inhibitory effects. Fractions ZL-2 and ZT-2 were purified through column chromatography using gradient-polarity binary eluent, and 12 purified compounds were obtained, i.e., L1–L6 and T1–T6. The results showed L2 (IC50 33.99 μg/mL) and T1 (IC50 42.08 μg/mL) had relatively high biological activity, respectively. Their structure was characterized using high-resolution mass spectrometry and 13C-NMR, indicating that L2 is a dimer with β-5 linkage (β-5, γ-CH3, and γ'-CH2OH), and T1 is also a dimer with β-5 linkage but different substituents (β-5, γ-CHO, and γ'-COOH). |
| format | Article |
| id | doaj-art-161cf9f8f6a94de18aa4650f4340d242 |
| institution | OA Journals |
| issn | 1930-2126 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | North Carolina State University |
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| series | BioResources |
| spelling | doaj-art-161cf9f8f6a94de18aa4650f4340d2422025-08-20T01:52:25ZengNorth Carolina State UniversityBioResources1930-21262025-02-01202290429212456Preparation of Lignin-like Polymers by Dehydrogenation of Lignin Precursors and Structure-activity Relationships of the Resulting Polymers against Live Cancer HepG2 CellsBoxuan Zhao0Zhijian Li1Zhi Wang2Yunbo Zhao3Yimin Xie4Research Institute of Pulp & Paper Engineering, Hubei University of Technology, Wuhan 430068 ChinaWuhan Children's Hospital (Wuhan Maternal and Child Health Hospital, Wuhan Women's and Children's Health Care Center), No.100 Xianggang Road, Wuhan, 430000 ChinaResearch Institute of Pulp & Paper Engineering, Hubei University of Technology, Wuhan 430068 ChinaResearch Institute of Pulp & Paper Engineering, Hubei University of Technology, Wuhan 430068 ChinaResearch 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 ChinaLignin can be used as a natural anticancer drug because of its potential biological activity and low cytotoxicity. This research focuses on oligomeric dehydrogenation polymers (DHPs) of lignin. The lignin precursor coniferin was used to yield Zulaufverfahren dehydrogenation polymers (ZL-DHPs) and Zutropfverfahren dehydropolymers (ZT-DHPs) catalyzed by mixed enzymes. The 13C-NMR determination showed that the DHPs obtained were similar to natural lignin, and ZL-DHP had a slightly higher β-5 content than ZT-DHP. ZL-DHPs and ZT-DHPs were subjected to organic solvent extraction with different polarities to obtain eight fractions, i.e., ZL-1-ZL-4 and ZT-1-ZT-4. The antitumor activity showed ZL-2 (IC50 181.99 μg/mL) and ZT-2 (IC50 246.76 μg/mL) had significant inhibitory effects. Fractions ZL-2 and ZT-2 were purified through column chromatography using gradient-polarity binary eluent, and 12 purified compounds were obtained, i.e., L1–L6 and T1–T6. The results showed L2 (IC50 33.99 μg/mL) and T1 (IC50 42.08 μg/mL) had relatively high biological activity, respectively. Their structure was characterized using high-resolution mass spectrometry and 13C-NMR, indicating that L2 is a dimer with β-5 linkage (β-5, γ-CH3, and γ'-CH2OH), and T1 is also a dimer with β-5 linkage but different substituents (β-5, γ-CHO, and γ'-COOH).https://ojs.bioresources.com/index.php/BRJ/article/view/24195lignindehydrogenation polymersanticancermass spectrometrystructure-activity relationship |
| spellingShingle | Boxuan Zhao Zhijian Li Zhi Wang Yunbo Zhao Yimin Xie Preparation of Lignin-like Polymers by Dehydrogenation of Lignin Precursors and Structure-activity Relationships of the Resulting Polymers against Live Cancer HepG2 Cells BioResources lignin dehydrogenation polymers anticancer mass spectrometry structure-activity relationship |
| title | Preparation of Lignin-like Polymers by Dehydrogenation of Lignin Precursors and Structure-activity Relationships of the Resulting Polymers against Live Cancer HepG2 Cells |
| title_full | Preparation of Lignin-like Polymers by Dehydrogenation of Lignin Precursors and Structure-activity Relationships of the Resulting Polymers against Live Cancer HepG2 Cells |
| title_fullStr | Preparation of Lignin-like Polymers by Dehydrogenation of Lignin Precursors and Structure-activity Relationships of the Resulting Polymers against Live Cancer HepG2 Cells |
| title_full_unstemmed | Preparation of Lignin-like Polymers by Dehydrogenation of Lignin Precursors and Structure-activity Relationships of the Resulting Polymers against Live Cancer HepG2 Cells |
| title_short | Preparation of Lignin-like Polymers by Dehydrogenation of Lignin Precursors and Structure-activity Relationships of the Resulting Polymers against Live Cancer HepG2 Cells |
| title_sort | preparation of lignin like polymers by dehydrogenation of lignin precursors and structure activity relationships of the resulting polymers against live cancer hepg2 cells |
| topic | lignin dehydrogenation polymers anticancer mass spectrometry structure-activity relationship |
| url | https://ojs.bioresources.com/index.php/BRJ/article/view/24195 |
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